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class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Concepts_and_techniques"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Concepts and techniques</span> </div> </a> <ul id="toc-Concepts_and_techniques-sublist" class="vector-toc-list"> </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">3</span> <span>History</span> </div> </a> <button aria-controls="toc-History-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 History subsection</span> </button> <ul id="toc-History-sublist" class="vector-toc-list"> <li id="toc-Organometallic_chemistry_timeline" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Organometallic_chemistry_timeline"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Organometallic chemistry timeline</span> </div> </a> <ul id="toc-Organometallic_chemistry_timeline-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Scope" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Scope"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Scope</span> </div> </a> <ul id="toc-Scope-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Industrial_applications" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Industrial_applications"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Industrial applications</span> </div> </a> <ul id="toc-Industrial_applications-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Organometallic_reactions" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Organometallic_reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Organometallic reactions</span> </div> </a> <ul id="toc-Organometallic_reactions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Catalysis" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Catalysis"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Catalysis</span> </div> </a> <ul id="toc-Catalysis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Environmental_concerns" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Environmental_concerns"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>Environmental concerns</span> </div> </a> <ul id="toc-Environmental_concerns-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">10</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Sources" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Sources"> <div class="vector-toc-text"> <span class="vector-toc-numb">11</span> <span>Sources</span> </div> </a> <ul id="toc-Sources-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">12</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">Organometallic chemistry</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 43 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-43" 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">43 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/Organometaalchemie" title="Organometaalchemie – Afrikaans" lang="af" hreflang="af" data-title="Organometaalchemie" 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/%D9%83%D9%8A%D9%85%D9%8A%D8%A7%D8%A1_%D8%B9%D8%B6%D9%88%D9%8A%D8%A9_%D9%81%D9%84%D8%B2%D9%8A%D8%A9" title="كيمياء عضوية فلزية – Arabic" lang="ar" hreflang="ar" data-title="كيمياء عضوية فلزية" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-ast mw-list-item"><a href="https://ast.wikipedia.org/wiki/Qu%C3%ADmica_organomet%C3%A1lica" title="Química organometálica – Asturian" lang="ast" hreflang="ast" data-title="Química organometálica" data-language-autonym="Asturianu" data-language-local-name="Asturian" class="interlanguage-link-target"><span>Asturianu</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%9C%E0%A7%88%E0%A6%AC-%E0%A6%A7%E0%A6%BE%E0%A6%A4%E0%A6%AC_%E0%A6%B0%E0%A6%B8%E0%A6%BE%E0%A6%AF%E0%A6%BC%E0%A6%A8" title="জৈব-ধাতব রসায়ন – Bangla" lang="bn" hreflang="bn" data-title="জৈব-ধাতব রসায়ন" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%9C%D0%B5%D1%82%D0%B0%D0%BB%D0%BE%D0%BE%D1%80%D0%B3%D0%B0%D0%BD%D0%B8%D1%87%D0%BD%D0%B0_%D1%85%D0%B8%D0%BC%D0%B8%D1%8F" title="Металоорганична химия – Bulgarian" lang="bg" hreflang="bg" data-title="Металоорганична химия" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Qu%C3%ADmica_organomet%C3%A0l%C2%B7lica" title="Química organometàl·lica – Catalan" lang="ca" hreflang="ca" data-title="Química organometàl·lica" 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/Organokovov%C3%A1_chemie" title="Organokovová chemie – Czech" lang="cs" hreflang="cs" data-title="Organokovová chemie" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Organometallisk_kemi" title="Organometallisk kemi – Danish" lang="da" hreflang="da" data-title="Organometallisk kemi" 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/Metallorganische_Chemie" title="Metallorganische Chemie – German" lang="de" hreflang="de" data-title="Metallorganische Chemie" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Qu%C3%ADmica_organomet%C3%A1lica" title="Química organometálica – Spanish" lang="es" hreflang="es" data-title="Química organometálica" 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/Organometala_%C4%A5emio" title="Organometala ĥemio – Esperanto" lang="eo" hreflang="eo" data-title="Organometala ĥemio" 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/Kimika_organometaliko" title="Kimika organometaliko – Basque" lang="eu" hreflang="eu" data-title="Kimika organometaliko" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%B4%DB%8C%D9%85%DB%8C_%D8%A2%D9%84%DB%8C_%D9%81%D9%84%D8%B2%DB%8C" title="شیمی آلی فلزی – Persian" lang="fa" hreflang="fa" data-title="شیمی آلی فلزی" 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/Chimie_organom%C3%A9tallique" title="Chimie organométallique – French" lang="fr" hreflang="fr" data-title="Chimie organométallique" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%9C%A0%EA%B8%B0%EA%B8%88%EC%86%8D%ED%99%94%ED%95%99" title="유기금속화학 – Korean" lang="ko" hreflang="ko" data-title="유기금속화학" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%95%E0%A4%BE%E0%A4%B0%E0%A5%8D%E0%A4%AC%E0%A4%A7%E0%A4%BE%E0%A4%A4%E0%A5%81%E0%A4%95_%E0%A4%AF%E0%A5%8C%E0%A4%97%E0%A4%BF%E0%A4%95" title="कार्बधातुक यौगिक – Hindi" lang="hi" hreflang="hi" data-title="कार्बधातुक यौगिक" 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/Kimia_organologam" title="Kimia organologam – Indonesian" lang="id" hreflang="id" data-title="Kimia organologam" 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/Chimica_metallorganica" title="Chimica metallorganica – Italian" lang="it" hreflang="it" data-title="Chimica metallorganica" 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%9B%D7%99%D7%9E%D7%99%D7%94_%D7%90%D7%95%D7%A8%D7%92%D7%A0%D7%95-%D7%9E%D7%AA%D7%9B%D7%AA%D7%99%D7%AA" title="כימיה אורגנו-מתכתית – Hebrew" lang="he" hreflang="he" data-title="כימיה אורגנו-מתכתית" 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%9D%E1%83%A0%E1%83%92%E1%83%90%E1%83%9C%E1%83%9D%E1%83%9B%E1%83%94%E1%83%A2%E1%83%90%E1%83%9A%E1%83%A3%E1%83%A0%E1%83%98_%E1%83%A5%E1%83%98%E1%83%9B%E1%83%98%E1%83%90" title="ორგანომეტალური ქიმია – Georgian" lang="ka" hreflang="ka" data-title="ორგანომეტალური ქიმია" data-language-autonym="ქართული" data-language-local-name="Georgian" class="interlanguage-link-target"><span>ქართული</span></a></li><li class="interlanguage-link interwiki-la mw-list-item"><a href="https://la.wikipedia.org/wiki/Chemia_organometallica" title="Chemia organometallica – Latin" lang="la" hreflang="la" data-title="Chemia organometallica" data-language-autonym="Latina" data-language-local-name="Latin" class="interlanguage-link-target"><span>Latina</span></a></li><li class="interlanguage-link interwiki-lb mw-list-item"><a href="https://lb.wikipedia.org/wiki/Organometallchimie" title="Organometallchimie – Luxembourgish" lang="lb" hreflang="lb" data-title="Organometallchimie" data-language-autonym="Lëtzebuergesch" data-language-local-name="Luxembourgish" class="interlanguage-link-target"><span>Lëtzebuergesch</span></a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Organometaliniai_junginiai" title="Organometaliniai