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<li id="toc-Definitions_and_general_characteristics" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Definitions_and_general_characteristics"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.1</span> <span>Definitions and general characteristics</span> </div> </a> <ul id="toc-Definitions_and_general_characteristics-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Bond_strength" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Bond_strength"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.2</span> <span>Bond strength</span> </div> </a> <ul id="toc-Bond_strength-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Resonance_assisted_hydrogen_bond" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Resonance_assisted_hydrogen_bond"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.3</span> <span>Resonance assisted hydrogen bond</span> </div> </a> <ul id="toc-Resonance_assisted_hydrogen_bond-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Structural_details" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Structural_details"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.4</span> <span>Structural details</span> </div> </a> <ul id="toc-Structural_details-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Spectroscopy" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Spectroscopy"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.5</span> <span>Spectroscopy</span> </div> </a> <ul id="toc-Spectroscopy-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Theoretical_considerations" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Theoretical_considerations"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.6</span> <span>Theoretical considerations</span> </div> </a> <ul id="toc-Theoretical_considerations-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-History" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#History"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>History</span> </div> </a> <ul id="toc-History-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Hydrogen_bonds_in_small_molecules" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Hydrogen_bonds_in_small_molecules"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Hydrogen bonds in small molecules</span> </div> </a> <button aria-controls="toc-Hydrogen_bonds_in_small_molecules-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 Hydrogen bonds in small molecules subsection</span> </button> <ul id="toc-Hydrogen_bonds_in_small_molecules-sublist" class="vector-toc-list"> <li id="toc-Water" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Water"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Water</span> </div> </a> <ul id="toc-Water-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Bifurcated_and_over-coordinated_hydrogen_bonds_in_water" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Bifurcated_and_over-coordinated_hydrogen_bonds_in_water"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Bifurcated and over-coordinated hydrogen bonds in water</span> </div> </a> <ul id="toc-Bifurcated_and_over-coordinated_hydrogen_bonds_in_water-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Other_liquids" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Other_liquids"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.3</span> <span>Other liquids</span> </div> </a> <ul id="toc-Other_liquids-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Further_manifestations_of_solvent_hydrogen_bonding" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Further_manifestations_of_solvent_hydrogen_bonding"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.4</span> <span>Further manifestations of solvent hydrogen bonding</span> </div> </a> <ul id="toc-Further_manifestations_of_solvent_hydrogen_bonding-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Hydrogen_bonds_in_polymers" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Hydrogen_bonds_in_polymers"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Hydrogen bonds in polymers</span> </div> </a> <button aria-controls="toc-Hydrogen_bonds_in_polymers-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 Hydrogen bonds in polymers subsection</span> </button> <ul id="toc-Hydrogen_bonds_in_polymers-sublist" class="vector-toc-list"> <li id="toc-DNA" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#DNA"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>DNA</span> </div> </a> <ul id="toc-DNA-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Proteins" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Proteins"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2</span> <span>Proteins</span> </div> </a> <ul id="toc-Proteins-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Other_polymers" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Other_polymers"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.3</span> <span>Other polymers</span> </div> </a> <ul id="toc-Other_polymers-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Symmetric_hydrogen_bond" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Symmetric_hydrogen_bond"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Symmetric hydrogen bond</span> </div> </a> <ul id="toc-Symmetric_hydrogen_bond-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Dihydrogen_bond" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Dihydrogen_bond"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Dihydrogen bond</span> </div> </a> <ul id="toc-Dihydrogen_bond-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Application_to_drugs" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Application_to_drugs"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Application to drugs</span> </div> </a> <ul id="toc-Application_to_drugs-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</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 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Further_reading"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</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 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">10</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">Hydrogen bond</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 67 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-67" 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">67 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/Waterstofbinding" title="Waterstofbinding – Afrikaans" lang="af" hreflang="af" data-title="Waterstofbinding" 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%B1%D8%A7%D8%A8%D8%B7%D8%A9_%D9%87%D9%8A%D8%AF%D8%B1%D9%88%D8%AC%D9%8A%D9%86%D9%8A%D8%A9" title="رابطة هيدروجينية – Arabic" lang="ar" hreflang="ar" data-title="رابطة هيدروجينية" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-an mw-list-item"><a href="https://an.wikipedia.org/wiki/Vinclo_d%27hidrocheno" title="Vinclo d'hidrocheno – Aragonese" lang="an" hreflang="an" data-title="Vinclo d'hidrocheno" data-language-autonym="Aragonés" data-language-local-name="Aragonese" class="interlanguage-link-target"><span>Aragonés</span></a></li><li class="interlanguage-link interwiki-ast mw-list-item"><a href="https://ast.wikipedia.org/wiki/Fuercia_per_ponte_d%27hidr%C3%B3xenu" title="Fuercia per ponte d'hidróxenu – Asturian" lang="ast" hreflang="ast" data-title="Fuercia per ponte d'hidróxenu" 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/Hidrogen_rabit%C9%99si" title="Hidrogen rabitəsi – Azerbaijani" lang="az" hreflang="az" data-title="Hidrogen rabitəsi" 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%B9%E0%A6%BE%E0%A6%87%E0%A6%A1%E0%A7%8D%E0%A6%B0%E0%A7%8B%E0%A6%9C%E0%A7%87%E0%A6%A8_%E0%A6%AC%E0%A6%A8%E0%A7%8D%E0%A6%A7%E0%A6%A8" title="হাইড্রোজেন বন্ধন – Bangla" lang="bn" hreflang="bn" data-title="হাইড্রোজেন বন্ধন" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-zh-min-nan mw-list-item"><a href="https://zh-min-nan.wikipedia.org/wiki/Ch%C3%BAi-s%C3%B2%CD%98_kiat-ha%CC%8Dp" title="Chúi-sò͘ kiat-ha̍p – Minnan" lang="nan" hreflang="nan" data-title="Chúi-sò͘ kiat-ha̍p" data-language-autonym="閩南語 / Bân-lâm-gú" data-language-local-name="Minnan" class="interlanguage-link-target"><span>閩南語 / Bân-lâm-gú</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%92%D0%B0%D0%B4%D0%B0%D1%80%D0%BE%D0%B4%D0%BD%D0%B0%D1%8F_%D1%81%D1%83%D0%B2%D1%8F%D0%B7%D1%8C" title="Вадародная сувязь – Belarusian" lang="be" hreflang="be" data-title="Вадародная сувязь" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%92%D0%BE%D0%B4%D0%BE%D1%80%D0%BE%D0%B4%D0%BD%D0%B0_%D0%B2%D1%80%D1%8A%D0%B7%D0%BA%D0%B0" title="Водородна връзка – Bulgarian" lang="bg" hreflang="bg" data-title="Водородна връзка" 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/Vodikova_veza" title="Vodikova veza – Bosnian" lang="bs" hreflang="bs" data-title="Vodikova veza" 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/Enlla%C3%A7_per_pont_d%27hidrogen" title="Enllaç per pont d'hidrogen – Catalan" lang="ca" hreflang="ca" data-title="Enllaç per pont d'hidrogen" 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/Vod%C3%ADkov%C3%A1_vazba" title="Vodíková vazba – Czech" lang="cs" hreflang="cs" data-title="Vodíková vazba" 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/Bond_hydrogen" title="Bond hydrogen – Welsh" lang="cy" hreflang="cy" data-title="Bond hydrogen" 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/Hydrogenbinding" title="Hydrogenbinding – Danish" lang="da" hreflang="da" data-title="Hydrogenbinding" 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/Wasserstoffbr%C3%BCckenbindung" title="Wasserstoffbrückenbindung – German" lang="de" hreflang="de" data-title="Wasserstoffbrückenbindung" 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/Vesinikside" title="Vesinikside – Estonian" lang="et" hreflang="et" data-title="Vesinikside" 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%94%CE%B5%CF%83%CE%BC%CF%8C%CF%82_%CF%85%CE%B4%CF%81%CE%BF%CE%B3%CF%8C%CE%BD%CE%BF%CF%85" title="Δεσμός υδρογόνου – Greek" lang="el" hreflang="el" data-title="Δεσμός υδρογόνου" 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/Enlace_de_hidr%C3%B3geno" title="Enlace de hidrógeno – Spanish" lang="es" hreflang="es" data-title="Enlace de hidrógeno" 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/Hidrogena_ligo" title="Hidrogena ligo – Esperanto" lang="eo" hreflang="eo" data-title="Hidrogena ligo" 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/Hidrogeno_lotura" title="Hidrogeno lotura – Basque" lang="eu" hreflang="eu" data-title="Hidrogeno lotura" 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/%D9%BE%DB%8C%D9%88%D9%86%D8%AF_%D9%87%DB%8C%D8%AF%D8%B1%D9%88%DA%98%D9%86%DB%8C" title="پیوند هیدروژنی – Persian" lang="fa" hreflang="fa" data-title="پیوند