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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-Classification_of_amines" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Classification_of_amines"> <div class="vector-toc-text"> <span class="vector-toc-numb">1</span> <span>Classification of amines</span> </div> </a> <ul id="toc-Classification_of_amines-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Naming_conventions" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Naming_conventions"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Naming conventions</span> </div> </a> <ul id="toc-Naming_conventions-sublist" class="vector-toc-list"> </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">3</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-Spectroscopic_identification" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Spectroscopic_identification"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Spectroscopic identification</span> </div> </a> <ul id="toc-Spectroscopic_identification-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Structure" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Structure"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Structure</span> </div> </a> <button aria-controls="toc-Structure-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 Structure subsection</span> </button> <ul id="toc-Structure-sublist" class="vector-toc-list"> <li id="toc-Alkyl_amines" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Alkyl_amines"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>Alkyl amines</span> </div> </a> <ul id="toc-Alkyl_amines-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Aromatic_amines" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Aromatic_amines"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2</span> <span>Aromatic amines</span> </div> </a> <ul id="toc-Aromatic_amines-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Basicity" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Basicity"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Basicity</span> </div> </a> <button aria-controls="toc-Basicity-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 Basicity subsection</span> </button> <ul id="toc-Basicity-sublist" class="vector-toc-list"> <li id="toc-Electronic_effects" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Electronic_effects"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>Electronic effects</span> </div> </a> <ul id="toc-Electronic_effects-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Solvation_effects" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Solvation_effects"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2</span> <span>Solvation effects</span> </div> </a> <ul id="toc-Solvation_effects-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Synthesis" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Synthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Synthesis</span> </div> </a> <button aria-controls="toc-Synthesis-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 Synthesis subsection</span> </button> <ul id="toc-Synthesis-sublist" class="vector-toc-list"> <li id="toc-From_alcohols" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#From_alcohols"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.1</span> <span>From alcohols</span> </div> </a> <ul id="toc-From_alcohols-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-From_alkyl_and_aryl_halides" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#From_alkyl_and_aryl_halides"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.2</span> <span>From alkyl and aryl halides</span> </div> </a> <ul id="toc-From_alkyl_and_aryl_halides-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-From_alkenes" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#From_alkenes"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.3</span> <span>From alkenes</span> </div> </a> <ul id="toc-From_alkenes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Reductive_routes" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Reductive_routes"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.4</span> <span>Reductive routes</span> </div> </a> <ul id="toc-Reductive_routes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Specialized_methods" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Specialized_methods"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.5</span> <span>Specialized methods</span> </div> </a> <ul id="toc-Specialized_methods-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Reactions" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Reactions</span> </div> </a> <button aria-controls="toc-Reactions-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 Reactions subsection</span> </button> <ul id="toc-Reactions-sublist" class="vector-toc-list"> <li id="toc-Alkylation,_acylation,_and_sulfonation,_etc." class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Alkylation,_acylation,_and_sulfonation,_etc."> <div class="vector-toc-text"> <span class="vector-toc-numb">7.1</span> <span>Alkylation, acylation, and sulfonation, etc.</span> </div> </a> <ul id="toc-Alkylation,_acylation,_and_sulfonation,_etc.-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Diazotization" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Diazotization"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.2</span> <span>Diazotization</span> </div> </a> <ul id="toc-Diazotization-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Conversion_to_imines" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Conversion_to_imines"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.3</span> <span>Conversion to imines</span> </div> </a> <ul id="toc-Conversion_to_imines-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Overview" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Overview"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.4</span> <span>Overview</span> </div> </a> <ul id="toc-Overview-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Biological_activity" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Biological_activity"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>Biological activity</span> </div> </a> <button aria-controls="toc-Biological_activity-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 Biological activity subsection</span> </button> <ul id="toc-Biological_activity-sublist" class="vector-toc-list"> <li id="toc-Amine_hormones" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Amine_hormones"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.1</span> <span>Amine hormones</span> </div> </a> <ul id="toc-Amine_hormones-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Application_of_amines" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Application_of_amines"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>Application of amines</span> </div> </a> <button aria-controls="toc-Application_of_amines-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 Application of amines subsection</span> </button> <ul id="toc-Application_of_amines-sublist" class="vector-toc-list"> <li id="toc-Dyes" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Dyes"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.1</span> <span>Dyes</span> </div> </a> <ul id="toc-Dyes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Drugs" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Drugs"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.2</span> <span>Drugs</span> </div> </a> <ul id="toc-Drugs-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Gas_treatment" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Gas_treatment"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.3</span> <span>Gas treatment</span> </div> </a> <ul id="toc-Gas_treatment-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Epoxy_resin_curing_agents" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Epoxy_resin_curing_agents"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.4</span> <span>Epoxy resin curing agents</span> </div> </a> <ul id="toc-Epoxy_resin_curing_agents-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Safety" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Safety"> <div class="vector-toc-text"> <span class="vector-toc-numb">10</span> <span>Safety</span> </div> </a> <ul id="toc-Safety-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">11</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">12</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">13</span> <span>Further reading</span> </div> </a> <ul id="toc-Further_reading-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">14</span> <span>External links</span> </div> </a> <ul id="toc-External_links-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">Amine</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 72 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-72" 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">72 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/Amien" title="Amien – Afrikaans" lang="af" hreflang="af" data-title="Amien" 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%85%D9%8A%D9%86_(%D9%83%D9%8A%D9%85%D9%8A%D8%A7%D8%A1)" title="أمين (كيمياء) – Arabic" lang="ar" hreflang="ar" data-title="أمين (كيمياء)" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-ast mw-list-item"><a href="https://ast.wikipedia.org/wiki/Amina" title="Amina – Asturian" lang="ast" hreflang="ast" data-title="Amina" 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/Aminl%C9%99r" title="Aminlər – Azerbaijani" lang="az" hreflang="az" data-title="Aminlər" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</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%AE%E0%A6%BF%E0%A6%A8" title="অ্যামিন – Bangla" lang="bn" hreflang="bn" data-title="অ্যামিন" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%90%D0%BC%D1%96%D0%BD%D1%8B" title="Аміны – Belarusian" lang="be" hreflang="be" data-title="Аміны" 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%BC%D1%96%D0%BD%D1%8B" title="Аміны – Belarusian (Taraškievica orthography)" lang="be-tarask" hreflang="be-tarask" data-title="Аміны" 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-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%90%D0%BC%D0%B8%D0%BD" title="Амин – Bulgarian" lang="bg" hreflang="bg" data-title="Амин" 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/Amin_(hemija)" title="Amin (hemija) – Bosnian" lang="bs" hreflang="bs" data-title="Amin (hemija)" 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/Amina" title="Amina – Catalan" lang="ca" hreflang="ca" data-title="Amina" 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/Aminy" title="Aminy – Czech" lang="cs" hreflang="cs" data-title="Aminy" 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/Amin" title="Amin – Welsh" lang="cy" hreflang="cy" data-title="Amin" 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/Amin" title="Amin – Danish" lang="da" hreflang="da" data-title="Amin" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Amine" title="Amine – German" lang="de" hreflang="de" data-title="Amine" 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/Amiinid" title="Amiinid – Estonian" lang="et" hreflang="et" data-title="Amiinid" 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%BC%CE%AF%CE%BD%CE%B5%CF%82" title="Αμίνες – Greek" lang="el" hreflang="el" data-title="Αμίνες" 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/Amina" title="Amina – Spanish" lang="es" hreflang="es" data-title="Amina" 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/Amino" title="Amino – Esperanto" lang="eo" hreflang="eo" data-title="Amino" 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/Amina" title="Amina – Basque" lang="eu" hreflang="eu" data-title="Amina" 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%85%DB%8C%D9%86_(%D8%B4%DB%8C%D9%85%DB%8C)" title="آمین (شیمی) – Persian" lang="fa" hreflang="fa" data-title="آمین (شیمی)" 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/Amin" title="Amin – Faroese" lang="fo" hreflang="fo" data-title="Amin" 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/Amine_(chimie)" title="Amine (chimie) – French" lang="fr" hreflang="fr" data-title="Amine (chimie)" 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/Aim%C3%ADn%C3%AD" title="Aimíní – Irish" lang="ga" hreflang="ga" data-title="Aimíní" 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/Amina" title="Amina – Galician" lang="gl" hreflang="gl" data-title="Amina" 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%84%EB%AF%BC" title="아민 – Korean" lang="ko" hreflang="ko" data-title="아민" 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%B4%D5%AB%D5%B6%D5%B6%D5%A5%D6%80" title="Ամիններ – Armenian" lang="hy" hreflang="hy" data-title="Ամիններ" 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%8F%E0%A4%AE%E0%A5%80%E0%A4%A8" title="एमीन – Hindi" lang="hi" hreflang="hi" data-title="एमीन" 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/Amini_(kemija)" title="Amini (kemija) – Croatian" lang="hr" hreflang="hr" data-title="Amini (kemija)" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-io mw-list-item"><a href="https://io.wikipedia.org/wiki/Amino" title="Amino – Ido" lang="io" hreflang="io" data-title="Amino" data-language-autonym="Ido" data-language-local-name="Ido" class="interlanguage-link-target"><span>Ido</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Amina" title="Amina – Indonesian" lang="id" hreflang="id" data-title="Amina" 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-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Ammine" title="Ammine – Italian" lang="it" hreflang="it" data-title="Ammine" 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%9E%D7%99%D7%9F" title="אמין – Hebrew" lang="he" hreflang="he" data-title="אמין" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-kn mw-list-item"><a href="https://kn.wikipedia.org/wiki/%E0%B2%85%E0%B2%AE%E0%B3%80%E0%B2%A8%E0%B3%8D%E2%80%8D%E0%B2%97%E0%B2%B3%E0%B3%81" title="ಅಮೀನ್‍ಗಳು – Kannada" lang="kn" hreflang="kn" data-title="ಅಮೀನ್‍ಗಳು" 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%9B%E1%83%98%E1%83%9C%E1%83%94%E1%83%91%E1%83%98" title="ამინები – Georgian" lang="ka" hreflang="ka" data-title="ამინები" 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%BC%D0%B8%D0%BD%D0%B4%D0%B5%D1%80" title="Аминдер – Kazakh" lang="kk" hreflang="kk" data-title="Аминдер" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-ky mw-list-item"><a