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data-event-name="pinnable-header.vector-toc.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-toc.unpin">hide</button> </div> <ul class="vector-toc-contents" id="mw-panel-toc-list"> <li id="toc-mw-content-text" class="vector-toc-list-item vector-toc-level-1"> <a href="#" class="vector-toc-link"> <div class="vector-toc-text">(Top)</div> </a> </li> <li id="toc-Structure_and_classification" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Structure_and_classification"> <div class="vector-toc-text"> <span class="vector-toc-numb">1</span> <span>Structure and classification</span> </div> </a> <ul id="toc-Structure_and_classification-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Isomerism" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Isomerism"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Isomerism</span> </div> </a> <ul id="toc-Isomerism-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Nomenclature" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Nomenclature"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Nomenclature</span> </div> </a> <button aria-controls="toc-Nomenclature-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Nomenclature subsection</span> </button> <ul id="toc-Nomenclature-sublist" class="vector-toc-list"> <li id="toc-Linear_alkanes" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Linear_alkanes"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Linear alkanes</span> </div> </a> <ul id="toc-Linear_alkanes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Branched_alkanes" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Branched_alkanes"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Branched alkanes</span> </div> </a> <ul id="toc-Branched_alkanes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Saturated_cyclic_hydrocarbons" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Saturated_cyclic_hydrocarbons"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.3</span> <span>Saturated cyclic hydrocarbons</span> </div> </a> <ul id="toc-Saturated_cyclic_hydrocarbons-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Trivial/common_names" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Trivial/common_names"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.4</span> <span>Trivial/common names</span> </div> </a> <ul id="toc-Trivial/common_names-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Physical_properties" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Physical_properties"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Physical properties</span> </div> </a> <button aria-controls="toc-Physical_properties-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Physical properties subsection</span> </button> <ul id="toc-Physical_properties-sublist" class="vector-toc-list"> <li id="toc-Table_of_alkanes" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Table_of_alkanes"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>Table of alkanes</span> </div> </a> <ul id="toc-Table_of_alkanes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Boiling_point" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Boiling_point"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2</span> <span>Boiling point</span> </div> </a> <ul id="toc-Boiling_point-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Melting_points" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Melting_points"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.3</span> <span>Melting points</span> </div> </a> <ul id="toc-Melting_points-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Conductivity_and_solubility" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Conductivity_and_solubility"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.4</span> <span>Conductivity and solubility</span> </div> </a> <ul id="toc-Conductivity_and_solubility-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Molecular_geometry" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Molecular_geometry"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.5</span> <span>Molecular geometry</span> </div> </a> <ul id="toc-Molecular_geometry-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Bond_lengths_and_bond_angles" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Bond_lengths_and_bond_angles"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.6</span> <span>Bond lengths and bond angles</span> </div> </a> <ul id="toc-Bond_lengths_and_bond_angles-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Conformation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Conformation"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.7</span> <span>Conformation</span> </div> </a> <ul id="toc-Conformation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Spectroscopic_properties" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Spectroscopic_properties"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.8</span> <span>Spectroscopic properties</span> </div> </a> <ul id="toc-Spectroscopic_properties-sublist" class="vector-toc-list"> <li id="toc-Infrared_spectroscopy" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Infrared_spectroscopy"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.8.1</span> <span>Infrared spectroscopy</span> </div> </a> <ul id="toc-Infrared_spectroscopy-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-NMR_spectroscopy" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#NMR_spectroscopy"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.8.2</span> <span>NMR spectroscopy</span> </div> </a> <ul id="toc-NMR_spectroscopy-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Mass_spectrometry" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Mass_spectrometry"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.8.3</span> <span>Mass spectrometry</span> </div> </a> <ul id="toc-Mass_spectrometry-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> </ul> </li> <li id="toc-Chemical_properties" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Chemical_properties"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Chemical properties</span> </div> </a> <button aria-controls="toc-Chemical_properties-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Chemical properties subsection</span> </button> <ul id="toc-Chemical_properties-sublist" class="vector-toc-list"> <li id="toc-Acid-base_behavior" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Acid-base_behavior"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>Acid-base behavior</span> </div> </a> <ul id="toc-Acid-base_behavior-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Reactions_with_oxygen_(combustion_reaction)" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Reactions_with_oxygen_(combustion_reaction)"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2</span> <span>Reactions with oxygen (combustion reaction)</span> </div> </a> <ul id="toc-Reactions_with_oxygen_(combustion_reaction)-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Biodegradation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Biodegradation"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.3</span> <span>Biodegradation</span> </div> </a> <ul id="toc-Biodegradation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Free_radical_reactions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Free_radical_reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.4</span> <span>Free radical reactions</span> </div> </a> <ul id="toc-Free_radical_reactions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-C-H_activation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#C-H_activation"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.5</span> <span>C-H activation</span> </div> </a> <ul id="toc-C-H_activation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Cracking" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Cracking"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.6</span> <span>Cracking</span> </div> </a> <ul id="toc-Cracking-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Isomerization_and_reformation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Isomerization_and_reformation"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.7</span> <span>Isomerization and reformation</span> </div> </a> <ul id="toc-Isomerization_and_reformation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Other_reactions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Other_reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.8</span> <span>Other reactions</span> </div> </a> <ul id="toc-Other_reactions-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Occurrence" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Occurrence"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Occurrence</span> </div> </a> <button aria-controls="toc-Occurrence-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Occurrence subsection</span> </button> <ul id="toc-Occurrence-sublist" class="vector-toc-list"> <li id="toc-Occurrence_of_alkanes_in_the_Universe" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Occurrence_of_alkanes_in_the_Universe"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.1</span> <span>Occurrence of alkanes in the Universe</span> </div> </a> <ul id="toc-Occurrence_of_alkanes_in_the_Universe-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Occurrence_of_alkanes_on_Earth" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Occurrence_of_alkanes_on_Earth"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.2</span> <span>Occurrence of alkanes on Earth</span> </div> </a> <ul id="toc-Occurrence_of_alkanes_on_Earth-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Biological_occurrence" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Biological_occurrence"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.3</span> <span>Biological occurrence</span> </div> </a> <ul id="toc-Biological_occurrence-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Coal" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Coal"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.4</span> <span>Coal</span> </div> </a> <ul id="toc-Coal-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Laboratory_preparation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Laboratory_preparation"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.5</span> <span>Laboratory preparation</span> </div> </a> <ul id="toc-Laboratory_preparation-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Applications" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Applications"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Applications</span> </div> </a> <button aria-controls="toc-Applications-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Applications subsection</span> </button> <ul id="toc-Applications-sublist" class="vector-toc-list"> <li id="toc-Fuels" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Fuels"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.1</span> <span>Fuels</span> </div> </a> <ul id="toc-Fuels-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Precursors_to_chemicals" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Precursors_to_chemicals"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.2</span> <span>Precursors to chemicals</span> </div> </a> <ul id="toc-Precursors_to_chemicals-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Other" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Other"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.3</span> <span>Other</span> </div> </a> <ul id="toc-Other-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Hazards" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Hazards"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>Hazards</span> </div> </a> <ul id="toc-Hazards-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">10</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Further_reading" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Further_reading"> <div class="vector-toc-text"> <span class="vector-toc-numb">11</span> <span>Further reading</span> </div> </a> <ul id="toc-Further_reading-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Alkane</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. Available in 94 languages" > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-94" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">94 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-af mw-list-item"><a href="https://af.wikipedia.org/wiki/Alkaan" title="Alkaan – Afrikaans" lang="af" hreflang="af" data-title="Alkaan" data-language-autonym="Afrikaans" data-language-local-name="Afrikaans" class="interlanguage-link-target"><span>Afrikaans</span></a></li><li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%A3%D9%84%D9%83%D8%A7%D9%86" title="ألكان – Arabic" lang="ar" hreflang="ar" data-title="ألكان" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-as mw-list-item"><a href="https://as.wikipedia.org/wiki/%E0%A6%8F%E0%A6%B2%E0%A6%95%E0%A7%87%E0%A6%A8" title="এলকেন – Assamese" lang="as" hreflang="as" data-title="এলকেন" data-language-autonym="অসমীয়া" data-language-local-name="Assamese" class="interlanguage-link-target"><span>অসমীয়া</span></a></li><li class="interlanguage-link interwiki-ast mw-list-item"><a href="https://ast.wikipedia.org/wiki/Alcano" title="Alcano – Asturian" lang="ast" hreflang="ast" data-title="Alcano" data-language-autonym="Asturianu" data-language-local-name="Asturian" class="interlanguage-link-target"><span>Asturianu</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Alkanlar" title="Alkanlar – Azerbaijani" lang="az" hreflang="az" data-title="Alkanlar" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%A2%D9%84%DA%A9%D8%A7%D9%86" title="آلکان – South Azerbaijani" lang="azb" hreflang="azb" data-title="آلکان" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%85%E0%A7%8D%E0%A6%AF%E0%A6%BE%E0%A6%B2%E0%A6%95%E0%A7%87%E0%A6%A8" title="অ্যালকেন – Bangla" lang="bn" hreflang="bn" data-title="অ্যালকেন" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-zh-min-nan mw-list-item"><a href="https://zh-min-nan.wikipedia.org/wiki/Alkane" title="Alkane – Minnan" lang="nan" hreflang="nan" data-title="Alkane" data-language-autonym="閩南語 / Bân-lâm-gú" data-language-local-name="Minnan" class="interlanguage-link-target"><span>閩南語 / Bân-lâm-gú</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%90%D0%BB%D0%BA%D0%B0%D0%BD%D1%8B" title="Алканы – Belarusian" lang="be" hreflang="be" data-title="Алканы" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-be-x-old mw-list-item"><a href="https://be-tarask.wikipedia.org/wiki/%D0%90%D0%BB%D1%8C%D0%BA%D0%B0%D0%BD%D1%8B" title="Альканы – Belarusian (Taraškievica orthography)" lang="be-tarask" hreflang="be-tarask" data-title="Альканы" data-language-autonym="Беларуская (тарашкевіца)" data-language-local-name="Belarusian (Taraškievica orthography)" class="interlanguage-link-target"><span>Беларуская (тарашкевіца)</span></a></li><li class="interlanguage-link interwiki-bcl mw-list-item"><a href="https://bcl.wikipedia.org/wiki/Alkano" title="Alkano – Central Bikol" lang="bcl" hreflang="bcl" data-title="Alkano" data-language-autonym="Bikol Central" data-language-local-name="Central Bikol" class="interlanguage-link-target"><span>Bikol Central</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%90%D0%BB%D0%BA%D0%B0%D0%BD" title="Алкан – Bulgarian" lang="bg" hreflang="bg" data-title="Алкан" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Alkani" title="Alkani – Bosnian" lang="bs" hreflang="bs" data-title="Alkani" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Alc%C3%A0" title="Alcà – Catalan" lang="ca" hreflang="ca" data-title="Alcà" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Alkany" title="Alkany – Czech" lang="cs" hreflang="cs" data-title="Alkany" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-cy mw-list-item"><a href="https://cy.wikipedia.org/wiki/Alcan" title="Alcan – Welsh" lang="cy" hreflang="cy" data-title="Alcan" data-language-autonym="Cymraeg" data-language-local-name="Welsh" class="interlanguage-link-target"><span>Cymraeg</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Alkan" title="Alkan – Danish" lang="da" hreflang="da" data-title="Alkan" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de badge-Q17437796 badge-featuredarticle mw-list-item" title="featured article badge"><a href="https://de.wikipedia.org/wiki/Alkane" title="Alkane – German" lang="de" hreflang="de" data-title="Alkane" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Alkaanid" title="Alkaanid – Estonian" lang="et" hreflang="et" data-title="Alkaanid" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%91%CE%BB%CE%BA%CE%AC%CE%BD%CE%B9%CE%B1" title="Αλκάνια – Greek" lang="el" hreflang="el" data-title="Αλκάνια" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Alcano" title="Alcano – Spanish" lang="es" hreflang="es" data-title="Alcano" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Alkano" title="Alkano – Esperanto" lang="eo" hreflang="eo" data-title="Alkano" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Alkano" title="Alkano – Basque" lang="eu" hreflang="eu" data-title="Alkano" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A2%D9%84%DA%A9%D8%A7%D9%86" title="آلکان – Persian" lang="fa" hreflang="fa" data-title="آلکان" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fo mw-list-item"><a href="https://fo.wikipedia.org/wiki/Alkan" title="Alkan – Faroese" lang="fo" hreflang="fo" data-title="Alkan" data-language-autonym="Føroyskt" data-language-local-name="Faroese" class="interlanguage-link-target"><span>Føroyskt</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Alcane" title="Alcane – French" lang="fr" hreflang="fr" data-title="Alcane" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ga mw-list-item"><a href="https://ga.wikipedia.org/wiki/Alc%C3%A1n" title="Alcán – Irish" lang="ga" hreflang="ga" data-title="Alcán" data-language-autonym="Gaeilge" data-language-local-name="Irish" class="interlanguage-link-target"><span>Gaeilge</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Alcano" title="Alcano – Galician" lang="gl" hreflang="gl" data-title="Alcano" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%95%8C%EC%BC%80%EC%9D%B8" title="알케인 – Korean" lang="ko" hreflang="ko" data-title="알케인" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D4%B1%D5%AC%D5%AF%D5%A1%D5%B6%D5%B6%D5%A5%D6%80" title="Ալկաններ – Armenian" lang="hy" hreflang="hy" data-title="Ալկաններ" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%85%E0%A4%B2%E0%A5%8D%E0%A4%95%E0%A5%87%E0%A4%A8" title="अल्केन – Hindi" lang="hi" hreflang="hi" data-title="अल्केन" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Alkani" title="Alkani – Croatian" lang="hr" hreflang="hr" data-title="Alkani" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Alkana" title="Alkana – Indonesian" lang="id" hreflang="id" data-title="Alkana" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-is mw-list-item"><a href="https://is.wikipedia.org/wiki/Alkanar" title="Alkanar – Icelandic" lang="is" hreflang="is" data-title="Alkanar" data-language-autonym="Íslenska" data-language-local-name="Icelandic" class="interlanguage-link-target"><span>Íslenska</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Alcani" title="Alcani – Italian" lang="it" hreflang="it" data-title="Alcani" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%90%D7%9C%D7%A7%D7%90%D7%9F" title="אלקאן – Hebrew" lang="he" hreflang="he" data-title="אלקאן" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-jv mw-list-item"><a href="https://jv.wikipedia.org/wiki/Alkana" title="Alkana – Javanese" lang="jv" hreflang="jv" data-title="Alkana" data-language-autonym="Jawa" data-language-local-name="Javanese" class="interlanguage-link-target"><span>Jawa</span></a></li><li class="interlanguage-link interwiki-kn mw-list-item"><a href="https://kn.wikipedia.org/wiki/%E0%B2%86%E0%B2%B2%E0%B3%8D%E0%B2%95%E0%B3%87%E0%B2%A8%E0%B3%8D%E2%80%8C%E0%B2%97%E0%B2%B3%E0%B3%81" title="ಆಲ್ಕೇನ್‌ಗಳು – Kannada" lang="kn" hreflang="kn" data-title="ಆಲ್ಕೇನ್‌ಗಳು" data-language-autonym="ಕನ್ನಡ" data-language-local-name="Kannada" class="interlanguage-link-target"><span>ಕನ್ನಡ</span></a></li><li class="interlanguage-link interwiki-ka mw-list-item"><a href="https://ka.wikipedia.org/wiki/%E1%83%90%E1%83%9A%E1%83%99%E1%83%90%E1%83%9C%E1%83%98" title="ალკანი – Georgian" lang="ka" hreflang="ka" data-title="ალკანი" data-language-autonym="ქართული" data-language-local-name="Georgian" class="interlanguage-link-target"><span>ქართული</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%90%D0%BB%D0%BA%D0%B0%D0%BD%D0%B4%D0%B0%D1%80" title="Алкандар – Kazakh" lang="kk" hreflang="kk" data-title="Алкандар" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-ku mw-list-item"><a href="https://ku.wikipedia.org/wiki/Alkan" title="Alkan – Kurdish" lang="ku" hreflang="ku" data-title="Alkan" data-language-autonym="Kurdî" data-language-local-name="Kurdish" class="interlanguage-link-target"><span>Kurdî</span></a></li><li class="interlanguage-link interwiki-la mw-list-item"><a href="https://la.wikipedia.org/wiki/Alcanum" title="Alcanum – Latin" lang="la" hreflang="la" data-title="Alcanum" data-language-autonym="Latina" data-language-local-name="Latin" class="interlanguage-link-target"><span>Latina</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Alk%C4%81ni" title="Alkāni – Latvian" lang="lv" hreflang="lv" data-title="Alkāni" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-lb mw-list-item"><a href="https://lb.wikipedia.org/wiki/Alkanen" title="Alkanen – Luxembourgish" lang="lb" hreflang="lb" data-title="Alkanen" data-language-autonym="Lëtzebuergesch" data-language-local-name="Luxembourgish" class="interlanguage-link-target"><span>Lëtzebuergesch</span></a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Alkanas" title="Alkanas – Lithuanian" lang="lt" hreflang="lt" data-title="Alkanas" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target"><span>Lietuvių</span></a></li><li class="interlanguage-link interwiki-lmo mw-list-item"><a href="https://lmo.wikipedia.org/wiki/Alcan" title="Alcan – Lombard" lang="lmo" hreflang="lmo" data-title="Alcan" data-language-autonym="Lombard" data-language-local-name="Lombard" class="interlanguage-link-target"><span>Lombard</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Alk%C3%A1nok" title="Alkánok – Hungarian" lang="hu" hreflang="hu" data-title="Alkánok" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%90%D0%BB%D0%BA%D0%B0%D0%BD" title="Алкан – Macedonian" lang="mk" hreflang="mk" data-title="Алкан" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-ml mw-list-item"><a href="https://ml.wikipedia.org/wiki/%E0%B4%86%E0%B5%BD%E0%B4%95%E0%B5%8D%E0%B4%95%E0%B5%86%E0%B4%AF%E0%B5%8D%E0%B5%BB" title="ആൽക്കെയ്ൻ – Malayalam" lang="ml" hreflang="ml" data-title="ആൽക്കെയ്ൻ" data-language-autonym="മലയാളം" data-language-local-name="Malayalam" class="interlanguage-link-target"><span>മലയാളം</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Alkana" title="Alkana – Malay" lang="ms" hreflang="ms" data-title="Alkana" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-mn mw-list-item"><a href="https://mn.wikipedia.org/wiki/%D0%90%D0%BB%D0%BA%D0%B0%D0%BD" title="Алкан – Mongolian" lang="mn" hreflang="mn" data-title="Алкан" data-language-autonym="Монгол" data-language-local-name="Mongolian" class="interlanguage-link-target"><span>Монгол</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Alkaan" title="Alkaan – Dutch" lang="nl" hreflang="nl" data-title="Alkaan" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%A2%E3%83%AB%E3%82%AB%E3%83%B3" title="アルカン – Japanese" lang="ja" hreflang="ja" data-title="アルカン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Alkaner" title="Alkaner – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Alkaner" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-nn mw-list-item"><a href="https://nn.wikipedia.org/wiki/Alkan" title="Alkan – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Alkan" data-language-autonym="Norsk nynorsk" data-language-local-name="Norwegian Nynorsk" class="interlanguage-link-target"><span>Norsk nynorsk</span></a></li><li class="interlanguage-link interwiki-nrm mw-list-item"><a href="https://nrm.wikipedia.org/wiki/Alcane" title="Alcane – Norman" lang="nrf" hreflang="nrf" data-title="Alcane" data-language-autonym="Nouormand" data-language-local-name="Norman" class="interlanguage-link-target"><span>Nouormand</span></a></li><li class="interlanguage-link interwiki-oc mw-list-item"><a href="https://oc.wikipedia.org/wiki/Alcan" title="Alcan – Occitan" lang="oc" hreflang="oc" data-title="Alcan" data-language-autonym="Occitan" data-language-local-name="Occitan" class="interlanguage-link-target"><span>Occitan</span></a></li><li class="interlanguage-link interwiki-om mw-list-item"><a href="https://om.wikipedia.org/wiki/Alkeenii" title="Alkeenii – Oromo" lang="om" hreflang="om" data-title="Alkeenii" data-language-autonym="Oromoo" data-language-local-name="Oromo" class="interlanguage-link-target"><span>Oromoo</span></a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/To%CA%BByingan_uglevodorodlar" title="Toʻyingan uglevodorodlar – Uzbek" lang="uz" hreflang="uz" data-title="Toʻyingan uglevodorodlar" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="Uzbek" class="interlanguage-link-target"><span>Oʻzbekcha / ўзбекча</span></a></li><li class="interlanguage-link interwiki-pa mw-list-item"><a href="https://pa.wikipedia.org/wiki/%E0%A8%85%E0%A8%B2%E0%A8%95%E0%A9%87%E0%A8%A8" title="ਅਲਕੇਨ – Punjabi" lang="pa" hreflang="pa" data-title="ਅਲਕੇਨ" data-language-autonym="ਪੰਜਾਬੀ" data-language-local-name="Punjabi" class="interlanguage-link-target"><span>ਪੰਜਾਬੀ</span></a></li><li class="interlanguage-link interwiki-ps mw-list-item"><a href="https://ps.wikipedia.org/wiki/%D8%A7%D9%84%DA%A9%D8%A7%D9%86" title="الکان – Pashto" lang="ps" hreflang="ps" data-title="الکان" data-language-autonym="پښتو" data-language-local-name="Pashto" class="interlanguage-link-target"><span>پښتو</span></a></li><li class="interlanguage-link interwiki-pms mw-list-item"><a href="https://pms.wikipedia.org/wiki/Parafin-a" title="Parafin-a – Piedmontese" lang="pms" hreflang="pms" data-title="Parafin-a" data-language-autonym="Piemontèis" data-language-local-name="Piedmontese" class="interlanguage-link-target"><span>Piemontèis</span></a></li><li class="interlanguage-link interwiki-nds mw-list-item"><a href="https://nds.wikipedia.org/wiki/Alkan" title="Alkan – Low German" lang="nds" hreflang="nds" data-title="Alkan" data-language-autonym="Plattdüütsch" data-language-local-name="Low German" class="interlanguage-link-target"><span>Plattdüütsch</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Alkany" title="Alkany – Polish" lang="pl" hreflang="pl" data-title="Alkany" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Alcano" title="Alcano – Portuguese" lang="pt" hreflang="pt" data-title="Alcano" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Alcan" title="Alcan – Romanian" lang="ro" hreflang="ro" data-title="Alcan" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-rue mw-list-item"><a href="https://rue.wikipedia.org/wiki/%D0%90%D0%BB%D0%BA%D0%B0%D0%BD%D1%8B" title="Алканы – Rusyn" lang="rue" hreflang="rue" data-title="Алканы" data-language-autonym="Русиньскый" data-language-local-name="Rusyn" class="interlanguage-link-target"><span>Русиньскый</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%90%D0%BB%D0%BA%D0%B0%D0%BD%D1%8B" title="Алканы – Russian" lang="ru" hreflang="ru" data-title="Алканы" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-stq mw-list-item"><a href="https://stq.wikipedia.org/wiki/Alkane" title="Alkane – Saterland Frisian" lang="stq" hreflang="stq" data-title="Alkane" data-language-autonym="Seeltersk" data-language-local-name="Saterland Frisian" class="interlanguage-link-target"><span>Seeltersk</span></a></li><li class="interlanguage-link interwiki-sq mw-list-item"><a href="https://sq.wikipedia.org/wiki/Alkanet" title="Alkanet – Albanian" lang="sq" hreflang="sq" data-title="Alkanet" data-language-autonym="Shqip" data-language-local-name="Albanian" class="interlanguage-link-target"><span>Shqip</span></a></li><li class="interlanguage-link interwiki-scn mw-list-item"><a href="https://scn.wikipedia.org/wiki/Alcani" title="Alcani – Sicilian" lang="scn" hreflang="scn" data-title="Alcani" data-language-autonym="Sicilianu" data-language-local-name="Sicilian" class="interlanguage-link-target"><span>Sicilianu</span></a></li><li class="interlanguage-link interwiki-si mw-list-item"><a href="https://si.wikipedia.org/wiki/%E0%B6%87%E0%B6%BD%E0%B7%8A%E0%B6%9A%E0%B7%9A%E0%B6%B1" title="ඇල්කේන – Sinhala" lang="si" hreflang="si" data-title="ඇල්කේන" data-language-autonym="සිංහල" data-language-local-name="Sinhala" class="interlanguage-link-target"><span>සිංහල</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Alkane" title="Alkane – Simple English" lang="en-simple" hreflang="en-simple" data-title="Alkane" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target"><span>Simple English</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Alk%C3%A1n" title="Alkán – Slovak" lang="sk" hreflang="sk" data-title="Alkán" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sl badge-Q17437796 badge-featuredarticle mw-list-item" title="featured article badge"><a href="https://sl.wikipedia.org/wiki/Alkan" title="Alkan – Slovenian" lang="sl" hreflang="sl" data-title="Alkan" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-ckb mw-list-item"><a href="https://ckb.wikipedia.org/wiki/%D8%A6%DB%95%D9%84%DA%A9%D8%A7%D9%86" title="ئەلکان – Central Kurdish" lang="ckb" hreflang="ckb" data-title="ئەلکان" data-language-autonym="کوردی" data-language-local-name="Central Kurdish" class="interlanguage-link-target"><span>کوردی</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/%D0%90%D0%BB%D0%BA%D0%B0%D0%BD" title="Алкан – Serbian" lang="sr" hreflang="sr" data-title="Алкан" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Alkani" title="Alkani – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Alkani" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-su mw-list-item"><a href="https://su.wikipedia.org/wiki/Alkana" title="Alkana – Sundanese" lang="su" hreflang="su" data-title="Alkana" data-language-autonym="Sunda" data-language-local-name="Sundanese" class="interlanguage-link-target"><span>Sunda</span></a></li><li class="interlanguage-link interwiki-fi 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href="https://kab.wikipedia.org/wiki/Alkan" title="Alkan – Kabyle" lang="kab" hreflang="kab" data-title="Alkan" data-language-autonym="Taqbaylit" data-language-local-name="Kabyle" class="interlanguage-link-target"><span>Taqbaylit</span></a></li><li class="interlanguage-link interwiki-te mw-list-item"><a href="https://te.wikipedia.org/wiki/%E0%B0%86%E0%B0%B2%E0%B1%8D%E0%B0%95%E0%B1%87%E0%B0%A8%E0%B1%8D" title="ఆల్కేన్ – Telugu" lang="te" hreflang="te" data-title="ఆల్కేన్" data-language-autonym="తెలుగు" data-language-local-name="Telugu" class="interlanguage-link-target"><span>తెలుగు</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B9%81%E0%B8%AD%E0%B8%A5%E0%B9%80%E0%B8%84%E0%B8%99" title="แอลเคน – Thai" lang="th" hreflang="th" data-title="แอลเคน" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a 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class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Type of saturated hydrocarbon compound</div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Not to be confused with <a href="/wiki/Alkene" title="Alkene">alkene</a>, <a href="/wiki/Alkyne" title="Alkyne">alkyne</a>, <a href="/wiki/Alkali" title="Alkali">alkali</a>, or <a href="/wiki/Alkali" title="Alkali">alkaline</a>.