junginiai – Lithuanian" lang="lt" hreflang="lt" data-title="Organometaliniai junginiai" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target"><span>Lietuvių</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/F%C3%A9morganikus_k%C3%A9mia" title="Fémorganikus kémia – Hungarian" lang="hu" hreflang="hu" data-title="Fémorganikus kémia" 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%9E%D1%80%D0%B3%D0%B0%D0%BD%D0%BE%D0%BC%D0%B5%D1%82%D0%B0%D0%BB%D0%BD%D0%B0_%D1%85%D0%B5%D0%BC%D0%B8%D1%98%D0%B0" title="Органометална хемија – Macedonian" lang="mk" hreflang="mk" data-title="Органометална хемија" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Organometaalchemie" title="Organometaalchemie – Dutch" lang="nl" hreflang="nl" data-title="Organometaalchemie" 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%9C%89%E6%A9%9F%E9%87%91%E5%B1%9E%E5%8C%96%E5%AD%A6" title="有機金属化学 – Japanese" lang="ja" hreflang="ja" data-title="有機金属化学" 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-oc mw-list-item"><a href="https://oc.wikipedia.org/wiki/Quimia_organometallica" title="Quimia organometallica – Occitan" lang="oc" hreflang="oc" data-title="Quimia organometallica" data-language-autonym="Occitan" data-language-local-name="Occitan" class="interlanguage-link-target"><span>Occitan</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Qu%C3%ADmica_organomet%C3%A1lica" title="Química organometálica – Portuguese" lang="pt" hreflang="pt" data-title="Química organometálica" 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/Chimie_organometalic%C4%83" title="Chimie organometalică – Romanian" lang="ro" hreflang="ro" data-title="Chimie organometalică" 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%9C%D0%B5%D1%82%D0%B0%D0%BB%D0%BB%D0%BE%D0%BE%D1%80%D0%B3%D0%B0%D0%BD%D0%B8%D1%87%D0%B5%D1%81%D0%BA%D0%B0%D1%8F_%D1%85%D0%B8%D0%BC%D0%B8%D1%8F" title="Металлоорганическая химия – Russian" lang="ru" hreflang="ru" data-title="Металлоорганическая химия" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Organometallic_chemistry" title="Organometallic chemistry – Simple English" lang="en-simple" hreflang="en-simple" data-title="Organometallic chemistry" 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-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Organometalna_hemija" title="Organometalna hemija – Serbian" lang="sr" hreflang="sr" data-title="Organometalna hemija" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Organometalna_hemija" title="Organometalna hemija – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Organometalna hemija" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-su mw-list-item"><a href="https://su.wikipedia.org/wiki/Kimia_organologam" title="Kimia organologam – Sundanese" lang="su" hreflang="su" data-title="Kimia organologam" data-language-autonym="Sunda" data-language-local-name="Sundanese" class="interlanguage-link-target"><span>Sunda</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Metallorganisk_kemi" title="Metallorganisk kemi – Swedish" lang="sv" hreflang="sv" data-title="Metallorganisk kemi" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%95%E0%AE%B0%E0%AE%BF%E0%AE%AE_%E0%AE%89%E0%AE%B2%E0%AF%8B%E0%AE%95_%E0%AE%B5%E0%AF%87%E0%AE%A4%E0%AE%BF%E0%AE%AF%E0%AE%BF%E0%AE%AF%E0%AE%B2%E0%AF%8D" title="கரிம உலோக வேதியியல் – Tamil" lang="ta" hreflang="ta" data-title="கரிம உலோக வேதியியல்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li 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class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:N-butyllithium-tetramer-3D-balls.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/97/N-butyllithium-tetramer-3D-balls.png/200px-N-butyllithium-tetramer-3D-balls.png" decoding="async" width="200" height="220" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/97/N-butyllithium-tetramer-3D-balls.png/300px-N-butyllithium-tetramer-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/97/N-butyllithium-tetramer-3D-balls.png/400px-N-butyllithium-tetramer-3D-balls.png 2x" data-file-width="1001" data-file-height="1100" /></a><figcaption><a href="/wiki/N-Butyllithium" title="N-Butyllithium"><i>n</i>-Butyllithium</a>, an organometallic compound. Four lithium atoms (in purple) form a <a href="/wiki/Tetrahedron" title="Tetrahedron">tetrahedron</a>, with four <a href="/wiki/Butyl" class="mw-redirect" title="Butyl">butyl</a> groups attached to the faces (carbon is black, hydrogen is white).</figcaption></figure> <p><b>Organometallic chemistry</b> is the study of <b>organometallic compounds</b>, <a href="/wiki/Chemical_compound" title="Chemical compound">chemical compounds</a> containing at least one <a href="/wiki/Chemical_bond" title="Chemical bond">chemical bond</a> between a <a href="/wiki/Carbon" title="Carbon">carbon</a> atom of an <a href="/wiki/Organic_molecule" class="mw-redirect" title="Organic molecule">organic molecule</a> and a <a href="/wiki/Metal" title="Metal">metal</a>, including <a href="/wiki/Alkali" title="Alkali">alkali</a>, <a href="/wiki/Alkaline_earth" class="mw-redirect" title="Alkaline earth">alkaline earth</a>, and <a href="/wiki/Transition_metals" class="mw-redirect" title="Transition metals">transition metals</a>, and sometimes broadened to include <a href="/wiki/Metalloids" class="mw-redirect" title="Metalloids">metalloids</a> like boron, silicon, and selenium, as well.<sup id="cite_ref-FOOTNOTECrabtree2009[[Category:Wikipedia_articles_needing_page_number_citations_from_October_2021]]<sup_class="noprint_Inline-Template_"_style="white-space:nowrap;">&#91;<i>[[Wikipedia:Citing_sources|<span_title="This_citation_requires_a_reference_to_the_specific_page_or_range_of_pages_in_which_the_material_appears.&#32;(October_2021)">page&nbsp;needed</span>]]</i>&#93;</sup>_1-0" class="reference"><a href="#cite_note-FOOTNOTECrabtree2009[[Category:Wikipedia_articles_needing_page_number_citations_from_October_2021]]<sup_class="noprint_Inline-Template_"_style="white-space:nowrap;">&#91;<i>[[Wikipedia:Citing_sources|<span_title="This_citation_requires_a_reference_to_the_specific_page_or_range_of_pages_in_which_the_material_appears.&#32;(October_2021)">page&nbsp;needed</span>]]</i>&#93;</sup>-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:0_2-0" class="reference"><a href="#cite_note-:0-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Aside from bonds to <a href="/wiki/Organyl" class="mw-redirect" title="Organyl">organyl</a> fragments or molecules, bonds to 'inorganic' carbon, like <a href="/wiki/Carbon_monoxide" title="Carbon monoxide">carbon monoxide</a> (<a href="/wiki/Metal_carbonyl" title="Metal carbonyl">metal carbonyls</a>), <a href="/wiki/Cyanide" title="Cyanide">cyanide</a>, or <a href="/wiki/Carbide" title="Carbide">carbide</a>, are generally considered to be organometallic as well. Some related compounds such as <a href="/wiki/Transition_metal_hydride" title="Transition metal hydride">transition metal hydrides</a> and <a href="/wiki/Metal_phosphine_complexes" class="mw-redirect" title="Metal phosphine complexes">metal phosphine complexes</a> are often included in discussions of organometallic compounds, though strictly speaking, they are not necessarily organometallic. The related but distinct term "<a href="/wiki/Metalorganics" class="mw-redirect" title="Metalorganics">metalorganic compound</a>" refers to metal-containing compounds lacking direct metal-carbon bonds but which contain organic ligands. Metal β-diketonates, <a href="/wiki/Alkoxide" title="Alkoxide">alkoxides</a>, dialkylamides, and metal phosphine complexes are representative members of this class. The field of organometallic chemistry combines aspects of traditional <a href="/wiki/Inorganic_chemistry" title="Inorganic chemistry">inorganic</a> and <a href="/wiki/Organic_chemistry" title="Organic chemistry">organic chemistry</a>.