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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">5</span> <span>References</span> </div> </a> <ul id="toc-References-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" title="Table of Contents" > <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 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Available in 42 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-42" 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">42 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <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_%D8%AB%D9%86%D8%A7%D8%A6%D9%8A%D8%A9" title="رابطة ثنائية – Arabic" lang="ar" hreflang="ar" data-title="رابطة ثنائية" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%94%D0%B2%D0%BE%D0%B9%D0%BD%D0%B0_%D0%B2%D1%80%D1%8A%D0%B7%D0%BA%D0%B0" title="Двойна връзка – Bulgarian" lang="bg" hreflang="bg" data-title="Двойна 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/Dvostruka_veza" title="Dvostruka veza – Bosnian" lang="bs" hreflang="bs" data-title="Dvostruka 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/Doble_enlla%C3%A7" title="Doble enllaç – Catalan" lang="ca" hreflang="ca" data-title="Doble enllaç" 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/Dvojn%C3%A1_vazba_(chemie)" title="Dvojná vazba (chemie) – Czech" lang="cs" hreflang="cs" data-title="Dvojná vazba (chemie)" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Doppelbindung" title="Doppelbindung – German" lang="de" hreflang="de" data-title="Doppelbindung" 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/Kaksikside" title="Kaksikside – Estonian" lang="et" hreflang="et" data-title="Kaksikside" 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%B9%CF%80%CE%BB%CF%8C%CF%82_%CE%B4%CE%B5%CF%83%CE%BC%CF%8C%CF%82" title="Διπλός δεσμός – Greek" lang="el" hreflang="el" data-title="Διπλός δεσμός" 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_doble" title="Enlace doble – Spanish" lang="es" hreflang="es" data-title="Enlace doble" 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/Duobla_ligo" title="Duobla ligo – Esperanto" lang="eo" hreflang="eo" data-title="Duobla 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/Lotura_bikoitz" title="Lotura bikoitz – Basque" lang="eu" hreflang="eu" data-title="Lotura bikoitz" 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_%D8%AF%D9%88%DA%AF%D8%A7%D9%86%D9%87" title="پیوند دوگانه – Persian" lang="fa" hreflang="fa" data-title="پیوند دوگانه" 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_double" title="Liaison double – French" lang="fr" hreflang="fr" data-title="Liaison double" 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_d%C3%BAbailte" title="Nasc dúbailte – Irish" lang="ga" hreflang="ga" data-title="Nasc dúbailte" 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/Dobre_enlace" title="Dobre enlace – Galician" lang="gl" hreflang="gl" data-title="Dobre enlace" 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%9D%B4%EC%A4%91_%EA%B2%B0%ED%95%A9" title="이중 결합 – Korean" lang="ko" hreflang="ko" data-title="이중 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/%D4%BF%D6%80%D5%AF%D5%B6%D5%A1%D5%AF%D5%AB_%D5%AF%D5%A1%D5%BA" title="Կրկնակի կապ – Armenian" lang="hy" hreflang="hy" data-title="Կրկնակի 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%A6%E0%A5%8D%E0%A4%B5%E0%A4%BF-%E0%A4%86%E0%A4%AC%E0%A4%A8%E0%A5%8D%E0%A4%A7" title="द्वि-आबन्ध – Hindi" lang="hi" hreflang="hi" data-title="द्वि-आबन्ध" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Ikatan_ganda" title="Ikatan ganda – Indonesian" lang="id" hreflang="id" data-title="Ikatan ganda" 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/Doppio_legame" title="Doppio legame – Italian" lang="it" hreflang="it" data-title="Doppio legame" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-ka mw-list-item"><a href="https://ka.wikipedia.org/wiki/%E1%83%9D%E1%83%A0%E1%83%9B%E1%83%90%E1%83%92%E1%83%98_%E1%83%91%E1%83%9B%E1%83%90" title="ორმაგი ბმა – Georgian" lang="ka" hreflang="ka" data-title="ორმაგი ბმა" data-language-autonym="ქართული" data-language-local-name="Georgian" class="interlanguage-link-target"><span>ქართული</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Kett%C5%91s_k%C3%B6t%C3%A9s" title="Kettős kötés – Hungarian" lang="hu" hreflang="hu" data-title="Kettős kötés" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%94%D0%B2%D0%BE%D1%98%D0%BD%D0%B0_%D0%B2%D1%80%D1%81%D0%BA%D0%B0" title="Двојна врска – Macedonian" lang="mk" hreflang="mk" data-title="Двојна врска" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Ikatan_ganda_dua" title="Ikatan ganda dua – Malay" lang="ms" hreflang="ms" data-title="Ikatan ganda