href="https://ky.wikipedia.org/wiki/%D0%90%D0%BC%D0%B8%D0%BD%D0%B4%D0%B5%D1%80" title="Аминдер – Kyrgyz" lang="ky" hreflang="ky" data-title="Аминдер" data-language-autonym="Кыргызча" data-language-local-name="Kyrgyz" class="interlanguage-link-target"><span>Кыргызча</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Am%C4%ABni" title="Amīni – Latvian" lang="lv" hreflang="lv" data-title="Amīni" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Aminai" title="Aminai – Lithuanian" lang="lt" hreflang="lt" data-title="Aminai" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target"><span>Lietuvių</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Aminok" title="Aminok – Hungarian" lang="hu" hreflang="hu" data-title="Aminok" 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%BC%D0%B8%D0%BD_(%D1%85%D0%B5%D0%BC%D0%B8%D1%98%D0%B0)" title="Амин (хемија) – Macedonian" lang="mk" hreflang="mk" data-title="Амин (хемија)" 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%85%E0%B4%AE%E0%B5%80%E0%B4%A8%E0%B5%81%E0%B4%95%E0%B5%BE" title="അമീനുകൾ – Malayalam" lang="ml" hreflang="ml" data-title="അമീനുകൾ" 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/Amina" title="Amina – Malay" lang="ms" hreflang="ms" data-title="Amina" 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-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Amine" title="Amine – Dutch" lang="nl" hreflang="nl" data-title="Amine" 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%9F%E3%83%B3" title="アミン – Japanese" lang="ja" hreflang="ja" data-title="アミン" 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/Amin" title="Amin – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Amin" 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/Amin" title="Amin – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Amin" 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-oc mw-list-item"><a href="https://oc.wikipedia.org/wiki/Amina" title="Amina – Occitan" lang="oc" hreflang="oc" data-title="Amina" data-language-autonym="Occitan" data-language-local-name="Occitan" class="interlanguage-link-target"><span>Occitan</span></a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Aminlar" title="Aminlar – Uzbek" lang="uz" hreflang="uz" data-title="Aminlar" 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-pnb mw-list-item"><a href="https://pnb.wikipedia.org/wiki/%D8%A7%D9%85%D8%A7%D8%A6%D9%86" title="امائن – Western Punjabi" lang="pnb" hreflang="pnb" data-title="امائن" data-language-autonym="پنجابی" data-language-local-name="Western Punjabi" class="interlanguage-link-target"><span>پنجابی</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Aminy" title="Aminy – Polish" lang="pl" hreflang="pl" data-title="Aminy" 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/Amina" title="Amina – Portuguese" lang="pt" hreflang="pt" data-title="Amina" 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/Amin%C4%83" title="Amină – Romanian" lang="ro" hreflang="ro" data-title="Amină" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%90%D0%BC%D0%B8%D0%BD%D1%8B" title="Амины – Russian" lang="ru" hreflang="ru" data-title="Амины" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sco mw-list-item"><a href="https://sco.wikipedia.org/wiki/Amine" title="Amine – Scots" lang="sco" hreflang="sco" data-title="Amine" data-language-autonym="Scots" data-language-local-name="Scots" class="interlanguage-link-target"><span>Scots</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Amine" title="Amine – Simple English" lang="en-simple" hreflang="en-simple" data-title="Amine" 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/Am%C3%ADn" title="Amín – Slovak" lang="sk" hreflang="sk" data-title="Amín" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Amin" title="Amin – Slovenian" lang="sl" hreflang="sl" data-title="Amin" 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%85%DB%8C%D9%86_(%DA%A9%DB%8C%D9%85%DB%8C%D8%A7)" title="ئەمین (کیمیا) – Central Kurdish" lang="ckb" hreflang="ckb" data-title="ئەمین (کیمیا)" 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/Amin_(hemija)" title="Amin (hemija) – Serbian" lang="sr" hreflang="sr" data-title="Amin (hemija)" 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/Amin_(hemija)" title="Amin (hemija) – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Amin (hemija)" 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-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Amiinit" title="Amiinit – Finnish" lang="fi" hreflang="fi" data-title="Amiinit" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Amin" title="Amin – Swedish" lang="sv" hreflang="sv" data-title="Amin" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%85%E0%AE%AE%E0%AF%80%E0%AE%A9%E0%AF%8D" title="அமீன் – Tamil" lang="ta" hreflang="ta" data-title="அமீன்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B9%80%E0%B8%AD%E0%B8%A1%E0%B8%B5%E0%B8%99" title="เอมีน – Thai" lang="th" hreflang="th" data-title="เอมีน" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-tg mw-list-item"><a href="https://tg.wikipedia.org/wiki/%D0%90%D0%BC%D0%B8%D0%BD%D2%B3%D0%BE" title="Аминҳо – Tajik" lang="tg" hreflang="tg" data-title="Аминҳо" data-language-autonym="Тоҷикӣ" data-language-local-name="Tajik" class="interlanguage-link-target"><span>Тоҷикӣ</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Amin_(kimya)" title="Amin (kimya) – Turkish" lang="tr" hreflang="tr" data-title="Amin (kimya)" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%90%D0%BC%D1%96%D0%BD%D0%B8" title="Аміни – Ukrainian" lang="uk" hreflang="uk" data-title="Аміни" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Amin" title="Amin – Vietnamese" lang="vi" hreflang="vi" data-title="Amin" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-war mw-list-item"><a href="https://war.wikipedia.org/wiki/Amine" title="Amine – Waray" lang="war" hreflang="war" data-title="Amine" data-language-autonym="Winaray" data-language-local-name="Waray" class="interlanguage-link-target"><span>Winaray</span></a></li><li class="interlanguage-link interwiki-wuu mw-list-item"><a href="https://wuu.wikipedia.org/wiki/%E8%83%BA" title="胺 – Wu" lang="wuu" hreflang="wuu" data-title="胺" data-language-autonym="吴语" data-language-local-name="Wu" class="interlanguage-link-target"><span>吴语</span></a></li><li class="interlanguage-link interwiki-zh-yue mw-list-item"><a href="https://zh-yue.wikipedia.org/wiki/%E8%83%BA" title="胺 – Cantonese" lang="yue" hreflang="yue" data-title="胺" data-language-autonym="粵語" data-language-local-name="Cantonese" class="interlanguage-link-target"><span>粵語</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E8%83%BA" title="胺 – Chinese" lang="zh" hreflang="zh" data-title="胺" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q167198#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> </div> </header> <div class="vector-page-toolbar"> <div class="vector-page-toolbar-container"> <div id="left-navigation"> <nav aria-label="Namespaces"> <div id="p-associated-pages" class="vector-menu vector-menu-tabs mw-portlet mw-portlet-associated-pages" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="ca-nstab-main" class="selected vector-tab-noicon mw-list-item"><a href="/wiki/Amine" title="View the content page [c]" 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.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">For other uses, see <a href="/wiki/Amine_(disambiguation)" class="mw-disambig" title="Amine (disambiguation)">Amine (disambiguation)</a>.</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">"Amino" redirects here. For other uses, see <a href="/wiki/Amino_(disambiguation)" class="mw-disambig" title="Amino (disambiguation)">Amino (disambiguation)</a>.</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Not to be confused with <a href="/wiki/Amin_(disambiguation)" class="mw-redirect mw-disambig" title="Amin (disambiguation)">Amin</a> or <a href="/wiki/Anime" title="Anime">Anime</a>.</div> <p class="mw-empty-elt"> </p> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Amine_Functional_Group.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d5/Amine_Functional_Group.png/164px-Amine_Functional_Group.png" decoding="async" width="164" height="68" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d5/Amine_Functional_Group.png/246px-Amine_Functional_Group.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d5/Amine_Functional_Group.png/328px-Amine_Functional_Group.png 2x" data-file-width="331" data-file-height="137" /></a><figcaption>Amine</figcaption></figure> <p>In <a href="/wiki/Chemistry" title="Chemistry">chemistry</a>, <b>amines</b> (<span class="rt-commentedText nowrap"><span class="IPA nopopups noexcerpt" lang="en-fonipa"><a href="/wiki/Help:IPA/English" title="Help:IPA/English">/<span style="border-bottom:1px dotted"><span title="/ə/: 'a' in 'about'">ə</span><span title="/ˈ/: primary stress follows">ˈ</span><span title="'m' in 'my'">m</span><span title="/iː/: 'ee' in 'fleece'">iː</span><span title="'n' in 'nigh'">n</span></span>,<span class="wrap"> </span><span style="border-bottom:1px dotted"><span title="/ˈ/: primary stress follows">ˈ</span><span title="/æ/: 'a' in 'bad'">æ</span><span title="'m' in 'my'">m</span><span title="/iː/: 'ee' in 'fleece'">iː</span><span title="'n' in 'nigh'">n</span></span>/</a></span></span>,<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><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> <span style="font-size:85%;">UK also</span> <span class="rt-commentedText nowrap"><span class="IPA nopopups noexcerpt" lang="en-fonipa"><a href="/wiki/Help:IPA/English" title="Help:IPA/English">/<span style="border-bottom:1px dotted"><span title="/ˈ/: primary stress follows">ˈ</span><span title="/eɪ/: 'a' in 'face'">eɪ</span><span title="'m' in 'my'">m</span><span title="/iː/: 'ee' in 'fleece'">iː</span><span title="'n' in 'nigh'">n</span></span>/</a></span></span><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>) are <a href="/wiki/Chemical_compound" title="Chemical compound">compounds</a> and <a href="/wiki/Functional_group" title="Functional group">functional groups</a> that contain a <a href="/wiki/Base_(chemistry)" title="Base (chemistry)">basic</a> <a href="/wiki/Nitrogen" title="Nitrogen">nitrogen</a> atom with a <a href="/wiki/Lone_pair" title="Lone pair">lone pair</a>. Formally, amines are <a href="/wiki/Derivative_(chemistry)" title="Derivative (chemistry)">derivatives</a> of <a href="/wiki/Ammonia" title="Ammonia">ammonia</a> (<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">NH<sub class="template-chem2-sub">3</sub></span>), wherein one or more <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a> atoms have been replaced by a <a href="/wiki/Substituent" title="Substituent">substituent</a> such as an <a href="/wiki/Alkyl" class="mw-redirect" title="Alkyl">alkyl</a> or <a href="/wiki/Aryl" class="mw-redirect" title="Aryl">aryl</a> group<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> (these may respectively be called alkylamines and arylamines; amines in which both types of substituent are attached to one <a href="/wiki/Nitrogen" title="Nitrogen">nitrogen</a> atom may be called alkylarylamines). Important amines include <a href="/wiki/Amino_acid" title="Amino acid">amino acids</a>, <a href="/wiki/Biogenic_amine" title="Biogenic amine">biogenic amines</a>, <a href="/wiki/Trimethylamine" title="Trimethylamine">trimethylamine</a>, and <a href="/wiki/Aniline" title="Aniline">aniline</a>. <a href="/wiki/Inorganic_compound" title="Inorganic compound">Inorganic</a> derivatives of <a href="/wiki/Ammonia" title="Ammonia">ammonia</a> are also called amines, such as <a href="/wiki/Monochloramine" title="Monochloramine">monochloramine</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">NClH<sub class="template-chem2-sub">2</sub></span>).<sup id="cite_ref-Ullmann_5-0" class="reference"><a href="#cite_note-Ullmann-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p>The substituent <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−NH<sub class="template-chem2-sub">2</sub></span> is called an amino group.<sup id="cite_ref-OChemSmith3E_6-0" class="reference"><a href="#cite_note-OChemSmith3E-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p><p>The chemical notation for amines contain the letter "R", where "R" is not an element, but a "R-group" which means "rest of the molecule" and in amines could be a single hydrogen or carbon atom, or could be a hydrocarbon chain. </p><p>Compounds with a <a href="/wiki/Nitrogen" title="Nitrogen">nitrogen</a> atom attached to a <a href="/wiki/Carbonyl_group" title="Carbonyl group">carbonyl group</a>, thus having the structure <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R−C(=O)−NR′R″</span>, are called <a href="/wiki/Amide" title="Amide">amides</a> and have different chemical properties from amines. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Classification_of_amines">Classification of amines</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Amine&action=edit&section=1" title="Edit section: Classification of amines"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Amines can be classified according to the nature and number of substituents on <a href="/wiki/Nitrogen" title="Nitrogen">nitrogen</a>. <b>Aliphatic amines</b> contain only H and alkyl substituents. <b><a href="/wiki/Aromatic_amine" title="Aromatic amine">Aromatic amines</a></b> have the nitrogen atom connected to an <a href="/wiki/Aromaticity" title="Aromaticity">aromatic</a> ring. </p> <table class="wikitable" style="margin:auto 1em auto 1em; float:right; text-align:center;"> <tbody><tr id="amino_group_connectivity_table"> <th>Primary (1°) amine</th> <th>Secondary (2°) amine</th> <th>Tertiary (3°) amine </th></tr> <tr> <td><span typeof="mw:File"><a href="/wiki/File:Primary-amine-2D-general.svg" class="mw-file-description" title="primary amine"><img alt="primary amine" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c6/Primary-amine-2D-general.svg/100px-Primary-amine-2D-general.svg.png" decoding="async" width="100" height="64" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c6/Primary-amine-2D-general.svg/150px-Primary-amine-2D-general.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c6/Primary-amine-2D-general.svg/200px-Primary-amine-2D-general.svg.png 2x" data-file-width="800" data-file-height="509" /></a></span> </td> <td><span typeof="mw:File"><a href="/wiki/File:Secondary-amine-2D-general.svg" class="mw-file-description" title="secondary amine"><img alt="secondary amine" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3c/Secondary-amine-2D-general.svg/100px-Secondary-amine-2D-general.svg.png" decoding="async" width="100" height="64" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3c/Secondary-amine-2D-general.svg/150px-Secondary-amine-2D-general.