</div> <p class="mw-empty-elt"> </p> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Methane-2D-stereo.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/92/Methane-2D-stereo.svg/220px-Methane-2D-stereo.svg.png" decoding="async" width="220" height="227" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/92/Methane-2D-stereo.svg/330px-Methane-2D-stereo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/92/Methane-2D-stereo.svg/440px-Methane-2D-stereo.svg.png 2x" data-file-width="512" data-file-height="528" /></a><figcaption>Chemical structure of <a href="/wiki/Methane" title="Methane">methane</a>, the simplest alkane</figcaption></figure> <p>In <a href="/wiki/Organic_chemistry" title="Organic chemistry">organic chemistry</a>, an <b>alkane</b>, or <b>paraffin</b> (a historical <a href="/wiki/Trivial_name" title="Trivial name">trivial name</a> that also has <a href="/wiki/Paraffin_(disambiguation)" class="mw-redirect mw-disambig" title="Paraffin (disambiguation)">other meanings</a>), is an <a href="/wiki/Open-chain_compound" title="Open-chain compound">acyclic</a> <a href="/wiki/Saturated_and_unsaturated_compounds" title="Saturated and unsaturated compounds">saturated</a> <a href="/wiki/Hydrocarbon" title="Hydrocarbon">hydrocarbon</a>. In other words, an alkane consists of <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a> and <a href="/wiki/Carbon" title="Carbon">carbon</a> atoms arranged in a <a href="/wiki/Tree_(graph_theory)" title="Tree (graph theory)">tree</a> structure in which all the <a href="/wiki/Carbon%E2%80%93carbon_bond" title="Carbon–carbon bond">carbon–carbon bonds</a> are <a href="/wiki/Single_bond" title="Single bond">single</a>.<sup id="cite_ref-GoldBook_alkanes_1-0" class="reference"><a href="#cite_note-GoldBook_alkanes-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Alkanes have the general chemical formula <style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">C<sub class="template-chem2-sub"><i>n</i></sub>H<sub class="template-chem2-sub">2<i>n</i>+2</sub></span>. The alkanes range in complexity from the simplest case of <a href="/wiki/Methane" title="Methane">methane</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">4</sub></span>), where <i>n</i> = 1 (sometimes called the parent molecule), to arbitrarily large and complex molecules, like <a href="/wiki/Higher_alkanes#Nonatetracontane_to_tetrapentacontane" class="mw-redirect" title="Higher alkanes">pentacontane</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">50</sub>H<sub class="template-chem2-sub">102</sub></span>) or 6-ethyl-2-methyl-5-(1-methylethyl) octane, an <a href="/wiki/Isomer" title="Isomer">isomer</a> of <a href="/wiki/Tetradecane" title="Tetradecane">tetradecane</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">14</sub>H<sub class="template-chem2-sub">30</sub></span>). </p><p>The <a href="/wiki/International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">International Union of Pure and Applied Chemistry</a> (IUPAC) defines alkanes as "acyclic branched or unbranched hydrocarbons having the general formula <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub"><i>n</i></sub>H<sub class="template-chem2-sub">2<i>n</i>+2</sub></span>, and therefore consisting entirely of hydrogen atoms and saturated carbon atoms". However, some sources use the term to denote <i>any</i> saturated hydrocarbon, including those that are either monocyclic (i.e. the <a href="/wiki/Cycloalkane" title="Cycloalkane">cycloalkanes</a>) or <a href="/wiki/Polycyclic_compound" title="Polycyclic compound">polycyclic</a>, despite them having a distinct general formula (e.g. cycloalkanes are <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub"><i>n</i></sub>H<sub class="template-chem2-sub">2<i>n</i></sub></span>). </p><p>In an alkane, each carbon atom is <a href="/wiki/Orbital_hybridisation" title="Orbital hybridisation">sp<sup>3</sup>-hybridized</a> with 4 <a href="/wiki/Sigma_bond" title="Sigma bond">sigma bonds</a> (either C–C or <a href="/wiki/Carbon%E2%80%93hydrogen_bond" title="Carbon–hydrogen bond">C–H</a>), and each hydrogen atom is joined to one of the carbon atoms (in a C–H bond). The longest series of linked carbon atoms in a molecule is known as its <a href="/wiki/Skeletal_formula" title="Skeletal formula">carbon skeleton</a> or carbon backbone. The number of carbon atoms may be considered as the size of the alkane. </p><p>One group of the <a href="/wiki/Higher_alkanes" class="mw-redirect" title="Higher alkanes">higher alkanes</a> are <a href="/wiki/Wax" title="Wax">waxes</a>, solids at <a href="/wiki/Standard_temperature_and_pressure" title="Standard temperature and pressure">standard ambient temperature and pressure</a> (SATP), for which the number of carbon atoms in the carbon backbone is greater than about 17. With their repeated –<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">2</sub></span> units, the alkanes constitute a <a href="/wiki/Homologous_series" title="Homologous series">homologous series</a> of organic compounds in which the members differ in <a href="/wiki/Molecular_mass" title="Molecular mass">molecular mass</a> by multiples of 14.03 <a href="/wiki/Dalton_(unit)" title="Dalton (unit)">u</a> (the total mass of each such <a href="/wiki/Methylene_bridge" title="Methylene bridge">methylene-bridge</a> unit, which comprises a single carbon atom of mass 12.01 u and two hydrogen atoms of mass ~1.01 u each). </p><p>Methane is produced by <a href="/wiki/Methanogen" title="Methanogen">methanogenic bacteria</a> and some long-chain alkanes function as pheromones in certain animal species or as protective waxes in plants and fungi. Nevertheless, most alkanes do not have much <a href="/wiki/Biological_activity" title="Biological activity">biological activity</a>. They can be viewed as molecular trees upon which can be hung the more active/reactive <a href="/wiki/Functional_group" title="Functional group">functional groups</a> of biological molecules. </p><p>The alkanes have two main commercial sources: <a href="/wiki/Petroleum" title="Petroleum">petroleum</a> (crude oil) and <a href="/wiki/Natural_gas" title="Natural gas">natural gas</a>. </p><p>An <a href="/wiki/Alkyl" class="mw-redirect" title="Alkyl">alkyl</a> group is an alkane-based molecular fragment that bears one open valence for bonding. They are generally abbreviated with the symbol for any <a href="/wiki/Organyl_group" title="Organyl group">organyl group</a>, R, although Alk is sometimes used to specifically symbolize an alkyl group (as opposed to an alkenyl group or aryl group). </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Structure_and_classification">Structure and classification</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkane&action=edit&section=1" title="Edit section: Structure and classification"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Ordinarily the C-C single bond distance is 1.53 <a href="/wiki/%C3%85ngstr%C3%B6m" class="mw-redirect" title="Ångström">ångströms</a> (1.53<span style="margin:0 .15em 0 .25em">×</span>10<sup>−10</sup> m).<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Saturated hydrocarbons can be linear, branched, or <a href="/wiki/Cyclic_compound" title="Cyclic compound">cyclic</a>. The third group is sometimes called <a href="/wiki/Cycloalkane" title="Cycloalkane">cycloalkanes</a>.<sup id="cite_ref-GoldBook_alkanes_1-1" class="reference"><a href="#cite_note-GoldBook_alkanes-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Very complicated structures are possible by combining linear, branch, cyclic alkanes. </p> <div class="mw-heading mw-heading2"><h2 id="Isomerism">Isomerism</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkane&action=edit&section=2" title="Edit section: Isomerism"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Saturated_C4_hydrocarbons_ball-and-stick_(C4H10_C4H8).png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5a/Saturated_C4_hydrocarbons_ball-and-stick_%28C4H10_C4H8%29.png/260px-Saturated_C4_hydrocarbons_ball-and-stick_%28C4H10_C4H8%29.png" decoding="async" width="260" height="208" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5a/Saturated_C4_hydrocarbons_ball-and-stick_%28C4H10_C4H8%29.png/390px-Saturated_C4_hydrocarbons_ball-and-stick_%28C4H10_C4H8%29.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5a/Saturated_C4_hydrocarbons_ball-and-stick_%28C4H10_C4H8%29.png/520px-Saturated_C4_hydrocarbons_ball-and-stick_%28C4H10_C4H8%29.png 2x" data-file-width="1360" data-file-height="1088" /></a><figcaption> C<sub>4</sub> alkanes and cycloalkanes (left to right): <a href="/wiki/N-butane" class="mw-redirect" title="N-butane"><i>n</i>-butane</a> and <a href="/wiki/Isobutane" title="Isobutane">isobutane</a> are the two C<sub>4</sub>H<sub>10</sub> isomers; <a href="/wiki/Cyclobutane" title="Cyclobutane">cyclobutane</a> and <a href="/wiki/Methylcyclopropane" title="Methylcyclopropane">methylcyclopropane</a> are the two C<sub>4</sub>H<sub>8</sub> isomers.</figcaption></figure> <style data-mw-deduplicate="TemplateStyles:r1237032888/mw-parser-output/.tmulti">.mw-parser-output .tmulti .multiimageinner{display:flex;flex-direction:column}.mw-parser-output .tmulti .trow{display:flex;flex-direction:row;clear:left;flex-wrap:wrap;width:100%;box-sizing:border-box}.mw-parser-output .tmulti .tsingle{margin:1px;float:left}.mw-parser-output .tmulti .theader{clear:both;font-weight:bold;text-align:center;align-self:center;background-color:transparent;width:100%}.mw-parser-output .tmulti .thumbcaption{background-color:transparent}.mw-parser-output .tmulti .text-align-left{text-align:left}.mw-parser-output .tmulti .text-align-right{text-align:right}.mw-parser-output .tmulti .text-align-center{text-align:center}@media all and (max-width:720px){.mw-parser-output .tmulti .thumbinner{width:100%!important;box-sizing:border-box;max-width:none!important;align-items:center}.mw-parser-output .tmulti .trow{justify-content:center}.mw-parser-output .tmulti .tsingle{float:none!important;max-width:100%!important;box-sizing:border-box;text-align:center}.mw-parser-output .tmulti .tsingle .thumbcaption{text-align:left}.mw-parser-output .tmulti .trow>.thumbcaption{text-align:center}}@media screen{html.skin-theme-clientpref-night .mw-parser-output .tmulti .multiimageinner img{background-color:white}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .tmulti .multiimageinner img{background-color:white}}</style><div class="thumb tmulti tright"><div class="thumbinner multiimageinner" style="width:262px;max-width:262px"><div class="trow"><div class="tsingle" style="width:139px;max-width:139px"><div class="thumbimage" style="height:112px;overflow:hidden"><span typeof="mw:File"><a href="/wiki/File:Saturated_C4_hydrocarbons_ball-and-stick_(C4H6).png" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d1/Saturated_C4_hydrocarbons_ball-and-stick_%28C4H6%29.png/137px-Saturated_C4_hydrocarbons_ball-and-stick_%28C4H6%29.png" decoding="async" width="137" height="113" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d1/Saturated_C4_hydrocarbons_ball-and-stick_%28C4H6%29.png/206px-Saturated_C4_hydrocarbons_ball-and-stick_%28C4H6%29.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d1/Saturated_C4_hydrocarbons_ball-and-stick_%28C4H6%29.png/274px-Saturated_C4_hydrocarbons_ball-and-stick_%28C4H6%29.png 2x" data-file-width="544" data-file-height="448" /></a></span></div><div class="thumbcaption"><a href="/wiki/Bicyclobutane" title="Bicyclobutane">Bicyclo[1.1.0]butane</a> is the only C<sub>4</sub>H<sub>6</sub> alkane and has no alkane isomer.</div></div><div class="tsingle" style="width:119px;max-width:119px"><div class="thumbimage" style="height:112px;overflow:hidden"><span typeof="mw:File"><a href="/wiki/File:Tetrahedrane-3D-balls.png" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/ee/Tetrahedrane-3D-balls.png/117px-Tetrahedrane-3D-balls.png" decoding="async" width="117" height="113" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/ee/Tetrahedrane-3D-balls.png/176px-Tetrahedrane-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/ee/Tetrahedrane-3D-balls.png/234px-Tetrahedrane-3D-balls.png 2x" data-file-width="1100" data-file-height="1058" /></a></span></div><div class="thumbcaption"><a href="/wiki/Tetrahedrane" title="Tetrahedrane">Tetrahedrane</a> is the only C<sub>4</sub>H<sub>4</sub> alkane and also has no alkane isomer.</div></div></div></div></div> <p>Alkanes with more than three <a href="/wiki/Carbon" title="Carbon">carbon</a> atoms can be arranged in various ways, forming <a href="/wiki/Structural_isomer" title="Structural isomer">structural isomers</a>. The simplest isomer of an alkane is the one in which the carbon atoms are arranged in a single chain with no branches. This isomer is sometimes called the <i>n</i>-isomer (<i>n</i> for "normal", although it is not necessarily the most common). However, the chain of carbon atoms may also be branched at one or more points. The number of possible isomers increases rapidly with the number of carbon atoms. For example, for acyclic alkanes:<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <ul><li>C<sub>1</sub>: <a href="/wiki/Methane" title="Methane">methane</a> only</li> <li>C<sub>2</sub>: <a href="/wiki/Ethane" title="Ethane">ethane</a> only</li> <li>C<sub>3</sub>: <a href="/wiki/Propane" title="Propane">propane</a> only</li> <li>C<sub>4</sub>: 2 isomers: <a href="/wiki/Butane" title="Butane">butane</a> and <a href="/wiki/Isobutane" title="Isobutane">isobutane</a></li> <li>C<sub>5</sub>: 3 isomers: <a href="/wiki/Pentane" title="Pentane">pentane</a>, <a href="/wiki/Isopentane" title="Isopentane">isopentane</a>, and <a href="/wiki/Neopentane" title="Neopentane">neopentane</a></li> <li>C<sub>6</sub>: 5 isomers: <a href="/wiki/Hexane" title="Hexane">hexane</a>, <a href="/wiki/2-Methylpentane" title="2-Methylpentane">2-methylpentane</a>, <a href="/wiki/3-Methylpentane" title="3-Methylpentane">3-methylpentane</a>, <a href="/wiki/2,2-Dimethylbutane" title="2,2-Dimethylbutane">2,2-dimethylbutane</a>, and <a href="/wiki/2,3-Dimethylbutane" title="2,3-Dimethylbutane">2,3-dimethylbutane</a></li> <li>C<sub>7</sub>: 9 isomers: <a href="/wiki/Heptane" title="Heptane">heptane</a>, <a href="/wiki/2-methylhexane" class="mw-redirect" title="2-methylhexane">2-methylhexane</a>, <a href="/wiki/3-methylhexane" class="mw-redirect" title="3-methylhexane">3-methylhexane</a>, <a href="/wiki/2,2-dimethylpentane" class="mw-redirect" title="2,2-dimethylpentane">2,2-dimethylpentane</a>, <a href="/wiki/2,3-dimethylpentane" class="mw-redirect" title="2,3-dimethylpentane">2,3-dimethylpentane</a>, <a href="/w/index.php?title=2,4-dimethylpentane&action=edit&redlink=1" class="new" title="2,4-dimethylpentane (page does not exist)">2,4-dimethylpentane</a>, <a href="/w/index.php?title=3,3-dimethylpentane&action=edit&redlink=1" class="new" title="3,3-dimethylpentane (page does not exist)">3,3-dimethylpentane</a>, <a href="/wiki/3-ethylpentane" class="mw-redirect" title="3-ethylpentane">3-ethylpentane</a>, <a href="/wiki/2,2,3-trimethylbutane" class="mw-redirect" title="2,2,3-trimethylbutane">2,2,3-trimethylbutane</a></li> <li>C<sub>8</sub>: 18 isomers: <a href="/wiki/Octane" title="Octane">octane</a>, <a href="/wiki/2-methylheptane" class="mw-redirect" title="2-methylheptane">2-methylheptane</a>, <a href="/wiki/3-methylheptane" class="mw-redirect" title="3-methylheptane">3-methylheptane</a>, <a href="/w/index.php?title=4-methylheptane&action=edit&redlink=1" class="new" title="4-methylheptane (page does not exist)">4-methylheptane</a>, <a href="/w/index.php?title=2,2-dimethylhexane&action=edit&redlink=1" class="new" title="2,2-dimethylhexane (page does not exist)">2,2-dimethylhexane</a>, <a href="/wiki/2,3-dimethylhexane" class="mw-redirect" title="2,3-dimethylhexane">2,3-dimethylhexane</a>, <a href="/w/index.php?title=2,4-dimethylhexane&action=edit&redlink=1" class="new" title="2,4-dimethylhexane (page does not exist)">2,4-dimethylhexane</a>, <a href="/wiki/2,5-dimethylhexane" class="mw-redirect" title="2,5-dimethylhexane">2,5-dimethylhexane</a>, <a href="/wiki/3,3-dimethylhexane" class="mw-redirect" title="3,3-dimethylhexane">3,3-dimethylhexane</a>, <a href="/w/index.php?title=3,4-dimethylhexane&action=edit&redlink=1" class="new" title="3,4-dimethylhexane (page does not exist)">3,4-dimethylhexane</a>, <a href="/w/index.php?title=3-ethylhexane&action=edit&redlink=1" class="new" title="3-ethylhexane (page does not exist)">3-ethylhexane</a>, <a href="/w/index.php?title=2,2,3-trimethylpentane&action=edit&redlink=1" class="new" title="2,2,3-trimethylpentane (page does not exist)">2,2,3-trimethylpentane</a>, <a href="/wiki/2,2,4-trimethylpentane" class="mw-redirect" title="2,2,4-trimethylpentane">2,2,4-trimethylpentane</a>, <a href="/wiki/2,3,3-trimethylpentane" class="mw-redirect" title="2,3,3-trimethylpentane">2,3,3-trimethylpentane</a>, <a href="/wiki/2,3,4-trimethylpentane" class="mw-redirect" title="2,3,4-trimethylpentane">2,3,4-trimethylpentane</a>, <a href="/w/index.php?title=3-ethyl-2-methylpentane&action=edit&redlink=1" class="new" title="3-ethyl-2-methylpentane (page does not exist)">3-ethyl-2-methylpentane</a>, <a href="/w/index.php?title=3-ethyl-3-methylpentane&action=edit&redlink=1" class="new" title="3-ethyl-3-methylpentane (page does not exist)">3-ethyl-3-methylpentane</a>, <a href="/wiki/2,2,3,3-tetramethylbutane" class="mw-redirect" title="2,2,3,3-tetramethylbutane">2,2,3,3-tetramethylbutane</a></li> <li>C<sub>9</sub>: <a href="/wiki/List_of_isomers_of_nonane" title="List of isomers of nonane">35 isomers</a></li> <li>C<sub>10</sub>: <a href="/wiki/List_of_isomers_of_decane" title="List of isomers of decane">75 isomers</a></li> <li>C<sub>12</sub>: <a href="/wiki/List_of_isomers_of_dodecane" title="List of isomers of dodecane">355 isomers</a></li> <li>C<sub>32</sub>: 27,711,253,769 isomers</li> <li>C<sub>60</sub>: 22,158,734,535,770,411,074,184 isomers, many of which are not stable</li></ul> <p>Branched alkanes can be <a href="/wiki/Chirality_(chemistry)" title="Chirality (chemistry)">chiral</a>. For example, <a href="/wiki/3-methylhexane" class="mw-redirect" title="3-methylhexane">3-methylhexane</a> and its higher <a href="/wiki/Homologous_series" title="Homologous series">homologues</a> are chiral due to their <a href="/wiki/Stereogenic_center" class="mw-redirect" title="Stereogenic center">stereogenic center</a> at carbon atom number 3. The above list only includes differences of connectivity, not stereochemistry. In addition to the alkane isomers, the chain of carbon atoms may form one or more rings. Such compounds are called <a href="/wiki/Cycloalkane" title="Cycloalkane">cycloalkanes</a>, and are also excluded from the above list because changing the number of rings changes the <a href="/wiki/Molecular_formula" class="mw-redirect" title="Molecular formula">molecular formula</a>. For example, <a href="/wiki/Cyclobutane" title="Cyclobutane">cyclobutane</a> and <a href="/wiki/Methylcyclopropane" title="Methylcyclopropane">methylcyclopropane</a> are isomers of each other (C<sub>4</sub>H<sub>8</sub>), but are not isomers of butane (C<sub>4</sub>H<sub>10</sub>). </p><p>Branched alkanes are more thermodynamically stable than their linear (or less branched) isomers. For example, the highly branched 2,2,3,3-tetramethylbutane is about 1.9 kcal/mol more stable than its linear isomer, <i>n</i>-octane.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Nomenclature">Nomenclature</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkane&action=edit&section=3" title="Edit section: Nomenclature"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/IUPAC_nomenclature_of_organic_chemistry" title="IUPAC nomenclature of organic chemistry">IUPAC nomenclature of organic chemistry</a></div> <p>The <a href="/wiki/IUPAC_nomenclature_of_organic_chemistry#Alkanes" title="IUPAC nomenclature of organic chemistry">IUPAC nomenclature</a> (systematic way of naming compounds) for alkanes is based on identifying hydrocarbon chains. Unbranched, saturated hydrocarbon chains are named systematically with a Greek numerical prefix denoting the number of carbons and the suffix "-ane".<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p>In 1866, <a href="/wiki/August_Wilhelm_von_Hofmann" title="August Wilhelm von Hofmann">August Wilhelm von Hofmann</a> suggested systematizing nomenclature by using the whole sequence of vowels a, e, i, o and u to create suffixes -ane, -ene, -ine (or -yne), -one, -une, for the <a href="/wiki/Hydrocarbons" class="mw-redirect" title="Hydrocarbons">hydrocarbons</a> C<sub><i>n</i></sub>H<sub>2<i>n</i>+2</sub>, C<sub><i>n</i></sub>H<sub>2<i>n</i></sub>, C<sub><i>n</i></sub>H<sub>2<i>n</i>−2</sub>, C<sub><i>n</i></sub>H<sub>2<i>n</i>−4</sub>, C<sub><i>n</i></sub>H<sub>2<i>n</i>−6</sub>.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> In modern nomenclature, the first three specifically name hydrocarbons with single, double and triple bonds;<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> while "-one" now represents a <a href="/wiki/Ketone" title="Ketone">ketone</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Linear_alkanes">Linear alkanes</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkane&action=edit&section=4" title="Edit section: Linear alkanes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Further information: <a href="/wiki/List_of_straight-chain_alkanes" title="List of straight-chain alkanes">List of straight-chain alkanes</a></div> <p>Straight-chain alkanes are sometimes indicated by the prefix "n-" or "<i>n</i>-"(for "normal") where a non-linear <a href="/wiki/Isomer" title="Isomer">isomer</a> exists. Although this is not strictly necessary and is not part of the IUPAC naming system, the usage is still common in cases where one wishes to emphasize or distinguish between the straight-chain and branched-chain isomers, e.g., "<a href="/wiki/Butane" title="Butane"><i>n</i>-butane</a>" rather than simply "butane" to differentiate it from <a href="/wiki/Isobutane" title="Isobutane">isobutane</a>. Alternative names for this group used in the petroleum industry are <b>linear paraffins</b> or <b><i>n</i>-paraffins</b>. </p><p>The first eight members of the series (in terms of number of carbon atoms) are named as follows: </p> <dl><dt><a href="/wiki/Methane" title="Methane">methane</a></dt> <dd>CH<sub>4</sub> – one carbon and 4 hydrogen</dd> <dt><a href="/wiki/Ethane" title="Ethane">ethane</a></dt> <dd>C<sub>2</sub>H<sub>6</sub> – two carbon and 6 hydrogen</dd> <dt><a href="/wiki/Propane" title="Propane">propane</a></dt> <dd>C<sub>3</sub>H<sub>8</sub> – three carbon and 8 hydrogen</dd> <dt><a href="/wiki/Butane" title="Butane">butane</a></dt> <dd>C<sub>4</sub>H<sub>10</sub> – four carbon and 10 hydrogen</dd> <dt><a href="/wiki/Pentane" title="Pentane">pentane</a></dt> <dd>C<sub>5</sub>H<sub>12</sub> – five carbon and 12 hydrogen</dd> <dt><a href="/wiki/Hexane" title="Hexane">hexane</a></dt> <dd>C<sub>6</sub>H<sub>14</sub> – six carbon and 14 hydrogen</dd> <dt><a href="/wiki/Heptane" title="Heptane">heptane</a></dt> <dd>C<sub>7</sub>H<sub>16</sub> – seven carbons and 16 hydrogen</dd> <dt><a href="/wiki/Octane" title="Octane">octane</a></dt> <dd>C<sub>8</sub>H<sub>18</sub> – eight carbons and 18 hydrogen</dd></dl> <p>The first four names were <a href="/wiki/Back-formation" title="Back-formation">derived</a> from <a href="/wiki/Methanol" title="Methanol">methanol</a>, <a href="/wiki/Diethyl_ether" title="Diethyl ether">ether</a>, <a href="/wiki/Propionic_acid" title="Propionic acid">propionic acid</a> and <a href="/wiki/Butyric_acid" title="Butyric acid">butyric acid</a>. Alkanes with five or more carbon atoms are named by adding the <a href="/wiki/Affix" title="Affix">suffix</a> <b>-ane</b> to the appropriate <a href="/wiki/IUPAC_numerical_multiplier" title="IUPAC numerical multiplier">numerical multiplier</a> prefix<sup id="cite_ref-reusch-nom_8-0" class="reference"><a href="#cite_note-reusch-nom-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> with <a href="/wiki/Elision" title="Elision">elision</a> of any terminal vowel (<i>-a</i> or <i>-o</i>) from the basic numerical term. Hence, <a href="/wiki/Pentane" title="Pentane">pentane</a>, C<sub>5</sub>H<sub>12</sub>; <a href="/wiki/Hexane" title="Hexane">hexane</a>, C<sub>6</sub>H<sub>14</sub>; <a href="/wiki/Heptane" title="Heptane">heptane</a>, C<sub>7</sub>H<sub>16</sub>; <a href="/wiki/Octane" title="Octane">octane</a>, C<sub>8</sub>H<sub>18</sub>; etc. The <a href="/wiki/Numeral_prefix" title="Numeral prefix">numeral prefix</a> is generally Greek; however, alkanes with a carbon atom count ending in nine, for example <a href="/wiki/Nonane" title="Nonane">nonane</a>, use the <a href="/wiki/Latin_language" class="mw-redirect" title="Latin language">Latin</a> prefix <b>non-</b>. </p> <div class="mw-heading mw-heading3"><h3 id="Branched_alkanes">Branched alkanes</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkane&action=edit&section=5" title="Edit section: Branched alkanes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Isopentane-numbered-3D-balls.