<sup id="cite_ref-ChrisE_3-0" class="reference"><a href="#cite_note-ChrisE-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p>Organometallic compounds are widely used both stoichiometrically in research and industrial chemical reactions, as well as in the role of catalysts to increase the rates of such reactions (e.g., as in uses of <a href="/wiki/Homogeneous_catalysis" title="Homogeneous catalysis">homogeneous catalysis</a>), where target molecules include polymers, pharmaceuticals, and many other types of practical products. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Organometallic_compounds">Organometallic compounds</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organometallic_chemistry&action=edit&section=1" title="Edit section: Organometallic compounds"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Magnesium_bis-cyclopentadienyl_bottle.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/33/Magnesium_bis-cyclopentadienyl_bottle.jpg/180px-Magnesium_bis-cyclopentadienyl_bottle.jpg" decoding="async" width="180" height="320" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/33/Magnesium_bis-cyclopentadienyl_bottle.jpg/270px-Magnesium_bis-cyclopentadienyl_bottle.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/33/Magnesium_bis-cyclopentadienyl_bottle.jpg/360px-Magnesium_bis-cyclopentadienyl_bottle.jpg 2x" data-file-width="1170" data-file-height="2080" /></a><figcaption>A steel bottle containing MgCp<sub>2</sub> <a href="/wiki/Magnesocene" title="Magnesocene">(magnesium bis-cyclopentadienyl)</a>, which, like several other organometallic compounds, is pyrophoric in air.</figcaption></figure> <p>Organometallic compounds are distinguished by the prefix "organo-" (e.g., organopalladium compounds), and include all compounds which contain a bond between a metal atom and a carbon atom of an <a href="/wiki/Organyl_group" title="Organyl group">organyl group</a>.<sup id="cite_ref-:0_2-1" class="reference"><a href="#cite_note-:0-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> In addition to the traditional metals (<a href="/wiki/Alkali_metal" title="Alkali metal">alkali metals</a>, <a href="/wiki/Alkali_earth_metal" class="mw-redirect" title="Alkali earth metal">alkali earth metals</a>, <a href="/wiki/Transition_metals" class="mw-redirect" title="Transition metals">transition metals</a>, and <a href="/wiki/Post_transition_metals" class="mw-redirect" title="Post transition metals">post transition metals</a>), <a href="/wiki/Lanthanide" title="Lanthanide">lanthanides</a>, <a href="/wiki/Actinide" title="Actinide">actinides</a>, semimetals, and the elements <a href="/wiki/Boron" title="Boron">boron</a>, <a href="/wiki/Silicon" title="Silicon">silicon</a>, <a href="/wiki/Arsenic" title="Arsenic">arsenic</a>, and <a href="/wiki/Selenium" title="Selenium">selenium</a> are considered to form organometallic compounds.<sup id="cite_ref-:0_2-2" class="reference"><a href="#cite_note-:0-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Examples of organometallic compounds include <a href="/wiki/Gilman_reagent" title="Gilman reagent">Gilman reagents</a>, which contain <a href="/wiki/Lithium" title="Lithium">lithium</a> and <a href="/wiki/Copper" title="Copper">copper</a>, and <a href="/wiki/Grignard_reagent" title="Grignard reagent">Grignard reagents</a>, which contain <a href="/wiki/Magnesium" title="Magnesium">magnesium</a>. Boron-containing organometallic compounds are often the result of <a href="/wiki/Hydroboration" title="Hydroboration">hydroboration</a> and <a href="/wiki/Carboboration" title="Carboboration">carboboration</a> reactions. <a href="/wiki/Tetracarbonyl_nickel" class="mw-redirect" title="Tetracarbonyl nickel">Tetracarbonyl nickel</a> and <a href="/wiki/Ferrocene" title="Ferrocene">ferrocene</a> are examples of organometallic compounds containing <a href="/wiki/Transition_metal" title="Transition metal">transition metals</a>. Other examples of organometallic compounds include <a href="/wiki/Organolithium" class="mw-redirect" title="Organolithium">organolithium</a> compounds such as <a href="/wiki/N-butyllithium" class="mw-redirect" title="N-butyllithium"><i>n</i>-butyllithium</a> (n-BuLi), <a href="/wiki/Organozinc" class="mw-redirect" title="Organozinc">organozinc</a> compounds such as <a href="/wiki/Diethylzinc" title="Diethylzinc">diethylzinc</a> (Et<sub>2</sub>Zn), <a href="/wiki/Organotin" class="mw-redirect" title="Organotin">organotin</a> compounds such as <a href="/wiki/Tributyltin_hydride" title="Tributyltin hydride">tributyltin hydride</a> (Bu<sub>3</sub>SnH), <a href="/wiki/Organoborane" class="mw-redirect" title="Organoborane">organoborane</a> compounds such as <a href="/wiki/Triethylborane" title="Triethylborane">triethylborane</a> (Et<sub>3</sub>B), and <a href="/wiki/Organoaluminium" class="mw-redirect" title="Organoaluminium">organoaluminium</a> compounds such as <a href="/wiki/Trimethylaluminium" title="Trimethylaluminium">trimethylaluminium</a> (Me<sub>3</sub>Al).<sup id="cite_ref-ChrisE_3-1" class="reference"><a href="#cite_note-ChrisE-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p>A naturally occurring organometallic complex is <a href="/wiki/Methylcobalamin" title="Methylcobalamin">methylcobalamin</a> (a form of <a href="/wiki/Vitamin_B12" title="Vitamin B12">Vitamin B<sub>12</sub></a>), which contains a <a href="/wiki/Cobalt" title="Cobalt">cobalt</a>-<a href="/wiki/Methyl" class="mw-redirect" title="Methyl">methyl</a> bond. This complex, along with other biologically relevant complexes are often discussed within the subfield of <a href="/wiki/Bioorganometallic_chemistry" title="Bioorganometallic chemistry">bioorganometallic chemistry</a>.<sup id="cite_ref-FOOTNOTELippardBerg1994[[Category:Wikipedia_articles_needing_page_number_citations_from_October_2021]]<sup_class="noprint_Inline-Template_"_style="white-space:nowrap;">&#91;<i>[[Wikipedia:Citing_sources|<span_title="This_citation_requires_a_reference_to_the_specific_page_or_range_of_pages_in_which_the_material_appears.&#32;(October_2021)">page&nbsp;needed</span>]]</i>&#93;</sup>_4-0" class="reference"><a href="#cite_note-FOOTNOTELippardBerg1994[[Category:Wikipedia_articles_needing_page_number_citations_from_October_2021]]<sup_class="noprint_Inline-Template_"_style="white-space:nowrap;">&#91;<i>[[Wikipedia:Citing_sources|<span_title="This_citation_requires_a_reference_to_the_specific_page_or_range_of_pages_in_which_the_material_appears.&#32;(October_2021)">page&nbsp;needed</span>]]</i>&#93;</sup>-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <ul class="gallery mw-gallery-traditional"> <li class="gallerycaption">Representative Organometallic Compounds</li> <li class="gallerybox" style="width: 175px"> <div class="thumb" style="width: 170px; height: 126px;"><span typeof="mw:File"><a href="/wiki/File:Ferrocene.svg" class="mw-file-description" title="Ferrocene is an archetypal organoiron complex. It is an air-stable, sublimable compound."><img alt="Ferrocene is an archetypal organoiron complex. It is an air-stable, sublimable compound." src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e9/Ferrocene.svg/57px-Ferrocene.svg.png" decoding="async" width="57" height="96" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e9/Ferrocene.svg/85px-Ferrocene.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e9/Ferrocene.svg/113px-Ferrocene.svg.png 2x" data-file-width="103" data-file-height="174" /></a></span></div> <div class="gallerytext"><a href="/wiki/Ferrocene" title="Ferrocene">Ferrocene</a> is an archetypal organoiron complex. It is an air-stable, sublimable compound.