هیدروژنی" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Liaison_hydrog%C3%A8ne" title="Liaison hydrogène – French" lang="fr" hreflang="fr" data-title="Liaison hydrogène" 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/Nasc_hidrigine" title="Nasc hidrigine – Irish" lang="ga" hreflang="ga" data-title="Nasc hidrigine" 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/Ponte_de_hidr%C3%B3xeno" title="Ponte de hidróxeno – Galician" lang="gl" hreflang="gl" data-title="Ponte de hidróxeno" 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%88%98%EC%86%8C_%EA%B2%B0%ED%95%A9" title="수소 결합 – Korean" lang="ko" hreflang="ko" data-title="수소 결합" 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/%D5%8B%D6%80%D5%A1%D5%AE%D5%B6%D5%A1%D5%B5%D5%AB%D5%B6_%D5%AF%D5%A1%D5%BA" title="Ջրածնային կապ – Armenian" lang="hy" hreflang="hy" data-title="Ջրածնային կապ" 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%B9%E0%A4%BE%E0%A4%87%E0%A4%A1%E0%A5%8D%E0%A4%B0%E0%A5%8B%E0%A4%9C%E0%A4%A8_%E0%A4%86%E0%A4%AC%E0%A4%82%E0%A4%A7" title="हाइड्रोजन आबंध – Hindi" lang="hi" hreflang="hi" data-title="हाइड्रोजन आबंध" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-hr badge-Q70893996 mw-list-item" title=""><a href="https://hr.wikipedia.org/wiki/Vodikova_veza" title="Vodikova veza – Croatian" lang="hr" hreflang="hr" data-title="Vodikova veza" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Ikatan_hidrogen" title="Ikatan hidrogen – Indonesian" lang="id" hreflang="id" data-title="Ikatan hidrogen" 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/Legame_a_idrogeno" title="Legame a idrogeno – Italian" lang="it" hreflang="it" data-title="Legame a idrogeno" 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%A7%D7%A9%D7%A8_%D7%9E%D7%99%D7%9E%D7%9F" title="קשר מימן – Hebrew" lang="he" hreflang="he" data-title="קשר מימן" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-ka mw-list-item"><a href="https://ka.wikipedia.org/wiki/%E1%83%AC%E1%83%A7%E1%83%90%E1%83%9A%E1%83%91%E1%83%90%E1%83%93%E1%83%A3%E1%83%A0%E1%83%98_%E1%83%91%E1%83%9B%E1%83%90" title="წყალბადური ბმა – Georgian" lang="ka" hreflang="ka" data-title="წყალბადური ბმა" 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%A1%D1%83%D1%82%D0%B5%D0%BA%D1%82%D1%96%D0%BA_%D0%B1%D0%B0%D0%B9%D0%BB%D0%B0%D0%BD%D1%8B%D1%81" title="Сутектік байланыс – Kazakh" lang="kk" hreflang="kk" data-title="Сутектік байланыс" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-ht mw-list-item"><a href="https://ht.wikipedia.org/wiki/Lyezon_idwoj%C3%A8n" title="Lyezon idwojèn – Haitian Creole" lang="ht" hreflang="ht" data-title="Lyezon idwojèn" data-language-autonym="Kreyòl ayisyen" data-language-local-name="Haitian Creole" class="interlanguage-link-target"><span>Kreyòl ayisyen</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/%C5%AAde%C5%86ra%C5%BEa_saite" title="Ūdeņraža saite – Latvian" lang="lv" hreflang="lv" data-title="Ūdeņraža saite" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%92%D0%BE%D0%B4%D0%BE%D1%80%D0%BE%D0%B4%D0%BD%D0%B0_%D0%B2%D1%80%D1%81%D0%BA%D0%B0" title="Водородна врска – Macedonian" lang="mk" hreflang="mk" data-title="Водородна врска" 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%B9%E0%B5%88%E0%B4%A1%E0%B5%8D%E0%B4%B0%E0%B4%9C%E0%B5%BB_%E0%B4%AC%E0%B4%A8%E0%B5%8D%E0%B4%A7%E0%B4%A8%E0%B4%82" title="ഹൈഡ്രജൻ ബന്ധനം – Malayalam" lang="ml" hreflang="ml" data-title="ഹൈഡ്രജൻ ബന്ധനം" 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/Ikatan_hidrogen" title="Ikatan hidrogen – Malay" lang="ms" hreflang="ms" data-title="Ikatan hidrogen" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-mn mw-list-item"><a href="https://mn.wikipedia.org/wiki/%D0%A3%D1%81%D1%82%D3%A9%D1%80%D3%A9%D0%B3%D1%87%D0%B8%D0%B9%D0%BD_%D1%85%D0%BE%D0%BB%D0%B1%D0%BE%D0%BE" title="Устөрөгчийн холбоо – Mongolian" lang="mn" hreflang="mn" data-title="Устөрөгчийн холбоо" data-language-autonym="Монгол" data-language-local-name="Mongolian" class="interlanguage-link-target"><span>Монгол</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Waterstofbrug" title="Waterstofbrug – Dutch" lang="nl" hreflang="nl" data-title="Waterstofbrug" 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/%E6%B0%B4%E7%B4%A0%E7%B5%90%E5%90%88" title="水素結合 – Japanese" lang="ja" hreflang="ja" data-title="水素結合" 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/Hydrogenbinding" title="Hydrogenbinding – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Hydrogenbinding" 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/Hydrogenbinding" title="Hydrogenbinding – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Hydrogenbinding" 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/Ligam_idrog%C3%A8n" title="Ligam idrogèn – Occitan" lang="oc" hreflang="oc" data-title="Ligam idrogèn" data-language-autonym="Occitan" data-language-local-name="Occitan" class="interlanguage-link-target"><span>Occitan</span></a></li><li class="interlanguage-link interwiki-om mw-list-item"><a href="https://om.wikipedia.org/wiki/Hidhoo_haayidiroojiinii" title="Hidhoo haayidiroojiinii – Oromo" lang="om" hreflang="om" data-title="Hidhoo haayidiroojiinii" data-language-autonym="Oromoo" data-language-local-name="Oromo" class="interlanguage-link-target"><span>Oromoo</span></a></li><li class="interlanguage-link interwiki-pa mw-list-item"><a href="https://pa.wikipedia.org/wiki/%E0%A8%B9%E0%A8%BE%E0%A8%88%E0%A8%A1%E0%A8%B0%E0%A9%8B%E0%A8%9C%E0%A8%A8_%E0%A8%9C%E0%A9%8B%E0%A9%9C" title="ਹਾਈਡਰੋਜਨ ਜੋੜ – Punjabi" lang="pa" hreflang="pa" data-title="ਹਾਈਡਰੋਜਨ ਜੋੜ" data-language-autonym="ਪੰਜਾਬੀ" data-language-local-name="Punjabi" class="interlanguage-link-target"><span>ਪੰਜਾਬੀ</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Wi%C4%85zanie_wodorowe" title="Wiązanie wodorowe – Polish" lang="pl" hreflang="pl" data-title="Wiązanie wodorowe" 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/Liga%C3%A7%C3%A3o_de_hidrog%C3%AAnio" title="Ligação de hidrogênio – Portuguese" lang="pt" hreflang="pt" data-title="Ligação de hidrogênio" 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/Leg%C4%83tur%C4%83_de_hidrogen" title="Legătură de hidrogen – Romanian" lang="ro" hreflang="ro" data-title="Legătură de hidrogen" 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%92%D0%BE%D0%B4%D0%BE%D1%80%D0%BE%D0%B4%D0%BD%D0%B0%D1%8F_%D1%81%D0%B2%D1%8F%D0%B7%D1%8C" title="Водородная связь – Russian" lang="ru" hreflang="ru" data-title="Водородная связь" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sq mw-list-item"><a href="https://sq.wikipedia.org/wiki/Lidhja_e_Hidrogjenit" title="Lidhja e Hidrogjenit – Albanian" lang="sq" hreflang="sq" data-title="Lidhja e Hidrogjenit" data-language-autonym="Shqip" data-language-local-name="Albanian" class="interlanguage-link-target"><span>Shqip</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Hydrogen_bond" title="Hydrogen bond – Simple English" lang="en-simple" hreflang="en-simple" data-title="Hydrogen bond" 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/Vod%C3%ADkov%C3%A1_v%C3%A4zba" title="Vodíková väzba – Slovak" lang="sk" hreflang="sk" data-title="Vodíková väzba" 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/Vodikova_vez" title="Vodikova vez – Slovenian" lang="sl" hreflang="sl" data-title="Vodikova vez" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/%D0%92%D0%BE%D0%B4%D0%BE%D0%BD%D0%B8%D1%87%D0%BD%D0%B0_%D0%B2%D0%B5%D0%B7%D0%B0" title="Водонична веза – Serbian" lang="sr" hreflang="sr" data-title="Водонична веза" 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/Vodoni%C4%8Dna_veza" title="Vodonična veza – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Vodonična veza" 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/Vetysidos" title="Vetysidos – Finnish" lang="fi" hreflang="fi" data-title="Vetysidos" 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/V%C3%A4tebindning" title="Vätebindning – Swedish" lang="sv" hreflang="sv" data-title="Vätebindning" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-tl mw-list-item"><a href="https://tl.wikipedia.org/wiki/Hydrogen_bond" title="Hydrogen bond – Tagalog" lang="tl" hreflang="tl" data-title="Hydrogen bond" data-language-autonym="Tagalog" data-language-local-name="Tagalog" class="interlanguage-link-target"><span>Tagalog</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%90%E0%AE%A4%E0%AE%B0%E0%AE%9A%E0%AE%A9%E0%AF%8D_%E0%AE%AA%E0%AE%BF%E0%AE%A3%E0%AF%88%E0%AE%AA%E0%AF%8D%E0%AE%AA%E0%AF%81" title="ஐதரசன் பிணைப்பு – Tamil" lang="ta" hreflang="ta" data-title="ஐதரசன் பிணைப்பு" 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%B8%9E%E0%B8%B1%E0%B8%99%E0%B8%98%E0%B8%B0%E0%B9%84%E0%B8%AE%E0%B9%82%E0%B8%94%E0%B8%A3%E0%B9%80%E0%B8%88%E0%B8%99" title="พันธะไฮโดรเจน – Thai" lang="th" hreflang="th" data-title="พันธะไฮโดรเจน" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Hidrojen_ba%C4%9F%C4%B1" title="Hidrojen bağı – Turkish" lang="tr" hreflang="tr" data-title="Hidrojen bağı" 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%92%D0%BE%D0%B4%D0%BD%D0%B5%D0%B2%D0%B8%D0%B9_%D0%B7%D0%B2%27%D1%8F%D0%B7%D0%BE%D0%BA" title="Водневий зв'язок – Ukrainian" lang="uk" hreflang="uk" data-title="Водневий зв'язок" 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/Li%C3%AAn_k%E1%BA%BFt_hydro" title="Liên kết hydro – Vietnamese" lang="vi" hreflang="vi" data-title="Liên kết hydro" 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-wuu mw-list-item"><a href="https://wuu.wikipedia.org/wiki/%E6%B0%A2%E9%94%AE" title="氢键 – Wu" lang="wuu" hreflang="wuu" data-title="氢键" 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/%E6%B0%AB%E9%8D%B5" title="氫鍵 – Cantonese" lang="yue" hreflang="yue" data-title="氫鍵" 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/%E6%B0%A2%E9%94%AE" title="氢键 – Chinese" lang="zh" hreflang="zh" data-title="氢键" 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/Q169324#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/Hydrogen_bond" title="View the content page [c]" 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typeof="mw:File/Thumb"><a href="/wiki/File:3D_model_hydrogen_bonds_in_water.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c6/3D_model_hydrogen_bonds_in_water.svg/220px-3D_model_hydrogen_bonds_in_water.svg.png" decoding="async" width="220" height="218" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c6/3D_model_hydrogen_bonds_in_water.svg/330px-3D_model_hydrogen_bonds_in_water.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c6/3D_model_hydrogen_bonds_in_water.svg/440px-3D_model_hydrogen_bonds_in_water.svg.png 2x" data-file-width="400" data-file-height="397" /></a><figcaption>Model of hydrogen bonds (1) between molecules of <a href="/wiki/Properties_of_water" title="Properties of water">water</a></figcaption></figure> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:NTCDI_AFM2a.