dua" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Dubbele_binding_(scheikunde)" title="Dubbele binding (scheikunde) – Dutch" lang="nl" hreflang="nl" data-title="Dubbele binding (scheikunde)" 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/%E4%BA%8C%E9%87%8D%E7%B5%90%E5%90%88" title="二重結合 – Japanese" lang="ja" hreflang="ja" data-title="二重結合" 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/Dobbeltbinding" title="Dobbeltbinding – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Dobbeltbinding" 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-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Leg%C4%83tur%C4%83_dubl%C4%83" title="Legătură dublă – Romanian" lang="ro" hreflang="ro" data-title="Legătură dublă" 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%94%D0%B2%D0%BE%D0%B9%D0%BD%D0%B0%D1%8F_%D1%81%D0%B2%D1%8F%D0%B7%D1%8C" title="Двойная связь – Russian" lang="ru" hreflang="ru" data-title="Двойная 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_dyfishe" title="Lidhja dyfishe – Albanian" lang="sq" hreflang="sq" data-title="Lidhja dyfishe" 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/Double_bond" title="Double bond – Simple English" lang="en-simple" hreflang="en-simple" data-title="Double 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/Dvojit%C3%A1_v%C3%A4zba" title="Dvojitá väzba – Slovak" lang="sk" hreflang="sk" data-title="Dvojitá väzba" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/%D0%94%D0%B2%D0%BE%D1%81%D1%82%D1%80%D1%83%D0%BA%D0%B0_%D0%B2%D0%B5%D0%B7%D0%B0" title="Двострука веза – Serbian" lang="sr" hreflang="sr" data-title="Двострука 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/Dvostruka_veza" title="Dvostruka veza – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Dvostruka 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/Kaksoissidos" title="Kaksoissidos – Finnish" lang="fi" hreflang="fi" data-title="Kaksoissidos" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%87%E0%AE%B0%E0%AE%9F%E0%AF%8D%E0%AE%9F%E0%AF%88%E0%AE%AA%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="இரட்டைப் பிணைப்பு – Tamil" lang="ta" hreflang="ta" data-title="இரட்டைப் பிணைப்பு" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/%C4%B0kili_ba%C4%9F" title="İkili bağ – Turkish" lang="tr" hreflang="tr" data-title="İkili bağ" 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%9F%D0%BE%D0%B4%D0%B2%D1%96%D0%B9%D0%BD%D0%B8%D0%B9_%D0%B7%D0%B2%27%D1%8F%D0%B7%D0%BE%D0%BA" title="Подвійний зв'язок – Ukrainian" lang="uk" hreflang="uk" data-title="Подвійний 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_%C4%91%C3%B4i" title="Liên kết đôi – Vietnamese" lang="vi" hreflang="vi" data-title="Liên kết đôi" 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/%E5%8F%8C%E9%94%AE" title="双键 – Wu" lang="wuu" hreflang="wuu" data-title="双键" 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/%E9%9B%99%E9%8D%B5" title="雙鍵 – Cantonese" lang="yue" hreflang="yue" data-title="雙鍵" 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/%E9%9B%99%E9%8D%B5" title="雙鍵 – Chinese" lang="zh" hreflang="zh" data-title="雙鍵" 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/Q258652#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> </div> </header> <div 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</nav> </div> </div> </div> <div class="vector-column-end"> <div class="vector-sticky-pinned-container"> <nav class="vector-page-tools-landmark" aria-label="Page tools"> <div id="vector-page-tools-pinned-container" class="vector-pinned-container"> </div> </nav> <nav class="vector-appearance-landmark" aria-label="Appearance"> <div id="vector-appearance-pinned-container" class="vector-pinned-container"> <div id="vector-appearance" class="vector-appearance vector-pinnable-element"> <div class="vector-pinnable-header vector-appearance-pinnable-header vector-pinnable-header-pinned" data-feature-name="appearance-pinned" data-pinnable-element-id="vector-appearance" data-pinned-container-id="vector-appearance-pinned-container" data-unpinned-container-id="vector-appearance-unpinned-container" > <div class="vector-pinnable-header-label">Appearance</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-appearance.