</div> </li> <li class="gallerybox" style="width: 175px"> <div class="thumb" style="width: 170px; height: 126px;"><span typeof="mw:File"><a href="/wiki/File:Cobaltocene.svg" class="mw-file-description" title="Cobaltocene is a structural analogue of ferrocene, but is highly reactive toward air."><img alt="Cobaltocene is a structural analogue of ferrocene, but is highly reactive toward air." src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2a/Cobaltocene.svg/76px-Cobaltocene.svg.png" decoding="async" width="76" height="96" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/2a/Cobaltocene.svg/115px-Cobaltocene.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/2a/Cobaltocene.svg/153px-Cobaltocene.svg.png 2x" data-file-width="184" data-file-height="231" /></a></span></div> <div class="gallerytext"><a href="/wiki/Cobaltocene" title="Cobaltocene">Cobaltocene</a> is a structural analogue of ferrocene, but is highly reactive toward air.</div> </li> <li class="gallerybox" style="width: 175px"> <div class="thumb" style="width: 170px; height: 126px;"><span typeof="mw:File"><a href="/wiki/File:HRh(CO)P3again.png" class="mw-file-description" title="Tris(triphenylphosphine)rhodium carbonyl hydride is used in the commercial production of many aldehyde-based fragrances."><img alt="Tris(triphenylphosphine)rhodium carbonyl hydride is used in the commercial production of many aldehyde-based fragrances." src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f2/HRh%28CO%29P3again.png/130px-HRh%28CO%29P3again.png" decoding="async" width="130" height="96" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f2/HRh%28CO%29P3again.png/196px-HRh%28CO%29P3again.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f2/HRh%28CO%29P3again.png/261px-HRh%28CO%29P3again.png 2x" data-file-width="1058" data-file-height="780" /></a></span></div> <div class="gallerytext"><a href="/wiki/Tris(triphenylphosphine)rhodium_carbonyl_hydride" title="Tris(triphenylphosphine)rhodium carbonyl hydride">Tris(triphenylphosphine)rhodium carbonyl hydride</a> is used in the commercial production of many aldehyde-based <a href="/wiki/Fragrance" class="mw-redirect" title="Fragrance">fragrances</a>.</div> </li> <li class="gallerybox" style="width: 175px"> <div class="thumb" style="width: 170px; height: 126px;"><span typeof="mw:File"><a href="/wiki/File:Zeise%27sSalt.png" class="mw-file-description" title="Zeise's salt is an example of a transition metal alkene complex."><img alt="Zeise's salt is an example of a transition metal alkene complex." src="//upload.wikimedia.org/wikipedia/commons/thumb/4/41/Zeise%27sSalt.png/138px-Zeise%27sSalt.png" decoding="async" width="138" height="96" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/41/Zeise%27sSalt.png/207px-Zeise%27sSalt.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/41/Zeise%27sSalt.png/276px-Zeise%27sSalt.png 2x" data-file-width="471" data-file-height="328" /></a></span></div> <div class="gallerytext"><a href="/wiki/Zeise%27s_salt" title="Zeise's salt">Zeise's salt</a> is an example of a <a href="/wiki/Transition_metal_alkene_complex" title="Transition metal alkene complex">transition metal alkene complex</a>.</div> </li> <li class="gallerybox" style="width: 175px"> <div class="thumb" style="width: 170px; height: 126px;"><span typeof="mw:File"><a href="/wiki/File:Trimethylaluminium-from-xtal-3D-bs-17.png" class="mw-file-description" title="Trimethylaluminium is an organometallic compound with a bridging methyl group. It is used in the industrial production of some alcohols."><img alt="Trimethylaluminium is an organometallic compound with a bridging methyl group. It is used in the industrial production of some alcohols." src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e9/Trimethylaluminium-from-xtal-3D-bs-17.png/120px-Trimethylaluminium-from-xtal-3D-bs-17.png" decoding="async" width="120" height="96" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e9/Trimethylaluminium-from-xtal-3D-bs-17.png/180px-Trimethylaluminium-from-xtal-3D-bs-17.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e9/Trimethylaluminium-from-xtal-3D-bs-17.png/240px-Trimethylaluminium-from-xtal-3D-bs-17.png 2x" data-file-width="2501" data-file-height="2000" /></a></span></div> <div class="gallerytext"><a href="/wiki/Trimethylaluminium" title="Trimethylaluminium">Trimethylaluminium</a> is an organometallic compound with a <a href="/wiki/Bridging_ligand" title="Bridging ligand">bridging</a> <a href="/wiki/Methyl_group" title="Methyl group">methyl group</a>. It is used in the industrial production of some alcohols.</div> </li> <li class="gallerybox" style="width: 175px"> <div class="thumb" style="width: 170px; height: 126px;"><span typeof="mw:File"><a href="/wiki/File:Dimethylzinc-3D-balls.png" class="mw-file-description" title="Dimethylzinc has a linear coordination. It is a volatile pyrophoric liquid that is used in the preparation of semiconducting films."><img alt="Dimethylzinc has a linear coordination. It is a volatile pyrophoric liquid that is used in the preparation of semiconducting films." src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4b/Dimethylzinc-3D-balls.png/140px-Dimethylzinc-3D-balls.png" decoding="async" width="140" height="75" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4b/Dimethylzinc-3D-balls.png/210px-Dimethylzinc-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4b/Dimethylzinc-3D-balls.png/280px-Dimethylzinc-3D-balls.png 2x" data-file-width="1100" data-file-height="592" /></a></span></div> <div class="gallerytext"><a href="/wiki/Dimethylzinc" title="Dimethylzinc">Dimethylzinc</a> has a linear coordination. It is a volatile pyrophoric liquid that is used in the preparation of semiconducting films.</div> </li> <li class="gallerybox" style="width: 175px"> <div class="thumb" style="width: 170px; height: 126px;"><span typeof="mw:File"><a href="/wiki/File:Lithium-diphenylcuprate-etherate-dimer-from-xtal-2D-skeletal.png" class="mw-file-description" title="Lithium diphenylcuprate bis(diethyl etherate) is an example of a Gilman reagent, a type of organocopper complex frequently employed in organic synthesis."><img alt="Lithium diphenylcuprate bis(diethyl etherate) is an example of a Gilman reagent, a type of organocopper complex frequently employed in organic synthesis." src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7e/Lithium-diphenylcuprate-etherate-dimer-from-xtal-2D-skeletal.png/118px-Lithium-diphenylcuprate-etherate-dimer-from-xtal-2D-skeletal.png" decoding="async" width="118" height="96" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/7e/Lithium-diphenylcuprate-etherate-dimer-from-xtal-2D-skeletal.png/177px-Lithium-diphenylcuprate-etherate-dimer-from-xtal-2D-skeletal.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/7e/Lithium-diphenylcuprate-etherate-dimer-from-xtal-2D-skeletal.png/237px-Lithium-diphenylcuprate-etherate-dimer-from-xtal-2D-skeletal.png 2x" data-file-width="1100" data-file-height="893" /></a></span></div> <div class="gallerytext">Lithium diphenylcuprate bis(diethyl etherate) is an example of a <a href="/wiki/Gilman_reagent" title="Gilman reagent">Gilman reagent</a>, a type of organocopper complex frequently employed in organic synthesis.</div> </li> <li class="gallerybox" style="width: 175px"> <div class="thumb" style="width: 170px; height: 126px;"><span typeof="mw:File"><a href="/wiki/File:AdoCbl-ColorCoded.png" class="mw-file-description" title="Adenosylcobalamin is a cofactor required by several crucial enzymatic reactions that take place in the human body. It is a rare example of a metal (cobalt) alkyl in biology."><img alt="Adenosylcobalamin is a cofactor required by several crucial enzymatic reactions that take place in the human body. It is a rare example of a metal (cobalt) alkyl in biology." src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1a/AdoCbl-ColorCoded.png/66px-AdoCbl-ColorCoded.png" decoding="async" width="66" height="96" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1a/AdoCbl-ColorCoded.png/99px-AdoCbl-ColorCoded.