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3c/Secondary-amine-2D-general.svg/200px-Secondary-amine-2D-general.svg.png 2x" data-file-width="800" data-file-height="509" /></a></span> </td> <td><span typeof="mw:File"><a href="/wiki/File:Amine-2D-general.svg" class="mw-file-description" title="tertiary amine"><img alt="tertiary amine" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/13/Amine-2D-general.svg/100px-Amine-2D-general.svg.png" decoding="async" width="100" height="64" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/13/Amine-2D-general.svg/150px-Amine-2D-general.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/13/Amine-2D-general.svg/200px-Amine-2D-general.svg.png 2x" data-file-width="800" data-file-height="509" /></a></span> </td></tr></tbody></table><p>Amines, alkyl and aryl alike, are organized into three subcategories <a href="#amino_group_connectivity_table"><small>(see table)</small></a> based on the number of <a href="/wiki/Carbon" title="Carbon">carbon</a> atoms adjacent to the nitrogen (how many hydrogen atoms of the <a href="/wiki/Ammonia" title="Ammonia">ammonia</a> molecule are replaced by <a href="/wiki/Hydrocarbon" title="Hydrocarbon">hydrocarbon</a> groups):<sup id="cite_ref-OChemSmith3E_6-1" class="reference"><a href="#cite_note-OChemSmith3E-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><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> </p><ul><li><b>Primary (1°) amines</b>—Primary amines arise when one of three hydrogen atoms in <a href="/wiki/Ammonia" title="Ammonia">ammonia</a> is replaced by an <a href="/wiki/Alkyl" class="mw-redirect" title="Alkyl">alkyl</a> or <a href="/wiki/Aromatic" class="mw-redirect" title="Aromatic">aromatic</a> group. Important primary alkyl amines include <a href="/wiki/Methylamine" title="Methylamine">methylamine</a>, most <a href="/wiki/Amino_acid" title="Amino acid">amino acids</a>, and the <a href="/wiki/Buffering_agent" class="mw-redirect" title="Buffering agent">buffering agent</a> <a href="/wiki/Tris" title="Tris">tris</a>, while primary aromatic amines include <a href="/wiki/Aniline" title="Aniline">aniline</a>.</li> <li><b>Secondary (2°) amines</b>—Secondary amines have two organic substituents (alkyl, aryl or both) bound to the nitrogen together with one hydrogen. Important representatives include <a href="/wiki/Dimethylamine" title="Dimethylamine">dimethylamine</a>, while an example of an <a href="/wiki/Aromatic_amine" title="Aromatic amine">aromatic amine</a> would be <a href="/wiki/Diphenylamine" title="Diphenylamine">diphenylamine</a>.</li> <li><b>Tertiary (3°) amines</b>—In tertiary amines, nitrogen has three organic substituents. Examples include <a href="/wiki/Trimethylamine" title="Trimethylamine">trimethylamine</a>, which has a distinctively fishy smell, and <a href="/wiki/EDTA" class="mw-redirect" title="EDTA">EDTA</a>.</li></ul> <p>A fourth subcategory is determined by the connectivity of the substituents attached to the nitrogen: </p> <ul><li><b>Cyclic amines</b>—<a href="/wiki/Cyclic_compound" title="Cyclic compound">Cyclic</a> amines are either secondary or tertiary amines. Examples of cyclic amines include the 3-membered ring <a href="/wiki/Aziridine" title="Aziridine">aziridine</a> and the six-membered ring <a href="/wiki/Piperidine" title="Piperidine">piperidine</a>. <i>N</i>-methylpiperidine and <i>N</i>-phenylpiperidine are examples of cyclic tertiary amines.</li></ul> <p>It is also possible to have four organic substituents on the nitrogen. These species are not amines but are <a href="/wiki/Quaternary_ammonium_cation" title="Quaternary ammonium cation">quaternary ammonium cations</a> and have a charged nitrogen center. Quaternary ammonium salts exist with many kinds of <a href="/wiki/Anions" class="mw-redirect" title="Anions">anions</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Naming_conventions">Naming conventions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Amine&action=edit&section=2" title="Edit section: Naming conventions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Amines are named in several ways. Typically, the compound is given the prefix "amino-" or the suffix "-amine". The prefix "<i>N</i>-" shows substitution on the nitrogen atom. An organic compound with multiple amino groups is called a <a href="/wiki/Diamine" title="Diamine">diamine</a>, <a href="/wiki/Triamine" class="mw-redirect" title="Triamine">triamine</a>, <a href="/wiki/Tetraamine" class="mw-redirect" title="Tetraamine">tetraamine</a> and so forth. </p><p>Lower amines are named with the suffix <i>-amine</i>. </p> <figure class="mw-default-size mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Butan-1-amine.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/56/Butan-1-amine.png/220px-Butan-1-amine.png" decoding="async" width="220" height="53" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/56/Butan-1-amine.png/330px-Butan-1-amine.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/56/Butan-1-amine.png/440px-Butan-1-amine.png 2x" data-file-width="655" data-file-height="158" /></a><figcaption><a href="/wiki/N-Butylamine" title="N-Butylamine">butan-1-amine</a></figcaption></figure> <p>Higher amines have the prefix <i>amino</i> as a functional group. IUPAC however does not recommend this convention,<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> but prefers the alkanamine form, e.g. butan-2-amine. </p> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:2-aminobutane.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b6/2-aminobutane.png/135px-2-aminobutane.png" decoding="async" width="135" height="100" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b6/2-aminobutane.png/203px-2-aminobutane.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b6/2-aminobutane.png/270px-2-aminobutane.png 2x" data-file-width="406" data-file-height="302" /></a><figcaption><a href="/wiki/Sec-Butylamine" title="Sec-Butylamine">2-aminobutane</a> (or butan-2-amine)</figcaption></figure> <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=Amine&action=edit&section=3" title="Edit section: Physical properties"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Hydrogen_bonding" class="mw-redirect" title="Hydrogen bonding">Hydrogen bonding</a> significantly influences the properties of primary and secondary amines. For example, <a href="/wiki/Methylamine" title="Methylamine">methyl</a> and <a href="/wiki/Ethylamine" title="Ethylamine">ethyl</a> amines are gases under standard conditions, whereas the corresponding <a href="/wiki/Methanol" title="Methanol">methyl</a> and <a href="/wiki/Ethanol" title="Ethanol">ethyl</a> alcohols are liquids. Amines possess a characteristic ammonia smell, liquid amines have a distinctive "fishy" and foul smell. </p><p>The nitrogen atom features a <a href="/wiki/Lone_electron_pair" class="mw-redirect" title="Lone electron pair">lone electron pair</a> that can bind H<sup>+</sup> to form an <a href="/wiki/Ammonium_ion" class="mw-redirect" title="Ammonium ion">ammonium ion</a> R<sub>3</sub>NH<sup>+</sup>. The lone electron pair is represented in this article by two dots above or next to the N. The water <a href="/wiki/Solubility" title="Solubility">solubility</a> of simple amines is enhanced by <a href="/wiki/Hydrogen_bonding" class="mw-redirect" title="Hydrogen bonding">hydrogen bonding</a> involving these lone electron pairs. Typically salts of ammonium compounds exhibit the following order of solubility in water: primary ammonium (<span class="chemf nowrap">RNH<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">+</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">3</sub></span></span></span>) > secondary ammonium (<span class="chemf nowrap">R<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span>NH<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">+</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span></span>) > tertiary ammonium (R<sub>3</sub>NH<sup>+</sup>). Small aliphatic amines display significant solubility in many <a href="/wiki/Solvent" title="Solvent">solvents</a>, whereas those with large substituents are lipophilic. Aromatic amines, such as <a href="/wiki/Aniline" title="Aniline">aniline</a>, have their lone pair electrons <a href="/wiki/Conjugated_system" title="Conjugated system">conjugated</a> into the benzene ring, thus their tendency to engage in hydrogen bonding is diminished. Their boiling points are high and their solubility in water is low. </p> <div class="mw-heading mw-heading3"><h3 id="Spectroscopic_identification">Spectroscopic identification</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Amine&action=edit&section=4" title="Edit section: Spectroscopic identification"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Typically the presence of an amine functional group is deduced by a combination of techniques, including mass spectrometry as well as NMR and IR spectroscopies. <sup>1</sup>H NMR signals for amines disappear upon treatment of the sample with D<sub>2</sub>O. In their <a href="/wiki/Infrared_spectrum" class="mw-redirect" title="Infrared spectrum">infrared spectrum</a> primary amines exhibit two N-H bands, whereas secondary amines exhibit only one.<sup id="cite_ref-OChemSmith3E_6-2" class="reference"><a href="#cite_note-OChemSmith3E-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> In their IR spectra, primary and secondary amines exhibit distinctive N-H stretching bands near 3300 cm<sup>-1</sup>. Somewhat less distinctive are the bands appearing below 1600 cm<sup>-1</sup>, which are weaker and overlap with C-C and C-H modes. For the case of <a href="/wiki/Propyl_amine" class="mw-redirect" title="Propyl amine">propyl amine</a>, the H-N-H scissor mode appears near 1600 cm<sup>-1</sup>, the C-N stretch near 1000 cm<sup>-1</sup>, and the R<sub>2</sub>N-H bend near 810 cm<sup>-1</sup>.<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> <div class="mw-heading mw-heading2"><h2 id="Structure">Structure</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Amine&action=edit&section=5" title="Edit section: Structure"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Alkyl_amines">Alkyl amines</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Amine&action=edit&section=6" title="Edit section: Alkyl amines"><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:Inversion_of_amine.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0f/Inversion_of_amine.svg/220px-Inversion_of_amine.svg.png" decoding="async" width="220" height="98" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0f/Inversion_of_amine.svg/330px-Inversion_of_amine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0f/Inversion_of_amine.svg/440px-Inversion_of_amine.svg.png 2x" data-file-width="443" data-file-height="198" /></a><figcaption>Inversion of an amine spatial configuration: Amine "flip-flop" like an umbrella turned over by the wind. The pair of dots represents the lone <a href="/wiki/Electron_pair" title="Electron pair">electron pair</a> on the nitrogen atom.</figcaption></figure> <p>Alkyl amines characteristically feature tetrahedral nitrogen centers. C-N-C and C-N-H angles approach the idealized angle of 109°. C-N distances are slightly shorter than C-C distances. The <a href="/wiki/Activation_energy" title="Activation energy">energy barrier</a> for the <a href="/wiki/Nitrogen_inversion" class="mw-redirect" title="Nitrogen inversion">nitrogen inversion</a> of the stereocenter is about 7 <a href="/wiki/Kcal/mol" class="mw-redirect" title="Kcal/mol">kcal/mol</a> for a trialkylamine. The interconversion has been compared to the inversion of an open umbrella into a strong wind. </p><p>Amines of the type NHRR' and NRR′R″ are <a href="/wiki/Chirality_(chemistry)" title="Chirality (chemistry)">chiral</a>: the nitrogen center bears four substituents counting the lone pair. Because of the low barrier to inversion, amines of the type NHRR' cannot be obtained in optical purity. For chiral tertiary amines, NRR′R″ can only be resolved when the R, R', and R″ groups are constrained in cyclic structures such as <i>N</i>-substituted <a href="/wiki/Aziridine" title="Aziridine">aziridines</a> (<a href="/wiki/Quaternary_ammonium_salt" class="mw-redirect" title="Quaternary ammonium salt">quaternary ammonium salts</a> are resolvable). </p> <div class="mw-heading mw-heading3"><h3 id="Aromatic_amines">Aromatic amines</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Amine&action=edit&section=7" title="Edit section: Aromatic amines"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In aromatic amines ("anilines"), nitrogen is often nearly planar owing to conjugation of the lone pair with the aryl substituent. The C-N distance is correspondingly shorter. In aniline, the C-N distance is the same as the C-C distances.<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> </p> <div class="mw-heading mw-heading2"><h2 id="Basicity">Basicity</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Amine&action=edit&section=8" title="Edit section: Basicity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Like ammonia, amines are <a href="/wiki/Base_(chemistry)" title="Base (chemistry)">bases</a>.