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-appearance.unpin">hide</button> </div> </div> </div> </nav> </div> </div> <div id="bodyContent" class="vector-body" aria-labelledby="firstHeading" data-mw-ve-target-container> <div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical bond involving four bonding electrons; has one sigma plus one pi bond</div> <p>In chemistry, a <b>double bond</b> is a <a href="/wiki/Covalent_bond" title="Covalent bond">covalent bond</a> between two <a href="/wiki/Atom" title="Atom">atoms</a> involving four <a href="/wiki/Electron_pair_bond" class="mw-redirect" title="Electron pair bond">bonding electrons</a> as opposed to two in a <a href="/wiki/Single_bond" title="Single bond">single bond</a>. Double bonds occur most commonly between two carbon atoms, for example in <a href="/wiki/Alkene" title="Alkene">alkenes</a>. Many double bonds exist between two different elements: for example, in a <a href="/wiki/Carbonyl" class="mw-redirect" title="Carbonyl">carbonyl</a> group between a carbon atom and an oxygen atom. Other common double bonds are found in <a href="/wiki/Azo_compound" title="Azo compound">azo compounds</a> (N=N), <a href="/wiki/Imine" title="Imine">imines</a> (C=N), and <a href="/wiki/Sulfoxide" title="Sulfoxide">sulfoxides</a> (S=O). In a <a href="/wiki/Skeletal_formula" title="Skeletal formula">skeletal formula</a>, a double bond is drawn as two parallel lines (=) between the two connected atoms; typographically, the <a href="/wiki/Equals_sign" title="Equals sign">equals sign</a> is used for this.<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Double bonds were introduced in chemical notation by <a href="/wiki/Russia" title="Russia">Russian</a> chemist <a href="/wiki/Alexander_Butlerov" title="Alexander Butlerov">Alexander Butlerov</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. (March 2017)">citation needed</span></a></i>]</sup> </p><p>Double bonds involving carbon are stronger and shorter than <a href="/wiki/Covalent_bond" title="Covalent bond">single bonds</a>. The <a href="/wiki/Bond_order" title="Bond order">bond order</a> is two. Double bonds are also electron-rich, which makes them potentially more reactive in the presence of a strong electron acceptor (as in <a href="/wiki/Halogen_addition_reaction" title="Halogen addition reaction">addition reactions of the halogens</a>). </p> <ul class="gallery mw-gallery-traditional"> <li class="gallerycaption">Chemical compounds with double bonds</li> <li class="gallerybox" style="width: 175px"> <div class="thumb" style="width: 170px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Ethene_structural.svg" class="mw-file-description" title="Ethylene Carbon–carbon double bond"><img alt="Ethylene Carbon–carbon double bond" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e9/Ethene_structural.svg/128px-Ethene_structural.svg.png" decoding="async" width="128" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e9/Ethene_structural.svg/191px-Ethene_structural.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e9/Ethene_structural.svg/255px-Ethene_structural.svg.png 2x" data-file-width="170" data-file-height="160" /></a></span></div> <div class="gallerytext"><a href="/wiki/Ethylene" title="Ethylene">Ethylene</a> <span class="nowrap">Carbon–carbon</span> double bond</div> </li> <li class="gallerybox" style="width: 175px"> <div class="thumb" style="width: 170px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Leuckart-Wallach-Reaktion_Aceton.svg" class="mw-file-description" title="Acetone Carbon–oxygen double bond"><img alt="Acetone Carbon–oxygen double bond" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/73/Leuckart-Wallach-Reaktion_Aceton.svg/140px-Leuckart-Wallach-Reaktion_Aceton.svg.png" decoding="async" width="140" height="102" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/73/Leuckart-Wallach-Reaktion_Aceton.svg/210px-Leuckart-Wallach-Reaktion_Aceton.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/73/Leuckart-Wallach-Reaktion_Aceton.svg/280px-Leuckart-Wallach-Reaktion_Aceton.svg.png 2x" data-file-width="171" data-file-height="124" /></a></span></div> <div class="gallerytext"><a href="/wiki/Acetone" title="Acetone">Acetone</a> <span class="nowrap">Carbon–oxygen</span> double bond</div> </li> <li class="gallerybox" style="width: 175px"> <div class="thumb" style="width: 170px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Dimethylsulfoxid.svg" class="mw-file-description" title="Dimethyl sulfoxide Sulfur–oxygen double bond"><img alt="Dimethyl sulfoxide Sulfur–oxygen double bond" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/ae/Dimethylsulfoxid.svg/140px-Dimethylsulfoxid.svg.png" decoding="async" width="140" height="83" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/ae/Dimethylsulfoxid.svg/210px-Dimethylsulfoxid.