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0c/NTCDI_AFM2a.jpg/220px-NTCDI_AFM2a.jpg" decoding="async" width="220" height="437" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/0/0c/NTCDI_AFM2a.jpg 1.5x" data-file-width="255" data-file-height="507" /></a><figcaption><a href="/wiki/Non-contact_atomic_force_microscopy" title="Non-contact atomic force microscopy">AFM</a> image of <a href="/wiki/Naphthalenetetracarboxylic_diimide" title="Naphthalenetetracarboxylic diimide">naphthalenetetracarboxylic diimide</a> molecules on silver-terminated silicon, interacting via hydrogen bonding, taken at 77 K.<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> ("Hydrogen bonds" in the top image are exaggerated by artifacts of the imaging technique.<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><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><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>)</figcaption></figure> <p>In <a href="/wiki/Chemistry" title="Chemistry">chemistry</a>, a <b>hydrogen bond</b> (or <b>H-bond</b>) is primarily an <a href="/wiki/Electrostatics" title="Electrostatics">electrostatic</a> force of attraction between a <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a> (H) atom which is <a href="/wiki/Covalent_bond" title="Covalent bond">covalently bonded</a> to a more <a href="/wiki/Electronegativity" title="Electronegativity">electronegative</a> "donor" atom or group (Dn), and another electronegative atom bearing a <a href="/wiki/Lone_pair" title="Lone pair">lone pair</a> of electrons—the hydrogen bond acceptor (Ac). Such an interacting system is generally denoted <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">Dn−H···Ac</span>, where the solid line denotes a polar <a href="/wiki/Covalent_bond" title="Covalent bond">covalent bond</a>, and the dotted or dashed line indicates the hydrogen bond.<sup id="cite_ref-:0_5-0" class="reference"><a href="#cite_note-:0-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> The most frequent donor and acceptor atoms are the <a href="/wiki/Period_2_elements" class="mw-redirect" title="Period 2 elements">period 2 elements</a> <a href="/wiki/Nitrogen" title="Nitrogen">nitrogen</a> (N), <a href="/wiki/Oxygen" title="Oxygen">oxygen</a> (O), and <a href="/wiki/Fluorine" title="Fluorine">fluorine</a> (F). </p><p>Hydrogen bonds can be <a href="/wiki/Intermolecular" class="mw-redirect" title="Intermolecular">intermolecular</a> (occurring between separate molecules) or <a href="/wiki/Intramolecular_force" title="Intramolecular force">intramolecular</a> (occurring among parts of the same molecule).<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><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><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><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> The energy of a hydrogen bond depends on the geometry, the environment, and the nature of the specific donor and acceptor atoms and can vary between 1 and 40 kcal/mol.<sup id="cite_ref-The_Hydrogen_Bond_in_the_Solid_Stat_10-0" class="reference"><a href="#cite_note-The_Hydrogen_Bond_in_the_Solid_Stat-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> This makes them somewhat stronger than a <a href="/wiki/Van_der_Waals_force" title="Van der Waals force">van der Waals interaction</a>, and weaker than fully <a href="/wiki/Covalent_bond" title="Covalent bond">covalent</a> or <a href="/wiki/Ionic_bond" class="mw-redirect" title="Ionic bond">ionic bonds</a>. This type of bond can occur in inorganic molecules such as water and in <a href="/wiki/Organic_molecules" class="mw-redirect" title="Organic molecules">organic molecules</a> like DNA and proteins. Hydrogen bonds are responsible for holding materials such as <a href="/wiki/Paper" title="Paper">paper</a> and <a href="/wiki/Wool" title="Wool">felted wool</a> together, and for causing separate sheets of paper to stick together after becoming wet and subsequently drying. </p><p>The hydrogen bond is also responsible for many of the physical and chemical properties of compounds of N, O, and F that seem unusual compared with other similar structures. In particular, intermolecular hydrogen bonding is responsible for the high boiling point of <a href="/wiki/Water" title="Water">water</a> (100 °C) compared to the other <a href="/wiki/Hydrogen_chalcogenide" title="Hydrogen chalcogenide">group-16 hydrides</a> that have much weaker hydrogen bonds.<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> Intramolecular hydrogen bonding is partly responsible for the <a href="/wiki/Secondary_structure" class="mw-redirect" title="Secondary structure">secondary</a> and <a href="/wiki/Tertiary_structure" class="mw-redirect" title="Tertiary structure">tertiary</a> structures of <a href="/wiki/Protein" title="Protein">proteins</a> and <a href="/wiki/Nucleic_acid" title="Nucleic acid">nucleic acids</a>. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Bonding">Bonding</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hydrogen_bond&action=edit&section=1" title="Edit section: Bonding"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Hydrogen_Bond_Quadruple_AngewChemIntEd_1998_v37_p75.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2d/Hydrogen_Bond_Quadruple_AngewChemIntEd_1998_v37_p75.jpg/300px-Hydrogen_Bond_Quadruple_AngewChemIntEd_1998_v37_p75.jpg" decoding="async" width="300" height="243" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/2d/Hydrogen_Bond_Quadruple_AngewChemIntEd_1998_v37_p75.jpg/450px-Hydrogen_Bond_Quadruple_AngewChemIntEd_1998_v37_p75.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/2d/Hydrogen_Bond_Quadruple_AngewChemIntEd_1998_v37_p75.jpg/600px-Hydrogen_Bond_Quadruple_AngewChemIntEd_1998_v37_p75.jpg 2x" data-file-width="1138" data-file-height="922" /></a><figcaption>An example of <a href="/wiki/Intermolecular" class="mw-redirect" title="Intermolecular">intermolecular</a> hydrogen bonding in a <a href="/wiki/Molecular_self-assembly" title="Molecular self-assembly">self-assembled</a> dimer complex.<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> The hydrogen bonds are represented by dotted lines.</figcaption></figure> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Acetylacetone_tautomerism.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3b/Acetylacetone_tautomerism.svg/300px-Acetylacetone_tautomerism.svg.png" decoding="async" width="300" height="37" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3b/Acetylacetone_tautomerism.svg/450px-Acetylacetone_tautomerism.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3b/Acetylacetone_tautomerism.svg/600px-Acetylacetone_tautomerism.svg.png 2x" data-file-width="415" data-file-height="51" /></a><figcaption><a href="/wiki/Intramolecular_force" title="Intramolecular force">Intramolecular</a> hydrogen bonding in <a href="/wiki/Acetylacetone" title="Acetylacetone">acetylacetone</a> helps stabilize the <a href="/wiki/Enol" title="Enol">enol</a> <a href="/wiki/Tautomer" title="Tautomer">tautomer</a>.</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Definitions_and_general_characteristics">Definitions and general characteristics</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hydrogen_bond&action=edit&section=2" title="Edit section: Definitions and general characteristics"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In a hydrogen bond, the electronegative atom not covalently attached to the hydrogen is named the proton acceptor, whereas the one covalently bound to the hydrogen is named the proton donor. This nomenclature is recommended by the IUPAC.<sup id="cite_ref-:0_5-1" class="reference"><a href="#cite_note-:0-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> The hydrogen of the donor is protic and therefore can act as a Lewis acid and the acceptor is the Lewis base. Hydrogen bonds are represented as <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">H···Y</span> system, where the dots represent the hydrogen bond. Liquids that display hydrogen bonding (such as water) are called <b>associated liquids</b>.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (June 2023)">citation needed</span></a></i>]</sup> </p> <figure typeof="mw:File/Thumb"><a href="/wiki/File:H-donor-acceptor.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8c/H-donor-acceptor.svg/299px-H-donor-acceptor.svg.png" decoding="async" width="299" height="320" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8c/H-donor-acceptor.svg/449px-H-donor-acceptor.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8c/H-donor-acceptor.svg/599px-H-donor-acceptor.svg.png 2x" data-file-width="550" data-file-height="588" /></a><figcaption>Examples of hydrogen bond donating (donors) and hydrogen bond accepting groups (acceptors)</figcaption></figure> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Acetic_Acid_Hydrogenbridge_V.1.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/be/Acetic_Acid_Hydrogenbridge_V.1.svg/300px-Acetic_Acid_Hydrogenbridge_V.1.svg.png" decoding="async" width="300" height="100" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/be/Acetic_Acid_Hydrogenbridge_V.1.svg/450px-Acetic_Acid_Hydrogenbridge_V.1.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/be/Acetic_Acid_Hydrogenbridge_V.1.svg/600px-Acetic_Acid_Hydrogenbridge_V.1.svg.png 2x" data-file-width="448" data-file-height="150" /></a><figcaption>Cyclic dimer of acetic acid; dashed <span style="color:green;"><b>green</b></span> lines represent hydrogen bonds</figcaption></figure> <p>Hydrogen bonds arise from a combination of electrostatics (multipole-multipole and multipole-induced multipole interactions), covalency (charge transfer by orbital overlap), and dispersion (<a href="/wiki/London_dispersion_force" title="London dispersion force">London forces</a>).<sup id="cite_ref-:0_5-2" class="reference"><a href="#cite_note-:0-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p>In weaker hydrogen bonds,<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> hydrogen atoms tend to bond to elements such as sulfur (S) or chlorine (Cl); even carbon (C) can serve as a donor, particularly when the carbon or one of its neighbors is electronegative (e.g., in chloroform, aldehydes and terminal acetylenes).<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> Gradually, it was recognized that there are many examples of weaker hydrogen bonding involving donor other than N, O, or F and/or acceptor Ac with electronegativity approaching that of hydrogen (rather than being much more electronegative). Although weak (≈1 kcal/mol), "non-traditional" hydrogen bonding interactions are ubiquitous and influence structures of many kinds of materials.