<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> Compared to alkali metal hydroxides, amines are weaker. </p> <table class="wikitable" style="float:center; margin:0 1em;"> <tbody><tr> <th>Alkylamine<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> or aniline<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> </th> <th>pK<sub>a</sub> of <br />protonated amine </th> <th><i>K</i><sub>b</sub><sup class="noprint Inline-Template" style="margin-left:0.1em; white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Please_clarify" title="Wikipedia:Please clarify"><span title="The text near this tag may need clarification or removal of jargon. (April 2022)">clarification needed</span></a></i>]</sup> </th></tr> <tr> <td><a href="/wiki/Methylamine" title="Methylamine">Methylamine</a> (MeNH<sub>2</sub>) </td> <td>10.62 </td> <td><span class="nowrap"><span data-sort-value="6996417000000000000♠"></span>4.17<span style="margin-left:0.25em;margin-right:0.15em;">×</span>10<sup>−4</sup></span> </td></tr> <tr> <td><a href="/wiki/Dimethylamine" title="Dimethylamine">Dimethylamine</a> (Me<sub>2</sub>NH) </td> <td>10.64 </td> <td><span class="nowrap"><span data-sort-value="6996437000000000000♠"></span>4.37<span style="margin-left:0.25em;margin-right:0.15em;">×</span>10<sup>−4</sup></span> </td></tr> <tr> <td><a href="/wiki/Trimethylamine" title="Trimethylamine">Trimethylamine</a> (Me<sub>3</sub>N) </td> <td><span style="padding-left:0.3em;"> </span>9.76 </td> <td><span class="nowrap"><span data-sort-value="6995575000000000000♠"></span>5.75<span style="margin-left:0.25em;margin-right:0.15em;">×</span>10<sup>−5</sup></span> </td></tr> <tr> <td><a href="/wiki/Ethylamine" title="Ethylamine">Ethylamine</a> (EtNH<sub>2</sub>) </td> <td>10.63 </td> <td><span class="nowrap"><span data-sort-value="6996427000000000000♠"></span>4.27<span style="margin-left:0.25em;margin-right:0.15em;">×</span>10<sup>−4</sup></span> </td></tr> <tr> <td><a href="/wiki/Aniline" title="Aniline">Aniline</a> (PhNH<sub>2</sub>) </td> <td><span style="padding-left:0.3em;"> </span>4.62 </td> <td><span class="nowrap"><span data-sort-value="6990417000000000000♠"></span>4.17<span style="margin-left:0.25em;margin-right:0.15em;">×</span>10<sup>−10</sup></span> </td></tr> <tr> <td><a href="/wiki/P-Anisidine" title="P-Anisidine">4-Methoxyaniline</a> (4-MeOC<sub>6</sub>H<sub>4</sub>NH<sub>2</sub>) </td> <td><span style="padding-left:0.3em;"> </span>5.36 </td> <td><span class="nowrap"><span data-sort-value="6991229000000000000♠"></span>2.29<span style="margin-left:0.25em;margin-right:0.15em;">×</span>10<sup>−9</sup></span> </td></tr> <tr> <td><a href="/wiki/Dimethylaniline" title="Dimethylaniline"><i>N</i>,<i>N</i>-Dimethylaniline</a> (PhNMe<sub>2</sub>) </td> <td><span style="padding-left:0.3em;"> </span>5.07 </td> <td><span class="nowrap"><span data-sort-value="6991117000000000000♠"></span>1.17<span style="margin-left:0.25em;margin-right:0.15em;">×</span>10<sup>−9</sup></span> </td></tr> <tr> <td><a href="/wiki/3-Nitroaniline" title="3-Nitroaniline">3-Nitroaniline</a> (3-NO<sub>2</sub>-C<sub>6</sub>H<sub>4</sub>NH<sub>2</sub>) </td> <td><span style="padding-left:0.3em;"> </span>2.46 </td> <td><span class="nowrap"><span data-sort-value="6988288000000000000♠"></span>2.88<span style="margin-left:0.25em;margin-right:0.15em;">×</span>10<sup>−12</sup></span> </td></tr> <tr> <td><a href="/wiki/4-Nitroaniline" title="4-Nitroaniline">4-Nitroaniline</a> (4-NO<sub>2</sub>-C<sub>6</sub>H<sub>4</sub>NH<sub>2</sub>) </td> <td><span style="padding-left:0.3em;"> </span>1.00 </td> <td><span class="nowrap"><span data-sort-value="6987100000000000000♠"></span>1.00<span style="margin-left:0.25em;margin-right:0.15em;">×</span>10<sup>−13</sup></span> </td></tr> <tr> <td>4-Trifluoromethylaniline (CF<sub>3</sub>C<sub>6</sub>H<sub>4</sub>NH<sub>2</sub>) </td> <td><span style="padding-left:0.3em;"> </span>2.75 </td> <td><span class="nowrap"><span data-sort-value="6988562000000000000♠"></span>5.62<span style="margin-left:0.25em;margin-right:0.15em;">×</span>10<sup>−12</sup></span> </td></tr></tbody></table> <p>The basicity of amines depends on: </p> <ol><li>The electronic properties of the substituents (alkyl groups enhance the basicity, aryl groups diminish it).</li> <li>The degree of solvation of the protonated amine, which includes <a href="/wiki/Steric_hindrance" class="mw-redirect" title="Steric hindrance">steric hindrance</a> by the groups on nitrogen.</li></ol> <div class="mw-heading mw-heading3"><h3 id="Electronic_effects">Electronic effects</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Amine&action=edit&section=9" title="Edit section: Electronic effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Owing to inductive effects, the basicity of an amine might be expected to increase with the number of alkyl groups on the amine. Correlations are complicated owing to the effects of solvation which are opposite the trends for inductive effects. Solvation effects also dominate the basicity of aromatic amines (anilines). For anilines, the lone pair of electrons on nitrogen delocalizes into the ring, resulting in decreased basicity. Substituents on the aromatic ring, and their positions relative to the amino group, also affect basicity as seen in the table. </p> <div class="mw-heading mw-heading3"><h3 id="Solvation_effects">Solvation effects</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Amine&action=edit&section=10" title="Edit section: Solvation effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Solvation significantly affects the basicity of amines. N-H groups strongly interact with water, especially in ammonium ions. Consequently, the basicity of ammonia is enhanced by 10<sup>11</sup> by solvation. The intrinsic basicity of amines, i.e. the situation where solvation is unimportant, has been evaluated in the gas phase. In the gas phase, amines exhibit the basicities predicted from the electron-releasing effects of the organic substituents. Thus tertiary amines are more basic than secondary amines, which are more basic than primary amines, and finally ammonia is least basic. The order of pK<sub>b</sub>'s (basicities in water) does not follow this order. Similarly aniline is more basic than ammonia in the gas phase, but ten thousand times less so in aqueous solution.<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> </p><p>In aprotic polar solvents such as <a href="/wiki/Dimethyl_sulfoxide" title="Dimethyl sulfoxide">DMSO</a>, <a href="/wiki/Dimethylformamide" title="Dimethylformamide">DMF</a>, and <a href="/wiki/Acetonitrile" title="Acetonitrile">acetonitrile</a> the energy of solvation is not as high as in protic polar solvents like water and methanol. For this reason, the basicity of amines in these aprotic solvents is almost solely governed by the electronic effects. </p> <div class="mw-heading mw-heading2"><h2 id="Synthesis">Synthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Amine&action=edit&section=11" title="Edit section: Synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="From_alcohols">From alcohols</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Amine&action=edit&section=12" title="Edit section: From alcohols"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Industrially significant alkyl amines are prepared from ammonia by <a href="/wiki/Alkylation" title="Alkylation">alkylation</a> with alcohols:<sup id="cite_ref-Ullmann_5-1" class="reference"><a href="#cite_note-Ullmann-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {ROH + NH3 -> RNH2 + H2O}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mtext>ROH</mtext> <mo>+</mo> <msubsup> <mtext>NH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo stretchy="false">⟶</mo> <msubsup> <mtext>RNH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo>+</mo> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>O</mtext> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {ROH + NH3 -> RNH2 + H2O}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/5a3723aef486f0e56727998c8d49718f03cd9ecf" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:31.435ex; height:2.843ex;" alt="{\displaystyle {\ce {ROH + NH3 -> RNH2 + H2O}}}"></span></dd></dl> <div class="mw-heading mw-heading3"><h3 id="From_alkyl_and_aryl_halides">From alkyl and aryl halides</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Amine&action=edit&section=13" title="Edit section: From alkyl and aryl halides"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Unlike the reaction of amines with alcohols the reaction of amines and ammonia with alkyl halides is used for synthesis in the laboratory: </p> <dl><dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {RX + 2 R'NH2 -> RR'NH + [RR'NH2]X}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mtext>RX</mtext> <mo>+</mo> <mn>2</mn> <mspace width="thinmathspace" /> <msup> <mtext>R</mtext> <mo>′</mo> </msup> <msubsup> <mtext>NH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo stretchy="false">⟶</mo> <msup> <mtext>RR</mtext> <mo>′</mo> </msup> <mtext>NH</mtext> <mo>+</mo> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">[</mo> <msup> <mtext>RR</mtext> <mo>′</mo> </msup> <msubsup> <mtext>NH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo stretchy="false">]</mo> </mrow> <mtext>X</mtext> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {RX + 2 R'NH2 -> RR'NH + [RR'NH2]X}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/6794927305086253cb9a82bae6719d74c1ae1c83" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:41.991ex; height:3.176ex;" alt="{\displaystyle {\ce {RX + 2 R'NH2 -> RR'NH + [RR'NH2]X}}}"></span></dd></dl> <p>In such reactions, which are more useful for alkyl iodides and bromides, the degree of alkylation is difficult to control such that one obtains mixtures of primary, secondary, and tertiary amines, as well as quaternary ammonium salts.<sup id="cite_ref-Ullmann_5-2" class="reference"><a href="#cite_note-Ullmann-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p>Selectivity can be improved via the <a href="/wiki/Del%C3%A9pine_reaction" title="Delépine reaction">Delépine reaction</a>, although this is rarely employed on an industrial scale. Selectivity is also assured in the <a href="/wiki/Gabriel_synthesis" title="Gabriel synthesis">Gabriel synthesis</a>, which involves <a href="/wiki/Organohalide" class="mw-redirect" title="Organohalide">organohalide</a> reacting with <a href="/wiki/Potassium_phthalimide" title="Potassium phthalimide">potassium phthalimide</a>. </p><p>Aryl halides are much less reactive toward amines and for that reason are more controllable. A popular way to prepare aryl amines is the <a href="/wiki/Buchwald-Hartwig_reaction" class="mw-redirect" title="Buchwald-Hartwig reaction">Buchwald-Hartwig reaction</a>. </p> <div class="mw-heading mw-heading3"><h3 id="From_alkenes">From alkenes</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Amine&action=edit&section=14" title="Edit section: From alkenes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Disubstituted alkenes react with HCN in the presence of strong acids to give formamides, which can be decarbonylated. This method, the <a href="/wiki/Ritter_reaction" title="Ritter reaction">Ritter reaction</a>, is used industrially to produce tertiary amines such as <a href="/w/index.php?title=Tert-octylamine&action=edit&redlink=1" class="new" title="Tert-octylamine (page does not exist)"><i>tert</i>-octylamine</a>.<sup id="cite_ref-Ullmann_5-3" class="reference"><a href="#cite_note-Ullmann-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p>Hydroamination of alkenes is also widely practiced. The reaction is catalyzed by zeolite-based <a href="/wiki/Solid_acid" title="Solid acid">solid acids</a>.<sup id="cite_ref-Ullmann_5-4" class="reference"><a href="#cite_note-Ullmann-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Reductive_routes">Reductive routes</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Amine&action=edit&section=15" title="Edit section: Reductive routes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Via the process of <a href="/wiki/Hydrogenation" title="Hydrogenation">hydrogenation</a>, unsaturated N-containing functional groups are reduced to amines using hydrogen in the presence of a nickel catalyst. Suitable groups include <a href="/wiki/Nitrile" title="Nitrile">nitriles</a>, <a href="/wiki/Organic_azide" title="Organic azide">azides</a>, <a href="/wiki/Imine" title="Imine">imines</a> including <a href="/wiki/Oxime" title="Oxime">oximes</a>, amides, and <a href="/wiki/Nitro_compound" title="Nitro compound">nitro</a>. In the case of nitriles, reactions are sensitive to acidic or alkaline conditions, which can cause hydrolysis of the <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−CN</span> group. <a href="/wiki/Lithium_aluminium_hydride" title="Lithium aluminium hydride"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">LiAlH<sub class="template-chem2-sub">4</sub></span></a> is more commonly employed for the reduction of these same groups on the laboratory scale. </p><p>Many amines are produced from aldehydes and ketones via <a href="/wiki/Reductive_amination" title="Reductive amination">reductive amination</a>, which can either proceed catalytically or stoichiometrically. </p><p><a href="/wiki/Aniline" title="Aniline">Aniline</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>NH<sub class="template-chem2-sub">2</sub></span>) and its derivatives are prepared by reduction of the nitroaromatics. In industry, hydrogen is the preferred reductant, whereas, in the laboratory, tin and iron are often employed. </p> <div class="mw-heading mw-heading3"><h3 id="Specialized_methods">Specialized methods</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Amine&action=edit&section=16" title="Edit section: Specialized methods"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Many methods exist for the preparation of amines, many of these methods being rather specialized. </p> <table class="wikitable sortable" style="background:white; float:center; margin:0 1em;"> <tbody><tr> <th style="width:200px;">Reaction name</th> <th>Substrate</th> <th class="unsortable">Comment </th></tr> <tr> <td valign="top"><a href="/wiki/Staudinger_reduction" class="mw-redirect" title="Staudinger reduction">Staudinger reduction</a> </td> <td><a href="/wiki/Organic_azide" title="Organic azide">Organic azide</a> </td> <td>This reaction also takes place with a reducing agent such as <a href="/wiki/Lithium_aluminium_hydride" title="Lithium aluminium hydride">lithium aluminium hydride</a>. </td></tr> <tr> <td valign="top"><a href="/wiki/Schmidt_reaction" title="Schmidt reaction">Schmidt reaction</a> </td> <td valign="top"><a href="/wiki/Carboxylic_acid" title="Carboxylic acid">Carboxylic acid</a> </td> <td> </td></tr> <tr> <td valign="top"><a href="/wiki/Aza-Baylis%E2%80%93Hillman_reaction" title="Aza-Baylis–Hillman reaction">Aza-Baylis–Hillman reaction</a> </td> <td valign="top"><a href="/wiki/Imine" title="Imine">Imine</a> </td> <td>Synthesis of allylic amines </td></tr> <tr> <td valign="top"><a href="/wiki/Birch_reduction" title="Birch reduction">Birch reduction</a> </td> <td valign="top"><a href="/wiki/Imine" title="Imine">Imine</a> </td> <td>Useful for reactions that trap unstable imine intermediates, such as <a href="/wiki/Grignard_reaction" title="Grignard reaction">Grignard reactions</a> with <a href="/wiki/Nitrile" title="Nitrile">nitriles</a>.