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b7/Isopentane-numbered-3D-balls.png/220px-Isopentane-numbered-3D-balls.png" decoding="async" width="220" height="170" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b7/Isopentane-numbered-3D-balls.png/330px-Isopentane-numbered-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b7/Isopentane-numbered-3D-balls.png/440px-Isopentane-numbered-3D-balls.png 2x" data-file-width="1100" data-file-height="849" /></a><figcaption><a href="/wiki/Ball-and-stick_model" title="Ball-and-stick model">Ball-and-stick model</a> of <a href="/wiki/Isopentane" title="Isopentane">isopentane</a> (common name) or 2-methylbutane (IUPAC systematic name)</figcaption></figure> <p>Simple branched alkanes often have a common name using a prefix to distinguish them from linear alkanes, for example <a href="/wiki/Pentane" title="Pentane"><i>n</i>-pentane</a>, <a href="/wiki/Isopentane" title="Isopentane">isopentane</a>, and <a href="/wiki/Neopentane" title="Neopentane">neopentane</a>. </p><p>IUPAC naming conventions can be used to produce a systematic name. </p><p>The key steps in the naming of more complicated branched alkanes are as follows:<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <ul><li>Identify the longest continuous chain of carbon atoms</li> <li>Name this longest root chain using standard naming rules</li> <li>Name each side chain by changing the suffix of the name of the alkane from "-ane" to "-yl"</li> <li>Number the longest continuous chain in order to give the lowest possible numbers for the side-chains<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup></li> <li>Number and name the side chains before the name of the root chain</li> <li>If there are multiple side chains of the same type, use prefixes such as "di-" and "tri-" to indicate it as such, and number each one.</li> <li>Add side chain names in alphabetical (disregarding "di-" etc. prefixes) order in front of the name of the root chain</li></ul> <table class="wikitable" style="text-align:center"> <caption>Comparison of nomenclatures for three isomers of C<sub>5</sub>H<sub>12</sub> </caption> <tbody><tr> <th>Common name </th> <th><i>n</i>-pentane</th> <th>isopentane</th> <th>neopentane </th></tr> <tr> <th>IUPAC name </th> <th>pentane</th> <th>2-methylbutane</th> <th>2,2-dimethylpropane </th></tr> <tr> <th>Structure </th> <td><span typeof="mw:File"><a href="/wiki/File:Pentane-2D-Skeletal.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/38/Pentane-2D-Skeletal.svg/120px-Pentane-2D-Skeletal.svg.png" decoding="async" width="120" height="30" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/38/Pentane-2D-Skeletal.svg/180px-Pentane-2D-Skeletal.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/38/Pentane-2D-Skeletal.svg/240px-Pentane-2D-Skeletal.svg.png 2x" data-file-width="330" data-file-height="83" /></a></span></td> <td><span typeof="mw:File"><a href="/wiki/File:Isopentane-2D-skeletal.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6c/Isopentane-2D-skeletal.svg/90px-Isopentane-2D-skeletal.svg.png" decoding="async" width="90" height="55" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6c/Isopentane-2D-skeletal.svg/135px-Isopentane-2D-skeletal.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6c/Isopentane-2D-skeletal.svg/180px-Isopentane-2D-skeletal.svg.png 2x" data-file-width="141" data-file-height="86" /></a></span></td> <td><span typeof="mw:File"><a href="/wiki/File:Neopentane-2D-skeletal.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3f/Neopentane-2D-skeletal.png/70px-Neopentane-2D-skeletal.png" decoding="async" width="70" height="59" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3f/Neopentane-2D-skeletal.png/105px-Neopentane-2D-skeletal.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3f/Neopentane-2D-skeletal.png/140px-Neopentane-2D-skeletal.png 2x" data-file-width="800" data-file-height="672" /></a></span> </td></tr></tbody></table> <div class="mw-heading mw-heading3"><h3 id="Saturated_cyclic_hydrocarbons">Saturated cyclic hydrocarbons</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkane&action=edit&section=6" title="Edit section: Saturated cyclic hydrocarbons"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Cycloalkane" title="Cycloalkane">Cycloalkane</a></div> <p>Though technically distinct from the alkanes, this class of hydrocarbons is referred to by some as the "cyclic alkanes." As their description implies, they contain one or more rings. </p><p>Simple cycloalkanes have a prefix "cyclo-" to distinguish them from alkanes. Cycloalkanes are named as per their acyclic counterparts with respect to the number of carbon atoms in their backbones, e.g., <a href="/wiki/Cyclopentane" title="Cyclopentane">cyclopentane</a> (C<sub>5</sub>H<sub>10</sub>) is a cycloalkane with 5 carbon atoms just like <a href="/wiki/Pentane" title="Pentane">pentane</a> (C<sub>5</sub>H<sub>12</sub>), but they are joined up in a five-membered ring. In a similar manner, <a href="/wiki/Propane" title="Propane">propane</a> and <a href="/wiki/Cyclopropane" title="Cyclopropane">cyclopropane</a>, <a href="/wiki/Butane" title="Butane">butane</a> and <a href="/wiki/Cyclobutane" title="Cyclobutane">cyclobutane</a>, etc. </p><p>Substituted cycloalkanes are named similarly to substituted alkanes – the cycloalkane ring is stated, and the substituents are according to their position on the ring, with the numbering decided by the <a href="/wiki/Cahn%E2%80%93Ingold%E2%80%93Prelog_priority_rules" title="Cahn–Ingold–Prelog priority rules">Cahn–Ingold–Prelog priority rules</a>.<sup id="cite_ref-reusch-nom_8-1" class="reference"><a href="#cite_note-reusch-nom-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Trivial/common_names"><span id="Trivial.2Fcommon_names"></span>Trivial/common names</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkane&action=edit&section=7" title="Edit section: Trivial/common names"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/List_of_straight-chain_alkanes" title="List of straight-chain alkanes">List of straight-chain alkanes</a></div> <p>The trivial (non-<a href="/wiki/IUPAC_nomenclature" class="mw-redirect" title="IUPAC nomenclature">systematic</a>) name for alkanes is 'paraffins'. Together, alkanes are known as the 'paraffin series'. Trivial names for compounds are usually historical artifacts. They were coined before the development of systematic names, and have been retained due to familiar usage in industry. Cycloalkanes are also called naphthenes.<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p><p>Branched-chain alkanes are called <b>isoparaffins</b>. "Paraffin" is a general term and often does not distinguish between pure compounds and mixtures of <a href="/wiki/Isomer" title="Isomer">isomers</a>, i.e., compounds of the same <a href="/wiki/Chemical_formula" title="Chemical formula">chemical formula</a>, e.g., <a href="/wiki/Pentane" title="Pentane">pentane</a> and <a href="/wiki/Isopentane" title="Isopentane">isopentane</a>. </p> <dl><dt>In IUPAC</dt></dl> <p>The following trivial names are retained in the IUPAC system: </p> <ul><li><a href="/wiki/Isobutane" title="Isobutane">isobutane</a> for 2-methylpropane</li> <li><a href="/wiki/Isopentane" title="Isopentane">isopentane</a> for 2-methylbutane</li> <li><a href="/wiki/Neopentane" title="Neopentane">neopentane</a> for 2,2-dimethylpropane.</li></ul> <dl><dt>Non-IUPAC</dt></dl> <p>Some non-IUPAC trivial names are occasionally used: </p> <ul><li>cetane, for <a href="/wiki/Hexadecane" title="Hexadecane">hexadecane</a></li> <li>cerane, for <a href="/wiki/Hexacosane" class="mw-redirect" title="Hexacosane">hexacosane</a><sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup></li></ul> <div class="mw-heading mw-heading2"><h2 id="Physical_properties">Physical properties</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkane&action=edit&section=8" title="Edit section: Physical properties"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Higher_alkane" title="Higher alkane">Higher alkane</a> and <a href="/wiki/List_of_straight-chain_alkanes" title="List of straight-chain alkanes">List of straight-chain alkanes</a></div> <p>All alkanes are colorless.<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> Alkanes with the lowest molecular weights are gases, those of intermediate molecular weight are liquids, and the heaviest are waxy solids.<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Table_of_alkanes">Table of alkanes</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkane&action=edit&section=9" title="Edit section: Table of alkanes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <table class="wikitable"> <tbody><tr> <th>Alkane </th> <th>Formula </th> <th>Boiling point<sup id="cite_ref-prop_18-0" class="reference"><a href="#cite_note-prop-18"><span class="cite-bracket">[</span>note 1<span class="cite-bracket">]</span></a></sup><br />[°C] </th> <th>Melting point<sup id="cite_ref-prop_18-1" class="reference"><a href="#cite_note-prop-18"><span class="cite-bracket">[</span>note 1<span class="cite-bracket">]</span></a></sup><br />[°C] </th> <th>Density<sup id="cite_ref-prop_18-2" class="reference"><a href="#cite_note-prop-18"><span class="cite-bracket">[</span>note 1<span class="cite-bracket">]</span></a></sup><br />[kg/m<sup>3</sup>] (at 20 °C) </th> <th>Isomers<sup id="cite_ref-isomer_19-0" class="reference"><a href="#cite_note-isomer-19"><span class="cite-bracket">[</span>note 2<span class="cite-bracket">]</span></a></sup> </th></tr> <tr> <td><a href="/wiki/Methane" title="Methane">Methane</a> </td> <td>CH<sub>4</sub> </td> <td>−162 </td> <td>−182 </td> <td>0.656 (gas) </td> <td>1 </td></tr> <tr> <td><a href="/wiki/Ethane" title="Ethane">Ethane</a> </td> <td>C<sub>2</sub>H<sub>6</sub> </td> <td>−89 </td> <td>−183 </td> <td>1.26 (gas) </td> <td>1 </td></tr> <tr> <td><a href="/wiki/Propane" title="Propane">Propane</a> </td> <td>C<sub>3</sub>H<sub>8</sub> </td> <td>−42 </td> <td>−188 </td> <td>2.01 (gas) </td> <td>1 </td></tr> <tr> <td><a href="/wiki/Butane" title="Butane">Butane</a> </td> <td>C<sub>4</sub>H<sub>10</sub> </td> <td>0 </td> <td>−138 </td> <td>2.48 (gas) </td> <td>2 </td></tr> <tr> <td><a href="/wiki/Pentane" title="Pentane">Pentane</a> </td> <td>C<sub>5</sub>H<sub>12</sub> </td> <td>36 </td> <td>−130 </td> <td>626 (liquid) </td> <td>3 </td></tr> <tr> <td><a href="/wiki/Hexane" title="Hexane">Hexane</a> </td> <td>C<sub>6</sub>H<sub>14</sub> </td> <td>69 </td> <td>−95 </td> <td>659 (liquid) </td> <td>5 </td></tr> <tr> <td><a href="/wiki/Heptane" title="Heptane">Heptane</a> </td> <td>C<sub>7</sub>H<sub>16</sub> </td> <td>98 </td> <td>−91 </td> <td>684 (liquid) </td> <td>9 </td></tr> <tr> <td><a href="/wiki/Octane" title="Octane">Octane</a> </td> <td>C<sub>8</sub>H<sub>18</sub> </td> <td>126 </td> <td>−57 </td> <td>703 (liquid) </td> <td>18 </td></tr> <tr> <td><a href="/wiki/Nonane" title="Nonane">Nonane</a> </td> <td>C<sub>9</sub>H<sub>20</sub> </td> <td>151 </td> <td>−54 </td> <td>718 (liquid) </td> <td>35 </td></tr> <tr> <td><a href="/wiki/Decane" title="Decane">Decane</a> </td> <td>C<sub>10</sub>H<sub>22</sub> </td> <td>174 </td> <td>−30 </td> <td>730 (liquid) </td> <td>75 </td></tr> <tr> <td><a href="/wiki/Undecane" title="Undecane">Undecane</a> </td> <td>C<sub>11</sub>H<sub>24</sub> </td> <td>196 </td> <td>−26 </td> <td>740 (liquid) </td> <td>159 </td></tr> <tr> <td><a href="/wiki/Dodecane" title="Dodecane">Dodecane</a> </td> <td>C<sub>12</sub>H<sub>26</sub> </td> <td>216 </td> <td>−10 </td> <td>749 (liquid) </td> <td>355 </td></tr> <tr> <td><a href="/wiki/Tridecane" title="Tridecane">Tridecane</a> </td> <td>C<sub>13</sub>H<sub>28</sub> </td> <td>235 </td> <td>−5.4 </td> <td>756 (liquid) </td> <td>802 </td></tr> <tr> <td><a href="/wiki/Tetradecane" title="Tetradecane">Tetradecane</a> </td> <td>C<sub>14</sub>H<sub>30</sub> </td> <td>253 </td> <td>5.9 </td> <td>763 (liquid) </td> <td>1858 </td></tr> <tr> <td><a href="/wiki/Pentadecane" title="Pentadecane">Pentadecane</a> </td> <td>C<sub>15</sub>H<sub>32</sub> </td> <td>270 </td> <td>10 </td> <td>769 (liquid) </td> <td>4347 </td></tr> <tr> <td><a href="/wiki/Hexadecane" title="Hexadecane">Hexadecane</a> </td> <td>C<sub>16</sub>H<sub>34</sub> </td> <td>287 </td> <td>18 </td> <td>773 (liquid) </td> <td>10,359 </td></tr> <tr> <td><a href="/wiki/Heptadecane" title="Heptadecane">Heptadecane</a> </td> <td>C<sub>17</sub>H<sub>36</sub> </td> <td>303 </td> <td>22 </td> <td>777 (solid) </td> <td>24,894 </td></tr> <tr> <td><a href="/wiki/Octadecane" title="Octadecane">Octadecane</a> </td> <td>C<sub>18</sub>H<sub>38</sub> </td> <td>317 </td> <td>28 </td> <td>781 (solid) </td> <td>60,523 </td></tr> <tr> <td><a href="/wiki/Nonadecane" title="Nonadecane">Nonadecane</a> </td> <td>C<sub>19</sub>H<sub>40</sub> </td> <td>330 </td> <td>32 </td> <td>785 (solid) </td> <td>148,284 </td></tr> <tr> <td><a href="/wiki/Icosane" title="Icosane">Icosane</a> </td> <td>C<sub>20</sub>H<sub>42</sub> </td> <td>343 </td> <td>37 </td> <td>789 (solid) </td> <td>366,319 </td></tr> <tr> <td><a href="/wiki/Triacontane" class="mw-redirect" title="Triacontane">Triacontane</a> </td> <td>C<sub>30</sub>H<sub>62</sub> </td> <td>450 </td> <td>66 </td> <td>810 (solid) </td> <td>4,111,846,763 </td></tr> <tr> <td><a href="/wiki/Tetracontane" class="mw-redirect" title="Tetracontane">Tetracontane</a> </td> <td>C<sub>40</sub>H<sub>82</sub> </td> <td>525 </td> <td>82 </td> <td>817 (solid) </td> <td>62,481,801,147,341 </td></tr> <tr> <td><a href="/wiki/Pentacontane" class="mw-redirect" title="Pentacontane">Pentacontane</a> </td> <td>C<sub>50</sub>H<sub>102</sub> </td> <td>575 </td> <td>91 </td> <td>824 (solid) </td> <td>1,117,743,651,746,953,270 </td></tr> <tr> <td><a href="/wiki/Hexacontane" class="mw-redirect" title="Hexacontane">Hexacontane</a> </td> <td>C<sub>60</sub>H<sub>122</sub> </td> <td>625 </td> <td>100 </td> <td>829 (solid) </td> <td>2.21587345357704×10<sup>22</sup> </td></tr> <tr> <td>Heptacontane </td> <td>C<sub>70</sub>H<sub>142</sub> </td> <td>653 </td> <td>109 </td> <td>869 (solid) </td> <td>4.71484798515330×10<sup>26</sup> </td></tr> <tr> <td colspan="6"><style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-prop-18"><span class="mw-cite-backlink">^ <a href="#cite_ref-prop_18-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-prop_18-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-prop_18-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text">Physical properties of the straight-chain isomer</span> </li> <li id="cite_note-isomer-19"><span class="mw-cite-backlink"><b><a href="#cite_ref-isomer_19-0">^</a></b></span> <span class="reference-text">Total number of <a href="/wiki/Constitutional_isomer" class="mw-redirect" title="Constitutional isomer">constitutional isomers</a> for this molecular formula</span> </li> </ol></div></div> </td></tr></tbody></table> <div class="mw-heading mw-heading3"><h3 id="Boiling_point">Boiling point</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkane&action=edit&section=10" title="Edit section: Boiling point"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:AlkaneBoilingMeltingPoint.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/82/AlkaneBoilingMeltingPoint.png/420px-AlkaneBoilingMeltingPoint.png" decoding="async" width="420" height="210" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/82/AlkaneBoilingMeltingPoint.png/630px-AlkaneBoilingMeltingPoint.png 1.5x, //upload.wikimedia.org/wikipedia/commons/8/82/AlkaneBoilingMeltingPoint.png 2x" data-file-width="704" data-file-height="352" /></a><figcaption>Melting (blue) and boiling (orange) points of the first 16 <i>n</i>-alkanes in °C.</figcaption></figure> <p>Alkanes experience intermolecular <a href="/wiki/Van_der_Waals_force" title="Van der Waals force">van der Waals forces</a>. The cumulative effects of these intermolecular forces give rise to greater boiling points of alkanes.<sup id="cite_ref-m&b_20-0" class="reference"><a href="#cite_note-m&b-20"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p><p>Two factors influence the strength of the van der Waals forces: </p> <ul><li>the number of electrons surrounding the <a href="/wiki/Molecule" title="Molecule">molecule</a>, which increases with the alkane's molecular weight</li> <li>the surface area of the molecule</li></ul> <p>Under <a href="/wiki/Standard_conditions" class="mw-redirect" title="Standard conditions">standard conditions</a>, from CH<sub>4</sub> to C<sub>4</sub>H<sub>10</sub> alkanes are gaseous; from C<sub>5</sub>H<sub>12</sub> to C<sub>17</sub>H<sub>36</sub> they are liquids; and after C<sub>18</sub>H<sub>38</sub> they are solids. As the boiling point of alkanes is primarily determined by weight, it should not be a surprise that the boiling point has an almost linear relationship with the size (<a href="/wiki/Molecular_weight" class="mw-redirect" title="Molecular weight">molecular weight</a>) of the molecule. As a rule of thumb, the boiling point rises 20–30 °C for each carbon added to the chain; this rule applies to other homologous series.<sup id="cite_ref-m&b_20-1" class="reference"><a href="#cite_note-m&b-20"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p><p>A straight-chain alkane will have a boiling point higher than a branched-chain alkane due to the greater surface area in contact, and thus greater van der Waals forces, between adjacent molecules. For example, compare <a href="/wiki/Isobutane" title="Isobutane">isobutane</a> (2-methylpropane) and <a href="/wiki/N-butane" class="mw-redirect" title="N-butane">n-butane</a> (butane), which boil at −12 and 0 °C, and 2,2-dimethylbutane and 2,3-dimethylbutane which boil at 50 and 58 °C, respectively.<sup id="cite_ref-m&b_20-2" class="reference"><a href="#cite_note-m&b-20"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p><p>On the other hand, cycloalkanes tend to have higher boiling points than their linear counterparts due to the locked conformations of the molecules, which give a plane of intermolecular contact. </p> <div class="mw-heading mw-heading3"><h3 id="Melting_points">Melting points</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkane&action=edit&section=11" title="Edit section: Melting points"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The <a href="/wiki/Melting_point" title="Melting point">melting points</a> of the alkanes follow a similar trend to <a href="/wiki/Boiling_points" class="mw-redirect" title="Boiling points">boiling points</a> for the same reason as outlined above. That is, (all other things being equal) the larger the molecule the higher the melting point. There is one significant difference between boiling points and melting points. Solids have a more rigid and fixed structure than liquids. This rigid structure requires energy to break down. Thus the better put together solid structures will require more energy to break apart. For alkanes, this can be seen from the graph above (i.e., the blue line). The odd-numbered alkanes have a lower trend in melting points than even-numbered alkanes. This is because even-numbered alkanes pack well in the solid phase, forming a well-organized structure which requires more energy to break apart. The odd-numbered alkanes pack less well and so the "looser"-organized solid packing structure requires less energy to break apart.<sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> For a visualization of the crystal structures see.<sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p><p>The melting points of branched-chain alkanes can be either higher or lower than those of the corresponding straight-chain alkanes, again depending on the ability of the alkane in question to pack well in the solid phase. </p> <div class="mw-heading mw-heading3"><h3 id="Conductivity_and_solubility">Conductivity and solubility</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkane&action=edit&section=12" title="Edit section: Conductivity and solubility"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Alkanes do not conduct electricity in any way, nor are they substantially <a href="/wiki/Relative_static_permittivity" class="mw-redirect" title="Relative static permittivity">polarized</a> by an <a href="/wiki/Electric_field" title="Electric field">electric field</a>. For this reason, they do not form <a href="/wiki/Hydrogen_bond" title="Hydrogen bond">hydrogen bonds</a> and are insoluble in polar solvents such as water. Since the hydrogen bonds between individual water molecules are aligned away from an alkane molecule, the coexistence of an alkane and water leads to an increase in molecular order (a reduction in <a href="/wiki/Entropy" title="Entropy">entropy</a>). As there is no significant bonding between water molecules and alkane molecules, the <a href="/wiki/Second_law_of_thermodynamics" title="Second law of thermodynamics">second law of thermodynamics</a> suggests that this reduction in entropy should be minimized by minimizing the contact between alkane and water: Alkanes are said to be <a href="/wiki/Hydrophobe" title="Hydrophobe">hydrophobic</a> as they are insoluble in water. </p><p>Their solubility in nonpolar solvents is relatively high, a property that is called <a href="/wiki/Lipophilicity" title="Lipophilicity">lipophilicity</a>. Alkanes are, for example, miscible in all proportions among themselves. </p><p>The density of the alkanes usually increases with the number of carbon atoms but remains less than that of water. Hence, alkanes form the upper layer in an alkane–water mixture.<sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Molecular_geometry">Molecular geometry</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkane&action=edit&section=13" title="Edit section: Molecular geometry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Ch4_hybridization.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/bb/Ch4_hybridization.svg/170px-Ch4_hybridization.svg.png" decoding="async" width="170" height="159" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/bb/Ch4_hybridization.svg/255px-Ch4_hybridization.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/bb/Ch4_hybridization.svg/340px-Ch4_hybridization.svg.png 2x" data-file-width="756" data-file-height="707" /></a><figcaption>sp<sup>3</sup>-hybridization in methane.</figcaption></figure> <p>The molecular structure of the alkanes directly affects their physical and chemical characteristics. It is derived from the <a href="/wiki/Electron_configuration" title="Electron configuration">electron configuration</a> of <a href="/wiki/Carbon" title="Carbon">carbon</a>, which has four <a href="/wiki/Valence_electron" title="Valence electron">valence electrons</a>. The carbon atoms in alkanes are described as sp<sup>3</sup> hybrids; that is to say that, to a good approximation, the valence electrons are in orbitals directed towards the corners of a tetrahedron which are derived from the combination of the 2s orbital and the three 2p orbitals. Geometrically, the angle between the bonds are cos<sup>−1</sup>(−<style data-mw-deduplicate="TemplateStyles:r1214402035">.mw-parser-output .sfrac{white-space:nowrap}.mw-parser-output .sfrac.tion,.mw-parser-output .sfrac .tion{display:inline-block;vertical-align:-0.5em;font-size:85%;text-align:center}.mw-parser-output .sfrac .num{display:block;line-height:1em;margin:0.0em 0.1em;border-bottom:1px solid}.mw-parser-output .sfrac .den{display:block;line-height:1em;margin:0.1em 0.1em}.mw-parser-output .sr-only{border:0;clip:rect(0,0,0,0);clip-path:polygon(0px 0px,0px 0px,0px 0px);height:1px;margin:-1px;overflow:hidden;padding:0;position:absolute;width:1px}</style><span class="sfrac">⁠<span class="tion"><span class="num">1</span><span class="sr-only">/</span><span class="den">3</span></span>⁠</span>) ≈ 109.47°. This is exact for the case of methane, while larger alkanes containing a combination of C–H and C–C bonds generally have bonds that are within several degrees of this idealized value. </p> <div class="mw-heading mw-heading3"><h3 id="Bond_lengths_and_bond_angles">Bond lengths and bond angles</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkane&action=edit&section=14" title="Edit section: Bond lengths and bond angles"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Ch4-structure.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/55/Ch4-structure.png/170px-Ch4-structure.png" decoding="async" width="170" height="176" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/5/55/Ch4-structure.png 1.5x" data-file-width="172" data-file-height="178" /></a><figcaption>The tetrahedral structure of methane.</figcaption></figure> <p>An alkane has only C–H and C–C single bonds. The former result from the overlap of an sp<sup>3</sup> orbital of carbon with the 1s orbital of a hydrogen; the latter by the overlap of two sp<sup>3</sup> orbitals on adjacent carbon atoms. The <a href="/wiki/Bond_length" title="Bond length">bond lengths</a> amount to 1.09 × 10<sup>−10</sup> m for a C–H bond and 1.54 × 10<sup>−10</sup> m for a C–C bond. </p><p>The spatial arrangement of the bonds is similar to that of the four sp<sup>3</sup> orbitals—they are tetrahedrally arranged, with an angle of 109.47° between them. Structural formulae that represent the bonds as being at right angles to one another, while both common and useful, do not accurately depict the geometry. </p> <div class="mw-heading mw-heading3"><h3 id="Conformation">Conformation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkane&action=edit&section=15" title="Edit section: Conformation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Alkane_stereochemistry" class="mw-redirect" title="Alkane stereochemistry">Alkane stereochemistry</a></div> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Newman_projection_ethane.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e3/Newman_projection_ethane.png/220px-Newman_projection_ethane.png" decoding="async" width="220" height="105" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e3/Newman_projection_ethane.png/330px-Newman_projection_ethane.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e3/Newman_projection_ethane.png/440px-Newman_projection_ethane.png 2x" data-file-width="2022" data-file-height="964" /></a><figcaption>Newman projections of two of many conformations of ethane: eclipsed on the left, staggered on the right.</figcaption></figure> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Ethane-rotamers-3D-balls.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d0/Ethane-rotamers-3D-balls.png/220px-Ethane-rotamers-3D-balls.png" decoding="async" width="220" height="111" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d0/Ethane-rotamers-3D-balls.png/330px-Ethane-rotamers-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d0/Ethane-rotamers-3D-balls.png/440px-Ethane-rotamers-3D-balls.png 2x" data-file-width="1100" data-file-height="555" /></a><figcaption><a href="/wiki/Ball-and-stick_model" title="Ball-and-stick model">Ball-and-stick models</a> of the two rotamers of ethane</figcaption></figure> <p>The spatial arrangement of the C-C and C-H bonds are described by the torsion angles of the molecule is known as its <a href="/wiki/Conformational_isomerism" title="Conformational isomerism">conformation</a>. In <a href="/wiki/Ethane" title="Ethane">ethane</a>, the simplest case for studying the conformation of alkanes, there is nearly free rotation about a carbon–carbon single bond. Two limiting conformations are important: <a href="/wiki/Eclipsed" class="mw-redirect" title="Eclipsed">eclipsed</a> conformation and <a href="/wiki/Staggered_conformation" title="Staggered conformation">staggered conformation</a>. The staggered conformation is 12.6 kJ/mol (3.0 kcal/mol) lower in energy (more stable) than the eclipsed conformation (the least stable). In highly branched alkanes, the bond angle may differ from the optimal value (109.5°) to accommodate bulky groups. Such distortions introduce a tension in the molecule, known as <a href="/wiki/Steric_hindrance" class="mw-redirect" title="Steric hindrance">steric hindrance</a> or strain. Strain substantially increases reactivity.<sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Spectroscopic_properties">Spectroscopic properties</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkane&action=edit&section=16" title="Edit section: Spectroscopic properties"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Spectroscopic signatures for alkanes are obtainable by the major characterization techniques.<sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Infrared_spectroscopy">Infrared spectroscopy</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkane&action=edit&section=17" title="Edit section: Infrared spectroscopy"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The C-H stretching mode gives a strong absorptions between 2850 and 2960 <a href="/wiki/Wavenumber" title="Wavenumber">cm<sup>−1</sup></a> and weaker bands for the C-C stretching mode absorbs between 800 and 1300 cm<sup>−1</sup>. The carbon–hydrogen bending modes depend on the nature of the group: methyl groups show bands at 1450 cm<sup>−1</sup> and 1375 cm<sup>−1</sup>, while methylene groups show bands at 1465 cm<sup>−1</sup> and 1450 cm<sup>−1</sup>.<sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> Carbon chains with more than four carbon atoms show a weak absorption at around 725 cm<sup>−1</sup>. </p> <div class="mw-heading mw-heading4"><h4 id="NMR_spectroscopy">NMR spectroscopy</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkane&action=edit&section=18" title="Edit section: NMR spectroscopy"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The proton resonances of alkanes are usually found at <a href="/wiki/Chemical_shift" title="Chemical shift"><i>δ</i><sub>H</sub></a> = 0.5–1.5. The carbon-13 resonances depend on the number of hydrogen atoms attached to the carbon: <i>δ</i><sub>C</sub> = 8–30 (primary, methyl, –CH<sub>3</sub>), 15–55 (secondary, methylene, –CH<sub>2</sub>–), 20–60 (tertiary, methyne, C–H) and quaternary. The carbon-13 resonance of quaternary carbon atoms is characteristically weak, due to the lack of <a href="/wiki/Nuclear_Overhauser_effect" title="Nuclear Overhauser effect">nuclear Overhauser effect</a> and the long <a href="/wiki/Relaxation_time" class="mw-redirect" title="Relaxation time">relaxation time</a>, and can be missed in weak samples, or samples that have not been run for a sufficiently long time. </p> <div class="mw-heading mw-heading4"><h4 id="Mass_spectrometry">Mass spectrometry</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkane&action=edit&section=19" title="Edit section: Mass spectrometry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Since alkanes have high <a href="/wiki/Ionization_energy" title="Ionization energy">ionization energies</a>, their <a href="/wiki/Electron_ionization" title="Electron ionization">electron impact mass spectra</a> show weak currents for their molecular ions. The fragmentation pattern can be difficult to interpret, but in the case of branched chain alkanes, the carbon chain is preferentially cleaved at tertiary or quaternary carbons due to the relative stability of the resulting <a href="/wiki/Free_radical" class="mw-redirect" title="Free radical">free radicals</a>. The mass spectra for straight-chain alkanes is illustrated by that for <a href="/wiki/Dodecane" title="Dodecane">dodecane</a>: the fragment resulting from the loss of a single methyl group (<i>M</i> − 15) is absent, fragments are more intense than the molecular ion and are spaced by intervals of 14 mass units, corresponding to loss of CH<sub>2</sub> groups.<sup id="cite_ref-27" class="reference"><a href="#cite_note-27"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Chemical_properties">Chemical properties</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkane&action=edit&section=20" title="Edit section: Chemical properties"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Alkanes are only weakly reactive with most chemical compounds. They only reacts with the strongest of electrophilic reagents by virtue of their strong C–H bonds (~100 kcal/mol) and C–C bonds (~90 kcal/mol). They are also relatively unreactive toward free radicals. This inertness is the source of the term <i>paraffins</i> (with the meaning here of "lacking affinity"). In <a href="/wiki/Crude_oil" class="mw-redirect" title="Crude oil">crude oil</a> the alkane molecules have remained chemically unchanged for millions of years. </p> <div class="mw-heading mw-heading3"><h3 id="Acid-base_behavior">Acid-base behavior</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkane&action=edit&section=21" title="Edit section: Acid-base behavior"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The <a href="/wiki/Acid_dissociation_constant" title="Acid dissociation constant">acid dissociation constant</a> (p<i>K</i><sub>a</sub>) values of all alkanes are estimated to range from 50 to 70, depending on the extrapolation method, hence they are extremely weak acids that are practically inert to bases (see: <a href="/wiki/Carbon_acid" class="mw-redirect" title="Carbon acid">carbon acids</a>). They are also extremely weak bases, undergoing no observable protonation in pure <a href="/wiki/Sulfuric_acid" title="Sulfuric acid">sulfuric acid</a> (<i>H</i><sub>0</sub> ~ −12), although <a href="/wiki/Superacid" title="Superacid">superacids</a> that are at least millions of times stronger have been known to protonate them to give hypercoordinate alkanium ions (see: <a href="/wiki/Methanium" title="Methanium">methanium ion</a>). Thus, a mixture of <a href="/wiki/Antimony_pentafluoride" title="Antimony pentafluoride">antimony pentafluoride</a> (SbF<sub>5</sub>) and <a href="/wiki/Fluorosulfonic_acid" class="mw-redirect" title="Fluorosulfonic acid">fluorosulfonic acid</a> (HSO<sub>3</sub>F), called <a href="/wiki/Magic_acid" title="Magic acid">magic acid</a>, can protonate alkanes.<sup id="cite_ref-28" class="reference"><a href="#cite_note-28"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Reactions_with_oxygen_(combustion_reaction)"><span id="Reactions_with_oxygen_.28combustion_reaction.29"></span>Reactions with oxygen (combustion reaction)</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkane&action=edit&section=22" title="Edit section: Reactions with oxygen (combustion reaction)"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>All alkanes react with <a href="/wiki/Oxygen" title="Oxygen">oxygen</a> in a <a href="/wiki/Combustion" title="Combustion">combustion</a> reaction, although they become increasingly difficult to ignite as the number of carbon atoms increases. The general equation for complete combustion is: </p> <dl><dd>C<sub><i>n</i></sub>H<sub>2<i>n</i>+2</sub> + (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1214402035"><span class="sfrac">⁠<span class="tion"><span class="num">3</span><span class="sr-only">/</span><span class="den">2</span></span>⁠</span><i>n</i> + <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1214402035"><span class="sfrac">⁠<span class="tion"><span class="num">1</span><span class="sr-only">/</span><span class="den">2</span></span>⁠</span>) O<sub>2</sub> → (<i>n</i> + 1) H<sub>2</sub>O + <i>n</i> CO<sub>2</sub></dd> <dd>or C<sub><i>n</i></sub>H<sub>2<i>n</i>+2</sub> + (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1214402035"><span class="sfrac">⁠<span class="tion"><span class="num">3<i>n</i> + 1</span><span class="sr-only">/</span><span class="den">2</span></span>⁠</span>) O<sub>2</sub> → (<i>n</i> + 1) H<sub>2</sub>O + <i>n</i> CO<sub>2</sub></dd></dl> <p>In the absence of sufficient oxygen, <a href="/wiki/Carbon_monoxide" title="Carbon monoxide">carbon monoxide</a> or even <a href="/wiki/Soot" title="Soot">soot</a> can be formed, as shown below: </p> <dl><dd>C<sub><i>n</i></sub>H<sub>2<i>n</i>+2</sub> + (<i>n</i> + <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1214402035"><span class="sfrac">⁠<span class="tion"><span class="num">1</span><span class="sr-only">/</span><span class="den">2</span></span>⁠</span>) <a href="/wiki/Oxygen" title="Oxygen">O<sub>2</sub></a> → (<i>n</i> + 1) H<sub>2</sub>O + <i>n</i> <a href="/wiki/Carbon_monoxide" title="Carbon monoxide">CO</a></dd></dl> <dl><dd>C<sub><i>n</i></sub>H<sub>2<i>n</i>+2</sub> + (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1214402035"><span class="sfrac">⁠<span class="tion"><span class="num">1</span><span class="sr-only">/</span><span class="den">2</span></span>⁠</span><i>n</i> + <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1214402035"><span class="sfrac">⁠<span class="tion"><span class="num">1</span><span class="sr-only">/</span><span class="den">2</span></span>⁠</span>) <a href="/wiki/Oxygen" title="Oxygen">O<sub>2</sub></a> → (<i>n</i> + 1) H<sub>2</sub>O + <i>n</i> <a href="/wiki/Carbon" title="Carbon">C</a></dd></dl> <p>For example, <a href="/wiki/Methane" title="Methane">methane</a>: </p> <dl><dd>2 CH<sub>4</sub> + 3 O<sub>2</sub> → 4 H<sub>2</sub>O + 2 CO</dd> <dd>CH<sub>4</sub> + O<sub>2</sub> → 2 H<sub>2</sub>O + C</dd></dl> <p>See the <a href="/wiki/Standard_enthalpy_change_of_formation_(data_table)#Alkanes" class="mw-redirect" title="Standard enthalpy change of formation (data table)">alkane heat of formation table</a> for detailed data. The <a href="/wiki/Standard_enthalpy_change_of_combustion" class="mw-redirect" title="Standard enthalpy change of combustion">standard enthalpy change of combustion</a>, Δ<sub>c</sub><i>H</i><sup>⊖</sup>, for alkanes increases by about 650 kJ/mol per CH<sub>2</sub> group. Branched-chain alkanes have lower values of Δ<sub>c</sub><i>H</i><sup>⊖</sup> than straight-chain alkanes of the same number of carbon atoms, and so can be seen to be somewhat more stable. </p> <div class="mw-heading mw-heading3"><h3 id="Biodegradation">Biodegradation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkane&action=edit&section=23" title="Edit section: Biodegradation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Some organisms are capable of metalbolizing alkanes.<sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/Methane_monooxygenase" title="Methane monooxygenase">methane monooxygenases</a> convert methane to <a href="/wiki/Methanol" title="Methanol">methanol</a>. For higher alkanes, <a href="/wiki/Cytochrome_P450" title="Cytochrome P450">cytochrome P450</a> convert alkanes to alcohols, which are then susceptible to degradation. </p> <div class="mw-heading mw-heading3"><h3 id="Free_radical_reactions">Free radical reactions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkane&action=edit&section=24" title="Edit section: Free radical reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Free_radical" class="mw-redirect" title="Free radical">Free radicals</a>, molecules with unpaired electrons, play a large role in most reactions of alkanes. <a href="/wiki/Free_radical_halogenation" class="mw-redirect" title="Free radical halogenation">Free radical halogenation</a> reactions occur with halogens, leading to the production of <a href="/wiki/Haloalkanes" class="mw-redirect" title="Haloalkanes">haloalkanes</a>. The hydrogen atoms of the alkane are progressively replaced by halogen atoms. The reaction of alkanes and fluorine is highly <a href="/wiki/Exothermic_reaction" title="Exothermic reaction">exothermic</a> and can lead to an explosion.<sup id="cite_ref-31" class="reference"><a href="#cite_note-31"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> These reactions are an important industrial route to halogenated hydrocarbons. There are three steps: </p> <ul><li><b>Initiation</b> the halogen radicals form by <a href="/wiki/Homolysis_(chemistry)" title="Homolysis (chemistry)">homolysis</a>. Usually, energy in the form of heat or light is required.</li> <li><b>Chain reaction</b> or <b>Propagation</b> then takes place—the halogen radical abstracts a hydrogen from the alkane to give an alkyl radical. This reacts further.</li> <li><b>Chain termination</b> where the radicals recombine.</li></ul> <p>Experiments have shown that all halogenation produces a mixture of all possible isomers, indicating that all hydrogen atoms are susceptible to reaction. The mixture produced, however, is not statistical: Secondary and tertiary hydrogen atoms are preferentially replaced due to the greater stability of secondary and tertiary free-radicals. An example can be seen in the monobromination of propane:<sup id="cite_ref-m&b_20-3" class="reference"><a href="#cite_note-m&b-20"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Monobromination_of_propane.png" class="mw-file-description" title="Monobromination of propane"><img alt="Monobromination of propane" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8f/Monobromination_of_propane.png/500px-Monobromination_of_propane.png" decoding="async" width="500" height="113" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8f/Monobromination_of_propane.png/750px-Monobromination_of_propane.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8f/Monobromination_of_propane.png/1000px-Monobromination_of_propane.png 2x" data-file-width="1604" data-file-height="361" /></a><figcaption>Monobromination of <a href="/wiki/Propane" title="Propane">propane</a></figcaption></figure> <p>In the <a href="/wiki/Reed_reaction" title="Reed reaction">Reed reaction</a>, <a href="/wiki/Sulfur_dioxide" title="Sulfur dioxide">sulfur dioxide</a> and <a href="/wiki/Chlorine" title="Chlorine">chlorine</a> convert hydrocarbons to <a href="/wiki/Sulfonic_acid" title="Sulfonic acid">sulfonyl chlorides</a> under the influence of <a href="/wiki/Photochemistry" title="Photochemistry">light</a>. </p><p>Under some conditions, alkanes will undergo <a href="/wiki/Nitration" title="Nitration">Nitration</a>. </p> <div class="mw-heading mw-heading3"><h3 id="C-H_activation">C-H activation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkane&action=edit&section=25" title="Edit section: C-H activation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Certain transition metal complexes promote non-radical reactions with alkanes, resulting in so <a href="/wiki/Carbon-hydrogen_bond_activation" class="mw-redirect" title="Carbon-hydrogen bond activation">C–H bond activation</a> reactions.<sup id="cite_ref-32" class="reference"><a href="#cite_note-32"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Cracking">Cracking</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkane&action=edit&section=26" title="Edit section: Cracking"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Cracking_(chemistry)" title="Cracking (chemistry)">Cracking (chemistry)</a></div> <p>Cracking breaks larger molecules into smaller ones. This reaction requires heat and catalysts. The thermal cracking process follows a <a href="/wiki/Homolysis_(chemistry)" title="Homolysis (chemistry)">homolytic</a> mechanism with formation of <a href="/wiki/Radical_(chemistry)" title="Radical (chemistry)">free radicals</a>. The catalytic cracking process involves the presence of <a href="/wiki/Acid" title="Acid">acid</a> <a href="/wiki/Catalyst" class="mw-redirect" title="Catalyst">catalysts</a> (usually solid acids such as <a href="/wiki/Silica-alumina" class="mw-redirect" title="Silica-alumina">silica-alumina</a> and <a href="/wiki/Zeolite" title="Zeolite">zeolites</a>), which promote a <a href="/wiki/Heterolytic_cleavage" class="mw-redirect" title="Heterolytic cleavage">heterolytic</a> (asymmetric) breakage of bonds yielding pairs of ions of opposite charges, usually a <a href="/wiki/Carbocation" title="Carbocation">carbocation</a>. Carbon-localized free radicals and cations are both highly unstable and undergo processes of chain rearrangement, C–C scission in position <a href="/wiki/Beta_scission" title="Beta scission">beta</a> (i.e., cracking) and <a href="/wiki/Intramolecular_reaction" title="Intramolecular reaction">intra-</a> and <a href="/wiki/Intermolecular" class="mw-redirect" title="Intermolecular">intermolecular</a> hydrogen transfer or <a href="/wiki/Hydride" title="Hydride">hydride</a> transfer. In both types of processes, the corresponding <a href="/wiki/Reactive_intermediate" title="Reactive intermediate">reactive intermediates</a> (radicals, ions) are permanently regenerated, and thus they proceed by a self-propagating chain mechanism. The chain of reactions is eventually terminated by radical or ion recombination.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (January 2021)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading3"><h3 id="Isomerization_and_reformation">Isomerization and reformation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkane&action=edit&section=27" title="Edit section: Isomerization and reformation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Dragan and his colleague were the first to report about isomerization in alkanes.<sup id="cite_ref-Asinger,_Friedrich_1967_33-0" class="reference"><a href="#cite_note-Asinger,_Friedrich_1967-33"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> Isomerization and reformation are processes in which straight-chain alkanes are heated in the presence of a <a href="/wiki/Platinum" title="Platinum">platinum</a> catalyst. In isomerization, the alkanes become branched-chain isomers. In other words, it does not lose any carbons or hydrogens, keeping the same molecular weight.<sup id="cite_ref-Asinger,_Friedrich_1967_33-1" class="reference"><a href="#cite_note-Asinger,_Friedrich_1967-33"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> In reformation, the alkanes become <a href="/wiki/Cycloalkane" title="Cycloalkane">cycloalkanes</a> or <a href="/wiki/Aromatic_hydrocarbon" class="mw-redirect" title="Aromatic hydrocarbon">aromatic hydrocarbons</a>, giving off hydrogen as a by-product. Both of these processes raise the <a href="/wiki/Octane_number" class="mw-redirect" title="Octane number">octane number</a> of the substance. Butane is the most common alkane that is put under the process of isomerization, as it makes many branched alkanes with high octane numbers.<sup id="cite_ref-Asinger,_Friedrich_1967_33-2" class="reference"><a href="#cite_note-Asinger,_Friedrich_1967-33"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Other_reactions">Other reactions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkane&action=edit&section=28" title="Edit section: Other reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In <a href="/wiki/Steam_reforming" title="Steam reforming">steam reforming</a>, alkanes react with <a href="/wiki/Steam" title="Steam">steam</a> in the presence of a <a href="/wiki/Nickel" title="Nickel">nickel</a> <a href="/wiki/Catalyst" class="mw-redirect" title="Catalyst">catalyst</a> to give <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a> and carbon monoxide. </p> <div class="mw-heading mw-heading2"><h2 id="Occurrence">Occurrence</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkane&action=edit&section=29" title="Edit section: Occurrence"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Occurrence_of_alkanes_in_the_Universe">Occurrence of alkanes in the Universe</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkane&action=edit&section=30" title="Edit section: Occurrence of alkanes in the Universe"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Jupiter.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e2/Jupiter.jpg/220px-Jupiter.jpg" decoding="async" width="220" height="220" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e2/Jupiter.jpg/330px-Jupiter.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e2/Jupiter.jpg/440px-Jupiter.jpg 2x" data-file-width="840" data-file-height="840" /></a><figcaption><a href="/wiki/Methane" title="Methane">Methane</a> and <a href="/wiki/Ethane" title="Ethane">ethane</a> make up a tiny proportion of <a href="/wiki/Jupiter" title="Jupiter">Jupiter</a>'s atmosphere</figcaption></figure> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Oil_well.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/ce/Oil_well.jpg/220px-Oil_well.jpg" decoding="async" width="220" height="165" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/ce/Oil_well.jpg/330px-Oil_well.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/ce/Oil_well.jpg/440px-Oil_well.jpg 2x" data-file-width="640" data-file-height="480" /></a><figcaption>Extraction of oil, which contains many distinct <a href="/wiki/Hydrocarbon" title="Hydrocarbon">hydrocarbons</a> including alkanes</figcaption></figure> <p>Alkanes form a small portion of the <a href="/wiki/Celestial_body_atmosphere" class="mw-redirect" title="Celestial body atmosphere">atmospheres</a> of the outer gas planets such as <a href="/wiki/Jupiter" title="Jupiter">Jupiter</a> (0.1% methane, 2 <a href="/wiki/Parts_per_million" class="mw-redirect" title="Parts per million">ppm</a> ethane), <a href="/wiki/Saturn" title="Saturn">Saturn</a> (0.2% methane, 5 ppm ethane), <a href="/wiki/Uranus" title="Uranus">Uranus</a> (1.99% methane, 2.5 ppm ethane) and <a href="/wiki/Neptune" title="Neptune">Neptune</a> (1.5% methane, 1.5 ppm ethane). <a href="/wiki/Titan_(moon)" title="Titan (moon)">Titan</a> (1.6% methane), a satellite of Saturn, was examined by the <a href="/wiki/Huygens_(spacecraft)" title="Huygens (spacecraft)"><i>Huygens</i> probe</a>, which indicated that Titan's atmosphere periodically rains liquid methane onto the moon's surface.<sup id="cite_ref-34" class="reference"><a href="#cite_note-34"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> Also on Titan, the Cassini mission has imaged seasonal methane/ethane lakes near the polar regions of Titan. <a href="/wiki/Methane" title="Methane">Methane</a> and <a href="/wiki/Ethane" title="Ethane">ethane</a> have also been detected in the tail of the <a href="/wiki/Comet_Hyakutake" title="Comet Hyakutake">comet Hyakutake</a>. Chemical analysis showed that the abundances of ethane and methane were roughly equal, which is thought to imply that its ices formed in interstellar space, away from the Sun, which would have evaporated these volatile molecules.<sup id="cite_ref-35" class="reference"><a href="#cite_note-35"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> Alkanes have also been detected in <a href="/wiki/Meteorite" title="Meteorite">meteorites</a> such as <a href="/wiki/Carbonaceous_chondrite" title="Carbonaceous chondrite">carbonaceous chondrites</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Occurrence_of_alkanes_on_Earth">Occurrence of alkanes on Earth</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkane&action=edit&section=31" title="Edit section: Occurrence of alkanes on Earth"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Traces of methane gas (about 0.0002% or 1745 ppb) occur in the Earth's atmosphere, produced primarily by <a href="/wiki/Methanogenesis" title="Methanogenesis">methanogenic</a> microorganisms, such as <a href="/wiki/Archaea" title="Archaea">Archaea</a> in the gut of ruminants.<sup id="cite_ref-36" class="reference"><a href="#cite_note-36"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> </p><p>The most important commercial sources for alkanes are natural gas and <a href="/wiki/Petroleum" title="Petroleum">oil</a>.<sup id="cite_ref-m&b_20-4" class="reference"><a href="#cite_note-m&b-20"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> Natural gas contains primarily methane and ethane, with some <a href="/wiki/Propane" title="Propane">propane</a> and <a href="/wiki/Butane" title="Butane">butane</a>: oil is a mixture of liquid alkanes and other <a href="/wiki/Hydrocarbons" class="mw-redirect" title="Hydrocarbons">hydrocarbons</a>. These hydrocarbons were formed when marine animals and plants (zooplankton and phytoplankton) died and sank to the bottom of ancient seas and were covered with sediments in an <a href="https://en.wiktionary.org/wiki/anoxic" class="extiw" title="wikt:anoxic">anoxic</a> environment and converted over many millions of years at high temperatures and high pressure to their current form. Natural gas resulted thereby for example from the following reaction: </p> <dl><dd>C<sub>6</sub>H<sub>12</sub>O<sub>6</sub> → 3 CH<sub>4</sub> + 3 CO<sub>2</sub></dd></dl> <p>These hydrocarbon deposits, collected in porous rocks trapped beneath impermeable cap rocks, comprise commercial <a href="/wiki/Oil_fields" class="mw-redirect" title="Oil fields">oil fields</a>. They have formed over millions of years and once exhausted cannot be readily replaced. The depletion of these hydrocarbons reserves is the basis for what is known as the <a href="/wiki/Energy_crisis" title="Energy crisis">energy crisis</a>. </p><p>Alkanes have a low solubility in water, so the content in the oceans is negligible; however, at high pressures and low temperatures (such as at the bottom of the oceans), methane can co-crystallize with water to form a solid <a href="/wiki/Methane_clathrate" title="Methane clathrate">methane clathrate</a> (methane hydrate). Although this cannot be commercially exploited at the present time, the amount of combustible energy of the known methane clathrate fields exceeds the energy content of all the natural gas and oil deposits put together. Methane extracted from methane clathrate is, therefore, a candidate for future fuels. </p> <div class="mw-heading mw-heading3"><h3 id="Biological_occurrence">Biological occurrence</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkane&action=edit&section=32" title="Edit section: Biological occurrence"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Rotbuntes_Rind.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/78/Rotbuntes_Rind.jpg/220px-Rotbuntes_Rind.jpg" decoding="async" width="220" height="155" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/78/Rotbuntes_Rind.jpg/330px-Rotbuntes_Rind.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/78/Rotbuntes_Rind.jpg/440px-Rotbuntes_Rind.jpg 2x" data-file-width="1280" data-file-height="900" /></a><figcaption><a href="/wiki/Methanogen" title="Methanogen">Methanogenic</a> <a href="/wiki/Archaea" title="Archaea">archaea</a> in the gut of cows produce <a href="/wiki/Methane" title="Methane">methane</a>.</figcaption></figure> <p>Aside from petroleum and natural gas, alkanes occur significantly in nature only as methane, which is produced by some <a href="/wiki/Archaea" title="Archaea">archaea</a> by the process of <a href="/wiki/Methanogenesis" title="Methanogenesis">methanogenesis</a>. These organisms are found in the gut of termites<sup id="cite_ref-37" class="reference"><a href="#cite_note-37"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> and cows.<sup id="cite_ref-38" class="reference"><a href="#cite_note-38"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/Methane" title="Methane">methane</a> is produced from <a href="/wiki/Carbon_dioxide" title="Carbon dioxide">carbon dioxide</a> or other organic compounds. Energy is released by the oxidation of <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a>: </p> <dl><dd>CO<sub>2</sub> + 4 H<sub>2</sub> → CH<sub>4</sub> + 2 H<sub>2</sub>O</dd></dl> <p>It is probable that our current deposits of natural gas were formed in a similar way.