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (June 2023)">citation needed</span></a></i>]</sup> </p><p>The definition of hydrogen bonding has gradually broadened over time to include these weaker attractive interactions. In 2011, an <a href="/wiki/IUPAC" class="mw-redirect" title="IUPAC">IUPAC</a> Task Group recommended a modern evidence-based definition of hydrogen bonding, which was published in the IUPAC journal <i><a href="/wiki/Pure_and_Applied_Chemistry" title="Pure and Applied Chemistry">Pure and Applied Chemistry</a></i>. This definition specifies: </p> <style data-mw-deduplicate="TemplateStyles:r1244412712">.mw-parser-output .templatequote{overflow:hidden;margin:1em 0;padding:0 32px}.mw-parser-output .templatequotecite{line-height:1.5em;text-align:left;margin-top:0}@media(min-width:500px){.mw-parser-output .templatequotecite{padding-left:1.6em}}</style><blockquote class="templatequote"><p>The hydrogen bond is an attractive interaction between a hydrogen atom from a molecule or a molecular fragment <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">X−H</span> in which X is more electronegative than H, and an atom or a group of atoms in the same or another molecule, in which there is evidence of bond formation.<sup id="cite_ref-arunen2011_16-0" class="reference"><a href="#cite_note-arunen2011-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup></p></blockquote> <div class="mw-heading mw-heading3"><h3 id="Bond_strength">Bond strength</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hydrogen_bond&action=edit&section=3" title="Edit section: Bond strength"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Hydrogen bonds can vary in strength from weak (1–2 kJ/mol) to strong (161.5 kJ/mol in the <a href="/wiki/Bifluoride" title="Bifluoride">bifluoride</a> ion, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">HF<span class="template-chem2-su"><span>−</span><span>2</span></span></span>).<sup id="cite_ref-halide_17-0" class="reference"><a href="#cite_note-halide-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Emsley_18-0" class="reference"><a href="#cite_note-Emsley-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> Typical <a href="/wiki/Enthalpy" title="Enthalpy">enthalpies</a> in vapor include:<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> </p> <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">F−H···:F<sup class="template-chem2-sup">−</sup></span> (161.5 kJ/mol or 38.6 kcal/mol), illustrated uniquely by <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">HF<span class="template-chem2-su"><span>−</span><span>2</span></span></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">O−H···:N</span> (29 kJ/mol or 6.9 kcal/mol), illustrated water-ammonia</li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">O−H···:O</span> (21 kJ/mol or 5.0 kcal/mol), illustrated water-water, alcohol-alcohol</li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">N−H···:N</span> (13 kJ/mol or 3.1 kcal/mol), illustrated by ammonia-ammonia</li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">N−H···:O</span> (8 kJ/mol or 1.9 kcal/mol), illustrated water-amide</li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">OH<span class="template-chem2-su"><span>+</span><span>3</span></span>···:OH<sub class="template-chem2-sub">2</sub></span> (18 kJ/mol<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> or 4.3 kcal/mol)</li></ul> <p>The strength of intermolecular hydrogen bonds is most often evaluated by measurements of equilibria between molecules containing donor and/or acceptor units, most often in solution.<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> The strength of intramolecular hydrogen bonds can be studied with equilibria between conformers with and without hydrogen bonds. The most important method for the identification of hydrogen bonds also in complicated molecules is <a href="/wiki/Crystallography" title="Crystallography">crystallography</a>, sometimes also NMR-spectroscopy. Structural details, in particular distances between donor and acceptor which are smaller than the sum of the van der Waals radii can be taken as indication of the hydrogen bond strength. One scheme gives the following somewhat arbitrary classification: those that are 15 to 40 kcal/mol, 5 to 15 kcal/mol, and >0 to 5 kcal/mol are considered strong, moderate, and weak, respectively.<sup id="cite_ref-Emsley_18-1" class="reference"><a href="#cite_note-Emsley-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p><p>Hydrogen bonds involving C-H bonds are both very rare and weak.<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="Resonance_assisted_hydrogen_bond">Resonance assisted hydrogen bond</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hydrogen_bond&action=edit&section=4" title="Edit section: Resonance assisted hydrogen bond"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The <b>resonance assisted hydrogen bond</b> (commonly abbreviated as RAHB) is a strong type of hydrogen bond. It is characterized by the π-delocalization that involves the hydrogen and cannot be properly described by the <a href="/wiki/Electrostatic" class="mw-redirect" title="Electrostatic">electrostatic</a> model alone. This description of the hydrogen bond has been proposed to describe unusually short distances generally observed between <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">O=C−OH···</span> or <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">···O=C−C=C−OH</span>.<sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Structural_details">Structural details</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hydrogen_bond&action=edit&section=5" title="Edit section: Structural details"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">X−H</span> distance is typically ≈110 <a href="/wiki/Picometre" title="Picometre">pm</a>, whereas the <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">H···Y</span> distance is ≈160 to 200 pm. The typical length of a hydrogen bond in water is 197 pm. The ideal bond angle depends on the nature of the hydrogen bond donor. The following hydrogen bond angles between a hydrofluoric acid donor and various acceptors have been determined experimentally:<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> <table class="wikitable" style="text-align:left"> <tbody><tr> <th><span class="nowrap">Acceptor···donor</span></th> <th>VSEPR geometry</th> <th>Angle (°) </th></tr> <tr> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">HCN···HF</span></td> <td>linear</td> <td style="text-align:right">180 </td></tr> <tr> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>CO···HF</span></td> <td>trigonal planar</td> <td style="text-align:right">120 </td></tr> <tr> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>O···HF</span></td> <td>pyramidal</td> <td style="text-align:right">46 </td></tr> <tr> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>S···HF</span></td> <td>pyramidal</td> <td style="text-align:right">89 </td></tr> <tr> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">SO<sub class="template-chem2-sub">2</sub>···HF</span><sup class="noprint Inline-Template" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Verifiability" title="Wikipedia:Verifiability"><span title="Is it the oxygen(s) acceptor, or by analogy to rest of table should it be O2S...HF with S acceptor? (October 2022)">verification needed</span></a></i>]</sup></td> <td>trigonal</td> <td style="text-align:right">142 </td></tr> </tbody></table> <div class="mw-heading mw-heading3"><h3 id="Spectroscopy">Spectroscopy</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hydrogen_bond&action=edit&section=6" title="Edit section: Spectroscopy"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Strong hydrogen bonds are revealed by downfield shifts in the <a href="/wiki/Proton_NMR_spectroscopy" class="mw-redirect" title="Proton NMR spectroscopy"><sup>1</sup>H NMR spectrum</a>. For example, the acidic proton in the enol tautomer of <a href="/wiki/Acetylacetone" title="Acetylacetone">acetylacetone</a> appears at <span class="nowrap">⁠<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 \delta _{\text{H}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <msub> <mi>δ</mi> <mrow class="MJX-TeXAtom-ORD"> <mtext>H</mtext> </mrow> </msub> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle \delta _{\text{H}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/ff09c7bf039d31376f1b4c0e39fe85a495bab08e" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -0.671ex; width:2.497ex; height:2.676ex;" alt="{\displaystyle \delta _{\text{H}}}"></span>⁠</span> 15.5, which is about 10 ppm downfield of a conventional alcohol.<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> </p><p>In the IR spectrum, hydrogen bonding shifts the <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">X−H</span> stretching frequency to lower energy (i.e. the vibration frequency decreases). This shift reflects a weakening of the <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">X−H</span> bond. Certain hydrogen bonds - improper hydrogen bonds - show a blue shift of the <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">X−H</span> stretching frequency and a decrease in the bond length.<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> H-bonds can also be measured by IR vibrational mode shifts of the acceptor. The amide I mode of backbone carbonyls in α-helices shifts to lower frequencies when they form H-bonds with side-chain hydroxyl groups.<sup id="cite_ref-Feldblum_2014_4085–4090_27-0" class="reference"><a href="#cite_note-Feldblum_2014_4085–4090-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> The dynamics of hydrogen bond structures in water can be probed by this OH stretching vibration.<sup id="cite_ref-cowan_28-0" class="reference"><a href="#cite_note-cowan-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> In the hydrogen bonding network in protic organic ionic plastic crystals (POIPCs), which are a type of phase change material exhibiting solid-solid <a href="/wiki/Phase_transition" title="Phase transition">phase transitions</a> prior to melting, variable-temperature infrared spectroscopy can reveal the temperature dependence of hydrogen bonds and the dynamics of both the anions and the cations.<sup id="cite_ref-1,2,4-Triazolium_perfluorobutanesulfonate_as_an_archetypal_pure_protic_organic_ionic_plastic_crystal_electrolyte_for_all-solid-state_fuel_cells_29-0" class="reference"><a href="#cite_note-1,2,4-Triazolium_perfluorobutanesulfonate_as_an_archetypal_pure_protic_organic_ionic_plastic_crystal_electrolyte_for_all-solid-state_fuel_cells-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> The sudden weakening of hydrogen bonds during the solid-solid phase transition seems to be coupled with the onset of orientational or rotational disorder of the ions.