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1a/AdoCbl-ColorCoded.png/133px-AdoCbl-ColorCoded.png 2x" data-file-width="3278" data-file-height="4738" /></a></span></div> <div class="gallerytext"><a href="/wiki/Adenosylcobalamin" title="Adenosylcobalamin">Adenosylcobalamin</a> is a <a href="/wiki/Cofactor_(biochemistry)" title="Cofactor (biochemistry)">cofactor</a> required by several crucial enzymatic reactions that take place in the human body. It is a rare example of a metal (cobalt) alkyl in biology.</div> </li> <li class="gallerybox" style="width: 175px"> <div class="thumb" style="width: 170px; height: 126px;"><span typeof="mw:File"><a href="/wiki/File:IronPentacarbonylStructure.png" class="mw-file-description" title="Iron(0) pentacarbonyl is a red-orange liquid prepared directly from the union of finely divided iron and carbon monoxide gas under pressure."><img alt="Iron(0) pentacarbonyl is a red-orange liquid prepared directly from the union of finely divided iron and carbon monoxide gas under pressure." src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e9/IronPentacarbonylStructure.png/119px-IronPentacarbonylStructure.png" decoding="async" width="119" height="96" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e9/IronPentacarbonylStructure.png/178px-IronPentacarbonylStructure.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e9/IronPentacarbonylStructure.png/238px-IronPentacarbonylStructure.png 2x" data-file-width="903" data-file-height="730" /></a></span></div> <div class="gallerytext"><a href="/wiki/Iron_pentacarbonyl" title="Iron pentacarbonyl">Iron(0) pentacarbonyl</a> is a red-orange liquid prepared directly from the union of finely divided iron and carbon monoxide gas under pressure.</div> </li> <li class="gallerybox" style="width: 175px"> <div class="thumb" style="width: 170px; height: 126px;"><span typeof="mw:File"><a href="/wiki/File:Tc99_sestamibi_2D_structure.svg" class="mw-file-description" title="Technetium[99mTc] sestamibi is used to image the heart muscle in nuclear medicine."><img alt="Technetium[99mTc] sestamibi is used to image the heart muscle in nuclear medicine." src="//upload.wikimedia.org/wikipedia/commons/thumb/1/17/Tc99_sestamibi_2D_structure.svg/100px-Tc99_sestamibi_2D_structure.svg.png" decoding="async" width="100" height="96" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/17/Tc99_sestamibi_2D_structure.svg/149px-Tc99_sestamibi_2D_structure.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/17/Tc99_sestamibi_2D_structure.svg/199px-Tc99_sestamibi_2D_structure.svg.png 2x" data-file-width="1815" data-file-height="1749" /></a></span></div> <div class="gallerytext"><a href="/wiki/Technetium_(99mTc)_sestamibi" title="Technetium (99mTc) sestamibi">Technetium[<sup>99m</sup>Tc] sestamibi</a> is used to image the heart muscle in nuclear medicine.</div> </li> </ul> <div class="mw-heading mw-heading3"><h3 id="Distinction_from_coordination_compounds_with_organic_ligands">Distinction from coordination compounds with organic ligands</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organometallic_chemistry&action=edit&section=2" title="Edit section: Distinction from coordination compounds with organic ligands"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Many <a href="/wiki/Complex_(chemistry)" class="mw-redirect" title="Complex (chemistry)">complexes</a> feature <a href="/wiki/Coordination_bond" class="mw-redirect" title="Coordination bond">coordination bonds</a> between a metal and organic <a href="/wiki/Ligands" class="mw-redirect" title="Ligands">ligands</a>. Complexes where the organic ligands bind the metal through a <a href="/wiki/Heteroatom" title="Heteroatom">heteroatom</a> such as oxygen or nitrogen are considered coordination compounds (e.g., <a href="/wiki/Heme_A" title="Heme A">heme A</a> and <a href="/wiki/Tris(acetylacetonato)iron(III)" title="Tris(acetylacetonato)iron(III)">Fe(acac)<sub>3</sub></a>). However, if any of the ligands form a direct metal-carbon (M-C) bond, then the complex is considered to be organometallic. Although the IUPAC has not formally defined the term, some chemists use the term "metalorganic" to describe any coordination compound containing an organic ligand regardless of the presence of a direct M-C bond.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p>The status of compounds in which the <a href="/wiki/Resonance_(chemistry)" title="Resonance (chemistry)">canonical anion</a> has a negative charge that is shared between (<a href="/wiki/Delocalized_electrons" class="mw-redirect" title="Delocalized electrons">delocalized</a>) a carbon atom and an atom more <a href="/wiki/Electronegativity" title="Electronegativity">electronegative</a> than carbon (e.g. <a href="/wiki/Enolate" title="Enolate">enolates</a>) may vary with the nature of the anionic moiety, the metal ion, and possibly the medium. In the absence of direct structural evidence for a carbon–metal bond, such compounds are not considered to be organometallic.<sup id="cite_ref-:0_2-3" class="reference"><a href="#cite_note-:0-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> For instance, lithium enolates often contain only Li-O bonds and are not organometallic, while zinc enolates (<a href="/wiki/Reformatsky_reaction" title="Reformatsky reaction">Reformatsky reagents</a>) contain both Zn-O and Zn-C bonds, and are organometallic in nature.<sup id="cite_ref-ChrisE_3-2" class="reference"><a href="#cite_note-ChrisE-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Structure_and_properties">Structure and properties</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organometallic_chemistry&action=edit&section=3" title="Edit section: Structure and properties"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The metal-carbon bond in organometallic compounds is generally highly <a href="/wiki/Covalent" class="mw-redirect" title="Covalent">covalent</a>.<sup id="cite_ref-FOOTNOTECrabtree2009[[Category:Wikipedia_articles_needing_page_number_citations_from_October_2021]]<sup_class="noprint_Inline-Template_"_style="white-space:nowrap;">&#91;<i>[[Wikipedia:Citing_sources|<span_title="This_citation_requires_a_reference_to_the_specific_page_or_range_of_pages_in_which_the_material_appears.&#32;(October_2021)">page&nbsp;needed</span>]]</i>&#93;</sup>_1-1" class="reference"><a href="#cite_note-FOOTNOTECrabtree2009[[Category:Wikipedia_articles_needing_page_number_citations_from_October_2021]]<sup_class="noprint_Inline-Template_"_style="white-space:nowrap;">&#91;<i>[[Wikipedia:Citing_sources|<span_title="This_citation_requires_a_reference_to_the_specific_page_or_range_of_pages_in_which_the_material_appears.&#32;(October_2021)">page&nbsp;needed</span>]]</i>&#93;</sup>-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> For highly electropositive elements, such as lithium and sodium, the carbon ligand exhibits <a href="/wiki/Carbanion" title="Carbanion">carbanionic</a> character, but free carbon-based anions are extremely rare, an example being <a href="/wiki/Cyanide" title="Cyanide">cyanide</a>. </p> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Mn(II)_kompleksi_monokoristall.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/96/Mn%28II%29_kompleksi_monokoristall.jpg/220px-Mn%28II%29_kompleksi_monokoristall.jpg" decoding="async" width="220" height="191" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/96/Mn%28II%29_kompleksi_monokoristall.jpg/330px-Mn%28II%29_kompleksi_monokoristall.