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/ae/Dimethylsulfoxid.svg/280px-Dimethylsulfoxid.svg.png 2x" data-file-width="138" data-file-height="82" /></a></span></div> <div class="gallerytext"><a href="/wiki/Dimethyl_sulfoxide" title="Dimethyl sulfoxide">Dimethyl sulfoxide</a> <span class="nowrap">Sulfur–oxygen</span> double bond</div> </li> <li class="gallerybox" style="width: 175px"> <div class="thumb" style="width: 170px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Trans-diazene-2D.svg" class="mw-file-description" title="Diazene Nitrogen–nitrogen double bond"><img alt="Diazene Nitrogen–nitrogen double bond" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/30/Trans-diazene-2D.svg/250px-Trans-diazene-2D.svg.png" decoding="async" width="130" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/30/Trans-diazene-2D.svg/330px-Trans-diazene-2D.svg.png 2x" data-file-width="1011" data-file-height="935" /></a></span></div> <div class="gallerytext"><a href="/wiki/Diazene" class="mw-redirect" title="Diazene">Diazene</a> <span class="nowrap">Nitrogen–nitrogen</span> double bond</div> </li> </ul> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Double_bonds_in_alkenes">Double bonds in alkenes</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Double_bond&action=edit&section=1" title="Edit section: Double bonds in alkenes"><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:Ethylene-CRC-MW-dimensions-2D-Vector.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/43/Ethylene-CRC-MW-dimensions-2D-Vector.svg/220px-Ethylene-CRC-MW-dimensions-2D-Vector.svg.png" decoding="async" width="220" height="129" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/43/Ethylene-CRC-MW-dimensions-2D-Vector.svg/330px-Ethylene-CRC-MW-dimensions-2D-Vector.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/43/Ethylene-CRC-MW-dimensions-2D-Vector.svg/440px-Ethylene-CRC-MW-dimensions-2D-Vector.svg.png 2x" data-file-width="500" data-file-height="293" /></a><figcaption>Geometry of ethylene</figcaption></figure> <p>The type of bonding can be explained in terms of <a href="/wiki/Orbital_hybridisation" title="Orbital hybridisation">orbital hybridisation</a>. In <a href="/wiki/Ethylene" title="Ethylene">ethylene</a> each carbon atom has three <a href="/wiki/Orbital_hybridization#sp2_hybrids" class="mw-redirect" title="Orbital hybridization">sp<sup>2</sup></a> orbitals and one <a href="/wiki/Atomic_orbital" title="Atomic orbital">p-orbital</a>. The three sp<sup>2</sup> orbitals lie in a plane with ~120° angles. The p-orbital is perpendicular to this plane. When the carbon atoms approach each other, two of the sp<sup>2</sup> orbitals overlap to form a <a href="/wiki/Sigma_bond" title="Sigma bond">sigma bond</a>. At the same time, the two p-orbitals approach (again in the same plane) and together they form a <a href="/wiki/Pi_bond" title="Pi bond">pi bond</a>. For maximum overlap, the p-orbitals have to remain parallel, and, therefore, rotation around the central bond is not possible. This property gives rise to <a href="/wiki/Cis-trans_isomerism" class="mw-redirect" title="Cis-trans isomerism">cis-trans isomerism</a>. Double bonds are shorter than single bonds because p-orbital overlap is maximized. </p> <ul class="gallery mw-gallery-traditional"> <li class="gallerybox" style="width: 385px"> <div class="thumb" style="width: 380px; height: 280px;"><span typeof="mw:File"><a href="/wiki/File:Doppelbindung1.png" class="mw-file-description" title="2 sp2 orbitals (total of 3 such orbitals) approach to form a sp2-sp2 sigma bond"><img alt="2 sp2 orbitals (total of 3 such orbitals) approach to form a sp2-sp2 sigma bond" src="//upload.wikimedia.org/wikipedia/commons/thumb/9/95/Doppelbindung1.png/500px-Doppelbindung1.png" decoding="async" width="335" height="250" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/95/Doppelbindung1.png/960px-Doppelbindung1.png 1.5x" data-file-width="1126" data-file-height="840" /></a></span></div> <div class="gallerytext">2 sp<sup>2</sup> orbitals (total of 3 such orbitals) approach to form a sp<sup>2</sup>-sp<sup>2</sup> sigma bond</div> </li> <li class="gallerybox" style="width: 385px"> <div class="thumb" style="width: 380px; height: 280px;"><span typeof="mw:File"><a href="/wiki/File:Doppelbindung2.png" class="mw-file-description" title="Two p-orbitals overlap to form a pi-bond in a plane parallel to the sigma plane"><img alt="Two p-orbitals overlap to form a pi-bond in a plane parallel to the sigma plane" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b1/Doppelbindung2.png/500px-Doppelbindung2.png" decoding="async" width="335" height="250" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b1/Doppelbindung2.png/960px-Doppelbindung2.png 1.5x" data-file-width="1126" data-file-height="840" /></a></span></div> <div class="gallerytext">Two p-orbitals overlap to form a pi-bond in a plane parallel to the sigma plane</div> </li> <li class="gallerybox" style="width: 385px"> <div class="thumb" style="width: 380px; height: 280px;"><span typeof="mw:File"><a