<sup id="cite_ref-1,2,4-Triazolium_perfluorobutanesulfonate_as_an_archetypal_pure_protic_organic_ionic_plastic_crystal_electrolyte_for_all-solid-state_fuel_cells_29-1" class="reference"><a href="#cite_note-1,2,4-Triazolium_perfluorobutanesulfonate_as_an_archetypal_pure_protic_organic_ionic_plastic_crystal_electrolyte_for_all-solid-state_fuel_cells-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Theoretical_considerations">Theoretical considerations</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hydrogen_bond&action=edit&section=7" title="Edit section: Theoretical considerations"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Hydrogen bonding is of persistent theoretical interest.<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> According to a modern description <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">O:H−O</span> integrates both the intermolecular O:H lone pair ":" nonbond and the intramolecular <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">H−O</span> polar-covalent bond associated with <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">O−O</span> repulsive coupling.<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> </p><p>Quantum chemical calculations of the relevant interresidue potential constants (<a href="/wiki/Compliance_Constants" class="mw-redirect" title="Compliance Constants">compliance constants</a>) revealed<sup class="noprint Inline-Template" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Please_clarify" title="Wikipedia:Please clarify"><span title="Please clarify the preceding statement or statements with a good explanation from a reliable source. (December 2015)">how?</span></a></i>]</sup> large differences between individual H bonds of the same type. For example, the central interresidue <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">N−H···N</span> hydrogen bond between guanine and cytosine is much stronger in comparison to the <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">N−H···N</span> bond between the adenine-thymine pair.<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><p>Theoretically, the bond strength of the hydrogen bonds can be assessed using NCI index, <a href="/wiki/Non-covalent_interactions_index" title="Non-covalent interactions index">non-covalent interactions index</a>, which allows a visualization of these <a href="/wiki/Non-covalent_interactions" class="mw-redirect" title="Non-covalent interactions">non-covalent interactions</a>, as its name indicates, using the electron density of the system.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (June 2023)">citation needed</span></a></i>]</sup> </p><p>Interpretations of the <a href="/wiki/Anisotropy" title="Anisotropy">anisotropies</a> in the <a href="/wiki/Compton_scattering" title="Compton scattering">Compton profile</a> of ordinary ice claim that the hydrogen bond is partly covalent.<sup id="cite_ref-33" class="reference"><a href="#cite_note-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> However, this interpretation was challenged <sup id="cite_ref-34" class="reference"><a href="#cite_note-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> and subsequently clarified. <sup id="cite_ref-35" class="reference"><a href="#cite_note-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> </p><p>Most generally, the hydrogen bond can be viewed as a <a href="/wiki/Metric_(mathematics)" class="mw-redirect" title="Metric (mathematics)">metric</a>-dependent <a href="/wiki/Electrostatic" class="mw-redirect" title="Electrostatic">electrostatic</a> <a href="/wiki/Scalar_field" title="Scalar field">scalar field</a> between two or more intermolecular bonds. This is slightly different from the <a href="/wiki/Intramolecular_force" title="Intramolecular force">intramolecular</a> <a href="/wiki/Bound_states" class="mw-redirect" title="Bound states">bound states</a> of, for example, <a href="/wiki/Covalent_bond" title="Covalent bond">covalent</a> or <a href="/wiki/Ionic_bond" class="mw-redirect" title="Ionic bond">ionic bonds</a>. However, hydrogen bonding is generally still a <a href="/wiki/Bound_state" title="Bound state">bound state</a> phenomenon, since the <a href="/wiki/Interaction_energy" title="Interaction energy">interaction energy</a> has a net negative sum. The initial theory of hydrogen bonding proposed by <a href="/wiki/Linus_Pauling" title="Linus Pauling">Linus Pauling</a> suggested that the hydrogen bonds had a partial covalent nature. This interpretation remained controversial until <a href="/wiki/Nuclear_magnetic_resonance" title="Nuclear magnetic resonance">NMR techniques</a> demonstrated information transfer between hydrogen-bonded nuclei, a feat that would only be possible if the hydrogen bond contained some covalent character.<sup id="cite_ref-36" class="reference"><a href="#cite_note-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hydrogen_bond&action=edit&section=8" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The concept of hydrogen bonding once was challenging.<sup id="cite_ref-37" class="reference"><a href="#cite_note-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Linus_Pauling" title="Linus Pauling">Linus Pauling</a> credits T. S. Moore and T. F. Winmill with the first mention of the hydrogen bond, in 1912.<sup id="cite_ref-38" class="reference"><a href="#cite_note-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-39" class="reference"><a href="#cite_note-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> Moore and Winmill used the hydrogen bond to account for the fact that trimethylammonium hydroxide is a weaker base than <a href="/wiki/Tetramethylammonium_hydroxide" title="Tetramethylammonium hydroxide">tetramethylammonium hydroxide</a>. The description of hydrogen bonding in its better-known setting, water, came some years later, in 1920, from <a href="/wiki/Wendell_Mitchell_Latimer" title="Wendell Mitchell Latimer">Latimer</a> and Rodebush.<sup id="cite_ref-40" class="reference"><a href="#cite_note-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> In that paper, Latimer and Rodebush cited the work of a fellow scientist at their laboratory, <a href="/wiki/Maurice_Loyal_Huggins" title="Maurice Loyal Huggins">Maurice Loyal Huggins</a>, saying, "Mr. Huggins of this laboratory in some work as yet unpublished, has used the idea of a hydrogen kernel held between two atoms as a theory in regard to certain organic compounds." </p> <div class="mw-heading mw-heading2"><h2 id="Hydrogen_bonds_in_small_molecules">Hydrogen bonds in small molecules</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hydrogen_bond&action=edit&section=9" title="Edit section: Hydrogen bonds in small molecules"><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:Hex_ice.GIF" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5b/Hex_ice.GIF/220px-Hex_ice.GIF" decoding="async" width="220" height="187" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5b/Hex_ice.GIF/330px-Hex_ice.GIF 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5b/Hex_ice.GIF/440px-Hex_ice.GIF 2x" data-file-width="900" data-file-height="765" /></a><figcaption>Crystal structure of hexagonal ice. Gray dashed lines indicate hydrogen bonds</figcaption></figure> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:NIMGLO12.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5d/NIMGLO12.png/120px-NIMGLO12.png" decoding="async" width="120" height="181" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5d/NIMGLO12.png/180px-NIMGLO12.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5d/NIMGLO12.png/240px-NIMGLO12.png 2x" data-file-width="1200" data-file-height="1809" /></a><figcaption>Structure of <a href="/wiki/Nickel_bis(dimethylglyoximate)" title="Nickel bis(dimethylglyoximate)">nickel bis(dimethylglyoximate)</a>, which features two linear hydrogen-bonds.</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Water">Water</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hydrogen_bond&action=edit&section=10" title="Edit section: Water"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>An ubiquitous example of a hydrogen bond is found between <a href="/wiki/Water" title="Water">water</a> molecules. In a discrete water molecule, there are two hydrogen atoms and one oxygen atom. The simplest case is a pair of <a href="/wiki/Water" title="Water">water</a> molecules with one hydrogen bond between them, which is called the <a href="/wiki/Water_dimer" title="Water dimer">water dimer</a> and is often used as a model system. When more molecules are present, as is the case with liquid water, more bonds are possible because the oxygen of one water molecule has two lone pairs of electrons, each of which can form a hydrogen bond with a hydrogen on another water molecule. This can repeat such that every water molecule is H-bonded with up to four other molecules, as shown in the figure (two through its two lone pairs, and two through its two hydrogen atoms). Hydrogen bonding strongly affects the <a href="/wiki/Crystal_structure" title="Crystal structure">crystal structure</a> of <a href="/wiki/Ice" title="Ice">ice</a>, helping to create an open hexagonal lattice. The density of ice is less than the density of water at the same temperature; thus, the solid phase of water floats on the liquid, unlike most other substances.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (June 2023)">citation needed</span></a></i>]</sup> </p><p><a href="/wiki/Liquid" title="Liquid">Liquid</a> water's high <a href="/wiki/Boiling_point" title="Boiling point">boiling point</a> is due to the high number of hydrogen bonds each molecule can form, relative to its low <a href="/wiki/Molecular_mass" title="Molecular mass">molecular mass</a>. Owing to the difficulty of breaking these bonds, water has a very high boiling point, melting point, and viscosity compared to otherwise similar liquids not conjoined by hydrogen bonds. Water is unique because its oxygen atom has two lone pairs and two hydrogen atoms, meaning that the total number of bonds of a water molecule is up to four.<sup id="cite_ref-41" class="reference"><a href="#cite_note-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> </p><p>The number of hydrogen bonds formed by a molecule of liquid water fluctuates with time and temperature.<sup id="cite_ref-Jorgensen1985_42-0" class="reference"><a href="#cite_note-Jorgensen1985-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> From <a href="/wiki/Water_model" title="Water model">TIP4P</a> liquid water simulations at 25 °C, it was estimated that each water molecule participates in an average of 3.59 hydrogen bonds. At 100 °C, this number decreases to 3.24 due to the increased molecular motion and decreased density, while at 0 °C, the average number of hydrogen bonds increases to 3.69.