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/96/Mn%28II%29_kompleksi_monokoristall.jpg/440px-Mn%28II%29_kompleksi_monokoristall.jpg 2x" data-file-width="2773" data-file-height="2404" /></a><figcaption>a single crystal of a Mn(II) complex, [BnMIm]4[MnBr4]Br2. Its bright green color originates from spin-forbidden d-d transitions</figcaption></figure> <p>Most organometallic compounds are solids at room temperature, however some are liquids such as <a href="/wiki/Methylcyclopentadienyl_manganese_tricarbonyl" title="Methylcyclopentadienyl manganese tricarbonyl">methylcyclopentadienyl manganese tricarbonyl</a>, or even <a href="/wiki/Volatility_(chemistry)" title="Volatility (chemistry)">volatile</a> liquids such as <a href="/wiki/Nickel_tetracarbonyl" title="Nickel tetracarbonyl">nickel tetracarbonyl</a>.<sup id="cite_ref-FOOTNOTECrabtree2009[[Category:Wikipedia_articles_needing_page_number_citations_from_October_2021]]<sup_class="noprint_Inline-Template_"_style="white-space:nowrap;">&#91;<i>[[Wikipedia:Citing_sources|<span_title="This_citation_requires_a_reference_to_the_specific_page_or_range_of_pages_in_which_the_material_appears.&#32;(October_2021)">page&nbsp;needed</span>]]</i>&#93;</sup>_1-2" class="reference"><a href="#cite_note-FOOTNOTECrabtree2009[[Category:Wikipedia_articles_needing_page_number_citations_from_October_2021]]<sup_class="noprint_Inline-Template_"_style="white-space:nowrap;">&#91;<i>[[Wikipedia:Citing_sources|<span_title="This_citation_requires_a_reference_to_the_specific_page_or_range_of_pages_in_which_the_material_appears.&#32;(October_2021)">page&nbsp;needed</span>]]</i>&#93;</sup>-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Many organometallic compounds are <a href="/wiki/Air_sensitivity" title="Air sensitivity">air sensitive</a> (reactive towards oxygen and moisture), and thus they must be handled under an <a href="/wiki/Inert_gas" title="Inert gas">inert atmosphere</a>.<sup id="cite_ref-FOOTNOTECrabtree2009[[Category:Wikipedia_articles_needing_page_number_citations_from_October_2021]]<sup_class="noprint_Inline-Template_"_style="white-space:nowrap;">&#91;<i>[[Wikipedia:Citing_sources|<span_title="This_citation_requires_a_reference_to_the_specific_page_or_range_of_pages_in_which_the_material_appears.&#32;(October_2021)">page&nbsp;needed</span>]]</i>&#93;</sup>_1-3" class="reference"><a href="#cite_note-FOOTNOTECrabtree2009[[Category:Wikipedia_articles_needing_page_number_citations_from_October_2021]]<sup_class="noprint_Inline-Template_"_style="white-space:nowrap;">&#91;<i>[[Wikipedia:Citing_sources|<span_title="This_citation_requires_a_reference_to_the_specific_page_or_range_of_pages_in_which_the_material_appears.&#32;(October_2021)">page&nbsp;needed</span>]]</i>&#93;</sup>-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Some organometallic compounds such as <a href="/wiki/Triethylaluminium" title="Triethylaluminium">triethylaluminium</a> are <a href="/wiki/Pyrophoricity" title="Pyrophoricity">pyrophoric</a> and will <a href="/wiki/Combustion" title="Combustion">ignite</a> on contact with air.<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> </p> <div class="mw-heading mw-heading2"><h2 id="Concepts_and_techniques">Concepts and techniques</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organometallic_chemistry&action=edit&section=4" title="Edit section: Concepts and techniques"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>As in other areas of chemistry, <a href="/wiki/Electron_counting" title="Electron counting">electron counting</a> is useful for organizing organometallic chemistry. The <a href="/wiki/18-electron_rule" title="18-electron rule">18-electron rule</a> is helpful in predicting the stabilities of organometallic complexes, for example <a href="/wiki/Metal_carbonyl" title="Metal carbonyl">metal carbonyls</a> and <a href="/wiki/Transition_metal_hydride" title="Transition metal hydride">metal hydrides</a>. The 18e rule has two representative electron counting models, ionic and neutral (also known as covalent) ligand models, respectively.<sup id="cite_ref-:02_7-0" class="reference"><a href="#cite_note-:02-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> The hapticity of a metal-ligand complex, can influence the electron count.<sup id="cite_ref-:02_7-1" class="reference"><a href="#cite_note-:02-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Hapticity" title="Hapticity">Hapticity</a> (η, lowercase Greek eta), describes the number of contiguous ligands coordinated to a metal.<sup id="cite_ref-:02_7-2" class="reference"><a href="#cite_note-:02-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> For example, <a href="/wiki/Ferrocene" title="Ferrocene">ferrocene</a>, [(η<sup>5</sup>-C<sub>5</sub>H<sub>5</sub>)<sub>2</sub>Fe], has two <a href="/wiki/Cyclopentadienyl_ligand" class="mw-redirect" title="Cyclopentadienyl ligand">cyclopentadienyl ligands</a> giving a hapticity of 5, where all five carbon atoms of the C<sub>5</sub>H<sub>5</sub> ligand bond equally and contribute one electron to the iron center. Ligands that bind non-contiguous atoms are denoted the Greek letter kappa, κ.<sup id="cite_ref-:02_7-3" class="reference"><a href="#cite_note-:02-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Chelation" title="Chelation">Chelating</a> κ2-acetate is an example. The <a href="/wiki/Covalent_bond_classification_method" title="Covalent bond classification method">covalent bond classification method</a> identifies three classes of ligands, X,L, and Z; which are based on the electron donating interactions of the ligand. Many organometallic compounds do not follow the 18e rule. The metal atoms in organometallic compounds are frequently described by their <a href="/wiki/D_electron_count" title="D electron count">d electron count</a> and <a href="/wiki/Oxidation_state" title="Oxidation state">oxidation state</a>. These concepts can be used to help predict their reactivity and preferred <a href="/wiki/Molecular_geometry" title="Molecular geometry">geometry</a>. Chemical bonding and reactivity in organometallic compounds is often discussed from the perspective of the <a href="/wiki/Isolobal_principle" title="Isolobal principle">isolobal principle</a>. </p><p>A wide variety of physical techniques are used to determine the structure, composition, and properties of organometallic compounds. <a href="/wiki/X-ray_diffraction" title="X-ray diffraction">X-ray diffraction</a> is a particularly important technique that can locate the positions of atoms within a solid compound, providing a detailed description of its structure.<sup id="cite_ref-FOOTNOTECrabtree2009[[Category:Wikipedia_articles_needing_page_number_citations_from_October_2021]]<sup_class="noprint_Inline-Template_"_style="white-space:nowrap;">&#91;<i>[[Wikipedia:Citing_sources|<span_title="This_citation_requires_a_reference_to_the_specific_page_or_range_of_pages_in_which_the_material_appears.&#32;(October_2021)">page&nbsp;needed</span>]]</i>&#93;</sup>_1-4" class="reference"><a href="#cite_note-FOOTNOTECrabtree2009[[Category:Wikipedia_articles_needing_page_number_citations_from_October_2021]]<sup_class="noprint_Inline-Template_"_style="white-space:nowrap;">&#91;<i>[[Wikipedia:Citing_sources|<span_title="This_citation_requires_a_reference_to_the_specific_page_or_range_of_pages_in_which_the_material_appears.&#32;(October_2021)">page&nbsp;needed</span>]]</i>&#93;</sup>-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-FOOTNOTEShriverWellerOvertonArmstrong2014[[Category:Wikipedia_articles_needing_page_number_citations_from_October_2021]]<sup_class="noprint_Inline-Template_"_style="white-space:nowrap;">&#91;<i>[[Wikipedia:Citing_sources|<span_title="This_citation_requires_a_reference_to_the_specific_page_or_range_of_pages_in_which_the_material_appears.&#32;(October_2021)">page&nbsp;needed</span>]]</i>&#93;</sup>_8-0" class="reference"><a href="#cite_note-FOOTNOTEShriverWellerOvertonArmstrong2014[[Category:Wikipedia_articles_needing_page_number_citations_from_October_2021]]<sup_class="noprint_Inline-Template_"_style="white-space:nowrap;">&#91;<i>[[Wikipedia:Citing_sources|<span_title="This_citation_requires_a_reference_to_the_specific_page_or_range_of_pages_in_which_the_material_appears.