href="/wiki/File:Ethylene_3D.png" class="mw-file-description" title="pi bond (green) in ethylene"><img alt="pi bond (green) in ethylene" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e4/Ethylene_3D.png/250px-Ethylene_3D.png" decoding="async" width="224" height="250" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e4/Ethylene_3D.png/500px-Ethylene_3D.png 1.5x" data-file-width="549" data-file-height="613" /></a></span></div> <div class="gallerytext"><a href="/wiki/Pi_bond" title="Pi bond">pi bond</a> (green) in <a href="/wiki/Ethylene" title="Ethylene">ethylene</a></div> </li> </ul> <p>With 133 pm, the ethylene <a href="/wiki/Carbon%E2%80%93carbon_bond" title="Carbon–carbon bond">C=C</a> <a href="/wiki/Bond_length" title="Bond length">bond length</a> is shorter than the C−C length in <a href="/wiki/Ethane" title="Ethane">ethane</a> with 154 pm. The double bond is also stronger, 636 <a href="/wiki/Joule" title="Joule">kJ</a> <a href="/wiki/Mole_(unit)" title="Mole (unit)">mol</a><sup>−1</sup> versus 368 kJ mol<sup>−1</sup> but not twice as much as the pi-bond is weaker than the sigma bond due to less effective pi-overlap. </p><p>In an alternative representation, the double bond results from two overlapping sp<sup>3</sup> orbitals as in a <a href="/wiki/Bent_bond" title="Bent bond">bent bond</a>.<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Variations">Variations</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Double_bond&action=edit&section=2" title="Edit section: Variations"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In molecules with alternating double bonds and single bonds, p-orbital overlap can exist over multiple atoms in a chain, giving rise to a <a href="/wiki/Conjugated_system" title="Conjugated system">conjugated system</a>. Conjugation can be found in systems such as <a href="/wiki/Diene" title="Diene">dienes</a> and <a href="/wiki/Alpha-beta_Unsaturated_carbonyl_compounds" class="mw-redirect" title="Alpha-beta Unsaturated carbonyl compounds">enones</a>. In <a href="/wiki/Cyclic_compound" title="Cyclic compound">cyclic molecules</a>, conjugation can lead to <a href="/wiki/Aromaticity" title="Aromaticity">aromaticity</a>. In <a href="/wiki/Cumulene" title="Cumulene">cumulenes</a>, two double bonds are adjacent and do not overlap with each other. </p><p>Double bonds are common for <a href="/wiki/Period_2_element" title="Period 2 element">period 2 elements</a> <a href="/wiki/Carbon" title="Carbon">carbon</a>, <a href="/wiki/Nitrogen" title="Nitrogen">nitrogen</a>, and <a href="/wiki/Oxygen" title="Oxygen">oxygen</a>, and less common with elements of higher periods, a distinction called the <i><a href="/wiki/Double_bond_rule" title="Double bond rule">double bond rule</a></i>. Metals, too, can engage in multiple bonding in a <a href="/wiki/Metal%E2%80%93ligand_multiple_bond" title="Metal–ligand multiple bond">metal–ligand multiple bond</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Group_14_alkene_homologs">Group 14 alkene homologs</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Double_bond&action=edit&section=3" title="Edit section: Group 14 alkene homologs"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Double bonded compounds, <a href="/wiki/Alkene" title="Alkene">alkene</a> homologs, R<sub>2</sub>E=ER<sub>2</sub> are now known for all of the heavier <a href="/wiki/Carbon_group" title="Carbon group">group 14</a> elements. Unlike the alkenes these compounds are not planar but adopt twisted and/or trans bent structures. These effects become more pronounced for the heavier elements. The distannene (Me<sub>3</sub>Si)<sub>2</sub>CHSn=SnCH(SiMe<sub>3</sub>)<sub>2</sub> has a tin-tin bond length just a little shorter than a single bond, a trans bent structure with pyramidal coordination at each tin atom, and readily dissociates in solution to form (Me<sub>3</sub>Si)<sub>2</sub>CHSn: (stannanediyl, a carbene analog). The bonding comprises two weak donor acceptor bonds, the lone pair on each tin atom overlapping with the empty p orbital on the other.<sup id="cite_ref-Power1999_4-0" class="reference"><a href="#cite_note-Power1999-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Wang&Robinson2009_5-0" class="reference"><a href="#cite_note-Wang&Robinson2009-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> In contrast, in disilenes each silicon atom has planar coordination but the substituents are twisted so that the molecule as a whole is not planar. In diplumbenes the Pb=Pb bond length can be longer than that of many corresponding single bonds<sup id="cite_ref-Wang&Robinson2009_5-1" class="reference"><a href="#cite_note-Wang&Robinson2009-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Plumbenes and stannenes generally dissociate in solution into monomers with bond enthalpies that are just a fraction of the corresponding single bonds. Some double bonds plumbenes and stannenes are similar in strength to hydrogen bonds.