<sup id="cite_ref-Jorgensen1985_42-1" class="reference"><a href="#cite_note-Jorgensen1985-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> Another study found a much smaller number of hydrogen bonds: 2.357 at 25 °C.<sup id="cite_ref-43" class="reference"><a href="#cite_note-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> Defining and counting the hydrogen bonds is not straightforward however. </p><p>Because water may form hydrogen bonds with solute proton donors and acceptors, it may competitively inhibit the formation of solute intermolecular or intramolecular hydrogen bonds. Consequently, hydrogen bonds between or within solute molecules dissolved in water are almost always unfavorable relative to hydrogen bonds between water and the donors and acceptors for hydrogen bonds on those solutes.<sup id="cite_ref-44" class="reference"><a href="#cite_note-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup> Hydrogen bonds between water molecules have an average lifetime of 10<sup>−11</sup> seconds, or 10 picoseconds.<sup id="cite_ref-Dillon_45-0" class="reference"><a href="#cite_note-Dillon-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Bifurcated_and_over-coordinated_hydrogen_bonds_in_water">Bifurcated and over-coordinated hydrogen bonds in water</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hydrogen_bond&action=edit&section=11" title="Edit section: Bifurcated and over-coordinated hydrogen bonds in water"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A single hydrogen atom can participate in two hydrogen bonds. This type of bonding is called "bifurcated" (split in two or "two-forked"). It can exist, for instance, in complex organic molecules.<sup id="cite_ref-46" class="reference"><a href="#cite_note-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup> It has been suggested that a bifurcated hydrogen atom is an essential step in water reorientation.<sup id="cite_ref-47" class="reference"><a href="#cite_note-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> </p><p>Acceptor-type hydrogen bonds (terminating on an oxygen's lone pairs) are more likely to form bifurcation (it is called overcoordinated oxygen, OCO) than are donor-type hydrogen bonds, beginning on the same oxygen's hydrogens.<sup id="cite_ref-48" class="reference"><a href="#cite_note-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Other_liquids">Other liquids</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hydrogen_bond&action=edit&section=12" title="Edit section: Other liquids"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>For example, <a href="/wiki/Hydrogen_fluoride" title="Hydrogen fluoride">hydrogen fluoride</a>—which has three lone pairs on the F atom but only one H atom—can form only two bonds; (<a href="/wiki/Ammonia" title="Ammonia">ammonia</a> has the opposite problem: three hydrogen atoms but only one lone pair). </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 {H-F***H-F***H-F}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mtext>F</mtext> <mo>⋅</mo> <mo>⋅</mo> <mo>⋅</mo> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mtext>F</mtext> <mo>⋅</mo> <mo>⋅</mo> <mo>⋅</mo> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mtext>F</mtext> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {H-F***H-F***H-F}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/d1921d0ba708036ddce718f32853d82eaddb77cf" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -0.505ex; width:23.217ex; height:2.343ex;" alt="{\displaystyle {\ce {H-F***H-F***H-F}}}"></span></dd></dl> <div class="mw-heading mw-heading3"><h3 id="Further_manifestations_of_solvent_hydrogen_bonding">Further manifestations of solvent hydrogen bonding</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hydrogen_bond&action=edit&section=13" title="Edit section: Further manifestations of solvent hydrogen bonding"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li>Increase in the <a href="/wiki/Melting_point" title="Melting point">melting point</a>, <a href="/wiki/Boiling_point" title="Boiling point">boiling point</a>, <a href="/wiki/Solubility" title="Solubility">solubility</a>, and viscosity of many compounds can be explained by the concept of hydrogen bonding.</li> <li>Negative <a href="/wiki/Azeotrope" title="Azeotrope">azeotropy</a> of mixtures of HF and water.</li> <li>The fact that ice is less dense than liquid water is due to a crystal structure stabilized by hydrogen bonds.</li> <li>Dramatically higher boiling points of <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">NH<sub class="template-chem2-sub">3</sub></span>, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>O</span>, and HF compared to the heavier analogues <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">PH<sub class="template-chem2-sub">3</sub></span>, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>S</span>, and HCl, where hydrogen-bonding is absent.</li> <li>Viscosity of anhydrous <a href="/wiki/Phosphoric_acid" title="Phosphoric acid">phosphoric acid</a> and of <a href="/wiki/Glycerol" title="Glycerol">glycerol</a>.</li> <li>Dimer formation in <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acids</a> and hexamer formation in <a href="/wiki/Hydrogen_fluoride" title="Hydrogen fluoride">hydrogen fluoride</a>, which occur even in the gas phase, resulting in gross deviations from the <a href="/wiki/Ideal_gas_law" title="Ideal gas law">ideal gas law</a>.</li> <li>Pentamer formation of water and alcohols in apolar solvents.</li></ul> <div class="mw-heading mw-heading2"><h2 id="Hydrogen_bonds_in_polymers">Hydrogen bonds in polymers</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hydrogen_bond&action=edit&section=14" title="Edit section: Hydrogen bonds in polymers"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Hydrogen bonding plays an important role in determining the three-dimensional structures and the properties adopted by many proteins. Compared to the <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C−C</span>, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C−O</span>, and <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C−N</span> bonds that comprise most polymers, hydrogen bonds are far weaker, perhaps 5%. Thus, hydrogen bonds can be broken by chemical or mechanical means while retaining the basic structure of the polymer backbone. This hierarchy of bond strengths (covalent bonds being stronger than hydrogen-bonds being stronger than van der Waals forces) is relevant in the properties of many materials.<sup id="cite_ref-49" class="reference"><a href="#cite_note-49"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="DNA">DNA</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hydrogen_bond&action=edit&section=15" title="Edit section: DNA"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:DNA_animation.gif" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/0/0c/DNA_animation.gif" decoding="async" width="181" height="313" class="mw-file-element" data-file-width="181" data-file-height="313" /></a><figcaption>The structure of part of a DNA <a href="/wiki/Double_helix" class="mw-redirect" title="Double helix">double helix</a></figcaption></figure> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Base_pair_GC.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/64/Base_pair_GC.svg/220px-Base_pair_GC.svg.png" decoding="async" width="220" height="131" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/64/Base_pair_GC.svg/330px-Base_pair_GC.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/64/Base_pair_GC.svg/440px-Base_pair_GC.svg.png 2x" data-file-width="620" data-file-height="369" /></a><figcaption>Hydrogen bonding between <a href="/wiki/Guanine" title="Guanine">guanine</a> and <a href="/wiki/Cytosine" title="Cytosine">cytosine</a>, one of two types of <a href="/wiki/Base_pair" title="Base pair">base pairs</a> in DNA</figcaption></figure> <p>In these macromolecules, bonding between parts of the same macromolecule cause it to fold into a specific shape, which helps determine the molecule's physiological or biochemical role. For example, the double helical structure of <a href="/wiki/DNA" title="DNA">DNA</a> is due largely to hydrogen bonding between its <a href="/wiki/Base_pair" title="Base pair">base pairs</a> (as well as <a href="/wiki/Pi_stacking" class="mw-redirect" title="Pi stacking">pi stacking</a> interactions), which link one complementary strand to the other and enable <a href="/wiki/DNA_replication" title="DNA replication">replication</a>.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (June 2023)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading3"><h3 id="Proteins">Proteins</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hydrogen_bond&action=edit&section=16" title="Edit section: Proteins"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In the <a href="/wiki/Protein_secondary_structure" title="Protein secondary structure">secondary structure of proteins</a>, hydrogen bonds form between the backbone oxygens and <a href="/wiki/Amide" title="Amide">amide</a> hydrogens. When the spacing of the <a href="/wiki/Amino_acid" title="Amino acid">amino acid</a> residues participating in a hydrogen bond occurs regularly between positions <i>i</i> and <span class="nowrap"><i>i</i> + 4</span>, an <a href="/wiki/Alpha_helix" title="Alpha helix">alpha helix</a> is formed. When the spacing is less, between positions <i>i</i> and <span class="nowrap"><i>i</i> + 3</span>, then a <a href="/wiki/3_10_helix" class="mw-redirect" title="3 10 helix">3<sub>10</sub> helix</a> is formed. When two strands are joined by hydrogen bonds involving alternating residues on each participating strand, a <a href="/wiki/Beta_sheet" title="Beta sheet">beta sheet</a> is formed. Hydrogen bonds also play a part in forming the <a href="/wiki/Protein_tertiary_structure" title="Protein tertiary structure">tertiary structure of protein</a> through interaction of R-groups. (See also <a href="/wiki/Protein_folding" title="Protein folding">protein folding</a>). </p><p><a href="/w/index.php?title=Bifurcated_H-bond&action=edit&redlink=1" class="new" title="Bifurcated H-bond (page does not exist)">Bifurcated H-bond</a> systems are common in alpha-helical <a href="/wiki/Transmembrane_proteins" class="mw-redirect" title="Transmembrane proteins">transmembrane proteins</a> between the backbone amide <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C=O</span> of residue <i>i</i> as the H-bond acceptor and two H-bond donors from residue <span class="nowrap"><i>i</i> + 4</span>: the backbone amide <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">N−H</span> and a side-chain hydroxyl or thiol <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">H<sup class="template-chem2-sup">+</sup></span>. The energy preference of the bifurcated H-bond hydroxyl or thiol system is -3.4 kcal/mol or -2.6 kcal/mol, respectively. This type of bifurcated H-bond provides an intrahelical H-bonding partner for polar side-chains, such as <a href="/wiki/Serine" title="Serine">serine</a>, <a href="/wiki/Threonine" title="Threonine">threonine</a>, and <a href="/wiki/Cysteine" title="Cysteine">cysteine</a> within the hydrophobic membrane environments.