&#32;(October_2021)">page&nbsp;needed</span>]]</i>&#93;</sup>-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> Other techniques like <a href="/wiki/Infrared_spectroscopy" title="Infrared spectroscopy">infrared spectroscopy</a> and <a href="/wiki/Nuclear_magnetic_resonance_spectroscopy" title="Nuclear magnetic resonance spectroscopy">nuclear magnetic resonance spectroscopy</a> are also frequently used to obtain information on the structure and bonding of organometallic compounds.<sup id="cite_ref-FOOTNOTECrabtree2009[[Category:Wikipedia_articles_needing_page_number_citations_from_October_2021]]<sup_class="noprint_Inline-Template_"_style="white-space:nowrap;">&#91;<i>[[Wikipedia:Citing_sources|<span_title="This_citation_requires_a_reference_to_the_specific_page_or_range_of_pages_in_which_the_material_appears.&#32;(October_2021)">page&nbsp;needed</span>]]</i>&#93;</sup>_1-5" class="reference"><a href="#cite_note-FOOTNOTECrabtree2009[[Category:Wikipedia_articles_needing_page_number_citations_from_October_2021]]<sup_class="noprint_Inline-Template_"_style="white-space:nowrap;">&#91;<i>[[Wikipedia:Citing_sources|<span_title="This_citation_requires_a_reference_to_the_specific_page_or_range_of_pages_in_which_the_material_appears.&#32;(October_2021)">page&nbsp;needed</span>]]</i>&#93;</sup>-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-FOOTNOTEShriverWellerOvertonArmstrong2014[[Category:Wikipedia_articles_needing_page_number_citations_from_October_2021]]<sup_class="noprint_Inline-Template_"_style="white-space:nowrap;">&#91;<i>[[Wikipedia:Citing_sources|<span_title="This_citation_requires_a_reference_to_the_specific_page_or_range_of_pages_in_which_the_material_appears.&#32;(October_2021)">page&nbsp;needed</span>]]</i>&#93;</sup>_8-1" class="reference"><a href="#cite_note-FOOTNOTEShriverWellerOvertonArmstrong2014[[Category:Wikipedia_articles_needing_page_number_citations_from_October_2021]]<sup_class="noprint_Inline-Template_"_style="white-space:nowrap;">&#91;<i>[[Wikipedia:Citing_sources|<span_title="This_citation_requires_a_reference_to_the_specific_page_or_range_of_pages_in_which_the_material_appears.&#32;(October_2021)">page&nbsp;needed</span>]]</i>&#93;</sup>-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Ultraviolet-visible_spectroscopy" class="mw-redirect" title="Ultraviolet-visible spectroscopy">Ultraviolet-visible spectroscopy</a> is a common technique used to obtain information on the electronic structure of organometallic compounds. It is also used monitor the progress of organometallic reactions, as well as determine their <a href="/wiki/Chemical_kinetics" title="Chemical kinetics">kinetics</a>.<sup id="cite_ref-FOOTNOTEShriverWellerOvertonArmstrong2014[[Category:Wikipedia_articles_needing_page_number_citations_from_October_2021]]<sup_class="noprint_Inline-Template_"_style="white-space:nowrap;">&#91;<i>[[Wikipedia:Citing_sources|<span_title="This_citation_requires_a_reference_to_the_specific_page_or_range_of_pages_in_which_the_material_appears.&#32;(October_2021)">page&nbsp;needed</span>]]</i>&#93;</sup>_8-2" class="reference"><a href="#cite_note-FOOTNOTEShriverWellerOvertonArmstrong2014[[Category:Wikipedia_articles_needing_page_number_citations_from_October_2021]]<sup_class="noprint_Inline-Template_"_style="white-space:nowrap;">&#91;<i>[[Wikipedia:Citing_sources|<span_title="This_citation_requires_a_reference_to_the_specific_page_or_range_of_pages_in_which_the_material_appears.&#32;(October_2021)">page&nbsp;needed</span>]]</i>&#93;</sup>-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> The dynamics of organometallic compounds can be studied using <a href="/wiki/Dynamic_NMR_spectroscopy" class="mw-redirect" title="Dynamic NMR spectroscopy">dynamic NMR spectroscopy</a>.<sup id="cite_ref-FOOTNOTECrabtree2009[[Category:Wikipedia_articles_needing_page_number_citations_from_October_2021]]<sup_class="noprint_Inline-Template_"_style="white-space:nowrap;">&#91;<i>[[Wikipedia:Citing_sources|<span_title="This_citation_requires_a_reference_to_the_specific_page_or_range_of_pages_in_which_the_material_appears.&#32;(October_2021)">page&nbsp;needed</span>]]</i>&#93;</sup>_1-6" class="reference"><a href="#cite_note-FOOTNOTECrabtree2009[[Category:Wikipedia_articles_needing_page_number_citations_from_October_2021]]<sup_class="noprint_Inline-Template_"_style="white-space:nowrap;">&#91;<i>[[Wikipedia:Citing_sources|<span_title="This_citation_requires_a_reference_to_the_specific_page_or_range_of_pages_in_which_the_material_appears.&#32;(October_2021)">page&nbsp;needed</span>]]</i>&#93;</sup>-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Other notable techniques include <a href="/wiki/X-ray_absorption_spectroscopy" title="X-ray absorption spectroscopy">X-ray absorption spectroscopy</a>,<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> <a href="/wiki/Electron_paramagnetic_resonance_spectroscopy" class="mw-redirect" title="Electron paramagnetic resonance spectroscopy">electron paramagnetic resonance spectroscopy</a>, and <a href="/wiki/Elemental_analysis" title="Elemental analysis">elemental analysis</a>.<sup id="cite_ref-FOOTNOTECrabtree2009[[Category:Wikipedia_articles_needing_page_number_citations_from_October_2021]]<sup_class="noprint_Inline-Template_"_style="white-space:nowrap;">&#91;<i>[[Wikipedia:Citing_sources|<span_title="This_citation_requires_a_reference_to_the_specific_page_or_range_of_pages_in_which_the_material_appears.&#32;(October_2021)">page&nbsp;needed</span>]]</i>&#93;</sup>_1-7" class="reference"><a href="#cite_note-FOOTNOTECrabtree2009[[Category:Wikipedia_articles_needing_page_number_citations_from_October_2021]]<sup_class="noprint_Inline-Template_"_style="white-space:nowrap;">&#91;<i>[[Wikipedia:Citing_sources|<span_title="This_citation_requires_a_reference_to_the_specific_page_or_range_of_pages_in_which_the_material_appears.&#32;(October_2021)">page&nbsp;needed</span>]]</i>&#93;</sup>-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-FOOTNOTEShriverWellerOvertonArmstrong2014[[Category:Wikipedia_articles_needing_page_number_citations_from_October_2021]]<sup_class="noprint_Inline-Template_"_style="white-space:nowrap;">&#91;<i>[[Wikipedia:Citing_sources|<span_title="This_citation_requires_a_reference_to_the_specific_page_or_range_of_pages_in_which_the_material_appears.&#32;(October_2021)">page&nbsp;needed</span>]]</i>&#93;</sup>_8-3" class="reference"><a href="#cite_note-FOOTNOTEShriverWellerOvertonArmstrong2014[[Category:Wikipedia_articles_needing_page_number_citations_from_October_2021]]<sup_class="noprint_Inline-Template_"_style="white-space:nowrap;">&#91;<i>[[Wikipedia:Citing_sources|<span_title="This_citation_requires_a_reference_to_the_specific_page_or_range_of_pages_in_which_the_material_appears.&#32;(October_2021)">page&nbsp;needed</span>]]</i>&#93;</sup>-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p><p>Due to their high reactivity towards oxygen and moisture, organometallic compounds often must be handled using <a href="/wiki/Air-free_techniques" class="mw-redirect" title="Air-free techniques">air-free techniques</a>. Air-free handling of organometallic compounds typically requires the use of laboratory apparatuses such as a <a href="/wiki/Glovebox" title="Glovebox">glovebox</a> or <a href="/wiki/Schlenk_line" title="Schlenk line">Schlenk line</a>.<sup id="cite_ref-FOOTNOTECrabtree2009[[Category:Wikipedia_articles_needing_page_number_citations_from_October_2021]]<sup_class="noprint_Inline-Template_"_style="white-space:nowrap;">&#91;<i>[[Wikipedia:Citing_sources|<span_title="This_citation_requires_a_reference_to_the_specific_page_or_range_of_pages_in_which_the_material_appears.