<sup id="cite_ref-Power1999_4-1" class="reference"><a href="#cite_note-Power1999-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/Carter%E2%80%93Goddard%E2%80%93Malrieu%E2%80%93Trinquier_model" title="Carter–Goddard–Malrieu–Trinquier model">Carter–Goddard–Malrieu–Trinquier model</a> can be used to predict the nature of the bonding.<sup id="cite_ref-Power1999_4-2" class="reference"><a href="#cite_note-Power1999-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Types_of_double_bonds_between_atoms">Types of double bonds between atoms</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Double_bond&action=edit&section=4" title="Edit section: Types of double bonds between atoms"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <table class="wikitable" style="text-align:center;"> <tbody><tr> <th> </th> <th>C </th> <th>O </th> <th>N </th> <th>S </th> <th>Si </th> <th>Ge </th> <th>Sn </th> <th>Pb </th></tr> <tr> <th>C </th> <td><a href="/wiki/Alkene" title="Alkene">alkene</a> </td> <td><a href="/wiki/Carbonyl" class="mw-redirect" title="Carbonyl">carbonyl group</a> </td> <td><a href="/wiki/Imine" title="Imine">imine</a> </td> <td><a href="/wiki/Thioketone" title="Thioketone">thioketone</a>, <a href="/wiki/Thial" title="Thial">thial</a> </td> <td><a href="/wiki/Organosilicon#Silenes" class="mw-redirect" title="Organosilicon">alkylidenesilanes</a> </td> <td> </td> <td> </td> <td> </td></tr> <tr> <th>O </th> <td> </td> <td><a href="/wiki/Oxygen" title="Oxygen">dioxygen</a> </td> <td><a href="/wiki/Nitroso" title="Nitroso">nitroso compound</a> </td> <td><a href="/wiki/Sulfoxide" title="Sulfoxide">sulfoxide</a>, <a href="/wiki/Sulfone" title="Sulfone">sulfone</a>, <a href="/wiki/Sulfinic_acid" title="Sulfinic acid">sulfinic acid</a>, <a href="/wiki/Sulfonic_acid" title="Sulfonic acid">sulfonic acid</a> </td> <td> </td> <td> </td> <td> </td> <td> </td></tr> <tr> <th>N </th> <td> </td> <td> </td> <td><a href="/wiki/Azo_compound" title="Azo compound">azo compound</a> </td> <td> </td> <td> </td> <td> </td> <td> </td> <td> </td></tr> <tr> <th>S </th> <td> </td> <td> </td> <td> </td> <td><a href="/wiki/Disulfur" title="Disulfur">disulfur</a> </td> <td> </td> <td> </td> <td> </td> <td> </td></tr> <tr> <th>Si </th> <td> </td> <td> </td> <td> </td> <td> </td> <td><a href="/wiki/Silenes" title="Silenes">silenes</a> </td> <td> </td> <td> </td> <td> </td></tr> <tr> <th>Ge </th> <td> </td> <td> </td> <td> </td> <td> </td> <td> </td> <td><a href="/w/index.php?title=Germenes&action=edit&redlink=1" class="new" title="Germenes (page does not exist)">germenes</a> </td> <td> </td> <td> </td></tr> <tr> <th>Sn </th> <td> </td> <td> </td> <td> </td> <td> </td> <td> </td> <td> </td> <td><a href="/w/index.php?title=Stannenes&action=edit&redlink=1" class="new" title="Stannenes (page does not exist)">stannenes</a> </td> <td> </td></tr> <tr> <th>Pb </th> <td> </td> <td> </td> <td> </td> <td> </td> <td> </td> <td> </td> <td> </td> <td><a href="/w/index.php?title=Plumbenes&action=edit&redlink=1" class="new" title="Plumbenes (page does not exist)">plumbenes</a> </td></tr></tbody></table> <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=Double_bond&action=edit&section=5" 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 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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 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(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFMarch,_Jerry,_1929-1997.1985" class="citation book cs1">March, Jerry, 1929-1997. (1985). <a rel="nofollow" class="external text" href="https://www.worldcat.org/oclc/10998226"><i>Advanced organic chemistry : reactions, mechanisms, and structure</i></a> (3rd ed.). New York: Wiley. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0-471-88841-9" title="Special:BookSources/0-471-88841-9"><bdi>0-471-88841-9</bdi></a>. <a href="/wiki/OCLC_(identifier)" class="mw-redirect" title="OCLC (identifier)">OCLC</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/oclc/10998226">10998226</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20191210043257/https://www.worldcat.org/oclc/10998226">Archived</a> from the original on 2019-12-10<span class="reference-accessdate">. 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Boston, MA, USA. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-305-08048-5" title="Special:BookSources/978-1-305-08048-5"><bdi>978-1-305-08048-5</bdi></a>. <a href="/wiki/OCLC_(identifier)" class="mw-redirect" title="OCLC (identifier)">OCLC</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/oclc/907259297">907259297</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20240404115100/https://search.worldcat.org/title/907259297">Archived</a> from the original on 2024-04-04<span class="reference-accessdate">. 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New York: Springer. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-387-44897-8" title="Special:BookSources/978-0-387-44897-8"><bdi>978-0-387-44897-8</bdi></a>. <a href="/wiki/OCLC_(identifier)" class="mw-redirect" title="OCLC (identifier)">OCLC</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/oclc/154040953">154040953</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20240404115056/https://search.worldcat.org/title/154040953">Archived</a> from the original on 2024-04-04<span class="reference-accessdate">. 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.navbox-image img{max-width:none!important}@media print{body.ns-0 .mw-parser-output .navbox{display:none!important}}</style></div><div role="navigation" class="navbox" aria-labelledby="Chemical_bonding_theory174" style="padding:3px"><table class="nowraplinks hlist mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><style data-mw-deduplicate="TemplateStyles:r1239400231">.mw-parser-output .navbar{display:inline;font-size:88%;font-weight:normal}.mw-parser-output .navbar-collapse{float:left;text-align:left}.mw-parser-output .navbar-boxtext{word-spacing:0}.mw-parser-output .navbar ul{display:inline-block;white-space:nowrap;line-height:inherit}.mw-parser-output .navbar-brackets::before{margin-right:-0.125em;content:"[ "}.mw-parser-output .navbar-brackets::after{margin-left:-0.125em;content:" ]"}.mw-parser-output .navbar li{word-spacing:-0.125em}.mw-parser-output .navbar a>span,.mw-parser-output .navbar a>abbr{text-decoration:inherit}.mw-parser-output .navbar-mini abbr{font-variant:small-caps;border-bottom:none;text-decoration:none;cursor:inherit}.mw-parser-output .navbar-ct-full{font-size:114%;margin:0 7em}.mw-parser-output .navbar-ct-mini{font-size:114%;margin:0 4em}html.skin-theme-clientpref-night .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Chemical_bonding_theory" title="Template:Chemical bonding theory"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Chemical_bonding_theory" title="Template talk:Chemical bonding theory"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Chemical_bonding_theory" title="Special:EditPage/Template:Chemical bonding theory"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Chemical_bonding_theory174" style="font-size:114%;margin:0 4em"><a href="/wiki/Chemical_bond" title="Chemical bond">Chemical bonding</a> theory</div></th></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <ul><li><a href="/wiki/Atomic_orbital" title="Atomic orbital">Atomic orbital</a></li> <li><a href="/wiki/Quantum_mechanics" title="Quantum mechanics">Quantum mechanics</a> <ul><li><a href="/wiki/Introduction_to_quantum_mechanics" title="Introduction to quantum mechanics">Introduction to quantum mechanics</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Types of bonds</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">By symmetry</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/Sigma_bond" title="Sigma bond">Sigma (σ)</a></li> <li><a href="/wiki/Pi_bond" title="Pi bond">Pi (π)</a></li> <li><a href="/wiki/Delta_bond" title="Delta bond">Delta (δ)</a></li> <li><a href="/wiki/Phi_bond" title="Phi bond">Phi (φ)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">By <a href="/wiki/Bond_order" title="Bond order">multiplicity</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/Single_bond" title="Single bond">1 (single)</a></li> <li><a class="mw-selflink selflink">2 (double)</a></li> <li><a href="/wiki/Triple_bond" title="Triple bond">3 (triple)</a></li> <li><a href="/wiki/Quadruple_bond" title="Quadruple bond">4 (quadruple)</a></li> <li><a href="/wiki/Quintuple_bond" title="Quintuple bond">5 (quintuple)</a></li> <li><a href="/wiki/Sextuple_bond" title="Sextuple bond">6 (sextuple)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">By <a href="/wiki/Spin_(physics)" title="Spin (physics)">spin</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/Triplet_state" title="Triplet state">Triplet</a></li> <li><a href="/wiki/Singlet_state" title="Singlet state">Singlet</a></li> <li><a href="/wiki/Exchange_interaction" title="Exchange interaction">Exchange-coupled</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Valence_bond_theory" title="Valence bond theory">Valence bond theory</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">Concepts</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/Orbital_hybridisation" title="Orbital