<sup id="cite_ref-39" class="reference"><a href="#cite_note-39"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> </p><p><br /> </p> <pre>RCH2\sCH3}} (R = <a href="/wiki/Alkyl" class="mw-redirect" title="Alkyl">alkyl</a>) </pre> <p>Another route to alkanes is <a href="/wiki/Hydrogenolysis" title="Hydrogenolysis">hydrogenolysis</a>, which entails cleavage of C-heteroatom bonds using hydrogen. In industry, the main substrates are organonitrogen and organosulfur impurities, i.e. the heteroatoms are N and S. The specific processes are called <a href="/wiki/Hydrodenitrification" class="mw-redirect" title="Hydrodenitrification">hydrodenitrification</a> and <a href="/wiki/Hydrodesulfurization" title="Hydrodesulfurization">hydrodesulfurization</a>: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R<sub class="template-chem2-sub">3</sub>N + 3 H<sub class="template-chem2-sub">2</sub> → 3 RH + H<sub class="template-chem2-sub">3</sub>N</span></dd> <dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R<sub class="template-chem2-sub">2</sub>S + 2 H<sub class="template-chem2-sub">2</sub> → 2 RH + H<sub class="template-chem2-sub">2</sub>S</span></dd></dl> <p>Hydrogenolysis can be applied to the conversion of virtually any functional group into hydrocarbons. Substrates include haloalkanes, alcohols, aldehydes, ketones, carboxylic acids, etc. Both hydrogenolysis and hydrogenation are practiced in refineries. The can be effected by using <a href="/wiki/Lithium_aluminium_hydride" title="Lithium aluminium hydride">lithium aluminium hydride</a>, <a href="/wiki/Clemmenson_reduction" class="mw-redirect" title="Clemmenson reduction">Clemmenson reduction</a> and other specialized routes. </p> <div class="mw-heading mw-heading3"><h3 id="Coal">Coal</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkane&action=edit&section=33" title="Edit section: Coal"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Coal is a more traditional precursor to alkanes. A wide range of technologies have been intensively practiced for centuries.<sup id="cite_ref-Ull_40-0" class="reference"><a href="#cite_note-Ull-40"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> Simply heating coal gives alkanes, leaving behind <a href="/wiki/Coke_(fuel)" title="Coke (fuel)">coke</a>. Relevant technologies include the <a href="/wiki/Bergius_process" title="Bergius process">Bergius process</a> and <a href="/wiki/Coal_liquifaction" class="mw-redirect" title="Coal liquifaction">coal liquifaction</a>. Partial combustion of coal and related solid organic compounds generates <a href="/wiki/Carbon_monoxide" title="Carbon monoxide">carbon monoxide</a>, which can be hydrogenated using the <a href="/wiki/Fischer%E2%80%93Tropsch_process" title="Fischer–Tropsch process">Fischer–Tropsch process</a>. This technology allows the synthesize liquid hydrocarbons, including alkanes. This method is used to produce substitutes for <a href="/wiki/Petroleum_distillate" class="mw-redirect" title="Petroleum distillate">petroleum distillates</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Laboratory_preparation">Laboratory preparation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkane&action=edit&section=34" title="Edit section: Laboratory preparation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Rarely is there any interest in the synthesis of alkanes, since they are usually commercially available and less valued than virtually any precursor. The best-known method is <a href="/wiki/Hydrogenation" title="Hydrogenation">hydrogenation</a> of <a href="/wiki/Alkene" title="Alkene">alkenes</a>. Many C-X bonds can be converted to C-H bonds using <a href="/wiki/Lithium_aluminium_hydride" title="Lithium aluminium hydride">lithium aluminium hydride</a>, <a href="/wiki/Clemmenson_reduction" class="mw-redirect" title="Clemmenson reduction">Clemmenson reduction</a>, and other specialized routes.<sup id="cite_ref-41" class="reference"><a href="#cite_note-41"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> Hydrolysis of <a href="/wiki/Grignard_reagent" title="Grignard reagent">Alkyl Grignard reagents</a> and <a href="/wiki/Organolithium_compound" class="mw-redirect" title="Organolithium compound">alkyl lithium compounds</a> gives alkanes.<sup id="cite_ref-42" class="reference"><a href="#cite_note-42"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Applications">Applications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkane&action=edit&section=35" title="Edit section: Applications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Fuels">Fuels</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkane&action=edit&section=36" title="Edit section: Fuels"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The dominant use of alkanes is as fuels. <a href="/wiki/Propane" title="Propane">Propane</a> and <a href="/wiki/Butane" title="Butane">butane</a>, easily liquified gases, are commonly known as <a href="/wiki/Liquified_petroleum_gas" class="mw-redirect" title="Liquified petroleum gas">liquified petroleum gas</a> (LPG).<sup id="cite_ref-43" class="reference"><a href="#cite_note-43"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> From <a href="/wiki/Pentane" title="Pentane">pentane</a> to <a href="/wiki/Octane" title="Octane">octane</a> the alkanes are highly volatile liquids. They are used as fuels in <a href="/wiki/Internal_combustion_engine" title="Internal combustion engine">internal combustion engines</a>, as they vaporize easily on entry into the combustion chamber without forming droplets, which would impair the uniformity of the combustion. Branched-chain alkanes are preferred as they are much less prone to premature ignition, which causes <a href="/wiki/Engine_knocking" title="Engine knocking">knocking</a>, than their straight-chain homologues. This propensity to premature ignition is measured by the <a href="/wiki/Octane_rating" title="Octane rating">octane rating</a> of the fuel, where <a href="/wiki/2,2,4-Trimethylpentane" title="2,2,4-Trimethylpentane">2,2,4-trimethylpentane</a> (<i>isooctane</i>) has an arbitrary value of 100, and <a href="/wiki/Heptane" title="Heptane">heptane</a> has a value of zero. Apart from their use as fuels, the middle alkanes are also good <a href="/wiki/Solvent" title="Solvent">solvents</a> for nonpolar substances. Alkanes from <a href="/wiki/Nonane" title="Nonane">nonane</a> to, for instance, <a href="/wiki/Hexadecane" title="Hexadecane">hexadecane</a> (an alkane with sixteen carbon atoms) are liquids of higher <a href="/wiki/Viscosity" title="Viscosity">viscosity</a>, less and less suitable for use in gasoline. They form instead the major part of <a href="/wiki/Diesel_fuel" title="Diesel fuel">diesel</a> and <a href="/wiki/Aviation_fuel" title="Aviation fuel">aviation fuel</a>. Diesel fuels are characterized by their <a href="/wiki/Cetane_number" title="Cetane number">cetane number</a>, cetane being an old name for hexadecane. However, the higher melting points of these alkanes can cause problems at low temperatures and in polar regions, where the fuel becomes too thick to flow correctly. </p> <div class="mw-heading mw-heading3"><h3 id="Precursors_to_chemicals">Precursors to chemicals</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkane&action=edit&section=37" title="Edit section: Precursors to chemicals"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>By the process of <a href="/wiki/Cracking_(chemistry)" title="Cracking (chemistry)">cracking</a>, alkanes can be converted to <a href="/wiki/Alkene" title="Alkene">alkenes</a>. Simple alkenes are precursors to polymers, such as <a href="/wiki/Polyethylene" title="Polyethylene">polyethylene</a> and <a href="/wiki/Polypropylene" title="Polypropylene">polypropylene</a>. When the cracking is taken to extremes, alkanes can be converted to <a href="/wiki/Carbon_black" title="Carbon black">carbon black</a>, which is a significant tire component. </p><p>Chlorination of methane gives chloromethanes, which are used as solvents and building blocks for complex compounds. Similarly treatment of methane with sulfur gives <a href="/wiki/Carbon_disulfide" title="Carbon disulfide">carbon disulfide</a>. Still other chemicals are prepared by reaction with <a href="/wiki/Sulfur_trioxide" title="Sulfur trioxide">sulfur trioxide</a> and <a href="/wiki/Nitric_oxide" title="Nitric oxide">nitric oxide</a> </p> <div class="mw-heading mw-heading3"><h3 id="Other">Other</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkane&action=edit&section=38" title="Edit section: Other"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Some light hydrocarbons are used as <a href="/wiki/Aerosol_spray" class="mw-redirect" title="Aerosol spray">aerosol sprays</a>. </p><p>Alkanes from hexadecane upwards form the most important components of <a href="/wiki/Fuel_oil" title="Fuel oil">fuel oil</a> and <a href="/wiki/Lubricating_oil" class="mw-redirect" title="Lubricating oil">lubricating oil</a>. In the latter function, they work at the same time as anti-corrosive agents, as their hydrophobic nature means that water cannot reach the metal surface. Many solid alkanes find use as <a href="/wiki/Paraffin_wax" title="Paraffin wax">paraffin wax</a>, for example, in <a href="/wiki/Candle" title="Candle">candles</a>. This should not be confused however with true <a href="/wiki/Wax" title="Wax">wax</a>, which consists primarily of <a href="/wiki/Ester" title="Ester">esters</a>. </p><p>Alkanes with a chain length of approximately 35 or more carbon atoms are found in <a href="/wiki/Bitumen" title="Bitumen">bitumen</a>, used, for example, in road surfacing. However, the higher alkanes have little value and are usually split into lower alkanes by <a href="/wiki/Cracking_(chemistry)" title="Cracking (chemistry)">cracking</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Hazards">Hazards</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkane&action=edit&section=39" title="Edit section: Hazards"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Alkanes are highly flammable, but they have low toxicities. Methane "is toxicologically virtually inert." Alkanes can be asphyxiants and narcotic.<sup id="cite_ref-Ull_40-1" class="reference"><a href="#cite_note-Ull-40"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkane&action=edit&section=40" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1235681985">.mw-parser-output .side-box{margin:4px 0;box-sizing:border-box;border:1px solid #aaa;font-size:88%;line-height:1.25em;background-color:var(--background-color-interactive-subtle,#f8f9fa);display:flow-root}.mw-parser-output .side-box-abovebelow,.mw-parser-output .side-box-text{padding:0.25em 0.9em}.mw-parser-output .side-box-image{padding:2px 0 2px 0.9em;text-align:center}.mw-parser-output .side-box-imageright{padding:2px 0.9em 2px 0;text-align:center}@media(min-width:500px){.mw-parser-output .side-box-flex{display:flex;align-items:center}.mw-parser-output .side-box-text{flex:1;min-width:0}}@media(min-width:720px){.mw-parser-output .side-box{width:238px}.mw-parser-output .side-box-right{clear:right;float:right;margin-left:1em}.mw-parser-output .side-box-left{margin-right:1em}}</style><style data-mw-deduplicate="TemplateStyles:r1237033735">@media print{body.ns-0 .mw-parser-output .sistersitebox{display:none!important}}@media screen{html.skin-theme-clientpref-night .mw-parser-output .sistersitebox img[src*="Wiktionary-logo-en-v2.svg"]{background-color:white}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .sistersitebox img[src*="Wiktionary-logo-en-v2.svg"]{background-color:white}}</style><div class="side-box side-box-right plainlinks sistersitebox"><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style> <div class="side-box-flex"> <div class="side-box-image"><span class="noviewer" typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/30px-Commons-logo.svg.png" decoding="async" width="30" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/45px-Commons-logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/59px-Commons-logo.svg.png 2x" data-file-width="1024" data-file-height="1376" /></span></span></div> <div class="side-box-text plainlist">Wikimedia Commons has media related to <a href="https://commons.wikimedia.org/wiki/Category:Alkanes" class="extiw" title="commons:Category:Alkanes"><span style="font-style:italic; font-weight:bold;">Alkanes</span></a>.</div></div> </div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1235681985"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1237033735"><div class="side-box side-box-right plainlinks sistersitebox"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"> <div class="side-box-flex"> <div class="side-box-image"><span class="noviewer" typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/9/99/Wiktionary-logo-en-v2.svg/40px-Wiktionary-logo-en-v2.svg.png" decoding="async" width="40" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/99/Wiktionary-logo-en-v2.svg/60px-Wiktionary-logo-en-v2.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/99/Wiktionary-logo-en-v2.svg/80px-Wiktionary-logo-en-v2.svg.png 2x" data-file-width="512" data-file-height="512" /></span></span></div> <div class="side-box-text plainlist">Look up <i><b><a href="https://en.wiktionary.org/wiki/Special:Search/alkane" class="extiw" title="wiktionary:Special:Search/alkane">alkane</a></b></i> in Wiktionary, the free dictionary.</div></div> </div> <ul><li><a href="/wiki/Alkene" title="Alkene">Alkene</a></li> <li><a href="/wiki/Alkyne" title="Alkyne">Alkyne</a></li> <li><a href="/wiki/Cycloalkane" title="Cycloalkane">Cycloalkane</a></li> <li><a href="/wiki/Higher_alkanes" class="mw-redirect" title="Higher alkanes">Higher alkanes</a></li> <li><a href="/wiki/Aliphatic_compound" title="Aliphatic compound">Aliphatic compound</a></li></ul> <div style="clear:both;" class=""></div> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkane&action=edit&section=41" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239543626"><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-GoldBook_alkanes-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-GoldBook_alkanes_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-GoldBook_alkanes_1-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><a href="/wiki/International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">IUPAC</a>, <i><a href="/wiki/IUPAC_books#Gold_Book" class="mw-redirect" title="IUPAC books">Compendium of Chemical Terminology</a></i>, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "<a rel="nofollow" class="external text" href="https://goldbook.iupac.org/terms/view/A00222.html">alkanes</a>". <style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1351%2Fgoldbook.A00222">10.1351/goldbook.A00222</a></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSmith,_Michael_B.March,_Jerry2007" class="citation cs1">Smith, Michael B.; <a href="/wiki/Jerry_March" title="Jerry March">March, Jerry</a> (2007). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=JDR-nZpojeEC&printsec=frontcover"><i>Advanced Organic Chemistry: Reactions, Mechanisms, and Structure</i></a> (6th ed.). New York: Wiley-Interscience. p. 23. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-471-72091-1" title="Special:BookSources/978-0-471-72091-1"><bdi>978-0-471-72091-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Advanced+Organic+Chemistry%3A+Reactions%2C+Mechanisms%2C+and+Structure&rft.place=New+York&rft.pages=23&rft.edition=6th&rft.pub=Wiley-Interscience&rft.date=2007&rft.isbn=978-0-471-72091-1&rft.au=Smith%2C+Michael+B.&rft.au=March%2C+Jerry&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DJDR-nZpojeEC%26printsec%3Dfrontcover&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlkane" class="Z3988"></span></span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text"><a href="/wiki/On-Line_Encyclopedia_of_Integer_Sequences" title="On-Line Encyclopedia of Integer Sequences">On-Line Encyclopedia of Integer Sequences</a> (sequence <span class="nowrap external"><a href="//oeis.org/A000602" class="extiw" title="oeis:A000602">A000602</a></span> in the <a href="/wiki/On-Line_Encyclopedia_of_Integer_Sequences" title="On-Line Encyclopedia of Integer Sequences">OEIS</a>) Number of n-node unrooted quartic trees; number of n-carbon alkanes C(n)H(2n+2) ignoring stereoisomers</span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFAlabugin2016" class="citation book cs1">Alabugin, Igor V. (2016). <i>Stereoelectronic effects : a bridge between structure and reactivity</i>. Wiley. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-118-90637-8" title="Special:BookSources/978-1-118-90637-8"><bdi>978-1-118-90637-8</bdi></a>. <a href="/wiki/OCLC_(identifier)" class="mw-redirect" title="OCLC (identifier)">OCLC</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/oclc/957525299">957525299</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Stereoelectronic+effects+%3A+a+bridge+between+structure+and+reactivity&rft.pub=Wiley&rft.date=2016&rft_id=info%3Aoclcnum%2F957525299&rft.isbn=978-1-118-90637-8&rft.aulast=Alabugin&rft.aufirst=Igor+V.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlkane" class="Z3988"></span></span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFIUPAC,_Commission_on_Nomenclature_of_Organic_Chemistry1993" class="citation book cs1">IUPAC, Commission on Nomenclature of Organic Chemistry (1993). <a rel="nofollow" class="external text" href="http://www.acdlabs.com/iupac/nomenclature/93/r93_184.htm">"R-2.2.1: Hydrocarbons"</a>. <i>A Guide to IUPAC Nomenclature of Organic Compounds (Recommendations 1993)</i>. Blackwell Scientific. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-632-03488-8" title="Special:BookSources/978-0-632-03488-8"><bdi>978-0-632-03488-8</bdi></a><span class="reference-accessdate">. Retrieved <span class="nowrap">12 February</span> 2007</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=R-2.2.1%3A+Hydrocarbons&rft.btitle=A+Guide+to+IUPAC+Nomenclature+of+Organic+Compounds+%28Recommendations+1993%29&rft.pub=Blackwell+Scientific&rft.date=1993&rft.isbn=978-0-632-03488-8&rft.au=IUPAC%2C+Commission+on+Nomenclature+of+Organic+Chemistry&rft_id=http%3A%2F%2Fwww.acdlabs.com%2Fiupac%2Fnomenclature%2F93%2Fr93_184.htm&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlkane" class="Z3988"></span></span> </li> <li id="cite_note-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-6">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20120202091842/http://www.chem.yale.edu/~chem125/125/history99/5Valence/Nomenclature/alkanenames.html">"Alkane Nomenclature"</a>. Archived from <a rel="nofollow" class="external text" href="http://www.chem.yale.edu/~chem125/125/history99/5Valence/Nomenclature/alkanenames.html">the original</a> on 2 February 2012.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Alkane+Nomenclature&rft_id=http%3A%2F%2Fwww.chem.yale.edu%2F~chem125%2F125%2Fhistory99%2F5Valence%2FNomenclature%2Falkanenames.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlkane" class="Z3988"></span></span> </li> <li id="cite_note-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-7">^</a></b></span> <span class="reference-text">Thus, the ending "-diene" is applied in some cases where von Hofmann had "-ine"</span> </li> <li id="cite_note-reusch-nom-8"><span class="mw-cite-backlink">^ <a href="#cite_ref-reusch-nom_8-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-reusch-nom_8-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFReusch" class="citation web cs1">Reusch, William. <a rel="nofollow" class="external text" href="http://arquivo.pt/wayback/20160521131930/http://www.cem.msu.edu/~reusch/VirtualText/nomen1.htm">"Nomenclature – Alkanes"</a>. <i>Virtual Textbook of Organic Chemistry</i>. 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Retrieved <span class="nowrap">5 April</span> 2007</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Virtual+Textbook+of+Organic+Chemistry&rft.atitle=Nomenclature+%E2%80%93+Alkanes&rft.aulast=Reusch&rft.aufirst=William&rft_id=http%3A%2F%2Fwww.cem.msu.edu%2F~reusch%2FVirtualText%2Fnomen1.htm&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlkane" class="Z3988"></span></span> </li> <li id="cite_note-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-9">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFReusch" class="citation web cs1">Reusch, William. <a rel="nofollow" class="external text" href="http://arquivo.pt/wayback/20160521132003/http://www.cem.msu.edu/~reusch/VirtualText/nomexmp1.htm">"Examples of the IUPAC Rules in Practice"</a>. <i>Virtual Textbook of Organic Chemistry</i>. 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Retrieved <span class="nowrap">5 April</span> 2007</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Virtual+Textbook+of+Organic+Chemistry&rft.atitle=Examples+of+the+IUPAC+Rules+in+Practice&rft.aulast=Reusch&rft.aufirst=William&rft_id=http%3A%2F%2Fwww.cem.msu.edu%2F~reusch%2FVirtualText%2Fnomexmp1.htm&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlkane" class="Z3988"></span></span> </li> <li id="cite_note-10"><span class="mw-cite-backlink"><b><a href="#cite_ref-10">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.chem.uiuc.edu/GenChemReferences/nomenclature_rules.html">"IUPAC Rules"</a>. <i>www.chem.uiuc.edu</i><span class="reference-accessdate">. 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"n-Pentane". <i>Organic Syntheses</i>. <b>11</b>: 84. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.15227%2Forgsyn.011.0084">10.15227/orgsyn.011.0084</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Organic+Syntheses&rft.atitle=n-Pentane&rft.volume=11&rft.pages=84&rft.date=1931&rft_id=info%3Adoi%2F10.15227%2Forgsyn.011.0084&rft.aulast=Noller&rft.aufirst=C.R.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlkane" class="Z3988"></span></span> </li> <li id="cite_note-43"><span class="mw-cite-backlink"><b><a href="#cite_ref-43">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20131012000108/http://ferrellgas.com/Resource_/PageResource/LA_Transit_Case_Study.pdf">"Using propane as a fuel"</a> <span class="cs1-format">(PDF)</span>. Archived from <a rel="nofollow" class="external text" href="http://www.ferrellgas.com/Resource_/PageResource/LA_Transit_Case_Study.pdf">the original</a> <span class="cs1-format">(PDF)</span> on 12 October 2013<span class="reference-accessdate">. Retrieved <span class="nowrap">27 November</span> 2012</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Using+propane+as+a+fuel&rft_id=http%3A%2F%2Fwww.ferrellgas.com%2FResource_%2FPageResource%2FLA_Transit_Case_Study.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlkane" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="Further_reading">Further reading</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkane&action=edit&section=42" title="Edit section: Further reading"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a rel="nofollow" class="external text" href="https://www2.chemistry.msu.edu/faculty/reusch/VirtTxtJml/intro1.htm">Virtual Textbook of Organic Chemistry</a></li> <li><a rel="nofollow" class="external text" href="https://log-web.de/chemie/Start.htm?name=ethaneCryst&lang=en">A visualization of the crystal structures of alkanes up to nonan</a></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRedwood1911" class="citation encyclopaedia cs1">Redwood, Boverton (1911). <span class="cs1-ws-icon" title="s:1911 Encyclopædia Britannica/Paraffin"><a class="external text" href="https://en.wikisource.org/wiki/1911_Encyclop%C3%A6dia_Britannica/Paraffin">"Paraffin" </a></span>. <i><a href="/wiki/Encyclop%C3%A6dia_Britannica_Eleventh_Edition" title="Encyclopædia Britannica Eleventh Edition">Encyclopædia Britannica</a></i>. Vol. 20 (11th ed.). pp. 752–756.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Paraffin&rft.btitle=Encyclop%C3%A6dia+Britannica&rft.pages=752-756&rft.edition=11th&rft.date=1911&rft.aulast=Redwood&rft.aufirst=Boverton&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlkane" class="Z3988"></span></li></ul> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl dl,.mw-parser-output .hlist dl ol,.mw-parser-output .hlist dl ul,.mw-parser-output .hlist ol dl,.mw-parser-output .hlist ol ol,.mw-parser-output .hlist ol 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href="/wiki/Special:EditPage/Template:Hydrocarbons" title="Special:EditPage/Template:Hydrocarbons"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Hydrocarbons" style="font-size:114%;margin:0 4em"><a href="/wiki/Hydrocarbon" title="Hydrocarbon">Hydrocarbons</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:azzurro;">Saturated<br />aliphatic<br />hydrocarbons</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="AlkanesCnH2n_+_2" scope="row" class="navbox-group" style="width:8.5em"><a class="mw-selflink selflink">Alkanes</a><br />C<sub><i>n</i></sub>H<sub>2<i>n</i> + 2</sub></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em">Linear alkanes</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Methane" title="Methane">Methane</a></li> <li><a href="/wiki/Ethane" title="Ethane">Ethane</a></li> <li><a href="/wiki/Propane" title="Propane">Propane</a></li> <li><a href="/wiki/Butane" title="Butane">Butane</a></li> <li><a href="/wiki/Pentane" title="Pentane">Pentane</a></li> <li><a href="/wiki/Hexane" title="Hexane">Hexane</a></li> <li><a href="/wiki/Heptane" title="Heptane">Heptane</a></li> <li><a href="/wiki/Octane" title="Octane">Octane</a></li> <li><a href="/wiki/Nonane" title="Nonane">Nonane</a></li> <li><a href="/wiki/Decane" title="Decane">Decane</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Branched alkanes</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Isobutane" title="Isobutane">Isobutane</a></li> <li><a href="/wiki/Isopentane" title="Isopentane">Isopentane</a></li> <li><a href="/wiki/3-Methylpentane" title="3-Methylpentane">3-Methylpentane</a></li> <li><a href="/wiki/Neopentane" title="Neopentane">Neopentane</a></li> <li><a href="/wiki/2-Methylpentane" title="2-Methylpentane">Isohexane</a></li> <li><a href="/wiki/2-Methylhexane" title="2-Methylhexane">Isoheptane</a></li> <li><a href="/wiki/2,2,4-Trimethylpentane" title="2,2,4-Trimethylpentane">Isooctane</a></li> <li><a href="/wiki/2-Methyloctane" title="2-Methyloctane">Isononane</a></li> <li><a href="/w/index.php?title=Isodecane&action=edit&redlink=1" class="new" title="Isodecane (page does not exist)">Isodecane</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Cycloalkane" title="Cycloalkane">Cycloalkanes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cyclopropane" title="Cyclopropane">Cyclopropane</a></li> <li><a href="/wiki/Cyclobutane" title="Cyclobutane">Cyclobutane</a></li> <li><a href="/wiki/Cyclopentane" title="Cyclopentane">Cyclopentane</a></li> <li><a href="/wiki/Cyclohexane" title="Cyclohexane">Cyclohexane</a></li> <li><a href="/wiki/Cycloheptane" title="Cycloheptane">Cycloheptane</a></li> <li><a href="/wiki/Cyclooctane" title="Cyclooctane">Cyclooctane</a></li> <li><a href="/wiki/Cyclononane" title="Cyclononane">Cyclononane</a></li> <li><a href="/wiki/Cyclodecane" title="Cyclodecane">Cyclodecane</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/w/index.php?title=Alkylcycloalkane&action=edit&redlink=1" class="new" title="Alkylcycloalkane (page does not exist)">Alkylcycloalkanes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Methylcyclopropane" title="Methylcyclopropane">Methylcyclopropane</a></li> <li><a href="/w/index.php?title=Methylcyclobutane&action=edit&redlink=1" class="new" title="Methylcyclobutane (page does not exist)">Methylcyclobutane</a></li> <li><a href="/wiki/Methylcyclopentane" title="Methylcyclopentane">Methylcyclopentane</a></li> <li><a href="/wiki/Methylcyclohexane" title="Methylcyclohexane">Methylcyclohexane</a></li> <li><a href="/w/index.php?title=Isopropylcyclohexane&action=edit&redlink=1" class="new" title="Isopropylcyclohexane (page does not exist)">Isopropylcyclohexane</a></li> <li class="mw-empty-elt"></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/w/index.php?title=Bicycloalkane&action=edit&redlink=1" class="new" title="Bicycloalkane (page does not exist)">Bicycloalkanes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Housane" title="Housane">Housane</a> (bicyclo[2.1.0]pentane)</li> <li><a href="/wiki/Norbornane" title="Norbornane">Norbornane</a> (bicyclo[2.2.1]heptane)</li> <li><a href="/wiki/Decalin" title="Decalin">Decalin</a> (bicyclo[4.4.0]decane)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/w/index.php?title=Polycycloalkane&action=edit&redlink=1" class="new" title="Polycycloalkane (page does not exist)">Polycycloalkanes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Adamantane" title="Adamantane">Adamantane</a></li> <li><a href="/wiki/Diamondoid" title="Diamondoid">Diamondoid</a></li> <li><a href="/w/index.php?title=Perhydrophenanthrene&action=edit&redlink=1" class="new" title="Perhydrophenanthrene (page does not exist)">Perhydrophenanthrene</a></li> <li><a href="/wiki/Sterane" title="Sterane">Sterane</a></li> <li><a href="/wiki/Cubane" title="Cubane">Cubane</a></li> <li><a href="/wiki/Prismane" title="Prismane">Prismane</a></li> <li><a href="/wiki/Dodecahedrane" title="Dodecahedrane">Dodecahedrane</a></li> <li><a href="/wiki/Basketane" title="Basketane">Basketane</a></li> <li><a href="/wiki/Churchane" title="Churchane">Churchane</a></li> <li><a href="/wiki/Pagodane" title="Pagodane">Pagodane</a></li> <li><a href="/wiki/Twistane" title="Twistane">Twistane</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=Spiroalkane&action=edit&redlink=1" class="new" title="Spiroalkane (page does not exist)">Spiroalkanes</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:azzurro;"><a href="/wiki/Unsaturated_hydrocarbon" class="mw-redirect" title="Unsaturated hydrocarbon">Unsaturated</a><br />aliphatic<br />hydrocarbons</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Alkene" title="Alkene">Alkenes</a><br />C<sub><i>n</i></sub>H<sub>2<i>n</i></sub></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em">Linear alkenes</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ethylene" title="Ethylene">Ethene</a></li> <li><a href="/wiki/Propene" class="mw-redirect" title="Propene">Propene</a></li> <li><a href="/wiki/Butene" title="Butene">Butene</a></li> <li><a href="/wiki/Pentene" title="Pentene">Pentene</a></li> <li><a href="/wiki/Hexene" title="Hexene">Hexene</a></li> <li><a href="/wiki/Heptene" title="Heptene">Heptene</a></li> <li><a href="/wiki/Octene" title="Octene">Octene</a></li> <li><a href="/wiki/Nonene" title="Nonene">Nonene</a></li> <li><a href="/wiki/Decene" title="Decene">Decene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Branched alkenes</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Isobutylene" title="Isobutylene">Isobutene</a></li> <li><a href="/wiki/Isopentene" class="mw-redirect" title="Isopentene">Isopentene</a></li> <li><a href="/w/index.php?title=Isohexene&action=edit&redlink=1" class="new" title="Isohexene (page does not exist)">Isohexene</a></li> <li><a href="/w/index.php?title=Isoheptene&action=edit&redlink=1" class="new" title="Isoheptene (page does not exist)">Isoheptene</a></li> <li><a href="/w/index.php?title=Isooctene&action=edit&redlink=1" class="new" title="Isooctene (page does not exist)">Isooctene</a></li> <li><a href="/w/index.php?title=Isononene&action=edit&redlink=1" class="new" title="Isononene (page does not exist)">Isononene</a></li> <li><a href="/w/index.php?title=Isodecene&action=edit&redlink=1" class="new" title="Isodecene (page does not exist)">Isodecene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Alkyne" title="Alkyne">Alkynes</a><br />C<sub><i>n</i></sub>H<sub>2<i>n</i> − 2</sub></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em">Linear alkynes</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetylene" title="Acetylene">Ethyne</a></li> <li><a href="/wiki/Propyne" title="Propyne">Propyne</a></li> <li><a href="/wiki/Butyne" title="Butyne">Butyne</a></li> <li><a href="/wiki/Pentyne" title="Pentyne">Pentyne</a></li> <li><a href="/wiki/3-Hexyne" title="3-Hexyne">Hexyne</a></li> <li><a href="/wiki/Heptyne" title="Heptyne">Heptyne</a></li> <li><a href="/wiki/Octyne" title="Octyne">Octyne</a></li> <li><a href="/wiki/Nonyne" title="Nonyne">Nonyne</a></li> <li><a href="/wiki/1-Decyne" title="1-Decyne">Decyne</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Branched alkynes</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=Isopentyne&action=edit&redlink=1" class="new" title="Isopentyne (page does not exist)">Isopentyne</a></li> <li><a href="/w/index.php?title=Isohexyne&action=edit&redlink=1" class="new" title="Isohexyne (page does not exist)">Isohexyne</a></li> <li><a href="/w/index.php?title=Isoheptyne&action=edit&redlink=1" class="new" title="Isoheptyne (page does not exist)">Isoheptyne</a></li> <li><a href="/w/index.php?title=Isooctyne&action=edit&redlink=1" class="new" title="Isooctyne (page does not exist)">Isooctyne</a></li> <li><a href="/w/index.php?title=Isononyne&action=edit&redlink=1" class="new" title="Isononyne (page does not exist)">Isononyne</a></li> <li><a href="/w/index.php?title=Isodecyne&action=edit&redlink=1" class="new" title="Isodecyne (page does not exist)">Isodecyne</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Cycloalkene" title="Cycloalkene">Cycloalkenes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cyclopropene" title="Cyclopropene">Cyclopropene</a></li> <li><a href="/wiki/Cyclobutene" title="Cyclobutene">Cyclobutene</a></li> <li><a href="/wiki/Cyclopentene" title="Cyclopentene">Cyclopentene</a></li> <li><a href="/wiki/Cyclohexene" title="Cyclohexene">Cyclohexene</a></li> <li><a href="/wiki/Cycloheptene" title="Cycloheptene">Cycloheptene</a></li> <li><a href="/wiki/Cyclooctene" title="Cyclooctene">Cyclooctene</a></li> <li><a href="/wiki/Cyclononene" title="Cyclononene">Cyclononene</a></li> <li><a href="/wiki/Cyclodecene" title="Cyclodecene">Cyclodecene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/w/index.php?title=Alkylcycloalkene&action=edit&redlink=1" class="new" title="Alkylcycloalkene (page does not exist)">Alkylcycloalkenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/1-Methylcyclopropene" title="1-Methylcyclopropene">Methylcyclopropene</a></li> <li><a href="/w/index.php?title=Methylcyclobutene&action=edit&redlink=1" class="new" title="Methylcyclobutene (page does not exist)">Methylcyclobutene</a></li> <li><a href="/w/index.php?title=Methylcyclopentene&action=edit&redlink=1" class="new" title="Methylcyclopentene (page does not exist)">Methylcyclopentene</a></li> <li><a href="/wiki/Methylcyclohexene" title="Methylcyclohexene">Methylcyclohexene</a></li> <li><a href="/w/index.php?title=Isopropylcyclohexene&action=edit&redlink=1" class="new" title="Isopropylcyclohexene (page does not exist)">Isopropylcyclohexene</a></li> <li class="mw-empty-elt"></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/w/index.php?title=Bicycloalkene&action=edit&redlink=1" class="new" title="Bicycloalkene (page does not exist)">Bicycloalkenes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Norbornene" title="Norbornene">Norbornene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Cycloalkyne" title="Cycloalkyne">Cycloalkynes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cyclopropyne" class="mw-redirect" title="Cyclopropyne">Cyclopropyne</a></li> <li><a href="/wiki/Cyclobutyne" title="Cyclobutyne">Cyclobutyne</a></li> <li><a href="/wiki/Cyclopentyne" title="Cyclopentyne">Cyclopentyne</a></li> <li><a href="/w/index.php?title=Cyclohexyne&action=edit&redlink=1" class="new" title="Cyclohexyne (page does not exist)">Cyclohexyne</a></li> <li><a href="/w/index.php?title=Cycloheptyne&action=edit&redlink=1" class="new" title="Cycloheptyne (page does not exist)">Cycloheptyne</a></li> <li><a href="/wiki/Cyclooctyne" title="Cyclooctyne">Cyclooctyne</a></li> <li><a href="/w/index.php?title=Cyclononyne&action=edit&redlink=1" class="new" title="Cyclononyne (page does not exist)">Cyclononyne</a></li> <li><a href="/w/index.php?title=Cyclodecyne&action=edit&redlink=1" class="new" title="Cyclodecyne (page does not exist)">Cyclodecyne</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Diene" title="Diene">Dienes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Propadiene" title="Propadiene">Propadiene</a></li> <li><a href="/wiki/Butadiene" title="Butadiene">Butadiene</a></li> <li><a href="/wiki/Piperylene" title="Piperylene">Pentadiene</a></li> <li><a href="/wiki/1,5-Hexadiene" title="1,5-Hexadiene">Hexadiene</a></li> <li><a href="/w/index.php?title=Heptadiene&action=edit&redlink=1" class="new" title="Heptadiene (page does not exist)">Heptadiene</a></li> <li><a href="/wiki/1,7-Octadiene" title="1,7-Octadiene">Octadiene</a></li> <li><a href="/w/index.php?title=Nonadiene&action=edit&redlink=1" class="new" title="Nonadiene (page does not exist)">Nonadiene</a></li> <li><a href="/w/index.php?title=Decadiene&action=edit&redlink=1" class="new" title="Decadiene (page does not exist)">Decadiene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=Alkatriene&action=edit&redlink=1" class="new" title="Alkatriene (page does not exist)">Alkatriene</a></li> <li><a href="/w/index.php?title=Alkadiyne&action=edit&redlink=1" class="new" title="Alkadiyne (page does not exist)">Alkadiyne</a></li> <li><a href="/wiki/Cumulene" title="Cumulene">Cumulene</a></li> <li><a href="/wiki/Cyclooctatetraene" title="Cyclooctatetraene">Cyclooctatetraene</a></li> <li><a href="/wiki/Cyclododecatriene" title="Cyclododecatriene">Cyclododecatriene</a></li> <li><a href="/wiki/Enyne" title="Enyne">Enyne</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:azzurro;"><a href="/wiki/Aromatic_hydrocarbon" class="mw-redirect" title="Aromatic hydrocarbon">Aromatic<br />hydrocarbons</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Polycyclic_aromatic_hydrocarbon" title="Polycyclic aromatic hydrocarbon">PAHs</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Acene" title="Acene">Acenes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Naphthalene" title="Naphthalene">Naphthalene</a></li> <li><a href="/wiki/Anthracene" title="Anthracene">Anthracene</a></li> <li><a href="/wiki/Tetracene" title="Tetracene">Tetracene</a></li> <li><a href="/wiki/Pentacene" title="Pentacene">Pentacene</a></li> <li><a href="/wiki/Hexacene" title="Hexacene">Hexacene</a></li> <li><a href="/wiki/Heptacene" title="Heptacene">Heptacene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Azulene" title="Azulene">Azulene</a></li> <li><a href="/wiki/Fluorene" title="Fluorene">Fluorene</a></li> <li><a href="/wiki/Helicene" title="Helicene">Helicenes</a></li> <li><a href="/wiki/Circulene" title="Circulene">Circulenes</a></li> <li><a href="/wiki/Butalene" title="Butalene">Butalene</a></li> <li><a href="/wiki/Phenanthrene" title="Phenanthrene">Phenanthrene</a></li> <li><a href="/wiki/Chrysene" title="Chrysene">Chrysene</a></li> <li><a href="/wiki/Pyrene" title="Pyrene">Pyrene</a></li> <li><a href="/wiki/Corannulene" title="Corannulene">Corannulene</a></li> <li><a href="/wiki/Kekulene" title="Kekulene">Kekulene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Alkylbenzenes" class="mw-redirect" title="Alkylbenzenes">Alkylbenzenes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Toluene" title="Toluene">Toluene</a></li></ul> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/C2-Benzenes" title="C2-Benzenes">C2-Benzenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Xylene" title="Xylene">Xylenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/O-Xylene" title="O-Xylene"><i>o</i>-Xylene</a></li> <li><a href="/wiki/M-Xylene" title="M-Xylene"><i>m</i>-Xylene</a></li> <li><a href="/wiki/P-Xylene" title="P-Xylene"><i>p</i>-Xylene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ethylbenzene" title="Ethylbenzene">Ethylbenzene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/C3-Benzenes" title="C3-Benzenes">C3-Benzenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Trimethylbenzenes" class="mw-redirect" title="Trimethylbenzenes">Trimethylbenzenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Mesitylene" title="Mesitylene">Mesitylene</a></li> <li><a href="/wiki/Pseudocumene" class="mw-redirect" title="Pseudocumene">Pseudocumene</a></li> <li><a href="/wiki/Hemellitene" class="mw-redirect" title="Hemellitene">Hemellitene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cumene" title="Cumene">Cumene</a></li> <li><a href="/wiki/N-Propylbenzene" title="N-Propylbenzene"><i>n</i>-Propylbenzene</a></li> <li><a href="/wiki/4-Ethyltoluene" title="4-Ethyltoluene">4-Ethyltoluene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/C4-Benzenes" title="C4-Benzenes">C4-Benzenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Cymenes" class="mw-redirect" title="Cymenes">Cymenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/O-Cymene" title="O-Cymene"><i>o</i>-Cymene</a></li> <li><a href="/wiki/M-Cymene" title="M-Cymene"><i>m</i>-Cymene</a></li> <li><a href="/wiki/P-Cymene" title="P-Cymene"><i>p</i>-Cymene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Tetramethylbenzenes" class="mw-redirect" title="Tetramethylbenzenes">Tetramethylbenzenes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Durene" title="Durene">Durene</a></li> <li><a href="/wiki/Prehnitene" title="Prehnitene">Prehnitene</a></li> <li><a href="/wiki/Isodurene" title="Isodurene">Isodurene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/N-Butylbenzene" title="N-Butylbenzene"><i>n</i>-Butylbenzene</a></li> <li><a href="/wiki/Sec-Butylbenzene" title="Sec-Butylbenzene"><i>sec</i>-Butylbenzene</a></li> <li><a href="/wiki/Tert-Butylbenzene" title="Tert-Butylbenzene"><i>tert</i>-Butylbenzene</a></li> <li><a href="/wiki/Isobutylbenzene" title="Isobutylbenzene">Isobutylbenzene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Hexamethylbenzene" title="Hexamethylbenzene">Hexamethylbenzene</a></li> <li><a href="/wiki/2-Phenylhexane" title="2-Phenylhexane">2-Phenylhexane</a></li> <li><a href="/wiki/1,3,5-Triethylbenzene" title="1,3,5-Triethylbenzene">1,3,5-Triethylbenzene</a></li> <li><a href="/wiki/1,3,5-Triheptylbenzene" title="1,3,5-Triheptylbenzene">1,3,5-Triheptylbenzene</a></li></ul> </div></td></tr></tbody></table><div> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Vinylbenzenes</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Styrene" title="Styrene">Styrene</a></li> <li><a href="/wiki/Divinylbenzene" title="Divinylbenzene">Divinylbenzene</a></li> <li><a href="/wiki/4-Vinyltoluene" title="4-Vinyltoluene">4-Vinyltoluene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Benzene" title="Benzene">Benzene</a></li> <li><a href="/wiki/Cyclopropenylidene" title="Cyclopropenylidene">Cyclopropenylidene</a></li> <li><a href="/wiki/Phenylacetylene" title="Phenylacetylene">Phenylacetylene</a></li> <li><a href="/wiki/Trans-Propenylbenzene" title="Trans-Propenylbenzene"><i>trans</i>-Propenylbenzene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:azzurro;">Other</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Annulene" title="Annulene">Annulenes</a></li> <li><a href="/wiki/Annulyne" title="Annulyne">Annulynes</a></li> <li><a href="/wiki/Alicyclic_compound" title="Alicyclic compound">Alicyclic compounds</a></li> <li><a href="/wiki/Petroleum_jelly" title="Petroleum jelly">Petroleum jelly</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><link 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style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Alkanes" title="Template:Alkanes"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Alkanes" title="Template talk:Alkanes"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Alkanes" title="Special:EditPage/Template:Alkanes"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Alkanes" style="font-size:114%;margin:0 4em"><a class="mw-selflink selflink">Alkanes</a></div></th></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Methane" title="Methane">Methane</a> (<span class="chemf nowrap">CH<sub class="template-chem2-sub">4</sub></span>)</li> <li><a href="/wiki/Ethane" title="Ethane">Ethane</a> (<span class="chemf nowrap">C<sub class="template-chem2-sub">2</sub>H<sub class="template-chem2-sub">6</sub></span>)</li> <li><a href="/wiki/Propane" title="Propane">Propane</a> (<span class="chemf nowrap">C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">8</sub></span>)</li> <li><a href="/wiki/Butane" title="Butane">Butane</a> (<span class="chemf nowrap">C<sub class="template-chem2-sub">4</sub>H<sub class="template-chem2-sub">10</sub></span>)</li> <li><a href="/wiki/Pentane" title="Pentane">Pentane</a> (<span class="chemf nowrap">C<sub class="template-chem2-sub">5</sub>H<sub class="template-chem2-sub">12</sub></span>)</li> <li><a href="/wiki/Hexane" title="Hexane">Hexane</a> (<span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">14</sub></span>)</li> <li><a href="/wiki/Heptane" title="Heptane">Heptane</a> (<span class="chemf nowrap">C<sub class="template-chem2-sub">7</sub>H<sub class="template-chem2-sub">16</sub></span>)</li> <li><a href="/wiki/Octane" title="Octane">Octane</a> (<span class="chemf nowrap">C<sub class="template-chem2-sub">8</sub>H<sub class="template-chem2-sub">18</sub></span>)</li> <li><a href="/wiki/Nonane" title="Nonane">Nonane</a> (<span class="chemf nowrap">C<sub class="template-chem2-sub">9</sub>H<sub class="template-chem2-sub">20</sub></span>)</li> <li><a href="/wiki/Decane" title="Decane">Decane</a> (<span class="chemf nowrap">C<sub class="template-chem2-sub">10</sub>H<sub class="template-chem2-sub">22</sub></span>)</li> <li><a href="/wiki/Undecane" title="Undecane">Undecane</a> (<span class="chemf nowrap">C<sub class="template-chem2-sub">11</sub>H<sub class="template-chem2-sub">24</sub></span>)</li> <li><a href="/wiki/Dodecane" title="Dodecane">Dodecane</a> (<span class="chemf nowrap">C<sub class="template-chem2-sub">12</sub>H<sub class="template-chem2-sub">26</sub></span>)</li> <li><a href="/wiki/Tridecane" title="Tridecane">Tridecane</a> (<span class="chemf nowrap">C<sub class="template-chem2-sub">13</sub>H<sub class="template-chem2-sub">28</sub></span>)</li> <li><a href="/wiki/Tetradecane" title="Tetradecane">Tetradecane</a> (<span class="chemf nowrap">C<sub class="template-chem2-sub">14</sub>H<sub class="template-chem2-sub">30</sub></span>)</li> <li><a href="/wiki/Pentadecane" title="Pentadecane">Pentadecane</a> (<span class="chemf nowrap">C<sub class="template-chem2-sub">15</sub>H<sub class="template-chem2-sub">32</sub></span>)</li> <li><a href="/wiki/Hexadecane" title="Hexadecane">Hexadecane / Cetane</a> (<span class="chemf nowrap">C<sub class="template-chem2-sub">16</sub>H<sub class="template-chem2-sub">34</sub></span>)</li> <li><a href="/wiki/Heptadecane" title="Heptadecane">Heptadecane</a> (<span class="chemf nowrap">C<sub class="template-chem2-sub">17</sub>H<sub class="template-chem2-sub">36</sub></span>)</li> <li><a href="/wiki/Octadecane" title="Octadecane">Octadecane</a> (<span class="chemf nowrap">C<sub class="template-chem2-sub">18</sub>H<sub class="template-chem2-sub">38</sub></span>)</li> <li><a href="/wiki/Nonadecane" title="Nonadecane">Nonadecane</a> (<span class="chemf nowrap">C<sub class="template-chem2-sub">19</sub>H<sub class="template-chem2-sub">40</sub></span>)</li> <li><a href="/wiki/Icosane" title="Icosane">Icosane</a> (<span class="chemf nowrap">C<sub class="template-chem2-sub">20</sub>H<sub class="template-chem2-sub">42</sub></span>)</li> <li><a href="/wiki/Heneicosane" title="Heneicosane">Heneicosane</a> (<span class="chemf nowrap">C<sub class="template-chem2-sub">21</sub>H<sub class="template-chem2-sub">44</sub></span>)</li> <li><a href="/wiki/Tetracosane" title="Tetracosane">Tetracosane</a> (<span class="chemf nowrap">C<sub class="template-chem2-sub">24</sub>H<sub class="template-chem2-sub">50</sub></span>)</li> <li><a href="/wiki/Nonacosane" title="Nonacosane">Nonacosane</a> (<span class="chemf nowrap">C<sub class="template-chem2-sub">29</sub>H<sub class="template-chem2-sub">60</sub></span>)</li> <li><a href="/wiki/Hentriacontane" title="Hentriacontane">Hentriacontane</a> (<span class="chemf nowrap">C<sub class="template-chem2-sub">31</sub>H<sub class="template-chem2-sub">64</sub></span>)</li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <ul><li><a href="/wiki/Higher_alkanes" class="mw-redirect" title="Higher alkanes">Higher alkanes</a></li> <li><a href="/wiki/List_of_straight-chain_alkanes" title="List of straight-chain alkanes">List of alkanes</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"><style data-mw-deduplicate="TemplateStyles:r886047488">.mw-parser-output .nobold{font-weight:normal}</style><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r886047488"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r886047488"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r886047488"></div><div role="navigation" class="navbox" aria-labelledby="Functional_groups" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Functional_groups" title="Template:Functional groups"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Functional_groups" title="Template talk:Functional groups"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Functional_groups" title="Special:EditPage/Template:Functional groups"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Functional_groups" style="font-size:114%;margin:0 4em"><a href="/wiki/Functional_group" title="Functional group">Functional groups</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hydrocarbon" title="Hydrocarbon">Hydrocarbons</a> <br /><span class="nobold">(only C and H)</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Alkyl" class="mw-redirect" title="Alkyl">Alkyl</a> <ul><li><a href="/wiki/Methyl_group" title="Methyl group">Methyl</a></li> <li><a href="/wiki/Ethyl_group" title="Ethyl group">Ethyl</a></li> <li><a href="/wiki/Propyl_group" title="Propyl group">Propyl</a></li> <li><a href="/wiki/Cyclopropyl" class="mw-redirect" title="Cyclopropyl">Cyclopropyl</a></li> <li><a href="/wiki/Butyl_group" title="Butyl group">Butyl</a></li> <li><a href="/wiki/Pentyl_group" title="Pentyl group">Pentyl</a></li></ul></li> <li><a href="/wiki/Methylene_group" title="Methylene group">Methylene</a> <ul><li><a href="/wiki/Methylene_bridge" title="Methylene bridge">Bridge</a></li> <li><a href="/wiki/Methine_group" title="Methine group">Methine</a></li></ul></li> <li><a href="/wiki/Alkene" title="Alkene">Alkene</a> <ul><li><a href="/wiki/Vinyl_group" title="Vinyl group">Vinyl</a></li> <li><a href="/wiki/Allyl_group" title="Allyl group">Allyl</a></li> <li><a href="/wiki/Propenyl" title="Propenyl">1-Propenyl</a></li> <li><a href="/wiki/Crotyl_group" title="Crotyl group">Crotyl</a></li> <li><a href="/wiki/Allenes" title="Allenes">Allene</a></li> <li><a href="/wiki/Cumulene" title="Cumulene">Cumulene</a></li></ul></li> <li><a href="/wiki/Aryl" class="mw-redirect" title="Aryl">Aryl</a> <ul><li><a href="/wiki/Phenyl_group" title="Phenyl group">Phenyl</a></li> <li><a href="/wiki/Benzyl_group" title="Benzyl group">Benzyl</a></li></ul></li> <li><a href="/wiki/Alkyne" title="Alkyne">Alkyne</a></li> <li><a href="/wiki/Carbene" title="Carbene">Carbene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Only <a href="/wiki/Carbon" title="Carbon">carbon</a>, <br /><a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a>, <br />and <a href="/wiki/Oxygen" title="Oxygen">oxygen</a> <br /><span class="nobold">(only C, H and O)</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">R-O-R</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetal" title="Acetal">Acetal</a></li> <li><a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">Alcohol</a></li> <li><a href="/wiki/Alkoxy_group" title="Alkoxy group">Alkoxy</a> <ul><li><a href="/wiki/Methoxy_group" title="Methoxy group">Methoxy</a></li></ul></li> <li><a href="/wiki/Ether" title="Ether">Ether</a> <ul><li><a href="/wiki/Enol_ether" title="Enol ether">Enol ether</a></li> <li><a href="/wiki/Epoxide" title="Epoxide">Epoxide</a></li></ul></li> <li><a href="/wiki/Organic_peroxides" title="Organic peroxides">Peroxy</a> <ul><li><a href="/wiki/Hydroperoxide" title="Hydroperoxide">Hydroperoxy</a></li> <li><a href="/wiki/Dioxirane" title="Dioxirane">Dioxiranes</a></li></ul></li> <li><a href="/wiki/Ethylenedioxy" title="Ethylenedioxy">Ethylenedioxy</a></li> <li><a href="/wiki/Methylenedioxy" title="Methylenedioxy">Methylenedioxy</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Carbonyl_group" title="Carbonyl group">carbonyl</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acyl_group" title="Acyl group">Acyl</a> <ul><li><a href="/wiki/Acetyl_group" title="Acetyl group">Acetyl</a></li> <li><a href="/wiki/Acryloyl_group" class="mw-redirect" title="Acryloyl group">Acryloyl</a></li> <li><a href="/wiki/Benzoyl_group" title="Benzoyl group">Benzoyl</a></li></ul></li> <li><a href="/wiki/Aldehyde" title="Aldehyde">Aldehyde</a> <ul><li><a href="/wiki/Ketene" title="Ketene">Ketene</a></li></ul></li> <li><a href="/wiki/Ketone" title="Ketone">Ketone</a></li> <li><a href="/wiki/Ynone" title="Ynone">Ynone</a></li> <li><a href="/wiki/Reductone" title="Reductone">Reductone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">carboxy</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Carboxylic_acid" title="Carboxylic acid">Carboxyl</a> <ul><li><a href="/wiki/Acetoxy_group" title="Acetoxy group">Acetoxy</a></li> <li><a href="/wiki/Carboxylic_anhydride" class="mw-redirect" title="Carboxylic anhydride">Anhydride</a></li></ul></li> <li><a href="/wiki/Ester" title="Ester">Ester</a> <ul><li><a href="/wiki/Orthoester" class="mw-redirect" title="Orthoester">Orthoester</a></li></ul></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Only one <br />element, <br />not being <br />carbon, <br />hydrogen, <br />or oxygen <br /><span class="nobold">(one element, <br />not C, H or O)</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nitrogen" title="Nitrogen">Nitrogen</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Amine" title="Amine">Amine</a> <ul><li><a href="/wiki/Enamine" title="Enamine">Enamine</a></li> <li><a href="/wiki/Quaternary_ammonium_cation" title="Quaternary ammonium cation">Ammonium</a></li></ul></li> <li><a href="/wiki/Hydrazines" title="Hydrazines">Hydrazo</a></li> <li><a href="/wiki/Nitrene" title="Nitrene">Nitrene</a></li> <li><a href="/wiki/Imine" title="Imine">Imine</a></li> <li><a href="/wiki/Oxime" title="Oxime">Oxime</a></li> <li><a href="/wiki/Hydrazone" title="Hydrazone">Hydrazone</a></li> <li><a href="/wiki/Azo_compound" title="Azo compound">Azo</a></li> <li><a href="/wiki/Amide_(functional_group)" title="Amide (functional group)">Amide</a></li> <li><a href="/wiki/Imidate" class="mw-redirect" title="Imidate">Imidate</a></li> <li><a href="/wiki/Amidine" title="Amidine">Amidine</a></li> <li><a href="/wiki/Carbamate" title="Carbamate">Carbamate</a></li> <li><a href="/wiki/Imide" title="Imide">Imide</a></li> <li><a href="/wiki/Nitrile" title="Nitrile">Nitrile</a></li> <li><a href="/wiki/Isocyanide" title="Isocyanide">Isonitrile</a></li> <li><a href="/wiki/Cyanate_ester" title="Cyanate ester">Cyanate</a></li> <li><a href="/wiki/Isocyanate" title="Isocyanate">Isocyanate</a></li> <li><a href="/wiki/Nitrate_ester" title="Nitrate ester">Nitrate</a></li> <li><a href="/wiki/Nitrite_ester" class="mw-redirect" title="Nitrite ester">Nitrite</a></li> <li><a href="/wiki/Nitro_compound" title="Nitro compound">Nitro</a></li> <li><a href="/wiki/Nitroso" title="Nitroso">Nitroso</a></li> <li><a href="/wiki/NONOate" title="NONOate">NONOate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phosphorus" title="Phosphorus">Phosphorus</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Organophosphate" title="Organophosphate">Phosphate</a> <ul><li><a href="/wiki/Phosphodiester" class="mw-redirect" title="Phosphodiester">Phosphodiester</a></li></ul></li> <li><a href="/wiki/Phosphonate" title="Phosphonate">Phosphonate</a> <ul><li><a href="/wiki/Phosphite_ester" title="Phosphite ester">Phosphite</a></li></ul></li> <li><a href="/wiki/Phosphonite" title="Phosphonite">Phosphonous</a></li> <li><a href="/wiki/Phosphinate" title="Phosphinate">Phosphinate</a></li> <li><a href="/wiki/Phosphine_oxide" title="Phosphine oxide">Phosphine oxide</a></li> <li><a href="/wiki/Organophosphine" title="Organophosphine">Phosphine</a> <ul><li><a href="/wiki/Phosphonium" title="Phosphonium">Phosphonium</a></li></ul></li> <li><a href="/wiki/Phosphaalkene" title="Phosphaalkene">Phosphaalkene</a></li> <li><a href="/wiki/Phosphaalkyne" title="Phosphaalkyne">Phosphaalkyne</a></li> <li><a href="/wiki/1-Phosphaallenes" title="1-Phosphaallenes">Phosphaallene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sulfur" title="Sulfur">Sulfur</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Thiol" title="Thiol">Thiol</a></li> <li><a href="/wiki/Sulfide_(organic)" class="mw-redirect" title="Sulfide (organic)">Sulfide</a> <ul><li><a href="/wiki/Sulfonium" title="Sulfonium">Sulfonium</a></li></ul></li> <li><a href="/wiki/Persulfide" title="Persulfide">Persulfide</a></li> <li><a