<sup id="cite_ref-Feldblum_2014_4085–4090_27-1" class="reference"><a href="#cite_note-Feldblum_2014_4085–4090-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> </p><p>The role of hydrogen bonds in protein folding has also been linked to osmolyte-induced protein stabilization. Protective osmolytes, such as <a href="/wiki/Trehalose" title="Trehalose">trehalose</a> and <a href="/wiki/Sorbitol" title="Sorbitol">sorbitol</a>, shift the protein folding equilibrium toward the folded state, in a concentration dependent manner. While the prevalent explanation for osmolyte action relies on excluded volume effects that are entropic in nature, <a href="/wiki/Circular_dichroism" title="Circular dichroism">circular dichroism</a> (CD) experiments have shown osmolyte to act through an enthalpic effect.<sup id="cite_ref-50" class="reference"><a href="#cite_note-50"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup> The molecular mechanism for their role in protein stabilization is still not well established, though several mechanisms have been proposed. Computer <a href="/wiki/Molecular_dynamics" title="Molecular dynamics">molecular dynamics</a> simulations suggest that osmolytes stabilize proteins by modifying the hydrogen bonds in the protein hydration layer.<sup id="cite_ref-51" class="reference"><a href="#cite_note-51"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup> </p><p>Several studies have shown that hydrogen bonds play an important role for the stability between subunits in multimeric proteins. For example, a study of sorbitol dehydrogenase displayed an important hydrogen bonding network which stabilizes the tetrameric quaternary structure within the mammalian sorbitol dehydrogenase protein family.<sup id="cite_ref-52" class="reference"><a href="#cite_note-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> </p><p>A protein backbone hydrogen bond incompletely shielded from water attack is a <a href="/wiki/Dehydron" class="mw-redirect" title="Dehydron">dehydron</a>. Dehydrons promote the removal of water through proteins or <a href="/wiki/Ligand" title="Ligand">ligand binding</a>. The exogenous dehydration enhances the <a href="/wiki/Electrostatic" class="mw-redirect" title="Electrostatic">electrostatic</a> interaction between the <a href="/wiki/Amide" title="Amide">amide</a> and <a href="/wiki/Carbonyl" class="mw-redirect" title="Carbonyl">carbonyl</a> groups by de-shielding their <a href="/wiki/Charge_(physics)" title="Charge (physics)">partial charges</a>. Furthermore, the dehydration stabilizes the hydrogen bond by destabilizing the <a href="/wiki/Nonbonded_interactions" class="mw-redirect" title="Nonbonded interactions">nonbonded state</a> consisting of dehydrated <a href="/wiki/Charge_(physics)" title="Charge (physics)">isolated charges</a>.<sup id="cite_ref-53" class="reference"><a href="#cite_note-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Wool" title="Wool">Wool</a>, being a protein fibre, is held together by hydrogen bonds, causing wool to recoil when stretched. However, washing at high temperatures can permanently break the hydrogen bonds and a garment may permanently lose its shape. </p> <div class="mw-heading mw-heading3"><h3 id="Other_polymers">Other polymers</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hydrogen_bond&action=edit&section=17" title="Edit section: Other polymers"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Kevlar_chemical_structure_H-bonds.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/95/Kevlar_chemical_structure_H-bonds.svg/400px-Kevlar_chemical_structure_H-bonds.svg.png" decoding="async" width="400" height="192" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/95/Kevlar_chemical_structure_H-bonds.svg/600px-Kevlar_chemical_structure_H-bonds.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/95/Kevlar_chemical_structure_H-bonds.svg/800px-Kevlar_chemical_structure_H-bonds.svg.png 2x" data-file-width="512" data-file-height="246" /></a><figcaption>Para-aramid structure</figcaption></figure> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Cellulose_strand.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a4/Cellulose_strand.svg/260px-Cellulose_strand.svg.png" decoding="async" width="260" height="235" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a4/Cellulose_strand.svg/390px-Cellulose_strand.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a4/Cellulose_strand.svg/520px-Cellulose_strand.svg.png 2x" data-file-width="402" data-file-height="364" /></a><figcaption>A strand of cellulose (conformation I<sub>α</sub>), showing the hydrogen bonds (dashed) within and between cellulose molecules</figcaption></figure> <p>The properties of many polymers are affected by hydrogen bonds within and/or between the chains. Prominent examples include <a href="/wiki/Cellulose" title="Cellulose">cellulose</a> and its derived fibers, such as <a href="/wiki/Cotton" title="Cotton">cotton</a> and <a href="/wiki/Flax" title="Flax">flax</a>. In <a href="/wiki/Nylon" title="Nylon">nylon</a>, hydrogen bonds between <a href="/wiki/Carbonyl" class="mw-redirect" title="Carbonyl">carbonyl</a> and the <a href="/wiki/Amide" title="Amide">amide</a> N<i>H</i> effectively link adjacent chains, which gives the material mechanical strength. Hydrogen bonds also affect the <a href="/wiki/Aramid" title="Aramid">aramid</a> <a href="/wiki/Fibre" class="mw-redirect" title="Fibre">fibre</a>, where hydrogen bonds stabilize the linear chains laterally. The chain axes are aligned along the fibre axis, making the fibres extremely stiff and strong. Hydrogen-bond networks make both polymers sensitive to <a href="/wiki/Humidity" title="Humidity">humidity</a> levels in the atmosphere because water molecules can diffuse into the surface and disrupt the network. Some polymers are more sensitive than others. Thus <a href="/wiki/Nylon" title="Nylon">nylons</a> are more sensitive than <a href="/wiki/Aramid" title="Aramid">aramids</a>, and <a href="/wiki/Nylon_6" title="Nylon 6">nylon 6</a> more sensitive than <a href="/wiki/Nylon-11" class="mw-redirect" title="Nylon-11">nylon-11</a>.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (June 2023)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading2"><h2 id="Symmetric_hydrogen_bond">Symmetric hydrogen bond</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hydrogen_bond&action=edit&section=18" title="Edit section: Symmetric hydrogen bond"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A <a href="/wiki/Symmetric_hydrogen_bond" title="Symmetric hydrogen bond">symmetric hydrogen bond</a> is a special type of hydrogen bond in which the proton is spaced exactly halfway between two identical atoms. The strength of the bond to each of those atoms is equal. It is an example of a <a href="/wiki/Three-center_four-electron_bond" title="Three-center four-electron bond">three-center four-electron bond</a>. This type of bond is much stronger than a "normal" hydrogen bond. The effective bond order is 0.5, so its strength is comparable to a covalent bond. It is seen in ice at high pressure, and also in the solid phase of many anhydrous acids such as <a href="/wiki/Hydrofluoric_acid" title="Hydrofluoric acid">hydrofluoric acid</a> and <a href="/wiki/Formic_acid" title="Formic acid">formic acid</a> at high pressure. It is also seen in the <a href="/wiki/Bifluoride" title="Bifluoride">bifluoride</a> ion <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">[F···H···F]<sup class="template-chem2-sup">−</sup></span>. Due to severe steric constraint, the protonated form of Proton Sponge (1,8-bis(dimethylamino)naphthalene) and its derivatives also have symmetric hydrogen bonds (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">[N···H···N]<sup class="template-chem2-sup">+</sup></span>),<sup id="cite_ref-54" class="reference"><a href="#cite_note-54"><span class="cite-bracket">[</span>54<span class="cite-bracket">]</span></a></sup> although in the case of protonated Proton Sponge, the assembly is bent.<sup id="cite_ref-55" class="reference"><a href="#cite_note-55"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Dihydrogen_bond">Dihydrogen bond</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hydrogen_bond&action=edit&section=19" title="Edit section: Dihydrogen bond"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The hydrogen bond can be compared with the closely related <a href="/wiki/Dihydrogen_bond" title="Dihydrogen bond">dihydrogen bond</a>, which is also an <a href="/wiki/Intermolecular_force" title="Intermolecular force">intermolecular</a> bonding interaction involving hydrogen atoms. These structures have been known for some time, and well characterized by <a href="/wiki/X-ray_crystallography" title="X-ray crystallography">crystallography</a>;<sup id="cite_ref-crab_56-0" class="reference"><a href="#cite_note-crab-56"><span class="cite-bracket">[</span>56<span class="cite-bracket">]</span></a></sup> however, an understanding of their relationship to the conventional hydrogen bond, <a href="/wiki/Ionic_bond" class="mw-redirect" title="Ionic bond">ionic bond</a>, and <a href="/wiki/Covalent_bond" title="Covalent bond">covalent bond</a> remains unclear. Generally, the hydrogen bond is characterized by a proton acceptor that is a lone pair of electrons in nonmetallic atoms (most notably in the <a href="/wiki/Nitrogen_group" class="mw-redirect" title="Nitrogen group">nitrogen</a>, and <a href="/wiki/Chalcogen" title="Chalcogen">chalcogen</a> groups). In some cases, these proton acceptors may be <a href="/wiki/Pi-bond" class="mw-redirect" title="Pi-bond">pi-bonds</a> or <a href="/wiki/Metal_complexes" class="mw-redirect" title="Metal complexes">metal complexes</a>. In the dihydrogen bond, however, a metal hydride serves as a proton acceptor, thus forming a hydrogen-hydrogen interaction. <a href="/wiki/Neutron_diffraction" title="Neutron diffraction">Neutron diffraction</a> has shown that the <a href="/wiki/Molecular_geometry" title="Molecular geometry">molecular geometry</a> of these complexes is similar to hydrogen bonds, in that the bond length is very adaptable to the metal complex/hydrogen donor system.