hybridisation">Hybrid orbital</a></li> <li><a href="/wiki/Resonance_(chemistry)" title="Resonance (chemistry)">Resonance</a></li> <li><a href="/wiki/Lewis_structure" title="Lewis structure">Lewis structure</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Constituent units</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/Covalent_bond" title="Covalent bond">Covalent bond</a></li> <li><a href="/wiki/Lone_pair" title="Lone pair">Lone pair</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Molecular_orbital_theory" title="Molecular orbital theory">Molecular orbital theory</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">Concepts</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/Molecular_orbital" title="Molecular orbital">Molecular orbital</a></li> <li><a href="/wiki/Linear_combination_of_atomic_orbitals" title="Linear combination of atomic orbitals">LCAO</a></li> <li><a href="/wiki/Molecular_orbital_diagram" title="Molecular orbital diagram">MO diagram</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Constituent units</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/Bonding_molecular_orbital" title="Bonding molecular orbital">Bonding MO</a></li> <li><a href="/wiki/Non-bonding_orbital" title="Non-bonding orbital">Non-bonding MO</a></li> <li><a href="/wiki/Antibonding_molecular_orbital" title="Antibonding molecular orbital">Antibonding MO</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="Chemical_bonds164" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="3"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Chemical_bonds" title="Template:Chemical bonds"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Chemical_bonds" title="Template talk:Chemical bonds"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Chemical_bonds" title="Special:EditPage/Template:Chemical bonds"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Chemical_bonds164" 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 navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li class="mw-empty-elt"></li></ul> </div></td></tr></tbody></table><div></div></td><td class="noviewer navbox-image" rowspan="4" style="width:1px;padding:0 0 0 2px"><div><span typeof="mw:File"><a href="/wiki/File:Ligatio-covalens.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/Ligatio-covalens.svg/200px-Ligatio-covalens.svg.png" decoding="async" width="200" height="89" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/Ligatio-covalens.svg/300px-Ligatio-covalens.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/21/Ligatio-covalens.svg/400px-Ligatio-covalens.svg.png 2x" data-file-width="597" data-file-height="265" /></a></span><br /><span typeof="mw:File"><a href="/wiki/File:Chemfm_carbon_monoxide_3_1.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/77/Chemfm_carbon_monoxide_3_1.svg/200px-Chemfm_carbon_monoxide_3_1.svg.png" decoding="async" width="200" height="113" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/77/Chemfm_carbon_monoxide_3_1.svg/300px-Chemfm_carbon_monoxide_3_1.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/77/Chemfm_carbon_monoxide_3_1.svg/400px-Chemfm_carbon_monoxide_3_1.svg.png 2x" data-file-width="99" data-file-height="56" /></a></span><br /><span typeof="mw:File"><a href="/wiki/File:Pi-Bond.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/70/Pi-Bond.svg/250px-Pi-Bond.svg.png" decoding="async" width="200" height="113" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/70/Pi-Bond.svg/330px-Pi-Bond.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/70/Pi-Bond.svg/500px-Pi-Bond.svg.png 2x" data-file-width="1920" 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 href="/wiki/Hydrogen_bond" title="Hydrogen bond">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 supramolecular)">Salt bridge</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Bond_cleavage" title="Bond cleavage">Bond 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title="Spherical aromaticity">spherical</a></li></ul></li> <li><a href="/wiki/Polyhedral_skeletal_electron_pair_theory" title="Polyhedral skeletal electron pair theory">Polyhedral skeletal electron pair theory</a></li> <li><a href="/wiki/Jemmis_mno_rules" title="Jemmis mno rules">Jemmis mno rules</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox authority-control" aria-label="Navbox390" style="padding:3px"><table class="nowraplinks hlist navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Help:Authority_control" title="Help:Authority control">Authority control databases</a>: National <span class="mw-valign-text-top noprint" 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