href="/wiki/Disulfide" title="Disulfide">Disulfide</a></li> <li><a href="/wiki/Sulfenic_acid" title="Sulfenic acid">Sulfenic acid</a></li> <li><a href="/wiki/Thiosulfinate" title="Thiosulfinate">Thiosulfinate</a></li> <li><a href="/wiki/Sulfoxide" title="Sulfoxide">Sulfoxide</a></li> <li><a href="/wiki/Thiosulfonate" title="Thiosulfonate">Thiosulfonate</a></li> <li><a href="/wiki/Sulfinic_acid" title="Sulfinic acid">Sulfinic acid</a></li> <li><a href="/wiki/Sulfone" title="Sulfone">Sulfone</a></li> <li><a href="/wiki/Sulfonic_acid" title="Sulfonic acid">Sulfonic acid</a></li> <li><a href="/wiki/Thioketone" title="Thioketone">Thioketone</a></li> <li><a href="/wiki/Thial" title="Thial">Thial</a></li> <li><a href="/wiki/Thioester" title="Thioester">Thioester</a></li> <li><a href="/wiki/Thionoester" class="mw-redirect" title="Thionoester">Thionoester</a></li> <li><a href="/wiki/Thioxanthate" title="Thioxanthate">Thioxanthate</a></li> <li><a href="/wiki/Xanthate" title="Xanthate">Xanthate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Boron" title="Boron">Boron</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Boronic_acid" title="Boronic acid">Boronic acid</a></li> <li><a href="/wiki/Borinic_acid" title="Borinic acid">Borinic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Selenium" title="Selenium">Selenium</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Selenol" title="Selenol">Selenol</a></li> <li><a href="/wiki/Selenonic_acid" title="Selenonic acid">Selenonic acid</a></li> <li><a href="/wiki/Seleninic_acid" title="Seleninic acid">Seleninic acid</a></li> <li><a href="/wiki/Selenenic_acid" title="Selenenic acid">Selenenic acid</a></li> <li><a href="/wiki/Selone" title="Selone">Selone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Tellurium" title="Tellurium">Tellurium</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Tellurol" title="Tellurol">Tellurol</a></li> <li><a href="/wiki/Telluroketone" title="Telluroketone">Telluroketone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i><a href="/wiki/Halocarbon" title="Halocarbon">Halo</a></i></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Haloalkane" title="Haloalkane">Haloalkane</a> <ul><li><a href="/wiki/Fluoroethyl" title="Fluoroethyl">Fluoroethyl</a></li> <li><a href="/wiki/Trifluoromethyl" class="mw-redirect" title="Trifluoromethyl">Trifluoromethyl</a></li> <li><a href="/wiki/Trichloromethyl_group" title="Trichloromethyl group">Trichloromethyl</a></li> <li><a href="/wiki/Trifluoromethoxy_group" title="Trifluoromethoxy group">Trifluoromethoxy</a></li> <li><a href="/wiki/Iodane" class="mw-redirect" title="Iodane">Hypervalent iodine</a></li></ul></li> <li><a href="/wiki/Vinyl_halide" title="Vinyl halide">Vinyl halide</a> <ul><li><a href="/wiki/Vinyl_iodide_functional_group" title="Vinyl iodide functional group">Iodide</a></li></ul></li> <li><a href="/wiki/Acyl_halide" title="Acyl halide">Acyl halide</a> <ul><li><a href="/wiki/Acyl_chloride" title="Acyl chloride">Chloride</a></li></ul></li> <li><a href="/wiki/Perchlorate_ester" class="mw-redirect" title="Perchlorate ester">Perchlorate</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Isothiocyanate" title="Isothiocyanate">Isothiocyanate</a></li> <li><a href="/wiki/Phosphoramides" title="Phosphoramides">Phosphoramides</a></li> <li><a href="/wiki/Sulfenyl_chloride" title="Sulfenyl chloride">Sulfenyl chloride</a></li> <li><a href="/wiki/Sulfonamide" title="Sulfonamide">Sulfonamide</a></li> <li><a href="/wiki/Organic_thiocyanates" title="Organic thiocyanates">Thiocyanate</a></li> <li><a href="/wiki/Sulfinylamine" title="Sulfinylamine">Sulfinylamines</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt><span class="nobold">See also</span></dt> <dd><i><a href="/wiki/Chemical_classification" class="mw-redirect" title="Chemical classification">chemical classification</a></i></dd> <dd><i><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">chemical nomenclature</a></i> <dl><dd><a href="/wiki/IUPAC_nomenclature_of_inorganic_chemistry" title="IUPAC nomenclature of inorganic chemistry">inorganic</a></dd> <dd><a href="/wiki/IUPAC_nomenclature_of_organic_chemistry" title="IUPAC nomenclature of organic chemistry">organic</a></dd></dl></dd></dl> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Branches_of_chemistry" style="padding:3px"><table class="nowraplinks hlist mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Branches_of_chemistry" title="Template:Branches of chemistry"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Branches_of_chemistry" title="Template talk:Branches of chemistry"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Branches_of_chemistry" title="Special:EditPage/Template:Branches of chemistry"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Branches_of_chemistry" style="font-size:114%;margin:0 4em">Branches of <a href="/wiki/Chemistry" title="Chemistry">chemistry</a></div></th></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <ul><li><a href="/wiki/Glossary_of_chemical_formulae" title="Glossary of chemical formulae">Glossary of chemical formulae</a></li> <li><a href="/wiki/List_of_biomolecules" title="List of biomolecules">List of biomolecules</a></li> <li><a href="/wiki/List_of_inorganic_compounds" title="List of inorganic compounds">List of inorganic compounds</a></li> <li><a href="/wiki/Periodic_table" title="Periodic table">Periodic table</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Analytical_chemistry" title="Analytical chemistry">Analytical</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Instrumental_chemistry" title="Instrumental chemistry">Instrumental chemistry</a></li> <li><a href="/wiki/Electroanalytical_methods" title="Electroanalytical methods">Electroanalytical methods</a></li> <li><a href="/wiki/Spectroscopy" title="Spectroscopy">Spectroscopy</a> <ul><li><a href="/wiki/Infrared_spectroscopy" title="Infrared spectroscopy">IR</a></li> <li><a href="/wiki/Raman_spectroscopy" title="Raman spectroscopy">Raman</a></li> <li><a href="/wiki/Ultraviolet%E2%80%93visible_spectroscopy" title="Ultraviolet–visible spectroscopy">UV-Vis</a></li> <li><a href="/wiki/Nuclear_magnetic_resonance_spectroscopy" title="Nuclear magnetic resonance spectroscopy">NMR</a></li></ul></li> <li><a href="/wiki/Mass_spectrometry" title="Mass spectrometry">Mass spectrometry</a> <ul><li><a href="/wiki/Electron_ionization" title="Electron ionization">EI</a></li> <li><a href="/wiki/Inductively_coupled_plasma_mass_spectrometry" title="Inductively coupled plasma mass spectrometry">ICP</a></li> <li><a href="/wiki/Matrix-assisted_laser_desorption/ionization" title="Matrix-assisted laser desorption/ionization">MALDI</a></li></ul></li> <li><a href="/wiki/Separation_process" title="Separation process">Separation process</a></li> <li><a href="/wiki/Chromatography" title="Chromatography">Chromatography</a> <ul><li><a href="/wiki/Gas_chromatography" title="Gas chromatography">GC</a></li> <li><a href="/wiki/High-performance_liquid_chromatography" title="High-performance liquid chromatography">HPLC</a></li></ul></li> <li><a href="/wiki/Crystallography" title="Crystallography">Crystallography</a></li> <li><a href="/wiki/Characterization_(materials_science)" title="Characterization (materials science)">Characterization</a></li> <li><a href="/wiki/Titration" title="Titration">Titration</a></li> <li><a href="/wiki/Wet_chemistry" title="Wet chemistry">Wet chemistry</a></li> <li><a href="/wiki/Calorimetry" title="Calorimetry">Calorimetry</a></li> <li><a href="/wiki/Elemental_analysis" title="Elemental analysis">Elemental analysis</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Theoretical_chemistry" title="Theoretical chemistry">Theoretical</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Quantum_chemistry" title="Quantum chemistry">Quantum chemistry</a></li> <li><a href="/wiki/Computational_chemistry" title="Computational chemistry">Computational chemistry</a> <ul><li><a href="/wiki/Mathematical_chemistry" title="Mathematical chemistry">Mathematical chemistry</a></li></ul></li> <li><a href="/wiki/Molecular_modelling" title="Molecular modelling">Molecular modelling</a></li> <li><a href="/wiki/Molecular_mechanics" title="Molecular mechanics">Molecular mechanics</a></li> <li><a href="/wiki/Molecular_dynamics" title="Molecular dynamics">Molecular dynamics</a></li> <li><a href="/wiki/Molecular_geometry" title="Molecular geometry">Molecular geometry</a> <ul><li><a href="/wiki/VSEPR_theory" title="VSEPR theory">VSEPR theory</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Physical_chemistry" title="Physical chemistry">Physical</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Electrochemistry" title="Electrochemistry">Electrochemistry</a> <ul><li><a href="/wiki/Spectroelectrochemistry" title="Spectroelectrochemistry">Spectroelectrochemistry</a></li> <li><a href="/wiki/Photoelectrochemistry" title="Photoelectrochemistry">Photoelectrochemistry</a></li></ul></li> <li><a href="/wiki/Thermochemistry" title="Thermochemistry">Thermochemistry</a></li> <li><a href="/wiki/Chemical_thermodynamics" title="Chemical thermodynamics">Chemical thermodynamics</a></li> <li><a href="/wiki/Surface_science" title="Surface science">Surface science</a></li> <li><a href="/wiki/Interface_and_colloid_science" title="Interface and colloid science">Interface and colloid science</a> <ul><li><a href="/wiki/Micromeritics" title="Micromeritics">Micromeritics</a></li></ul></li> <li><a href="/wiki/Cryochemistry" title="Cryochemistry">Cryochemistry</a></li> <li><a href="/wiki/Sonochemistry" title="Sonochemistry">Sonochemistry</a></li> <li><a href="/wiki/Structural_chemistry" title="Structural chemistry">Structural chemistry</a></li> <li><a href="/wiki/Chemical_physics" title="Chemical physics">Chemical physics</a> <ul><li><a href="/wiki/Molecular_physics" title="Molecular physics">Molecular physics</a></li></ul></li> <li><a href="/wiki/Femtochemistry" title="Femtochemistry">Femtochemistry</a></li> <li><a href="/wiki/Chemical_kinetics" title="Chemical kinetics">Chemical kinetics</a></li> <li><a href="/wiki/Spectroscopy" title="Spectroscopy">Spectroscopy</a></li> <li><a href="/wiki/Photochemistry" title="Photochemistry">Photochemistry</a></li> <li><a href="/wiki/Spin_chemistry" title="Spin chemistry">Spin chemistry</a></li> <li><a href="/wiki/Microwave_chemistry" title="Microwave chemistry">Microwave chemistry</a></li> <li><a href="/wiki/Equilibrium_chemistry" title="Equilibrium chemistry">Equilibrium chemistry</a></li> <li><a href="/wiki/Mechanochemistry" title="Mechanochemistry">Mechanochemistry</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Inorganic_chemistry" title="Inorganic chemistry">Inorganic</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Coordination_complex" title="Coordination complex">Coordination chemistry</a></li> <li><a href="/wiki/Magnetochemistry" title="Magnetochemistry">Magnetochemistry</a></li> <li><a href="/wiki/Organometallic_chemistry" title="Organometallic chemistry">Organometallic chemistry</a> <ul><li><a href="/wiki/Organolanthanide_chemistry" title="Organolanthanide chemistry">Organolanthanide chemistry</a></li></ul></li> <li><a href="/wiki/Atom_cluster" class="mw-redirect" title="Atom cluster">Cluster chemistry</a></li> <li><a href="/wiki/Solid-state_chemistry" title="Solid-state chemistry">Solid-state chemistry</a></li> <li><a href="/wiki/Ceramic_chemistry" class="mw-redirect" title="Ceramic chemistry">Ceramic chemistry</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Organic_chemistry" title="Organic chemistry">Organic</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Stereochemistry" title="Stereochemistry">Stereochemistry</a> <ul><li><a href="/wiki/Alkane_stereochemistry" class="mw-redirect" title="Alkane stereochemistry">Alkane stereochemistry</a></li></ul></li> <li><a href="/wiki/Physical_organic_chemistry" title="Physical organic chemistry">Physical organic chemistry</a></li> <li><a href="/wiki/Organic_reactions" class="mw-redirect" title="Organic reactions">Organic reactions</a></li> <li><a href="/wiki/Organic_synthesis" title="Organic synthesis">Organic synthesis</a></li> <li><a href="/wiki/Retrosynthetic_analysis" title="Retrosynthetic analysis">Retrosynthetic analysis</a></li> <li><a href="/wiki/Enantioselective_synthesis" title="Enantioselective synthesis">Enantioselective synthesis</a></li> <li><a href="/wiki/Total_synthesis" title="Total synthesis">Total synthesis</a> / <a href="/wiki/Semisynthesis" title="Semisynthesis">Semisynthesis</a></li> <li><a href="/wiki/Fullerene_chemistry" title="Fullerene chemistry">Fullerene chemistry</a></li> <li><a href="/wiki/Polymer_chemistry" title="Polymer chemistry">Polymer chemistry</a></li> <li><a href="/wiki/Petrochemistry" class="mw-redirect" title="Petrochemistry">Petrochemistry</a></li> <li><a href="/wiki/Dynamic_covalent_chemistry" title="Dynamic covalent chemistry">Dynamic covalent chemistry</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Biochemistry" title="Biochemistry">Biological</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Biochemistry" title="Biochemistry">Biochemistry</a> <ul><li><a href="/wiki/Molecular_biology" title="Molecular biology">Molecular biology</a></li> <li><a href="/wiki/Cell_biology" title="Cell biology">Cell biology</a></li></ul></li> <li><a href="/wiki/Chemical_biology" title="Chemical biology">Chemical biology</a> <ul><li><a href="/wiki/Bioorthogonal_chemistry" title="Bioorthogonal chemistry">Bioorthogonal chemistry</a></li></ul></li> <li><a href="/wiki/Medicinal_chemistry" title="Medicinal chemistry">Medicinal chemistry</a> <ul><li><a href="/wiki/Pharmacology" title="Pharmacology">Pharmacology</a></li></ul></li> <li><a href="/wiki/Clinical_chemistry" title="Clinical chemistry">Clinical chemistry</a></li> <li><a href="/wiki/Neurochemistry" title="Neurochemistry">Neurochemistry</a></li> <li><a href="/wiki/Bioorganic_chemistry" title="Bioorganic chemistry">Bioorganic chemistry</a></li> <li><a href="/wiki/Bioorganometallic_chemistry" title="Bioorganometallic chemistry">Bioorganometallic chemistry</a></li> <li><a href="/wiki/Bioinorganic_chemistry" title="Bioinorganic chemistry">Bioinorganic chemistry</a></li> <li><a href="/wiki/Biophysical_chemistry" title="Biophysical chemistry">Biophysical chemistry</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Interdisciplinarity" title="Interdisciplinarity">Interdisciplinarity</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Nuclear_chemistry" title="Nuclear chemistry">Nuclear chemistry</a> <ul><li><a href="/wiki/Radiochemistry" title="Radiochemistry">Radiochemistry</a></li> <li><a href="/wiki/Radiation_chemistry" title="Radiation chemistry">Radiation chemistry</a></li> <li><a href="/wiki/Actinide_chemistry" title="Actinide chemistry">Actinide chemistry</a></li></ul></li> <li><a href="/wiki/Cosmochemistry" title="Cosmochemistry">Cosmochemistry</a> / <a href="/wiki/Astrochemistry" title="Astrochemistry">Astrochemistry</a> / <a href="/wiki/Stellar_chemistry" title="Stellar chemistry">Stellar chemistry</a></li> <li><a href="/wiki/Geochemistry" title="Geochemistry">Geochemistry</a> <ul><li><a href="/wiki/Biogeochemistry" title="Biogeochemistry">Biogeochemistry</a></li> <li><a href="/wiki/Photogeochemistry" title="Photogeochemistry">Photogeochemistry</a></li></ul></li></ul> <ul><li><a href="/wiki/Environmental_chemistry" title="Environmental chemistry">Environmental chemistry</a> <ul><li><a href="/wiki/Atmospheric_chemistry" title="Atmospheric chemistry">Atmospheric chemistry</a></li> <li><a href="/wiki/Ocean_chemistry" class="mw-redirect" title="Ocean chemistry">Ocean chemistry</a></li></ul></li> <li><a href="/wiki/Clay_chemistry" title="Clay chemistry">Clay chemistry</a></li> <li><a href="/wiki/Carbochemistry" title="Carbochemistry">Carbochemistry</a></li> <li><a href="/wiki/Food_chemistry" title="Food chemistry">Food chemistry</a> <ul><li><a href="/wiki/Carbohydrate_chemistry" class="mw-redirect" title="Carbohydrate chemistry">Carbohydrate chemistry</a></li> <li><a href="/wiki/Food_physical_chemistry" title="Food physical chemistry">Food physical chemistry</a></li></ul></li> <li><a href="/wiki/Agricultural_chemistry" title="Agricultural chemistry">Agricultural chemistry</a> <ul><li><a href="/wiki/Soil_chemistry" title="Soil chemistry">Soil chemistry</a></li></ul></li></ul> <ul><li><a href="/wiki/Chemistry_education" title="Chemistry education">Chemistry education</a> <ul><li><a href="/wiki/Amateur_chemistry" title="Amateur chemistry">Amateur chemistry</a></li> <li><a href="/wiki/General_chemistry" title="General chemistry">General chemistry</a></li></ul></li> <li><a href="/wiki/Clandestine_chemistry" title="Clandestine chemistry">Clandestine chemistry</a></li> <li><a href="/wiki/Forensic_chemistry" title="Forensic chemistry">Forensic chemistry</a> <ul><li><a href="/wiki/Forensic_toxicology" title="Forensic toxicology">Forensic toxicology</a></li> <li><a href="/wiki/Post-mortem_chemistry" title="Post-mortem chemistry">Post-mortem chemistry</a></li></ul></li></ul> <ul><li><a href="/wiki/Nanochemistry" title="Nanochemistry">Nanochemistry</a> <ul><li><a href="/wiki/Supramolecular_chemistry" title="Supramolecular chemistry">Supramolecular chemistry</a></li></ul></li> <li><a href="/wiki/Chemical_synthesis" title="Chemical synthesis">Chemical synthesis</a> <ul><li><a href="/wiki/Green_chemistry" title="Green chemistry">Green chemistry</a></li> <li><a href="/wiki/Click_chemistry" title="Click chemistry">Click chemistry</a></li> <li><a href="/wiki/Combinatorial_chemistry" title="Combinatorial chemistry">Combinatorial chemistry</a></li> <li><a href="/wiki/Biosynthesis" title="Biosynthesis">Biosynthesis</a></li></ul></li> <li><a href="/wiki/Chemical_engineering" title="Chemical engineering">Chemical engineering</a> <ul><li><a href="/wiki/Stoichiometry" title="Stoichiometry">Stoichiometry</a></li></ul></li> <li><a href="/wiki/Materials_science" title="Materials science">Materials science</a> <ul><li><a href="/wiki/Metallurgy" title="Metallurgy">Metallurgy</a></li> <li><a href="/wiki/Ceramic_engineering" title="Ceramic engineering">Ceramic engineering</a></li> <li><a href="/wiki/Polymer_science" title="Polymer science">Polymer science</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">See also</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/History_of_chemistry" title="History of chemistry">History of chemistry</a></li> <li><a href="/wiki/Nobel_Prize_in_Chemistry" title="Nobel Prize in Chemistry">Nobel Prize in Chemistry</a></li> <li><a href="/wiki/Timeline_of_chemistry" title="Timeline of chemistry">Timeline of chemistry</a> <ul><li><a href="/wiki/Discovery_of_chemical_elements" title="Discovery of chemical elements">of element discoveries</a></li></ul></li> <li>"<a href="/wiki/The_central_science" title="The central science">The central science</a>"</li> <li><a href="/wiki/Chemical_reaction" title="Chemical reaction">Chemical reaction</a> <ul><li><a href="/wiki/Catalysis" title="Catalysis">Catalysis</a></li></ul></li> <li><a href="/wiki/Chemical_element" title="Chemical element">Chemical element</a></li> <li><a href="/wiki/Chemical_compound" title="Chemical compound">Chemical compound</a></li> <li><a href="/wiki/Atom" title="Atom">Atom</a></li> <li><a href="/wiki/Molecule" title="Molecule">Molecule</a></li> <li><a href="/wiki/Ion" title="Ion">Ion</a></li> <li><a href="/wiki/Chemical_substance" title="Chemical substance">Chemical substance</a></li> <li><a href="/wiki/Chemical_bond" title="Chemical bond">Chemical bond</a></li> <li><a href="/wiki/Alchemy" title="Alchemy">Alchemy</a></li> <li><a href="/wiki/Quantum_mechanics" title="Quantum mechanics">Quantum mechanics</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <ul><li><span class="noviewer" typeof="mw:File"><span title="Category"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/16px-Symbol_category_class.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/23px-Symbol_category_class.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/31px-Symbol_category_class.svg.png 2x" data-file-width="180" data-file-height="185" /></span></span> <b><a href="/wiki/Category:Chemistry" title="Category:Chemistry">Category</a></b></li> <li><span class="noviewer" typeof="mw:File"><span title="Commons page"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/12px-Commons-logo.svg.png" decoding="async" width="12" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/18px-Commons-logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/24px-Commons-logo.svg.png 2x" data-file-width="1024" data-file-height="1376" /></span></span> <b><a href="https://commons.wikimedia.org/wiki/Category:Chemistry" class="extiw" title="commons:Category:Chemistry">Commons</a></b></li> <li><span class="noviewer" typeof="mw:File"><a href="/wiki/File:Symbol_portal_class.svg" class="mw-file-description" title="Portal"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/e/e2/Symbol_portal_class.svg/16px-Symbol_portal_class.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/e/e2/Symbol_portal_class.svg/23px-Symbol_portal_class.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/e/e2/Symbol_portal_class.svg/31px-Symbol_portal_class.svg.png 2x" data-file-width="180" data-file-height="185" /></a></span> <b><a href="/wiki/Portal:Chemistry" title="Portal:Chemistry">Portal</a></b></li> <li><span class="noviewer" typeof="mw:File"><span title="WikiProject"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/37/People_icon.svg/16px-People_icon.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/37/People_icon.svg/24px-People_icon.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/37/People_icon.svg/32px-People_icon.svg.png 2x" data-file-width="100" data-file-height="100" /></span></span> <b><a href="/wiki/Wikipedia:WikiProject_Chemistry" title="Wikipedia:WikiProject Chemistry">WikiProject</a></b></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Binary_compounds_of_hydrogen" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Hydrides_by_group" title="Template:Hydrides by group"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Hydrides_by_group" title="Template talk:Hydrides by group"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Hydrides_by_group" title="Special:EditPage/Template:Hydrides by group"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Binary_compounds_of_hydrogen" style="font-size:114%;margin:0 4em"><a href="/wiki/Binary_compounds_of_hydrogen" title="Binary compounds of hydrogen">Binary compounds of hydrogen</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hydride#Ionic_hydrides" title="Hydride">Alkali metal <br />(Group 1) hydrides</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Lithium_hydride" title="Lithium hydride">LiH</a></li> <li><a href="/wiki/Sodium_hydride" title="Sodium hydride">NaH</a></li> <li><a href="/wiki/Potassium_hydride" title="Potassium hydride">KH</a></li> <li><a href="/wiki/Rubidium_hydride" title="Rubidium hydride">RbH</a></li> <li><a href="/wiki/Caesium_hydride" title="Caesium hydride">CsH</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hydride#Ionic_hydrides" title="Hydride">Alkaline <br />(Group 2) <br />earth hydrides</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Monohydrides" scope="row" class="navbox-group" style="width:1%">Monohydrides</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Beryllium_monohydride" title="Beryllium monohydride">BeH</a></li> <li><a href="/wiki/Magnesium_monohydride" title="Magnesium monohydride">MgH</a></li> <li><a href="/wiki/Calcium_monohydride" title="Calcium monohydride">CaH</a></li> <li><a href="/w/index.php?title=Strontium_monohydride&action=edit&redlink=1" class="new" title="Strontium monohydride (page does not exist)">SrH</a></li> <li><a href="/w/index.php?title=Barium_monohydride&action=edit&redlink=1" class="new" title="Barium monohydride (page does not exist)">BaH</a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Dihydrides" scope="row" class="navbox-group" style="width:1%">Dihydrides</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Beryllium_hydride" title="Beryllium hydride">BeH<sub>2</sub></a></li> <li><a href="/wiki/Magnesium_hydride" title="Magnesium hydride">MgH<sub>2</sub></a></li> <li><a href="/wiki/Calcium_hydride" title="Calcium hydride">CaH<sub>2</sub></a></li> <li><a href="/wiki/Strontium_hydride" title="Strontium hydride">SrH<sub>2</sub></a></li> <li><a href="/wiki/Barium_hydride" title="Barium hydride">BaH<sub>2</sub></a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Group_13_hydride" title="Group 13 hydride">Group 13 <br />hydrides</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Boranes" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Boranes" title="Boranes">Boranes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Borane" title="Borane">BH<sub>3</sub></a></li> <li><a href="/wiki/Boron_monohydride" title="Boron monohydride">BH</a></li> <li><a href="/wiki/Diborane" title="Diborane">B<sub>2</sub>H<sub>6</sub></a></li> <li><a href="/wiki/Diborane(2)" title="Diborane(2)">B<sub>2</sub>H<sub>2</sub></a></li> <li><a href="/wiki/Diborane(4)" title="Diborane(4)">B<sub>2</sub>H<sub>4</sub></a></li> <li><a href="/wiki/Tetraborane" title="Tetraborane">B<sub>4</sub>H<sub>10</sub></a></li> <li><a href="/wiki/Pentaborane(9)" title="Pentaborane(9)">B<sub>5</sub>H<sub>9</sub></a></li> <li><a href="/wiki/Pentaborane(11)" title="Pentaborane(11)">B<sub>5</sub>H<sub>11</sub></a></li> <li><a href="/wiki/Hexaborane(10)" title="Hexaborane(10)">B<sub>6</sub>H<sub>10</sub></a></li> <li><a href="/wiki/Hexaborane(12)" title="Hexaborane(12)">B<sub>6</sub>H<sub>12</sub></a></li> <li><a href="/wiki/Decaborane" title="Decaborane">B<sub>10</sub>H<sub>14</sub></a></li> <li><a href="/wiki/Octadecaborane" title="Octadecaborane">B<sub>18</sub>H<sub>22</sub></a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Alanes" scope="row" class="navbox-group" style="width:1%">Alanes</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aluminium_hydride" title="Aluminium hydride">AlH<sub>3</sub></a></li> <li><a href="/wiki/Dialane" title="Dialane">Al<sub>2</sub>H<sub>6</sub></a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Gallanes" scope="row" class="navbox-group" style="width:1%">Gallanes</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Gallane" title="Gallane">GaH<sub>3</sub></a></li> <li><a href="/wiki/Digallane" title="Digallane">Ga<sub>2</sub>H<sub>6</sub></a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Indiganes" scope="row" class="navbox-group" style="width:1%">Indiganes</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Indium_trihydride" title="Indium trihydride">InH<sub>3</sub></a></li> <li><a href="/w/index.php?title=Diindigane&action=edit&redlink=1" class="new" title="Diindigane (page does not exist)">In<sub>2</sub>H<sub>6</sub></a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Thallanes" scope="row" class="navbox-group" style="width:1%">Thallanes</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Thallane" title="Thallane">TlH<sub>3</sub></a></li> <li><a href="/w/index.php?title=Dithallane&action=edit&redlink=1" class="new" title="Dithallane (page does not exist)">Tl<sub>2</sub>H<sub>6</sub></a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Nihonanes_(predicted)" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nihonium" title="Nihonium">Nihonanes</a> (<i>predicted</i>)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>NhH</i></li> <li><i>NhH<sub>3</sub></i></li> <li><i>Nh<sub>2</sub>H<sub>6</sub></i></li> <li><i>NhH<sub>5</sub></i></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Group_14_hydride" title="Group 14 hydride">Group 14 hydrides</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Hydrocarbons" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hydrocarbon" title="Hydrocarbon">Hydrocarbons</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a class="mw-selflink selflink">alkanes</a></li> <li><a href="/wiki/Alkene" title="Alkene">alkenes</a></li> <li><a href="/wiki/Alkyne" title="Alkyne">alkynes</a></li> <li><a href="/wiki/Cycloalkane" title="Cycloalkane">Cycloalkanes</a></li> <li><a href="/wiki/Cycloalkene" title="Cycloalkene">Cycloalkenes</a></li> <li><a href="/wiki/Cycloalkyne" title="Cycloalkyne">Cycloalkynes</a></li> <li><a href="/wiki/Annulenes" class="mw-redirect" title="Annulenes">Annulenes</a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Methylidyne_radical" title="Methylidyne radical">CH</a></li> <li><a href="/wiki/Methylene_(compound)" title="Methylene (compound)">CH<sub>2</sub></a></li> <li><a href="/wiki/Methyl_radical" title="Methyl radical">CH<sub>3</sub></a></li> <li><a href="/wiki/Ethynyl_radical" title="Ethynyl radical">C<sub>2</sub>H</a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Silanes" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Silanes" title="Silanes">Silanes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Silane" title="Silane">SiH<sub>4</sub></a></li> <li><a href="/wiki/Disilane" title="Disilane">Si<sub>2</sub>H<sub>6</sub></a></li> <li><a href="/wiki/Trisilane" title="Trisilane">Si<sub>3</sub>H<sub>8</sub></a></li> <li><a href="/wiki/Tetrasilane" title="Tetrasilane">Si<sub>4</sub>H<sub>10</sub></a></li> <li><a href="/wiki/Pentasilane" class="mw-redirect" title="Pentasilane">Si<sub>5</sub>H<sub>12</sub></a></li> <li><a href="/wiki/Hexasilane" class="mw-redirect" title="Hexasilane">Si<sub>6</sub>H<sub>14</sub></a></li> <li><a href="/w/index.php?title=Heptasilane&action=edit&redlink=1" class="new" title="Heptasilane (page does not exist)">Si<sub>7</sub>H<sub>16</sub></a></li> <li><a href="/w/index.php?title=Octasilane&action=edit&redlink=1" class="new" title="Octasilane (page does not exist)">Si<sub>8</sub>H<sub>18</sub></a></li> <li><a href="/w/index.php?title=Nonasilane&action=edit&redlink=1" class="new" title="Nonasilane (page does not exist)">Si<sub>9</sub>H<sub>20</sub></a></li> <li><a href="/w/index.php?title=Decasilane&action=edit&redlink=1" class="new" title="Decasilane (page does not exist)">Si<sub>10</sub>H<sub>22</sub></a></li> <li><a href="/wiki/Silanes" title="Silanes">more...