<sup id="cite_ref-crab_56-1" class="reference"><a href="#cite_note-crab-56"><span class="cite-bracket">[</span>56<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Application_to_drugs">Application to drugs</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hydrogen_bond&action=edit&section=20" title="Edit section: Application to drugs"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The Hydrogen bond is relevant to drug design. According to <a href="/wiki/Lipinski%27s_rule_of_five" title="Lipinski's rule of five">Lipinski's rule of five</a> the majority of orally active drugs have no more than five hydrogen bond donors and fewer than ten hydrogen bond acceptors. These interactions exist between <a href="/wiki/Nitrogen" title="Nitrogen">nitrogen</a>–<a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a> and <a href="/wiki/Oxygen" title="Oxygen">oxygen</a>–hydrogen centers.<sup id="cite_ref-Lipinski_2004_57-0" class="reference"><a href="#cite_note-Lipinski_2004-57"><span class="cite-bracket">[</span>57<span class="cite-bracket">]</span></a></sup> Many drugs do not, however, obey these "rules".<sup id="cite_ref-58" class="reference"><a href="#cite_note-58"><span class="cite-bracket">[</span>58<span class="cite-bracket">]</span></a></sup> </p> <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=Hydrogen_bond&action=edit&section=21" 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 reflist-columns references-column-width" style="column-width: 35em;"> <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="CITEREFSweetmanJarvisSangLekkas2014" class="citation journal cs1">Sweetman, A. 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Retrieved <span class="nowrap">2017-08-30</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Physical+Review+Letters&rft.atitle=Intermolecular+Contrast+in+Atomic+Force+Microscopy+Images+without+Intermolecular+Bonds&rft.volume=113&rft.issue=18&rft.pages=186102&rft.date=2014-10-31&rft_id=info%3Ahdl%2F1874%2F307996&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A8309018%23id-name%3DS2CID&rft_id=info%3Abibcode%2F2014PhRvL.113r6102H&rft_id=info%3Aarxiv%2F1410.1933&rft_id=info%3Apmid%2F25396382&rft_id=info%3Adoi%2F10.1103%2FPhysRevLett.113.186102&rft.aulast=H%C3%A4m%C3%A4l%C3%A4inen&rft.aufirst=Sampsa+K.&rft.au=van+der+Heijden%2C+Nadine&rft.au=van+der+Lit%2C+Joost&rft.au=den+Hartog%2C+Stephan&rft.au=Liljeroth%2C+Peter&rft.au=Swart%2C+Ingmar&rft_id=http%3A%2F%2Fdspace.library.uu.nl%3A8080%2Fhandle%2F1874%2F307996&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHydrogen+bond" class="Z3988"></span></span> </li> <li id="cite_note-:0-5"><span class="mw-cite-backlink">^ <a href="#cite_ref-:0_5-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-:0_5-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-:0_5-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFArunanDesirajuKleinSadlej2011" class="citation journal cs1">Arunan, Elangannan; Desiraju, Gautam R.; Klein, Roger A.; Sadlej, Joanna; Scheiner, Steve; Alkorta, Ibon; Clary, David C.; Crabtree, Robert H.; Dannenberg, Joseph J. (2011-07-08). <a rel="nofollow" class="external text" href="https://doi.org/10.1351%2FPAC-REC-10-01-02">"Definition of the hydrogen bond (IUPAC Recommendations 2011)"</a>. <i>Pure and Applied Chemistry</i>. <b>83</b> (8): 1637–1641. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1351%2FPAC-REC-10-01-02">10.1351/PAC-REC-10-01-02</a></span>. <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/1365-3075">1365-3075</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:97688573">97688573</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Pure+and+Applied+Chemistry&rft.atitle=Definition+of+the+hydrogen+bond+%28IUPAC+Recommendations+2011%29&rft.volume=83&rft.issue=8&rft.pages=1637-1641&rft.date=2011-07-08&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A97688573%23id-name%3DS2CID&rft.issn=1365-3075&rft_id=info%3Adoi%2F10.1351%2FPAC-REC-10-01-02&rft.aulast=Arunan&rft.aufirst=Elangannan&rft.au=Desiraju%2C+Gautam+R.&rft.au=Klein%2C+Roger+A.&rft.au=Sadlej%2C+Joanna&rft.au=Scheiner%2C+Steve&rft.au=Alkorta%2C+Ibon&rft.au=Clary%2C+David+C.&rft.au=Crabtree%2C+Robert+H.&rft.au=Dannenberg%2C+Joseph+J.&rft_id=https%3A%2F%2Fdoi.org%2F10.1351%252FPAC-REC-10-01-02&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHydrogen+bond" class="Z3988"></span></span> </li> <li id="cite_note-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-6">^</a></b></span> <span class="reference-text">Pimentel, G. <i>The Hydrogen Bond</i> Franklin Classics, 2018), <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0343171600" title="Special:BookSources/0343171600">0343171600</a></span> </li> <li id="cite_note-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-7">^</a></b></span> <span class="reference-text">Jeffrey, G. 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Jeffrey. <i>An Introduction to Hydrogen Bonding (Topics in Physical Chemistry)</i>. Oxford University Press, US (March 13, 1997). <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0-19-509549-9" title="Special:BookSources/0-19-509549-9">0-19-509549-9</a></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=Hydrogen_bond&action=edit&section=23" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20141203035841/http://www.magnet.fsu.edu/education/tutorials/slideshows/bubblewall/index.html">The Bubble Wall</a> (Audio slideshow from the National High Magnetic Field Laboratory explaining cohesion, surface tension and hydrogen bonds)</li> <li><a rel="nofollow" class="external text" href="http://scitation.aip.org/content/aip/journal/jcp/129/19/10.1063/1.3006032">isotopic effect on bond dynamics</a></li></ul> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl dl,.mw-parser-output .hlist dl ol,.mw-parser-output .hlist dl ul,.mw-parser-output .hlist ol dl,.mw-parser-output .hlist ol ol,.mw-parser-output .hlist ol ul,.mw-parser-output .hlist ul dl,.mw-parser-output .hlist ul ol,.mw-parser-output .hlist ul ul{display:inline}.mw-parser-output .hlist .mw-empty-li{display:none}.mw-parser-output .hlist dt::after{content:": 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style="font-size:114%;margin:0 4em"><a href="/wiki/Chemical_bond" title="Chemical bond">Chemical bonds</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Intramolecular_force" title="Intramolecular force">Intramolecular</a><br />(strong)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Covalent_bond" title="Covalent bond">Covalent</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/Electron_deficiency" title="Electron deficiency">Electron deficiency</a> <ul><li><a href="/wiki/Three-center_two-electron_bond" title="Three-center two-electron bond">3c–2e</a></li> <li><a href="/wiki/Four-center_two-electron_bond" title="Four-center two-electron bond">4c–2e</a></li> <li><a href="/wiki/Eight-center_two-electron_bond" class="mw-redirect" title="Eight-center two-electron bond">8c–2e</a></li></ul></li> <li><a href="/wiki/Hypervalent_molecule" title="Hypervalent molecule">Hypervalence</a> <ul><li><a href="/wiki/Three-center_four-electron_bond" title="Three-center four-electron bond">3c–4e</a></li></ul></li> <li><a href="/wiki/Agostic_interaction" title="Agostic interaction">Agostic</a></li> <li><a href="/wiki/Bent_bond" title="Bent bond">Bent</a></li> <li><a href="/wiki/Coordinate_covalent_bond" title="Coordinate covalent bond">Coordinate (dipolar)</a></li> <li><a href="/wiki/Pi_backbonding" title="Pi backbonding">Pi backbond</a></li> <li><a href="/wiki/Metal%E2%80%93ligand_multiple_bond" title="Metal–ligand multiple bond">Metal–ligand multiple bond</a></li> <li><a href="/wiki/Charge-shift_bond" title="Charge-shift bond">Charge-shift</a></li> <li><a href="/wiki/Hapticity" title="Hapticity">Hapticity</a></li> <li><a href="/wiki/Conjugated_system" title="Conjugated system">Conjugation</a></li> <li><a href="/wiki/Hyperconjugation" title="Hyperconjugation">Hyperconjugation</a></li> <li><a href="/wiki/Aromaticity" title="Aromaticity">Aromaticity</a> <ul><li><a href="/wiki/Homoaromaticity" title="Homoaromaticity">homo</a></li> <li><a href="/wiki/Bicycloaromaticity" title="Bicycloaromaticity">bicyclo</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Metallic_bonding" title="Metallic bonding">Metallic</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/Metal_aromaticity" title="Metal aromaticity">Metal aromaticity</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Ionic_bonding" title="Ionic bonding">Ionic</a></th><td class="navbox-list-with-group 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data-file-height="1080" /></a></span></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Intermolecular_force" title="Intermolecular force">Intermolecular</a><br />(weak)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Van_der_Waals_force" title="Van der Waals force">Van der Waals<br />forces</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/London_dispersion_force" title="London dispersion force">London dispersion</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a class="mw-selflink selflink">Hydrogen</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/Low-barrier_hydrogen_bond" title="Low-barrier hydrogen bond">Low-barrier</a></li> <li><a href="/wiki/Resonance-assisted_hydrogen_bond" class="mw-redirect" title="Resonance-assisted hydrogen bond">Resonance-assisted</a></li> <li><a href="/wiki/Symmetric_hydrogen_bond" title="Symmetric hydrogen bond">Symmetric</a></li> <li><a href="/wiki/Dihydrogen_bond" title="Dihydrogen bond">Dihydrogen bonds</a></li> <li><a href="/wiki/C%E2%80%93H%C2%B7%C2%B7%C2%B7O_interaction" title="C–H···O interaction">C–H···O interaction</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Non-covalent_interactions" class="mw-redirect" title="Non-covalent interactions">Noncovalent</a><br />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/Mechanically_interlocked_molecular_architectures" title="Mechanically interlocked molecular architectures">Mechanical</a></li> <li><a href="/wiki/Halogen_bond" title="Halogen bond">Halogen</a></li> <li><a href="/wiki/Chalcogen_bond" title="Chalcogen bond">Chalcogen</a></li> <li><a href="/wiki/Metallophilic_interaction" title="Metallophilic interaction">Metallophilic</a> (<a href="/wiki/Aurophilicity" title="Aurophilicity">aurophilic</a>)</li> <li><a href="/wiki/Intercalation_(chemistry)" title="Intercalation (chemistry)">Intercalation</a></li> <li><a href="/wiki/Stacking_(chemistry)" title="Stacking (chemistry)">Stacking</a></li> <li><a href="/wiki/Cation%E2%80%93pi_interaction" class="mw-redirect" title="Cation–pi interaction">Cation–pi</a></li> <li><a href="/wiki/Cation%E2%80%93pi_interaction#Anion–π_interaction" class="mw-redirect" title="Cation–pi interaction">Anion–pi</a></li> <li><a href="/wiki/Salt_bridge_(protein_and_supramolecular)" title="Salt bridge (protein and 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