<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> </td></tr> <tr> <td valign="top"><a href="/wiki/Hofmann_rearrangement" title="Hofmann rearrangement">Hofmann degradation</a> </td> <td valign="top"><a href="/wiki/Amide" title="Amide">Amide</a> </td> <td>This reaction is valid for preparation of primary amines only. Gives good yields of primary amines uncontaminated with other amines. </td></tr> <tr> <td valign="top"><a href="/wiki/Hofmann_elimination" title="Hofmann elimination">Hofmann elimination</a> </td> <td valign="top"><a href="/wiki/Quaternary_ammonium_salt" class="mw-redirect" title="Quaternary ammonium salt">Quaternary ammonium salt</a> </td> <td>Upon treatment with strong base </td></tr> <tr> <td valign="top"><a href="/wiki/Leuckart_reaction" title="Leuckart reaction">Leuckart reaction</a> </td> <td valign="top"><a href="/wiki/Ketone" title="Ketone">Ketones</a> and <a href="/wiki/Aldehyde" title="Aldehyde">aldehydes</a> </td> <td><a href="/wiki/Reductive_amination" title="Reductive amination">Reductive amination</a> with <a href="/wiki/Formic_acid" title="Formic acid">formic acid</a> and <a href="/wiki/Ammonia" title="Ammonia">ammonia</a> via an <a href="/wiki/Imine" title="Imine">imine</a> intermediate </td></tr> <tr> <td valign="top"><a href="/wiki/Hofmann%E2%80%93L%C3%B6ffler_reaction" title="Hofmann–Löffler reaction">Hofmann–Löffler reaction</a> </td> <td valign="top"><a href="/w/index.php?title=Haloamine&action=edit&redlink=1" class="new" title="Haloamine (page does not exist)">Haloamine</a> </td> <td> </td></tr> <tr> <td valign="top"><a href="/wiki/Eschweiler%E2%80%93Clarke_reaction" title="Eschweiler–Clarke reaction">Eschweiler–Clarke reaction</a> </td> <td valign="top">Amine </td> <td><a href="/wiki/Reductive_amination" title="Reductive amination">Reductive amination</a> with <a href="/wiki/Formic_acid" title="Formic acid">formic acid</a> and <a href="/wiki/Formaldehyde" title="Formaldehyde">formaldehyde</a> via an <a href="/wiki/Imine" title="Imine">imine</a> intermediate </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="Reactions">Reactions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Amine&action=edit&section=17" title="Edit section: Reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Alkylation,_acylation,_and_sulfonation,_etc."><span id="Alkylation.2C_acylation.2C_and_sulfonation.2C_etc."></span>Alkylation, acylation, and sulfonation, etc.</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Amine&action=edit&section=18" title="Edit section: Alkylation, acylation, and sulfonation, etc."><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Aside from their basicity, the dominant reactivity of amines is their <a href="/wiki/Nucleophilicity" class="mw-redirect" title="Nucleophilicity">nucleophilicity</a>.<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> Most primary amines are good <a href="/wiki/Ligand" title="Ligand">ligands</a> for metal ions to give <a href="/wiki/Coordination_complex" title="Coordination complex">coordination complexes</a>. Amines are alkylated by alkyl halides. <a href="/wiki/Acyl_chloride" title="Acyl chloride">Acyl chlorides</a> and <a href="/wiki/Organic_acid_anhydride" title="Organic acid anhydride">acid anhydrides</a> react with primary and secondary amines to form <a href="/wiki/Amide" title="Amide">amides</a> (the "<a href="/wiki/Schotten%E2%80%93Baumann_reaction" title="Schotten–Baumann reaction">Schotten–Baumann reaction</a>"). </p> <figure class="mw-default-size mw-halign-center" typeof="mw:File"><a href="/wiki/File:Amide_formation_from_amine.svg" class="mw-file-description" title="Amide formation"><img alt="Amide formation" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7a/Amide_formation_from_amine.svg/512px-Amide_formation_from_amine.svg.png" decoding="async" width="512" height="158" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/7a/Amide_formation_from_amine.svg/768px-Amide_formation_from_amine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/7a/Amide_formation_from_amine.svg/1024px-Amide_formation_from_amine.svg.png 2x" data-file-width="512" data-file-height="158" /></a><figcaption>Amide formation</figcaption></figure> <p>Similarly, with sulfonyl chlorides, one obtains <a href="/wiki/Sulfonamide" title="Sulfonamide">sulfonamides</a>. This transformation, known as the <a href="/wiki/Hinsberg_reaction" title="Hinsberg reaction">Hinsberg reaction</a>, is a chemical test for the presence of amines. </p><p>Because amines are basic, they neutralize <a href="/wiki/Acid" title="Acid">acids</a> to form the corresponding <a href="/wiki/Ammonium_salt" class="mw-redirect" title="Ammonium salt">ammonium salts</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R<sub class="template-chem2-sub">3</sub>NH<sup class="template-chem2-sup">+</sup></span>. When formed from carboxylic acids and primary and secondary amines, these salts thermally dehydrate to form the corresponding <a href="/wiki/Amide" title="Amide">amides</a>. </p> <dl><dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\underbrace {\ce {H-\!\!{\overset {\displaystyle R1 \atop |}{\underset {| \atop \displaystyle R2}{N}}}\!\!\!\!:}} _{\text{amine}}+\underbrace {\ce {R3-{\overset {\displaystyle O \atop \|}{C}}-OH}} _{\text{carboxylic acid}}->}\ \underbrace {\ce {{H-{\overset {\displaystyle R1 \atop |}{\underset {| \atop \displaystyle R2}{N+}}}-H}+R3-COO^{-}}} _{{\text{substituted-ammonium}} \atop {\text{carboxylate salt}}}{\ce {->[{\text{heat}}][{\text{dehydration}}]}}{\underbrace {\ce {{\overset {\displaystyle R1 \atop |}{\underset {| \atop \displaystyle R2}{N}}}\!\!-{\overset {\displaystyle O \atop \|}{C}}-R3}} _{\text{amide}}+\underbrace {\ce {H2O}} _{\text{water}}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <munder> <mrow class="MJX-TeXAtom-OP MJX-fixedlimits"> <munder> <mrow> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mspace width="negativethinmathspace" /> <mspace width="negativethinmathspace" /> <mrow class="MJX-TeXAtom-ORD"> <mover> <munder> <mtext>N</mtext> <mfrac linethickness="0"> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">|</mo> </mrow> <mstyle displaystyle="true" scriptlevel="0"> <msubsup> <mtext>R</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> </mstyle> </mfrac> </munder> <mfrac linethickness="0"> <mstyle displaystyle="true" scriptlevel="0"> <msubsup> <mtext>R</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>1</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> </mstyle> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">|</mo> </mrow> </mfrac> </mover> </mrow> <mspace width="negativethinmathspace" /> <mspace width="negativethinmathspace" /> <mspace width="negativethinmathspace" /> <mspace width="negativethinmathspace" /> <mo>:</mo> </mrow> <mo>⏟</mo> </munder> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mtext>amine</mtext> </mrow> </munder> <mo>+</mo> <munder> <mrow class="MJX-TeXAtom-OP MJX-fixedlimits"> <munder> <mrow> <msubsup> <mtext>R</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mover> <mtext>C</mtext> <mfrac linethickness="0"> <mstyle displaystyle="true" scriptlevel="0"> <mtext>O</mtext> </mstyle> <mo fence="false" stretchy="false">‖</mo> </mfrac> </mover> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mtext>OH</mtext> </mrow> <mo>⏟</mo> </munder> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mtext>carboxylic acid</mtext> </mrow> </munder> <mo>−</mo> <mo>></mo> </mrow> <mtext> </mtext> <munder> <mrow class="MJX-TeXAtom-OP MJX-fixedlimits"> <munder> <mrow> <mrow class="MJX-TeXAtom-ORD"> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mover> <munder> <msup> <mtext>N</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>+</mo> </mrow> </msup> <mfrac linethickness="0"> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">|</mo> </mrow> <mstyle displaystyle="true" scriptlevel="0"> <msubsup> <mtext>R</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> </mstyle> </mfrac> </munder> <mfrac linethickness="0"> <mstyle displaystyle="true" scriptlevel="0"> <msubsup> <mtext>R</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>1</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> </mstyle> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">|</mo> </mrow> </mfrac> </mover> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mtext>H</mtext> </mrow> <mo>+</mo> <msubsup> <mtext>R</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <msup> <mtext>COO</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> </msup> </mrow> <mo>⏟</mo> </munder> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mfrac linethickness="0"> <mrow class="MJX-TeXAtom-ORD"> <mtext>substituted-ammonium</mtext> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mtext>carboxylate salt</mtext> </mrow> </mfrac> </mrow> </munder> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-REL"> <munderover> <mo>→</mo> <mpadded width="+0.611em" lspace="0.278em" voffset="-.24em"> <mrow class="MJX-TeXAtom-ORD"> <mtext>dehydration</mtext> </mrow> </mpadded> <mpadded width="+0.611em" lspace="0.278em" voffset=".15em"> <mrow class="MJX-TeXAtom-ORD"> <mtext>heat</mtext> </mrow> </mpadded> </munderover> </mrow> </mrow> <mrow class="MJX-TeXAtom-ORD"> <munder> <mrow class="MJX-TeXAtom-OP MJX-fixedlimits"> <munder> <mrow> <mrow class="MJX-TeXAtom-ORD"> <mover> <munder> <mtext>N</mtext> <mfrac linethickness="0"> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">|</mo> </mrow> <mstyle displaystyle="true" scriptlevel="0"> <msubsup> <mtext>R</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> </mstyle> </mfrac> </munder> <mfrac linethickness="0"> <mstyle displaystyle="true" scriptlevel="0"> <msubsup> <mtext>R</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>1</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> </mstyle> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">|</mo> </mrow> </mfrac> </mover> </mrow> <mspace width="negativethinmathspace" /> <mspace width="negativethinmathspace" /> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mover> <mtext>C</mtext> <mfrac linethickness="0"> <mstyle displaystyle="true" scriptlevel="0"> <mtext>O</mtext> </mstyle> <mo fence="false" stretchy="false">‖</mo> </mfrac> </mover> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <msubsup> <mtext>R</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> </mrow> <mo>⏟</mo> </munder> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mtext>amide</mtext> </mrow> </munder> <mo>+</mo> <munder> <mrow class="MJX-TeXAtom-OP MJX-fixedlimits"> <munder> <mrow> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>O</mtext> </mrow> <mo>⏟</mo> </munder> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mtext>water</mtext> </mrow> </munder> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\underbrace {\ce {H-\!\!{\overset {\displaystyle R1 \atop |}{\underset {| \atop \displaystyle R2}{N}}}\!\!\!\!:}} _{\text{amine}}+\underbrace {\ce {R3-{\overset {\displaystyle O \atop \|}{C}}-OH}} _{\text{carboxylic acid}}->}\ \underbrace {\ce {{H-{\overset {\displaystyle R1 \atop |}{\underset {| \atop \displaystyle R2}{N+}}}-H}+R3-COO^{-}}} _{{\text{substituted-ammonium}} \atop {\text{carboxylate salt}}}{\ce {->[{\text{heat}}][{\text{dehydration}}]}}{\underbrace {\ce {{\overset {\displaystyle R1 \atop |}{\underset {| \atop \displaystyle R2}{N}}}\!\!-{\overset {\displaystyle O \atop \|}{C}}-R3}} _{\text{amide}}+\underbrace {\ce {H2O}} _{\text{water}}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/0fe12f730885534fda8c9f8c41b2bd6ba4371fcc" class="mwe-math-fallback-image-inline mw-invert skin-invert" title="Amine reaction with carboxylic acids" aria-hidden="true" style="vertical-align: -9.838ex; margin-right: -0.028ex; width:79.198ex; height:16.509ex;" alt="{\displaystyle {\underbrace {\ce {H-\!\!{\overset {\displaystyle R1 \atop |}{\underset {| \atop \displaystyle R2}{N}}}\!\!\!\!:}} _{\text{amine}}+\underbrace {\ce {R3-{\overset {\displaystyle O \atop \|}{C}}-OH}} _{\text{carboxylic acid}}->}\ \underbrace {\ce {{H-{\overset {\displaystyle R1 \atop |}{\underset {| \atop \displaystyle R2}{N+}}}-H}+R3-COO^{-}}} _{{\text{substituted-ammonium}} \atop {\text{carboxylate salt}}}{\ce {->[{\text{heat}}][{\text{dehydration}}]}}{\underbrace {\ce {{\overset {\displaystyle R1 \atop |}{\underset {| \atop \displaystyle R2}{N}}}\!\!-{\overset {\displaystyle O \atop \|}{C}}-R3}} _{\text{amide}}+\underbrace {\ce {H2O}} _{\text{water}}}}"></span></dd></dl> <p>Amines undergo <a href="/wiki/Sulfamation" title="Sulfamation">sulfamation</a> upon treatment with <a href="/wiki/Sulfur_trioxide" title="Sulfur trioxide">sulfur trioxide</a> or sources thereof: </p> <dl><dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {R2NH + SO3 -> R2NSO3H}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <msubsup> <mtext>R</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>NH</mtext> <mo>+</mo> <msubsup> <mtext>SO</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo stretchy="false">⟶</mo> <msubsup> <mtext>R</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msubsup> <mtext>NSO</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>H</mtext> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {R2NH + SO3 -> R2NSO3H}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/4ae061d4f134c16446de7bf637febf4958705210" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:28.748ex; height:2.843ex;" alt="{\displaystyle {\ce {R2NH + SO3 -> R2NSO3H}}}"></span></dd></dl> <div class="mw-heading mw-heading3"><h3 id="Diazotization">Diazotization</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Amine&action=edit&section=19" title="Edit section: Diazotization"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Amines reacts with <a href="/wiki/Nitrous_acid" title="Nitrous acid">nitrous acid</a> to give diazonium salts. The alkyl diazonium salts are of little importance because they are too unstable. The most important members are derivatives of aromatic amines such as <a href="/wiki/Aniline" title="Aniline">aniline</a> ("phenylamine") (A = aryl or naphthyl): </p> <dl><dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {ANH2 + HNO2 + HX -> AN2+ + X- + 2 H2O}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <msubsup> <mtext>ANH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo>+</mo> <msubsup> <mtext>HNO</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo>+</mo> <mtext>HX</mtext> <mo stretchy="false">⟶</mo> <msubsup> <mtext>AN</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mo>+</mo> </mrow> </msubsup> <mo>+</mo> <msup> <mtext>X</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> </msup> <mo>+</mo> <mn>2</mn> <mspace width="thinmathspace" /> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>O</mtext> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {ANH2 + HNO2 + HX -> AN2+ + X- + 2 H2O}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/e6b062678a9c0f085119b40538a75cde8bbeb7a6" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:46.982ex; height:3.176ex;" alt="{\displaystyle {\ce {ANH2 + HNO2 + HX -> AN2+ + X- + 2 H2O}}}"></span></dd></dl> <p>Anilines and naphthylamines form more stable <a href="/wiki/Diazonium" class="mw-redirect" title="Diazonium">diazonium</a> salts, which can be isolated in the crystalline form.