</a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Silenes" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Silenes" title="Silenes">Silenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Disilene" title="Disilene">Si<sub>2</sub>H<sub>4</sub></a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Silynes" scope="row" class="navbox-group" style="width:1%"><a href="/w/index.php?title=Silynes&action=edit&redlink=1" class="new" title="Silynes (page does not exist)">Silynes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Disilyne" title="Disilyne">Si<sub>2</sub>H<sub>2</sub></a></li> <li><a href="/wiki/Silicon_monohydride" class="mw-redirect" title="Silicon monohydride">SiH</a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Germanes" scope="row" class="navbox-group" style="width:1%"><a href="/w/index.php?title=Germanes&action=edit&redlink=1" class="new" title="Germanes (page does not exist)">Germanes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Germane" title="Germane">GeH<sub>4</sub></a></li> <li><a href="/wiki/Digermane" title="Digermane">Ge<sub>2</sub>H<sub>6</sub></a></li> <li><a href="/w/index.php?title=Trigermane&action=edit&redlink=1" class="new" title="Trigermane (page does not exist)">Ge<sub>3</sub>H<sub>8</sub></a></li> <li><a href="/w/index.php?title=Tetragermane&action=edit&redlink=1" class="new" title="Tetragermane (page does not exist)">Ge<sub>4</sub>H<sub>10</sub></a></li> <li><a href="/w/index.php?title=Pentagermane&action=edit&redlink=1" class="new" title="Pentagermane (page does not exist)">Ge<sub>5</sub>H<sub>12</sub></a></li></ul> </div></td></tr></tbody></table><div></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Stannanes" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Stannanes" class="mw-redirect" title="Stannanes">Stannanes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Stannane" title="Stannane">SnH<sub>4</sub></a></li> <li><a href="/w/index.php?title=Distannane&action=edit&redlink=1" class="new" title="Distannane (page does not exist)">Sn<sub>2</sub>H<sub>6</sub></a></li></ul> </div></td></tr></tbody></table><div></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Plumbanes" scope="row" class="navbox-group" style="width:1%">Plumbanes</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Plumbane" title="Plumbane">PbH<sub>4</sub></a></li></ul> </div></td></tr></tbody></table><div></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Flerovanes_(predicted)" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Flerovium" title="Flerovium">Flerovanes</a> (<i>predicted</i>)</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>FlH</i></li> <li><i>FlH<sub>2</sub></i></li> <li><i>FlH<sub>4</sub></i></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Pnictogen_hydride" title="Pnictogen hydride">Pnictogen <br />(Group 15) hydrides</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Azanes" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Azane" title="Azane">Azanes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ammonia" title="Ammonia">NH<sub>3</sub></a></li> <li><a href="/wiki/Hydrazine" title="Hydrazine">N<sub>2</sub>H<sub>4</sub></a></li> <li><a href="/wiki/Triazane" title="Triazane">N<sub>3</sub>H<sub>5</sub></a></li> <li><a href="/w/index.php?title=Tetrazane&action=edit&redlink=1" class="new" title="Tetrazane (page does not exist)">N<sub>4</sub>H<sub>6</sub></a></li> <li><a href="/w/index.php?title=Pentazane&action=edit&redlink=1" class="new" title="Pentazane (page does not exist)">N<sub>5</sub>H<sub>7</sub></a></li> <li><a href="/w/index.php?title=Hexazane&action=edit&redlink=1" class="new" title="Hexazane (page does not exist)">N<sub>6</sub>H<sub>8</sub></a></li> <li><a href="/w/index.php?title=Heptazane&action=edit&redlink=1" class="new" title="Heptazane (page does not exist)">N<sub>7</sub>H<sub>9</sub></a></li> <li><a href="/w/index.php?title=Octazane&action=edit&redlink=1" class="new" title="Octazane (page does not exist)">N<sub>8</sub>H<sub>10</sub></a></li> <li><a href="/w/index.php?title=Nonazane&action=edit&redlink=1" class="new" title="Nonazane (page does not exist)">N<sub>9</sub>H<sub>11</sub></a></li> <li><a href="/w/index.php?title=Decazane&action=edit&redlink=1" class="new" title="Decazane (page does not exist)">N<sub>10</sub>H<sub>12</sub></a></li> <li><a href="/wiki/Azane" title="Azane">more...</a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Azenes" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Azo_compound" title="Azo compound">Azenes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Diazene" class="mw-redirect" title="Diazene">N<sub>2</sub>H<sub>2</sub></a></li> <li><a href="/wiki/Triazene" title="Triazene">N<sub>3</sub>H<sub>3</sub></a></li> <li><a href="/wiki/Tetrazene" title="Tetrazene">N<sub>4</sub>H<sub>4</sub></a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Phosphanes" scope="row" class="navbox-group" style="width:1%"><a href="/w/index.php?title=Phosphanes&action=edit&redlink=1" class="new" title="Phosphanes (page does not exist)">Phosphanes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Phosphine" title="Phosphine">PH<sub>3</sub></a></li> <li><a href="/wiki/Diphosphane" title="Diphosphane">P<sub>2</sub>H<sub>4</sub></a></li> <li><a href="/wiki/Triphosphane" title="Triphosphane">P<sub>3</sub>H<sub>5</sub></a></li> <li><a href="/w/index.php?title=Tetraphosphane&action=edit&redlink=1" class="new" title="Tetraphosphane (page does not exist)">P<sub>4</sub>H<sub>6</sub></a></li> <li><a href="/w/index.php?title=Pentaphosphane&action=edit&redlink=1" class="new" title="Pentaphosphane (page does not exist)">P<sub>5</sub>H<sub>7</sub></a></li> <li><a href="/w/index.php?title=Hexaphosphane&action=edit&redlink=1" class="new" title="Hexaphosphane (page does not exist)">P<sub>6</sub>H<sub>8</sub></a></li> <li><a href="/w/index.php?title=Heptaphosphane&action=edit&redlink=1" class="new" title="Heptaphosphane (page does not exist)">P<sub>7</sub>H<sub>9</sub></a></li> <li><a href="/w/index.php?title=Octaphosphane&action=edit&redlink=1" class="new" title="Octaphosphane (page does not exist)">P<sub>8</sub>H<sub>10</sub></a></li> <li><a href="/w/index.php?title=Nonaphosphane&action=edit&redlink=1" class="new" title="Nonaphosphane (page does not exist)">P<sub>9</sub>H<sub>11</sub></a></li> <li><a href="/w/index.php?title=Decaphosphane&action=edit&redlink=1" class="new" title="Decaphosphane (page does not exist)">P<sub>10</sub>H<sub>12</sub></a></li> <li><a href="/w/index.php?title=Phosphanes&action=edit&redlink=1" class="new" title="Phosphanes (page does not exist)">more...</a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Phosphenes" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Diphosphenes" title="Diphosphenes">Phosphenes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Diphosphene" title="Diphosphene">P<sub>2</sub>H<sub>2</sub></a></li> <li><a href="/w/index.php?title=Triphosphene&action=edit&redlink=1" class="new" title="Triphosphene (page does not exist)">P<sub>3</sub>H<sub>3</sub></a></li> <li><a href="/w/index.php?title=Tetraphosphene&action=edit&redlink=1" class="new" title="Tetraphosphene (page does not exist)">P<sub>4</sub>H<sub>4</sub></a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Arsanes" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Arsane" class="mw-redirect" title="Arsane">Arsanes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Arsine" title="Arsine">AsH<sub>3</sub></a></li> <li><a href="/wiki/Diarsine" class="mw-redirect" title="Diarsine">As<sub>2</sub>H<sub>4</sub></a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Stibanes" scope="row" class="navbox-group" style="width:1%">Stibanes</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Stibine" title="Stibine">SbH<sub>3</sub></a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Bismuthanes" scope="row" class="navbox-group" style="width:1%">Bismuthanes</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Bismuthine" title="Bismuthine">BiH<sub>3</sub></a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Moscovanes" scope="row" class="navbox-group" style="width:1%">Moscovanes</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Moscovium" title="Moscovium">McH<sub>3</sub></a></i> (<i>predicted</i>)</li></ul> </div></td></tr></tbody></table><div> <ul><li><a href="/wiki/Hydrazoic_acid" title="Hydrazoic acid">HN<sub>3</sub></a></li> <li><a href="/wiki/Imidogen" title="Imidogen">NH</a></li> <li><a href="/wiki/Pentazole" title="Pentazole">HN<sub>5</sub></a></li> <li><a href="/wiki/Nitrogen_pentahydride" title="Nitrogen pentahydride">NH<sub>5</sub></a> <i>(hypothetical)</i></li></ul></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hydrogen_chalcogenide" title="Hydrogen chalcogenide">Hydrogen <br />chalcogenides <br />(Group 16 hydrides)</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Polyoxidanes" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hydrogen_polyoxide" title="Hydrogen polyoxide">Polyoxidanes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <li><a href="/wiki/Properties_of_water" title="Properties of water">H<sub>2</sub>O</a></li> <li><a href="/wiki/Hydrogen_peroxide" title="Hydrogen peroxide">H<sub>2</sub>O<sub>2</sub></a></li> <li><a href="/wiki/Trioxidane" title="Trioxidane">H<sub>2</sub>O<sub>3</sub></a></li> <li><a href="/wiki/Tetraoxidane" title="Tetraoxidane">H<sub>2</sub>O<sub>4</sub></a></li> <li><a href="/wiki/Pentaoxidane" title="Pentaoxidane">H<sub>2</sub>O<sub>5</sub></a></li> <li><a href="/wiki/Hydrogen_polyoxide" title="Hydrogen polyoxide">more...</a></li> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Polysulfanes" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Polysulfane" title="Polysulfane">Polysulfanes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Hydrogen_sulfide" title="Hydrogen sulfide">H<sub>2</sub>S</a></li> <li><a href="/wiki/Hydrogen_disulfide" title="Hydrogen disulfide">H<sub>2</sub>S<sub>2</sub></a></li> <li><a href="/wiki/Trisulfane" title="Trisulfane">H<sub>2</sub>S<sub>3</sub></a></li> <li><a href="/w/index.php?title=Hydrogen_tetrasulfide&action=edit&redlink=1" class="new" title="Hydrogen tetrasulfide (page does not exist)">H<sub>2</sub>S<sub>4</sub></a></li> <li><a href="/w/index.php?title=Hydrogen_pentasulfide&action=edit&redlink=1" class="new" title="Hydrogen pentasulfide (page does not exist)">H<sub>2</sub>S<sub>5</sub></a></li> <li><a href="/w/index.php?title=Hydrogen_hexasulfide&action=edit&redlink=1" class="new" title="Hydrogen hexasulfide (page does not exist)">H<sub>2</sub>S<sub>6</sub></a></li> <li><a href="/w/index.php?title=Hydrogen_heptasulfide&action=edit&redlink=1" class="new" title="Hydrogen heptasulfide (page does not exist)">H<sub>2</sub>S<sub>7</sub></a></li> <li><a href="/w/index.php?title=Hydrogen_octasulfide&action=edit&redlink=1" class="new" title="Hydrogen octasulfide (page does not exist)">H<sub>2</sub>S<sub>8</sub></a></li> <li><a href="/w/index.php?title=Hydrogen_nonasulfide&action=edit&redlink=1" class="new" title="Hydrogen nonasulfide (page does not exist)">H<sub>2</sub>S<sub>9</sub></a></li> <li><a href="/w/index.php?title=Hydrogen_decasulfide&action=edit&redlink=1" class="new" title="Hydrogen decasulfide (page does not exist)">H<sub>2</sub>S<sub>10</sub></a></li> <li><a href="/wiki/Polysulfane" title="Polysulfane">more...</a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Selanes" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Selanes" class="mw-redirect" title="Selanes">Selanes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Hydrogen_selenide" title="Hydrogen selenide">H<sub>2</sub>Se</a></li> <li><a href="/wiki/Hydrogen_diselenide" title="Hydrogen diselenide">H<sub>2</sub>Se<sub>2</sub></a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Tellanes" scope="row" class="navbox-group" style="width:1%">Tellanes</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Hydrogen_telluride" title="Hydrogen telluride">H<sub>2</sub>Te</a></li> <li><a href="/wiki/Hydrogen_ditelluride" title="Hydrogen ditelluride">H<sub>2</sub>Te<sub>2</sub></a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Polanes" scope="row" class="navbox-group" style="width:1%">Polanes</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Polonium_hydride" title="Polonium hydride">PoH<sub>2</sub></a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Livermoranes" scope="row" class="navbox-group" style="width:1%">Livermoranes</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Livermorium" title="Livermorium">LvH<sub>2</sub></a></i> (<i>predicted</i>)</li></ul> </div></td></tr></tbody></table><div> <ul><li><a href="/wiki/Hydroxyl_radical" title="Hydroxyl radical">HO</a></li> <li><a href="/wiki/Hydroperoxyl" title="Hydroperoxyl">HO<sub>2</sub></a></li> <li><a href="/wiki/Hydrogen_ozonide" title="Hydrogen ozonide">HO<sub>3</sub></a></li> <li><a href="/w/index.php?title=Oxywater&action=edit&redlink=1" class="new" title="Oxywater (page does not exist)">H<sub>2</sub>O<sup>+</sup>–O<sup>–</sup></a> <i>(hypothetical)</i></li> <li><a href="/wiki/Sulfanyl" title="Sulfanyl">HS</a></li> <li><a href="/wiki/Semiheavy_water" title="Semiheavy water">HDO</a></li> <li><a href="/wiki/Heavy_water" title="Heavy water">D<sub>2</sub>O</a></li> <li><a href="/wiki/Tritiated_water" title="Tritiated water">T<sub>2</sub>O</a></li></ul></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hydrogen_halide" title="Hydrogen halide">Hydrogen halides <br />(Group 17 hydrides)</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <li><a href="/wiki/Hydrogen_fluoride" title="Hydrogen fluoride">HF</a></li> <li><a href="/wiki/Hydrogen_chloride" title="Hydrogen chloride">HCl</a></li> <li><a href="/wiki/Hydrogen_bromide" title="Hydrogen bromide">HBr</a></li> <li><a href="/wiki/Hydrogen_iodide" title="Hydrogen iodide">HI</a></li> <li><a href="/wiki/Hydrogen_astatide" title="Hydrogen astatide">HAt</a></li> <li><i><a href="/wiki/Tennessine" title="Tennessine">HTs</a></i> (<i>predicted</i>)</li> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Transition_metal_hydrides" class="mw-redirect" title="Transition metal hydrides">Transition metal hydrides</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Scandium_hydride" title="Scandium hydride">ScH<sub>2</sub></a></li> <li><a href="/wiki/Yttrium_hydride" title="Yttrium hydride">YH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Yttrium_trihydride&action=edit&redlink=1" class="new" title="Yttrium trihydride (page does not exist)">YH<sub>3</sub></a></li> <li><a href="/w/index.php?title=Yttrium_hexahydride&action=edit&redlink=1" class="new" title="Yttrium hexahydride (page does not exist)">YH<sub>6</sub></a></li> <li><a href="/w/index.php?title=Yttrium_nonahydride&action=edit&redlink=1" class="new" title="Yttrium nonahydride (page does not exist)">YH<sub>9</sub></a></li> <li><a href="/w/index.php?title=Lutetium_dihydride&action=edit&redlink=1" class="new" title="Lutetium dihydride (page does not exist)">LuH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Lutetium_trihydride&action=edit&redlink=1" class="new" title="Lutetium trihydride (page does not exist)">LuH<sub>3</sub></a></li> <li><a href="/wiki/Titanium_hydride" title="Titanium hydride">TiH<sub>2</sub></a></li> <li><a href="/wiki/Titanium(IV)_hydride" title="Titanium(IV) hydride">TiH<sub>4</sub></a></li> <li><a href="/wiki/Zirconium(II)_hydride" title="Zirconium(II) hydride">ZrH<sub>2</sub></a></li> <li><a href="/wiki/Zirconium_hydride" title="Zirconium hydride">ZrH<sub>4</sub></a></li> <li><a href="/w/index.php?title=Hafnium(II)_hydride&action=edit&redlink=1" class="new" title="Hafnium(II) hydride (page does not exist)">HfH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Hafnium_hydride&action=edit&redlink=1" class="new" title="Hafnium hydride (page does not exist)">HfH<sub>4</sub></a></li> <li><a href="/w/index.php?title=Vanadium(I)_hydride&action=edit&redlink=1" class="new" title="Vanadium(I) hydride (page does not exist)">VH</a></li> <li><a href="/w/index.php?title=Vanadium(II)_hydride&action=edit&redlink=1" class="new" title="Vanadium(II) hydride (page does not exist)">VH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Niobium_monohydride&action=edit&redlink=1" class="new" title="Niobium monohydride (page does not exist)">NbH</a></li> <li><a href="/w/index.php?title=Niobium_dihydride&action=edit&redlink=1" class="new" title="Niobium dihydride (page does not exist)">NbH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Tantalum_monohydride&action=edit&redlink=1" class="new" title="Tantalum monohydride (page does not exist)">TaH</a></li> <li><a href="/w/index.php?title=Tantalum_dihydride&action=edit&redlink=1" class="new" title="Tantalum dihydride (page does not exist)">TaH<sub>2</sub></a></li> <li><a href="/wiki/Chromium(I)_hydride" title="Chromium(I) hydride">CrH</a></li> <li><a href="/wiki/Chromium(II)_hydride" title="Chromium(II) hydride">CrH<sub>2</sub></a></li> <li><a href="/wiki/Chromium_hydride" title="Chromium hydride">CrH<sub>x</sub></a></li> <li><a href="/wiki/Iron(I)_hydride" title="Iron(I) hydride">FeH</a></li> <li><a href="/wiki/Iron(II)_hydride" title="Iron(II) hydride">FeH<sub>2</sub></a></li> <li><a href="/wiki/Iron_pentahydride" title="Iron pentahydride">FeH<sub>5</sub></a></li> <li><a href="/wiki/Cobalt(II)_hydride" title="Cobalt(II) hydride">CoH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Rhodium_hydride&action=edit&redlink=1" class="new" title="Rhodium hydride (page does not exist)">RhH<sub>2</sub></a></li> <li><a href="/wiki/Iridium_trihydride" title="Iridium trihydride">IrH<sub>3</sub></a></li> <li><a href="/wiki/Nickel_hydride" title="Nickel hydride">NiH</a></li> <li><a href="/wiki/Palladium_hydride" title="Palladium hydride">PdH<sub><i>x</i></sub> (<i>x</i> < 1)</a></li> <li><a href="/w/index.php?title=Platinum_hydride&action=edit&redlink=1" class="new" title="Platinum hydride (page does not exist)">PtH<sub><i>x</i></sub> (<i>x</i>< 1) </a></li> <li><i><a href="/wiki/Darmstadtium" title="Darmstadtium">DsH<sub>2</sub></a></i> (<i>predicted</i>)</li> <li><a href="/wiki/Copper_hydride" title="Copper hydride">CuH</a></li> <li><i><a href="/wiki/Roentgenium" title="Roentgenium">RgH</a></i> (<i>predicted</i>)</li> <li><a href="/wiki/Zinc_hydride" title="Zinc hydride">ZnH<sub>2</sub></a></li> <li><a href="/wiki/Cadmium_hydride" title="Cadmium hydride">CdH<sub>2</sub></a></li> <li><a href="/wiki/Mercury(I)_hydride" title="Mercury(I) hydride">HgH</a></li> <li><a href="/wiki/Mercury(I)_hydride" title="Mercury(I) hydride">Hg<sub>2</sub>H<sub>2</sub></a></li> <li><a href="/wiki/Mercury(II)_hydride" title="Mercury(II) hydride">HgH<sub>2</sub></a></li> <li><i><a href="/wiki/Copernicium" title="Copernicium">CnH<sub>2</sub></a></i> (<i>predicted</i>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/w/index.php?title=Lanthanide_hydrides&action=edit&redlink=1" class="new" title="Lanthanide hydrides (page does not exist)">Lanthanide hydrides</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=Lanthanum_dihydride&action=edit&redlink=1" class="new" title="Lanthanum dihydride (page does not exist)">LaH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Lanthanum_trihydride&action=edit&redlink=1" class="new" title="Lanthanum trihydride (page does not exist)">LaH<sub>3</sub></a></li> <li><a href="/wiki/Lanthanum_decahydride" title="Lanthanum decahydride">LaH<sub>10</sub></a></li> <li><a href="/w/index.php?title=Cerium_dihydride&action=edit&redlink=1" class="new" title="Cerium dihydride (page does not exist)">CeH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Cerium_trihydride&action=edit&redlink=1" class="new" title="Cerium trihydride (page does not exist)">CeH<sub>3</sub></a></li> <li><a href="/w/index.php?title=Praseodymium_dihydride&action=edit&redlink=1" class="new" title="Praseodymium dihydride (page does not exist)">PrH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Praseodymium_hydride&action=edit&redlink=1" class="new" title="Praseodymium hydride (page does not exist)">PrH<sub>3</sub></a></li> <li><a href="/wiki/Neodymium(II)_hydride" title="Neodymium(II) hydride">NdH<sub>2</sub></a></li> <li><a href="/wiki/Neodymium(III)_hydride" title="Neodymium(III) hydride">NdH<sub>3</sub></a></li> <li><a href="/w/index.php?title=Samarium_dihydride&action=edit&redlink=1" class="new" title="Samarium dihydride (page does not exist)">SmH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Samarium_trihydride&action=edit&redlink=1" class="new" title="Samarium trihydride (page does not exist)">SmH<sub>3</sub></a></li> <li><a href="/wiki/Europium_hydride" title="Europium hydride">EuH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Gadolinium_dihydride&action=edit&redlink=1" class="new" title="Gadolinium dihydride (page does not exist)">GdH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Gadolinium_trihydride&action=edit&redlink=1" class="new" title="Gadolinium trihydride (page does not exist)">GdH<sub>3</sub></a></li> <li><a href="/w/index.php?title=Terbium_dihydride&action=edit&redlink=1" class="new" title="Terbium dihydride (page does not exist)">TbH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Terbium_trihydride&action=edit&redlink=1" class="new" title="Terbium trihydride (page does not exist)">TbH<sub>3</sub></a></li> <li><a href="/w/index.php?title=Dysprosium_dihydride&action=edit&redlink=1" class="new" title="Dysprosium dihydride (page does not exist)">DyH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Dysprosium_trihydride&action=edit&redlink=1" class="new" title="Dysprosium trihydride (page does not exist)">DyH<sub>3</sub></a></li> <li><a href="/w/index.php?title=Holmium_dihydride&action=edit&redlink=1" class="new" title="Holmium dihydride (page does not exist)">HoH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Holmium_trihydride&action=edit&redlink=1" class="new" title="Holmium trihydride (page does not exist)">HoH<sub>3</sub></a></li> <li><a href="/w/index.php?title=Erbium_dihydride&action=edit&redlink=1" class="new" title="Erbium dihydride (page does not exist)">ErH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Erbium_trihydride&action=edit&redlink=1" class="new" title="Erbium trihydride (page does not exist)">ErH<sub>3</sub></a></li> <li><a href="/w/index.php?title=Thulium_dihydride&action=edit&redlink=1" class="new" title="Thulium dihydride (page does not exist)">TmH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Thulium_trihydride&action=edit&redlink=1" class="new" title="Thulium trihydride (page does not exist)">TmH<sub>3</sub></a></li> <li><a href="/wiki/Ytterbium(II)_hydride" title="Ytterbium(II) hydride">YbH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Lutetium_dihydride&action=edit&redlink=1" class="new" title="Lutetium dihydride (page does not exist)">LuH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Lutetium_trihydride&action=edit&redlink=1" class="new" title="Lutetium trihydride (page does not exist)">LuH<sub>3</sub></a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/w/index.php?title=Actinide_hydrides&action=edit&redlink=1" class="new" title="Actinide hydrides (page does not exist)">Actinide hydrides</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=Actinium_dihydride&action=edit&redlink=1" class="new" title="Actinium dihydride (page does not exist)">AcH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Thorium_hydride&action=edit&redlink=1" class="new" title="Thorium hydride (page does not exist)">ThH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Thorium(IV)_hydride&action=edit&redlink=1" class="new" title="Thorium(IV) hydride (page does not exist)">ThH<sub>4</sub></a></li> <li>Th<sub>4</sub>H<sub>15</sub></li> <li><a href="/wiki/Protactinium_trihydride" title="Protactinium trihydride">PaH<sub>3</sub></a></li> <li><a href="/wiki/Uranium(III)_hydride" title="Uranium(III) hydride">UH<sub>3</sub></a></li> <li><a href="/wiki/Uranium(IV)_hydride" title="Uranium(IV) hydride">UH<sub>4</sub></a></li> <li><a href="/w/index.php?title=Neptunium_dihydride&action=edit&redlink=1" class="new" title="Neptunium dihydride (page does not exist)">NpH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Neptunium_trihydride&action=edit&redlink=1" class="new" title="Neptunium trihydride (page does not exist)">NpH<sub>3</sub></a></li> <li><a href="/wiki/Plutonium_hydride" title="Plutonium hydride">PuH<sub>2</sub></a></li> <li><a href="/wiki/Plutonium_hydride" title="Plutonium hydride">PuH<sub>3</sub></a></li> <li><a href="/w/index.php?title=Americium_dihydride&action=edit&redlink=1" class="new" title="Americium dihydride (page does not exist)">AmH<sub>2</sub></a></li> <li><a href="/wiki/Americium_trihydride" title="Americium trihydride">AmH<sub>3</sub></a></li> <li><a href="/w/index.php?title=Curium_hydride&action=edit&redlink=1" class="new" title="Curium hydride (page does not exist)">CmH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Berkelium_dihydride&action=edit&redlink=1" class="new" title="Berkelium dihydride (page does not exist)">BkH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Berkelium_trihydride&action=edit&redlink=1" class="new" title="Berkelium trihydride (page does not exist)">BkH<sub>3</sub></a></li> <li><a href="/w/index.php?title=Californium_dihydride&action=edit&redlink=1" class="new" title="Californium dihydride (page does not exist)">CfH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Californium_trihydride&action=edit&redlink=1" class="new" title="Californium trihydride (page does not exist)">CfH<sub>3</sub></a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Exotic_atoms" class="mw-redirect" title="Exotic atoms">Exotic matter hydrides</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Positronium_hydride" title="Positronium hydride">PsH</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"><style data-mw-deduplicate="TemplateStyles:r1038841319">.mw-parser-output .tooltip-dotted{border-bottom:1px dotted;cursor:help}</style><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1038841319"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1038841319"></div><div role="navigation" class="navbox authority-control" aria-label="Navbox" style="padding:3px"><table 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