<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> Diazonium salts undergo a variety of useful transformations involving replacement of the <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">N<sub class="template-chem2-sub">2</sub></span> group with anions. For example, <a href="/wiki/Copper(I)_cyanide" title="Copper(I) cyanide">cuprous cyanide</a> gives the corresponding nitriles: </p> <dl><dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {AN2+ + Y- -> AY + N2}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <msubsup> <mtext>AN</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mo>+</mo> </mrow> </msubsup> <mo>+</mo> <msup> <mtext>Y</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> </msup> <mo stretchy="false">⟶</mo> <mtext>AY</mtext> <mo>+</mo> <msubsup> <mtext>N</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {AN2+ + Y- -> AY + N2}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/74a06dba895cadef3662cab5279e68e9b0242fd9" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:25.311ex; height:3.176ex;" alt="{\displaystyle {\ce {AN2+ + Y- -> AY + N2}}}"></span></dd></dl> <p>Aryldiazoniums couple with electron-rich aromatic compounds such as a <a href="/wiki/Phenol" title="Phenol">phenol</a> to form <a href="/wiki/Azo_compound" title="Azo compound">azo compounds</a>. Such reactions are widely applied to the production of dyes.<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Conversion_to_imines">Conversion to imines</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Amine&action=edit&section=20" title="Edit section: Conversion to imines"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Alkylimino-de-oxo-bisubstitution" class="mw-redirect" title="Alkylimino-de-oxo-bisubstitution">Imine formation</a> is an important reaction. Primary amines react with <a href="/wiki/Ketone" title="Ketone">ketones</a> and <a href="/wiki/Aldehyde" title="Aldehyde">aldehydes</a> to form <a href="/wiki/Imine" title="Imine">imines</a>. In the case of <a href="/wiki/Formaldehyde" title="Formaldehyde">formaldehyde</a> (R' = H), these products typically exist as cyclic <a href="/wiki/Trimer_(chemistry)" title="Trimer (chemistry)">trimers</a>: <span class="mwe-math-element"><span class="mwe-math-mathml-display mwe-math-mathml-a11y" style="display: none;"><math display="block" xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {RNH2 + R'_2C=O -> R'_2C=NR + H2O}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <msubsup> <mtext>RNH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo>+</mo> <msubsup> <mtext>R</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow> <mo class="MJX-variant">′</mo> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </mrow> </msubsup> <mtext>C</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>=</mo> </mrow> <mtext>O</mtext> <mo stretchy="false">⟶</mo> <msubsup> <mtext>R</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow> <mo class="MJX-variant">′</mo> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </mrow> </msubsup> <mtext>C</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>=</mo> </mrow> <mtext>NR</mtext> <mo>+</mo> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>O</mtext> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {RNH2 + R'_2C=O -> R'_2C=NR + H2O}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/02cb3c0b2e1f7f3fcfe0b9b2f0b5e7b5b6e16d3e" class="mwe-math-fallback-image-display mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:39.397ex; height:3.509ex;" alt="{\displaystyle {\ce {RNH2 + R'_2C=O -> R'_2C=NR + H2O}}}"></span> Reduction of these imines gives secondary amines: <span class="mwe-math-element"><span class="mwe-math-mathml-display mwe-math-mathml-a11y" style="display: none;"><math display="block" xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {R'_2C=NR + H2 -> R'_2CH-NHR}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <msubsup> <mtext>R</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow> <mo class="MJX-variant">′</mo> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </mrow> </msubsup> <mtext>C</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>=</mo> </mrow> <mtext>NR</mtext> <mo>+</mo> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo stretchy="false">⟶</mo> <msubsup> <mtext>R</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow> <mo class="MJX-variant">′</mo> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </mrow> </msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mtext>NHR</mtext> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {R'_2C=NR + H2 -> R'_2CH-NHR}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/e66fafa91d6e61ab13d6dee177b54faccd992082" class="mwe-math-fallback-image-display mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:33.629ex; height:3.509ex;" alt="{\displaystyle {\ce {R'_2C=NR + H2 -> R'_2CH-NHR}}}"></span> </p><p>Similarly, secondary amines react with ketones and aldehydes to form <a href="/wiki/Enamine" title="Enamine">enamines</a>: <span class="mwe-math-element"><span class="mwe-math-mathml-display mwe-math-mathml-a11y" style="display: none;"><math display="block" xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {R2NH + R'(R''CH2)C=O -> R''CH=C(NR2)R' + H2O}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <msubsup> <mtext>R</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>NH</mtext> <mo>+</mo> <msup> <mtext>R</mtext> <mo>′</mo> </msup> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msup> <mtext>R</mtext> <mo>″</mo> </msup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo stretchy="false">)</mo> </mrow> <mtext>C</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>=</mo> </mrow> <mtext>O</mtext> <mo stretchy="false">⟶</mo> <msup> <mtext>R</mtext> <mo>″</mo> </msup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>=</mo> </mrow> <mtext>C</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msubsup> <mtext>NR</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo stretchy="false">)</mo> </mrow> <msup> <mtext>R</mtext> <mo>′</mo> </msup> <mo>+</mo> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>O</mtext> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {R2NH + R'(R''CH2)C=O -> R''CH=C(NR2)R' + H2O}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/706b2526cc8858c1e3ddaca98aeb54a642f43feb" class="mwe-math-fallback-image-display mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:56.923ex; height:3.176ex;" alt="{\displaystyle {\ce {R2NH + R'(R''CH2)C=O -> R''CH=C(NR2)R' + H2O}}}"></span> </p><p><a href="/wiki/Mercuric" class="mw-redirect" title="Mercuric">Mercuric</a> ions reversibly oxidize <a href="/wiki/Tertiary_amine" class="mw-redirect" title="Tertiary amine">tertiary amines</a> with an <a href="/wiki/Locant" title="Locant">α</a> hydrogen to <a href="/wiki/Iminium" title="Iminium">iminium</a> ions:<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> <span class="mwe-math-element"><span class="mwe-math-mathml-display mwe-math-mathml-a11y" style="display: none;"><math display="block" xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {Hg^2+ + R2NCH2R' <=> Hg + [R2N=CHR']+ + H+}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <msup> <mtext>Hg</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> <mo>+</mo> </mrow> </msup> <mo>+</mo> <msubsup> <mtext>R</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msubsup> <mtext>NCH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msup> <mtext>R</mtext> <mo>′</mo> </msup> <mrow class="MJX-TeXAtom-REL"> <mover> <mrow class="MJX-TeXAtom-OP MJX-fixedlimits"> <mrow class="MJX-TeXAtom-ORD"> <mpadded height="0" depth="0"> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">↽</mo> </mrow> <mspace width="negativethinmathspace" /> <mspace width="negativethinmathspace" /> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> </mpadded> </mrow> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="false" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mspace width="negativethinmathspace" /> <mspace width="negativethinmathspace" /> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">⇀</mo> </mrow> </mrow> </mstyle> </mrow> </mover> </mrow> <mtext>Hg</mtext> <mo>+</mo> <msup> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">[</mo> <msubsup> <mtext>R</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>N</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>=</mo> </mrow> <msup> <mtext>CHR</mtext> <mo>′</mo> </msup> <mo stretchy="false">]</mo> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mo>+</mo> </mrow> </msup> <mo>+</mo> <msup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>+</mo> </mrow> </msup> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {Hg^2+ + R2NCH2R' <=> Hg + [R2N=CHR']+ + H+}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/577bae0e4c2a18b653c850439a5ad969c30ef050" class="mwe-math-fallback-image-display mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:50.883ex; height:3.509ex;" alt="{\displaystyle {\ce {Hg^2+ + R2NCH2R' <=> Hg + [R2N=CHR']+ + H+}}}"></span> </p> <div class="mw-heading mw-heading3"><h3 id="Overview">Overview</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Amine&action=edit&section=21" title="Edit section: Overview"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>An overview of the reactions of amines is given below: </p> <table class="wikitable sortable" style="background:white; float:center; margin:0 1em;"> <tbody><tr> <th style="width:200px;">Reaction name</th> <th>Reaction product</th> <th class="unsortable">Comment </th></tr> <tr> <td valign="top"><a href="/wiki/Amine_alkylation" title="Amine alkylation">Amine alkylation</a> </td> <td valign="top">Amines </td> <td>Degree of substitution increases </td></tr> <tr> <td valign="top"><a href="/wiki/Schotten%E2%80%93Baumann_reaction" title="Schotten–Baumann reaction">Schotten–Baumann reaction</a> </td> <td valign="top"><a href="/wiki/Amide" title="Amide">Amide</a> </td> <td>Reagents: <a href="/wiki/Acyl_chloride" title="Acyl chloride">acyl chlorides</a>, <a href="/wiki/Acid_anhydride" title="Acid anhydride">acid anhydrides</a> </td></tr> <tr> <td valign="top"><a href="/wiki/Hinsberg_reaction" title="Hinsberg reaction">Hinsberg reaction</a> </td> <td valign="top"><a href="/wiki/Sulfonamide" title="Sulfonamide">Sulfonamides</a> </td> <td>Reagents: <a href="/wiki/Sulfonyl_chloride" class="mw-redirect" title="Sulfonyl chloride">sulfonyl chlorides</a> </td></tr> <tr> <td valign="top"><a href="/wiki/Amine-carbonyl_condensation" class="mw-redirect" title="Amine-carbonyl condensation">Amine–carbonyl condensation</a> </td> <td valign="top"><a href="/wiki/Imines" class="mw-redirect" title="Imines">Imines</a> </td></tr> <tr> <td valign="top"><a href="/wiki/Organic_oxidation" class="mw-redirect" title="Organic oxidation">Organic oxidation</a> </td> <td valign="top"><a href="/wiki/Nitroso" title="Nitroso">Nitroso</a> compounds </td> <td>Reagent: <a href="/wiki/Peroxymonosulfuric_acid" title="Peroxymonosulfuric acid">peroxymonosulfuric acid</a> </td></tr> <tr> <td valign="top"><a href="/wiki/Organic_oxidation" class="mw-redirect" title="Organic oxidation">Organic oxidation</a> </td> <td valign="top"><a href="/wiki/Diazonium_salt" class="mw-redirect" title="Diazonium salt">Diazonium salt</a> </td> <td>Reagent: <a href="/wiki/Nitrous_acid" title="Nitrous acid">nitrous acid</a> </td></tr> <tr> <td valign="top"><a href="/wiki/Zincke_reaction" title="Zincke reaction">Zincke reaction</a> </td> <td><a href="/wiki/Zincke_aldehyde" title="Zincke aldehyde">Zincke aldehyde</a> </td> <td>Reagent: <a href="/wiki/Pyridinium" title="Pyridinium">pyridinium</a> salts, with primary and secondary amines </td></tr> <tr> <td valign="top"><a href="/wiki/Emde_degradation" title="Emde degradation">Emde degradation</a> </td> <td valign="top"><a href="/wiki/Tertiary_amine" class="mw-redirect" title="Tertiary amine">Tertiary amine</a> </td> <td>Reduction of <a href="/wiki/Quaternary_ammonium_cation" title="Quaternary ammonium cation">quaternary ammonium cations</a> </td></tr> <tr> <td valign="top"><a href="/wiki/Hofmann%E2%80%93Martius_rearrangement" title="Hofmann–Martius rearrangement">Hofmann–Martius rearrangement</a> </td> <td valign="top">Aryl-substituted <a href="/wiki/Aniline" title="Aniline">anilines</a> </td></tr> <tr> <td valign="top"><a href="/wiki/Von_Braun_reaction" title="Von Braun reaction">von Braun reaction</a> </td> <td valign="top"><a href="/wiki/Nitrile#Organic_cyanamides" title="Nitrile">Organic cyanamide</a> </td> <td>By cleavage (tertiary amines only) with cyanogen bromide </td></tr> <tr> <td valign="top"><a href="/wiki/Hofmann_elimination" title="Hofmann elimination">Hofmann elimination</a> </td> <td valign="top"><a href="/wiki/Alkene" title="Alkene">Alkene</a> </td> <td>Proceeds by β-elimination of less hindered carbon </td></tr> <tr> <td valign="top"><a href="/wiki/Cope_reaction" title="Cope reaction">Cope reaction</a> </td> <td valign="top"><a href="/wiki/Alkene" title="Alkene">Alkene</a> </td> <td>Similar to <a href="/wiki/Hofmann_elimination" title="Hofmann elimination">Hofmann elimination</a> </td></tr> <tr> <td valign="top"><a href="/wiki/Carbylamine_reaction" title="Carbylamine reaction">Carbylamine reaction</a> </td> <td valign="top"><a href="/wiki/Isonitrile" class="mw-redirect" title="Isonitrile">Isonitrile</a> </td> <td>Primary amines only </td></tr> <tr> <td valign="top">Hoffmann's mustard oil test </td> <td valign="top"><a href="/wiki/Isothiocyanate" title="Isothiocyanate">Isothiocyanate</a> </td> <td><a href="/wiki/Carbon_disulfide" title="Carbon disulfide">Carbon disulfide</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CS<sub class="template-chem2-sub">2</sub></span> and <a href="/wiki/Mercury(II)_chloride" title="Mercury(II) chloride">mercury(II) chloride</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">HgCl<sub class="template-chem2-sub">2</sub></span> are used. Thiocyanate smells like mustard. </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="Biological_activity">Biological activity</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Amine&action=edit&section=22" title="Edit section: Biological activity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Amines are ubiquitous in biology. The breakdown of <a href="/wiki/Amino_acid" title="Amino acid">amino acids</a> releases amines, famously in the case of decaying fish which smell of <a href="/wiki/Trimethylamine" title="Trimethylamine">trimethylamine</a>. Many <a href="/wiki/Neurotransmitter" title="Neurotransmitter">neurotransmitters</a> are amines, including <a href="/wiki/Epinephrine" class="mw-redirect" title="Epinephrine">epinephrine</a>, <a href="/wiki/Norepinephrine" title="Norepinephrine">norepinephrine</a>, <a href="/wiki/Dopamine" title="Dopamine">dopamine</a>, <a href="/wiki/Serotonin" title="Serotonin">serotonin</a>, and <a href="/wiki/Histamine" title="Histamine">histamine</a>. <a href="/wiki/Protonated" class="mw-redirect" title="Protonated">Protonated</a> <a href="/wiki/Amino_group" class="mw-redirect" title="Amino group">amino groups</a> (<span class="chemf nowrap">–NH<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">+</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">3</sub></span></span></span>) are the most common positively charged moieties in <a href="/wiki/Protein" title="Protein">proteins</a>, specifically in the amino acid <a href="/wiki/Lysine" title="Lysine">lysine</a>.<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> The anionic polymer <a href="/wiki/DNA" title="DNA">DNA</a> is typically bound to various amine-rich proteins.<sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> Additionally, the terminal charged primary ammonium on lysine forms <a href="/wiki/Salt_bridge_(protein_and_supramolecular)" title="Salt bridge (protein and supramolecular)">salt bridges</a> with <a href="/wiki/Carboxylate" title="Carboxylate">carboxylate</a> groups of other amino acids in <a href="/wiki/Polypeptide" class="mw-redirect" title="Polypeptide">polypeptides</a>, which is one of the primary influences on the three-dimensional structures of proteins.<sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Amine_hormones">Amine hormones</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Amine&action=edit&section=23" title="Edit section: Amine hormones"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Hormone" title="Hormone">Hormones</a> derived from the modification of amino acids are referred to as amine hormones. Typically, the original structure of the amino acid is modified such that a –COOH, or carboxyl, group is removed, whereas the <span class="chemf nowrap">–NH<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">+</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">3</sub></span></span></span>, or amine, group remains. Amine hormones are synthesized from the amino acids <a href="/wiki/Tryptophan" title="Tryptophan">tryptophan</a> or <a href="/wiki/Tyrosine" title="Tyrosine">tyrosine</a>.<sup id="cite_ref-Openstax_Anatomy_&_Physiology_attribution_23-0" class="reference"><a href="#cite_note-Openstax_Anatomy_&_Physiology_attribution-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Application_of_amines">Application of amines</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Amine&action=edit&section=24" title="Edit section: Application of amines"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Dyes">Dyes</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Amine&action=edit&section=25" title="Edit section: Dyes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Primary aromatic amines are used as a starting material for the manufacture of <a href="/wiki/Azo_dye" title="Azo dye">azo dyes</a>. It reacts with nitrous acid to form diazonium salt, which can undergo coupling reaction to form an azo compound. As azo-compounds are highly coloured, they are widely used in dyeing industries, such as: </p> <ul><li><a href="/wiki/Methyl_orange" title="Methyl orange">Methyl orange</a></li> <li>Direct brown 138</li> <li><a href="/wiki/Sunset_yellow" class="mw-redirect" title="Sunset yellow">Sunset yellow</a> FCF</li> <li><a href="/wiki/Ponceau_4R" title="Ponceau 4R">Ponceau</a></li></ul> <div class="mw-heading mw-heading3"><h3 id="Drugs">Drugs</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Amine&action=edit&section=26" title="Edit section: Drugs"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Most drugs and drug candidates contain amine functional groups:<sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p> <ul><li><a href="/wiki/Chlorpheniramine" class="mw-redirect" title="Chlorpheniramine">Chlorpheniramine</a> is an <a href="/wiki/Antihistamine" title="Antihistamine">antihistamine</a> that helps to relieve allergic disorders due to cold, hay fever, itchy skin, insect bites and stings.</li> <li><a href="/wiki/Chlorpromazine" title="Chlorpromazine">Chlorpromazine</a> is a tranquilizer that sedates without inducing sleep. It is used to relieve anxiety, excitement, restlessness or even mental disorder.</li> <li><a href="/wiki/Ephedrine" title="Ephedrine">Ephedrine</a> and <a href="/wiki/Phenylephrine" title="Phenylephrine">phenylephrine</a>, as amine hydrochlorides, are used as decongestants.</li> <li><a href="/wiki/Amphetamine" title="Amphetamine">Amphetamine</a>, <a href="/wiki/Methamphetamine" title="Methamphetamine">methamphetamine</a>, and <a href="/wiki/Methcathinone" title="Methcathinone">methcathinone</a> are psychostimulant amines that are listed as controlled substances by the US <a href="/wiki/Drug_Enforcement_Administration" title="Drug Enforcement Administration">DEA</a>.</li> <li><a href="/wiki/Thioridazine" title="Thioridazine">Thioridazine</a>, an antipsychotic drug, is an amine which is believed to exhibit its antipsychotic effects, in part, due to its effects on other amines.<sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Amitriptyline" title="Amitriptyline">Amitriptyline</a>, <a href="/wiki/Imipramine" title="Imipramine">imipramine</a>, <a href="/wiki/Lofepramine" title="Lofepramine">lofepramine</a> and <a href="/wiki/Clomipramine" title="Clomipramine">clomipramine</a> are <a href="/wiki/Tricyclic_antidepressant" title="Tricyclic antidepressant">tricyclic antidepressants</a> and tertiary amines.</li> <li><a href="/wiki/Nortriptyline" title="Nortriptyline">Nortriptyline</a>, <a href="/wiki/Desipramine" title="Desipramine">desipramine</a>, and <a href="/wiki/Amoxapine" title="Amoxapine">amoxapine</a> are <a href="/wiki/Tricyclic_antidepressants" class="mw-redirect" title="Tricyclic antidepressants">tricyclic antidepressants</a> and secondary amines. (The tricyclics are grouped by the nature of the final amino group on the side chain.)</li> <li><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Substituted tryptamines</a> and <a href="/wiki/Substituted_phenethylamine" title="Substituted phenethylamine">phenethylamines</a> are key basic structures for a large variety of <a href="/wiki/Psychedelic_drug" title="Psychedelic drug">psychedelic drugs</a>.</li> <li><a href="/wiki/Opiate" title="Opiate">Opiate</a> <a href="/wiki/Analgesic" title="Analgesic">analgesics</a> such as <a href="/wiki/Morphine" title="Morphine">morphine</a>, <a href="/wiki/Codeine" title="Codeine">codeine</a>, and <a href="/wiki/Heroin" title="Heroin">heroin</a> are <a href="/wiki/Tertiary_(chemistry)" title="Tertiary (chemistry)">tertiary</a> amines.</li></ul> <div class="mw-heading mw-heading3"><h3 id="Gas_treatment">Gas treatment</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Amine&action=edit&section=27" title="Edit section: Gas treatment"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Aqueous <a href="/wiki/Monoethanolamine" class="mw-redirect" title="Monoethanolamine">monoethanolamine</a> (MEA), <a href="/w/index.php?title=Diglycolamine&action=edit&redlink=1" class="new" title="Diglycolamine (page does not exist)">diglycolamine</a> (DGA), <a href="/wiki/Diethanolamine" title="Diethanolamine">diethanolamine</a> (DEA), <a href="/wiki/Diisopropanolamine" title="Diisopropanolamine">diisopropanolamine</a> (DIPA) and <a href="/wiki/N-methyl-diethanolamine" class="mw-redirect" title="N-methyl-diethanolamine">methyldiethanolamine</a> (MDEA) are widely used industrially for removing <a href="/wiki/Carbon_dioxide" title="Carbon dioxide">carbon dioxide</a> (CO<sub>2</sub>) and <a href="/wiki/Hydrogen_sulfide" title="Hydrogen sulfide">hydrogen sulfide</a> (H<sub>2</sub>S) from natural gas and refinery process streams. They may also be used to remove CO<sub>2</sub> from combustion gases and <a href="/wiki/Flue_gas" title="Flue gas">flue gases</a> and may have potential for abatement of <a href="/wiki/Greenhouse_gas" title="Greenhouse gas">greenhouse gases</a>. Related processes are known as <a href="/wiki/Amine_gas_treating" title="Amine gas treating">sweetening</a>.<sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Epoxy_resin_curing_agents">Epoxy resin curing agents</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Amine&action=edit&section=28" title="Edit section: Epoxy resin curing agents"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Amines are often used as epoxy resin curing agents.<sup id="cite_ref-27" class="reference"><a href="#cite_note-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-28" class="reference"><a href="#cite_note-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> These include <a href="/wiki/Dimethylethylamine" class="mw-redirect" title="Dimethylethylamine">dimethylethylamine</a>, <a href="/wiki/Cyclohexylamine" title="Cyclohexylamine">cyclohexylamine</a>, and a variety of diamines such as 4,4-diaminodicyclohexylmethane.<sup id="cite_ref-Ullmann_5-5" class="reference"><a href="#cite_note-Ullmann-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Multifunctional amines such as <a href="/wiki/Tetraethylenepentamine" title="Tetraethylenepentamine">tetraethylenepentamine</a> and <a href="/wiki/Triethylenetetramine" title="Triethylenetetramine">triethylenetetramine</a> are also widely used in this capacity.<sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> The reaction proceeds by the lone pair of electrons on the amine nitrogen attacking the outermost carbon on the oxirane ring of the epoxy resin. This relieves ring strain on the epoxide and is the driving force of the reaction.<sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> Molecules with tertiary amine functionality are often used to accelerate the epoxy-amine curing reaction and include substances such as <a href="/wiki/2,4,6-Tris(dimethylaminomethyl)phenol" title="2,4,6-Tris(dimethylaminomethyl)phenol">2,4,6-Tris(dimethylaminomethyl)phenol</a>. It has been stated that this is the most widely used room temperature accelerator for two-component epoxy resin systems.<sup id="cite_ref-31" class="reference"><a href="#cite_note-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-32" class="reference"><a href="#cite_note-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Safety">Safety</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Amine&action=edit&section=29" title="Edit section: Safety"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Low molecular weight simple amines, such as <a href="/wiki/Ethylamine" title="Ethylamine">ethylamine</a>, are only weakly toxic with <a href="/wiki/Median_lethal_dose" title="Median lethal dose">LD<sub style="font-size:-1">50</sub></a> between 100 and 1000 mg/kg. They are skin irritants, especially as some are easily absorbed through the skin.<sup id="cite_ref-Ullmann_5-6" class="reference"><a href="#cite_note-Ullmann-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Amines are a broad class of compounds, and more complex members of the class can be extremely bioactive, for example <a href="/wiki/Strychnine" title="Strychnine">strychnine</a>. </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=Amine&action=edit&section=30" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Acid-base_extraction" class="mw-redirect" title="Acid-base extraction">Acid-base extraction</a></li> <li><a href="/wiki/Amine_value" title="Amine value">Amine value</a></li> <li><a href="/wiki/Amine_gas_treating" title="Amine gas treating">Amine gas treating</a></li> <li><a href="/wiki/Ammine" class="mw-redirect" title="Ammine">Ammine</a></li> <li><a href="/wiki/Biogenic_amine" title="Biogenic amine">Biogenic amine</a></li> <li><a href="/wiki/Ligand_isomerism" title="Ligand isomerism">Ligand isomerism</a></li> <li><a href="/wiki/IUPAC_nomenclature_of_organic_chemistry#Amines" title="IUPAC nomenclature of organic chemistry">Official naming rules for amines</a> as determined by the International Union of Pure and Applied Chemistry (<a href="/wiki/IUPAC" class="mw-redirect" title="IUPAC">IUPAC</a>)</li></ul> <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=Amine&action=edit&section=31" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <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 mw-references-columns"><ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><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><cite id="Reference-AHD-amine" class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.ahdictionary.com/word/search.html?q=amine">"amine"</a>. <i><a href="/wiki/The_American_Heritage_Dictionary_of_the_English_Language" title="The American Heritage Dictionary of the English Language">The American Heritage Dictionary of the English Language</a></i> (5th ed.). HarperCollins.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=The+American+Heritage+Dictionary+of+the+English+Language&rft.atitle=amine&rft_id=https%3A%2F%2Fwww.ahdictionary.com%2Fword%2Fsearch.html%3Fq%3Damine&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAmine" class="Z3988"></span></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 class="citation encyclopaedia cs1"><a rel="nofollow" class="external text" href="https://www.collinsdictionary.com/dictionary/english/amine">"Amine definition and meaning"</a>. <i>Collins English Dictionary</i>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20150223133401/http://www.collinsdictionary.com/dictionary/english/amine">Archived</a> from the original on 23 February 2015<span class="reference-accessdate">. Retrieved <span class="nowrap">28 March</span> 2017</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Amine+definition+and+meaning&rft.btitle=Collins+English+Dictionary&rft_id=http%3A%2F%2Fwww.collinsdictionary.com%2Fdictionary%2Fenglish%2Famine&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAmine" 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"><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/20150223133030/http://www.oxforddictionaries.com/us/definition/english/amine">"amine – definition of amine in English"</a>. Oxford Dictionaries. 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Weinheim: Wiley-VCH. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F14356007.a02_001">10.1002/14356007.a02_001</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/3527306730" title="Special:BookSources/3527306730"><bdi>3527306730</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Amines%2C+Aliphatic&rft.btitle=Ullmann%27s+Encyclopedia+of+Industrial+Chemistry&rft.place=Weinheim&rft.pub=Wiley-VCH&rft.date=2005&rft_id=info%3Adoi%2F10.1002%2F14356007.a02_001&rft.isbn=3527306730&rft.aulast=Eller&rft.aufirst=K&rft.au=Henkes%2C+E&rft.au=Rossbacher%2C+R&rft.au=H%C3%B6ke%2C+H&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAmine" class="Z3988"></span></span> </li> <li id="cite_note-30"><span class="mw-cite-backlink"><b><a href="#cite_ref-30">^</a></b></span> <span class="reference-text">Howarth G.A "Synthesis of a legislation compliant corrosion protection coating system based on urethane, oxazolidine and waterborne epoxy technology" pages 12, Chapter 1.3.1 Master of Science Thesis April 1997 Imperial College London</span> </li> <li id="cite_note-31"><span class="mw-cite-backlink"><b><a href="#cite_ref-31">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSeoYuiSeo2019" class="citation journal cs1">Seo, Jiae; Yui, Nobuhiko; Seo, Ji-Hun (January 2019). <a rel="nofollow" class="external text" href="https://doi.org/10.1016/j.cej.2018.09.020">"Development of a supramolecular accelerator simultaneously to increase the cross-linking density and ductility of an epoxy resin"</a>. <i>Chemical Engineering Journal</i>. <b>356</b>: 303–311. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2019ChEnJ.356..303S">2019ChEnJ.356..303S</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.cej.2018.09.020">10.1016/j.cej.2018.09.020</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/1385-8947">1385-8947</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chemical+Engineering+Journal&rft.atitle=Development+of+a+supramolecular+accelerator+simultaneously+to+increase+the+cross-linking+density+and+ductility+of+an+epoxy+resin&rft.volume=356&rft.pages=303-311&rft.date=2019-01&rft.issn=1385-8947&rft_id=info%3Adoi%2F10.1016%2Fj.cej.2018.09.020&rft_id=info%3Abibcode%2F2019ChEnJ.356..303S&rft.aulast=Seo&rft.aufirst=Jiae&rft.au=Yui%2C+Nobuhiko&rft.au=Seo%2C+Ji-Hun&rft_id=https%3A%2F%2Fdoi.org%2F10.1016%2Fj.cej.2018.09.020&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAmine" class="Z3988"></span></span> </li> <li id="cite_note-32"><span class="mw-cite-backlink"><b><a href="#cite_ref-32">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFChenLiuDu2023" class="citation journal cs1">Chen, Fengjun; Liu, Fan; Du, Xiaogang (10 January 2023). <a rel="nofollow" class="external text" href="https://onlinelibrary.wiley.com/doi/10.1002/app.53302">"Molecular dynamics simulation of crosslinking process and mechanical properties of epoxy under the accelerator"</a>. <i>Journal of Applied Polymer Science</i>. <b>140</b> (2). <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fapp.53302">10.1002/app.53302</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0021-8995">0021-8995</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Applied+Polymer+Science&rft.atitle=Molecular+dynamics+simulation+of+crosslinking+process+and+mechanical+properties+of+epoxy+under+the+accelerator&rft.volume=140&rft.issue=2&rft.date=2023-01-10&rft_id=info%3Adoi%2F10.1002%2Fapp.53302&rft.issn=0021-8995&rft.aulast=Chen&rft.aufirst=Fengjun&rft.au=Liu%2C+Fan&rft.au=Du%2C+Xiaogang&rft_id=https%3A%2F%2Fonlinelibrary.wiley.com%2Fdoi%2F10.1002%2Fapp.53302&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAmine" 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=Amine&action=edit&section=32" title="Edit section: Further reading"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://courses.lumenlearning.com/introchem/chapter/amines/#:~:text=The%20amine%20functional%20group%20contains,by%20a%20carbon-containing%20substituent.&text=Amine%20groups%20bonded%20to%20an,are%20known%20as%20aromatic%20amines.">"Amines | Introduction to Chemistry"</a>. <i>courses.lumenlearning.com</i><span class="reference-accessdate">. Retrieved <span class="nowrap">22 July</span> 2021</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=courses.lumenlearning.com&rft.atitle=Amines+%7C+Introduction+to+Chemistry&rft_id=https%3A%2F%2Fcourses.lumenlearning.com%2Fintrochem%2Fchapter%2Famines%2F%23%3A~%3Atext%3DThe%2520amine%2520functional%2520group%2520contains%2Cby%2520a%2520carbon-containing%2520substituent.%26text%3DAmine%2520groups%2520bonded%2520to%2520an%2Care%2520known%2520as%2520aromatic%2520amines.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAmine" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFlick1993" class="citation book cs1">Flick, Ernest W. (1993). <a rel="nofollow" class="external text" href="https://www.worldcat.org/oclc/915134542"><i>Epoxy Resins, Curing Agents, Compounds, and Modifiers: An Industrial Guide</i></a>. Park Ridge, NJ: Noyes Publications. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-8155-1708-5" title="Special:BookSources/978-0-8155-1708-5"><bdi>978-0-8155-1708-5</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/915134542">915134542</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Epoxy+Resins%2C+Curing+Agents%2C+Compounds%2C+and+Modifiers%3A+An+Industrial+Guide&rft.place=Park+Ridge%2C+NJ&rft.pub=Noyes+Publications&rft.date=1993&rft_id=info%3Aoclcnum%2F915134542&rft.isbn=978-0-8155-1708-5&rft.aulast=Flick&rft.aufirst=Ernest+W.&rft_id=https%3A%2F%2Fwww.worldcat.org%2Foclc%2F915134542&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAmine" class="Z3988"></span></li></ul> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Amine&action=edit&section=33" title="Edit section: External links"><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 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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 class="mw-selflink selflink">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"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"></div><div role="navigation" class="navbox" aria-labelledby="Nitrogen_species" 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:Nitrogen_compounds" title="Template:Nitrogen compounds"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Nitrogen_compounds" title="Template talk:Nitrogen compounds"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Nitrogen_compounds" title="Special:EditPage/Template:Nitrogen compounds"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Nitrogen_species" style="font-size:114%;margin:0 4em"><a href="/wiki/Nitrogen" title="Nitrogen">Nitrogen</a> species</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Hydrides</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/Ammonia" title="Ammonia">NH<sub>3</sub></a></li> <li><a href="/wiki/Ammonium" title="Ammonium"><span class="chemf nowrap">NH<span class="template-chem2-su"><span>+</span><span>4</span></span></span></a></li> <li><a href="/wiki/Metal_amides#Alkali_metal_amides" title="Metal amides"><span class="chemf nowrap">NH<span class="template-chem2-su"><span>−</span><span>2</span></span></span></a></li> <li><a href="/wiki/Nitride" title="Nitride">N<sup>3−</sup></a></li> <li><a href="/wiki/Hydroxylamine" title="Hydroxylamine">NH<sub>2</sub>OH</a></li> <li><a href="/wiki/Hydrazine" title="Hydrazine">N<sub>2</sub>H<sub>4</sub></a></li> <li><a href="/wiki/Hydrazoic_acid" title="Hydrazoic acid">HN<sub>3</sub></a></li> <li><a href="/wiki/Azide" title="Azide"><span class="chemf nowrap">N<span class="template-chem2-su"><span>−</span><span>3</span></span></span></a></li> <li><a href="/wiki/Nitrogen_pentahydride" title="Nitrogen pentahydride"><i>NH<sub>5</sub></i></a> (?)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Organic</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 class="mw-selflink selflink">NR<sub>3</sub></a></li> <li><a href="/wiki/Imine" title="Imine">>C=NR</a></li> <li><a href="/wiki/Amide" title="Amide">−CONR<sub>2</sub></a></li> <li><a href="/wiki/Nitrile" title="Nitrile">−CN</a></li> <li><a href="/wiki/Hydrogen_cyanide" title="Hydrogen cyanide">HCN</a></li> <li><a href="/wiki/Cyanide" title="Cyanide">CN<sup>−</sup></a></li> <li><a href="/wiki/Cyanogen" title="Cyanogen">(CN)<sub>2</sub></a></li> <li><a href="/wiki/Cyanamide" title="Cyanamide">H<sub>2</sub>NCN</a></li> <li><a href="/wiki/Cyanate" title="Cyanate">HOCN</a></li> <li><a href="/wiki/Isocyanate" title="Isocyanate">HNCO</a></li> <li><a href="/wiki/Isothiocyanate" title="Isothiocyanate">HNCS</a></li> <li><a href="/wiki/Diazomethane" title="Diazomethane">CH<sub>2</sub>N<sub>2</sub></a></li> <li><a href="/wiki/Nitroso" title="Nitroso">−NO</a></li> <li><a href="/wiki/Nitro_compound" title="Nitro compound">−NO<sub>2</sub></a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nitrogen_oxide" title="Nitrogen oxide">Oxides</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/Nitric_oxide" title="Nitric oxide">NO</a> / <a href="/wiki/Dinitrogen_dioxide" title="Dinitrogen dioxide">(NO)<sub>2</sub></a></li> <li><a href="/wiki/Dinitrogen_trioxide" title="Dinitrogen trioxide">N<sub>2</sub>O<sub>3</sub></a></li> <li><a href="/wiki/Nitrous_acid" title="Nitrous acid">HNO<sub>2</sub></a> / <a href="/wiki/Nitrite" title="Nitrite"><span class="chemf nowrap">NO<span class="template-chem2-su"><span>−</span><span>2</span></span></span></a> / <a href="/wiki/Nitrosonium" title="Nitrosonium">NO<sup>+</sup></a></li> <li><a href="/wiki/Nitrogen_dioxide" title="Nitrogen dioxide">NO<sub>2</sub></a> / <a href="/wiki/Dinitrogen_tetroxide" title="Dinitrogen tetroxide">(NO<sub>2</sub>)<sub>2</sub></a></li> <li><a href="/wiki/Dinitrogen_pentoxide" title="Dinitrogen pentoxide">N<sub>2</sub>O<sub>5</sub></a></li> <li><a href="/wiki/Nitric_acid" title="Nitric acid">HNO<sub>3</sub></a> / <a href="/wiki/Nitrate" title="Nitrate"><span class="chemf nowrap">NO<span class="template-chem2-su"><span>−</span><span>3</span></span></span></a> / <a href="/wiki/Nitronium" class="mw-redirect" title="Nitronium"><span class="chemf nowrap">NO<span class="template-chem2-su"><span>+</span><span>2</span></span></span></a></li> <li><a href="/wiki/Nitrate_radical" title="Nitrate radical">NO<sub>3</sub></a></li> <li><a href="/wiki/Nitroxyl" title="Nitroxyl">HNO</a> / <a href="/wiki/Hyponitrous_acid" title="Hyponitrous acid">(HON)<sub>2</sub></a> / <a href="/wiki/Hyponitrite" title="Hyponitrite"><span class="chemf nowrap">N<sub class="template-chem2-sub">2</sub>O<span class="template-chem2-su"><span>−</span><span>2</span></span></span></a> / <a href="/wiki/Nitrous_oxide" title="Nitrous oxide">N<sub>2</sub>O</a></li> <li><a href="/wiki/Nitramide" title="Nitramide">H<sub>2</sub>NNO<sub>2</sub></a></li> <li><a href="/wiki/Peroxynitrous_acid" title="Peroxynitrous acid">HO<sub>2</sub>NO</a> / <a href="/wiki/Peroxynitrite" title="Peroxynitrite">ONOO<sup>−</sup></a></li> <li><a href="/wiki/Peroxynitric_acid" title="Peroxynitric acid">HO<sub>2</sub>NO<sub>2</sub></a> / <a href="/wiki/Peroxynitrate" title="Peroxynitrate">O<sub>2</sub>NOO<sup>−</sup></a></li> <li><a href="/wiki/Orthonitrate" title="Orthonitrate"><span class="chemf nowrap">NO<span class="template-chem2-su"><span>−</span><span>4</span></span></span></a></li> <li><a href="/wiki/Nitroxylic_acid" title="Nitroxylic acid">H<sub>4</sub>N<sub>2</sub>O<sub>4</sub></a> / <a href="/wiki/Angeli%27s_salt" title="Angeli's salt"><span class="chemf nowrap">N<sub class="template-chem2-sub">2</sub>O<span class="template-chem2-su"><span>2−</span><span>3</span></span></span></a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Halides</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/Nitrogen_monofluoride" title="Nitrogen monofluoride">NF</a></li> <li><a href="/wiki/Nitrogen_difluoride" title="Nitrogen difluoride">NF<sub>2</sub></a></li> <li><a href="/wiki/Nitrogen_trifluoride" title="Nitrogen trifluoride">NF<sub>3</sub></a></li> <li><a href="/wiki/Nitrogen_pentafluoride" title="Nitrogen pentafluoride"><i>NF<sub>5</sub></i></a> (?)</li> <li><a href="/wiki/Nitrogen_trichloride" title="Nitrogen trichloride">NCl<sub>3</sub></a></li> <li><a href="/wiki/Nitrogen_tribromide" title="Nitrogen tribromide">NBr<sub>3</sub></a></li> <li><a href="/wiki/Nitrogen_triiodide" title="Nitrogen triiodide">NI<sub>3</sub></a></li> <li><a href="/wiki/Fluorine_azide" title="Fluorine azide">FN<sub>3</sub></a></li> <li><a href="/wiki/Chlorine_azide" title="Chlorine azide">ClN<sub>3</sub></a></li> <li><a href="/wiki/Bromine_azide" title="Bromine azide">BrN<sub>3</sub></a></li> <li><a href="/wiki/Iodine_azide" title="Iodine azide">IN<sub>3</sub></a></li> <li><a href="/wiki/Fluoroamine" title="Fluoroamine">NH<sub>2</sub>F</a></li> <li><a href="/wiki/Dinitrogen_difluoride" title="Dinitrogen difluoride">N<sub>2</sub>F<sub>2</sub></a></li> <li><a href="/wiki/Monochloramine" title="Monochloramine">NH<sub>2</sub>Cl</a></li> <li><a href="/w/index.php?title=Difluoramine&action=edit&redlink=1" class="new" title="Difluoramine (page does not exist)">NHF<sub>2</sub></a></li> <li><a href="/wiki/Dichloramine" title="Dichloramine">NHCl<sub>2</sub></a></li> <li><a href="/w/index.php?title=Dibromamine&action=edit&redlink=1" class="new" title="Dibromamine (page does not exist)">NHBr<sub>2</sub></a></li> <li><a href="/w/index.php?title=Diiodoamine&action=edit&redlink=1" class="new" title="Diiodoamine (page does not exist)">NHI<sub>2</sub></a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Oxidation_state" title="Oxidation state">Oxidation states</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"><span style="font-size:112%;"><b><a href="/wiki/Nitride" title="Nitride">−3</a></b></span>, <a href="/wiki/Hydrazine" title="Hydrazine">−2</a>, <a href="/wiki/Hydroxylamine" title="Hydroxylamine">−1</a>, 0, <a href="/wiki/Nitroxyl" title="Nitroxyl">+1</a>, <a href="/wiki/Nitric_oxide" title="Nitric oxide">+2</a>, <span style="font-size:112%;"><b><a href="/wiki/Nitrite" title="Nitrite">+3</a></b></span>, <a href="/wiki/Nitrogen_dioxide" title="Nitrogen dioxide">+4</a>, <span style="font-size:112%;"><b><a href="/wiki/Nitrate" title="Nitrate">+5</a></b></span> (a strongly <a href="/wiki/Acid" title="Acid">acidic</a> oxide)</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"></div><div role="navigation" 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