&#32;(October_2021)">page&nbsp;needed</span>]]</i>&#93;</sup>_1-8" class="reference"><a href="#cite_note-FOOTNOTECrabtree2009[[Category:Wikipedia_articles_needing_page_number_citations_from_October_2021]]<sup_class="noprint_Inline-Template_"_style="white-space:nowrap;">&#91;<i>[[Wikipedia:Citing_sources|<span_title="This_citation_requires_a_reference_to_the_specific_page_or_range_of_pages_in_which_the_material_appears.&#32;(October_2021)">page&nbsp;needed</span>]]</i>&#93;</sup>-1"><span class="cite-bracket">[</span>1<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=Organometallic_chemistry&action=edit&section=5" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Early developments in organometallic chemistry include <a href="/wiki/Louis_Claude_Cadet_de_Gassicourt" title="Louis Claude Cadet de Gassicourt">Louis Claude Cadet</a>'s synthesis of methyl arsenic compounds related to <a href="/wiki/Cacodyl" title="Cacodyl">cacodyl</a>, <a href="/wiki/William_Christopher_Zeise" title="William Christopher Zeise">William Christopher Zeise</a>'s<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Zeise%27s_salt" title="Zeise's salt">platinum-ethylene complex</a>,<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Edward_Frankland" title="Edward Frankland">Edward Frankland</a>'s discovery of <a href="/wiki/Diethylzinc" title="Diethylzinc">diethyl-</a> and <a href="/wiki/Dimethyl_zinc" class="mw-redirect" title="Dimethyl zinc">dimethylzinc</a>, <a href="/wiki/Ludwig_Mond" title="Ludwig Mond">Ludwig Mond</a>'s discovery of <a href="/wiki/Tetracarbonyl_nickel" class="mw-redirect" title="Tetracarbonyl nickel">Ni(CO)<sub>4</sub></a>,<sup id="cite_ref-FOOTNOTECrabtree2009[[Category:Wikipedia_articles_needing_page_number_citations_from_October_2021]]<sup_class="noprint_Inline-Template_"_style="white-space:nowrap;">&#91;<i>[[Wikipedia:Citing_sources|<span_title="This_citation_requires_a_reference_to_the_specific_page_or_range_of_pages_in_which_the_material_appears.&#32;(October_2021)">page&nbsp;needed</span>]]</i>&#93;</sup>_1-9" class="reference"><a href="#cite_note-FOOTNOTECrabtree2009[[Category:Wikipedia_articles_needing_page_number_citations_from_October_2021]]<sup_class="noprint_Inline-Template_"_style="white-space:nowrap;">&#91;<i>[[Wikipedia:Citing_sources|<span_title="This_citation_requires_a_reference_to_the_specific_page_or_range_of_pages_in_which_the_material_appears.&#32;(October_2021)">page&nbsp;needed</span>]]</i>&#93;</sup>-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> and <a href="/wiki/Victor_Grignard" title="Victor Grignard">Victor Grignard</a>'s organomagnesium compounds. (Although not always acknowledged as an organometallic compound, <a href="/wiki/Prussian_blue" title="Prussian blue">Prussian blue</a>, a mixed-valence iron-cyanide complex, was first prepared in 1706 by paint maker <a href="/wiki/Johann_Jacob_Diesbach" title="Johann Jacob Diesbach">Johann Jacob Diesbach</a> as the first <a href="/wiki/Coordination_polymer" title="Coordination polymer">coordination polymer</a> and synthetic material containing a metal-carbon bond.<sup id="cite_ref-FOOTNOTECrabtree200998_12-0" class="reference"><a href="#cite_note-FOOTNOTECrabtree200998-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup>) The abundant and diverse products from coal and petroleum led to <a href="/wiki/Ziegler%E2%80%93Natta" class="mw-redirect" title="Ziegler–Natta">Ziegler–Natta</a>, <a href="/wiki/Fischer%E2%80%93Tropsch" class="mw-redirect" title="Fischer–Tropsch">Fischer–Tropsch</a>, <a href="/wiki/Hydroformylation" title="Hydroformylation">hydroformylation</a> catalysis which employ CO, H<sub>2</sub>, and alkenes as feedstocks and ligands. </p><p>Recognition of organometallic chemistry as a distinct subfield culminated in the Nobel Prizes to <a href="/wiki/Ernst_Otto_Fischer" title="Ernst Otto Fischer">Ernst Fischer</a> and <a href="/wiki/Geoffrey_Wilkinson" title="Geoffrey Wilkinson">Geoffrey Wilkinson</a> for work on <a href="/wiki/Metallocene" title="Metallocene">metallocenes</a>. In 2005, <a href="/wiki/Yves_Chauvin" title="Yves Chauvin">Yves Chauvin</a>, <a href="/wiki/Robert_H._Grubbs" title="Robert H. Grubbs">Robert H. Grubbs</a> and <a href="/wiki/Richard_R._Schrock" title="Richard R. Schrock">Richard R. Schrock</a> shared the Nobel Prize for metal-catalyzed <a href="/wiki/Olefin_metathesis" title="Olefin metathesis">olefin metathesis</a>.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Organometallic_chemistry_timeline">Organometallic chemistry timeline</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organometallic_chemistry&action=edit&section=6" title="Edit section: Organometallic chemistry timeline"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li>1760 <a href="/wiki/Louis_Claude_Cadet_de_Gassicourt" title="Louis Claude Cadet de Gassicourt">Louis Claude Cadet de Gassicourt</a> isolates the <a href="/w/index.php?title=Organoarenic_compound&action=edit&redlink=1" class="new" title="Organoarenic compound (page does not exist)">organoarenic compound</a> <a href="/wiki/Cacodyl" title="Cacodyl">cacodyl</a></li> <li>1827 <a href="/wiki/William_Christopher_Zeise" title="William Christopher Zeise">William Christopher Zeise</a> produces <a href="/wiki/Zeise%27s_salt" title="Zeise's salt">Zeise's salt</a>; the first <a href="/wiki/Platinum" title="Platinum">platinum</a> / <a href="/wiki/Olefin" class="mw-redirect" title="Olefin">olefin</a> complex</li> <li>1848 <a href="/wiki/Edward_Frankland" title="Edward Frankland">Edward Frankland</a> discovers <a href="/wiki/Diethylzinc" title="Diethylzinc">diethylzinc</a></li> <li>1890 <a href="/wiki/Ludwig_Mond" title="Ludwig Mond">Ludwig Mond</a> discovers <a href="/wiki/Nickel_carbonyl" class="mw-redirect" title="Nickel carbonyl">nickel carbonyl</a></li> <li>1899 <a href="/wiki/John_Ulric_Nef_(chemist)" title="John Ulric Nef (chemist)">John Ulric Nef</a> discovers <a href="/wiki/Alkynylation" title="Alkynylation">alkynylation</a> using sodium <a href="/wiki/Acetylide" title="Acetylide">acetylides</a>.</li> <li>1909 <a href="/wiki/Paul_Ehrlich" title="Paul Ehrlich">Paul Ehrlich</a> introduces <a href="/wiki/Salvarsan" class="mw-redirect" title="Salvarsan">Salvarsan</a> for the treatment of syphilis, an early arsenic based organometallic compound</li> <li>1912 <a href="/wiki/Nobel_Prize_in_Chemistry" title="Nobel Prize in Chemistry">Nobel Prize</a> <a href="/wiki/Victor_Grignard" title="Victor Grignard">Victor Grignard</a> and <a href="/wiki/Paul_Sabatier_(chemist)" title="Paul Sabatier (chemist)">Paul Sabatier</a></li> <li>1930 <a href="/wiki/Henry_Gilman" title="Henry Gilman">Henry Gilman</a> invents lithium cuprates, see <a href="/wiki/Gilman_reagent" title="Gilman reagent">Gilman reagent</a></li> <li>1940 <a href="/wiki/Eugene_G._Rochow" title="Eugene G. Rochow">Eugene G. Rochow</a> and <a href="/wiki/Richard_M%C3%BCller_(chemist)" title="Richard Müller (chemist)">Richard Müller</a> discover the <a href="/wiki/Direct_process" title="Direct process">direct process</a> for preparing <a href="/wiki/Organosilicon" class="mw-redirect" title="Organosilicon">organosilicon</a> compounds</li> <li>1930's and 1940's <a href="/wiki/Otto_Roelen" title="Otto Roelen">Otto Roelen</a> and <a href="/wiki/Walter_Reppe" title="Walter Reppe">Walter Reppe</a> develop metal-catalyzed <a href="/wiki/Hydroformylation" title="Hydroformylation">hydroformylation</a> and acetylene chemistry</li> <li>1951 <a href="/wiki/Walter_Hieber" title="Walter Hieber">Walter Hieber</a> was awarded the <a href="/wiki/Alfred_Stock" title="Alfred Stock">Alfred Stock</a> prize for his work with <a href="/wiki/Metal_carbonyl" title="Metal carbonyl">metal carbonyl</a> chemistry.</li> <li>1951 <a href="/wiki/Ferrocene" title="Ferrocene">Ferrocene</a> is discovered</li> <li>1956 <a href="/wiki/Dorothy_Hodgkin" title="Dorothy Hodgkin">Dorothy Crawfoot Hodgkin</a> determines the structure of <a href="/wiki/Vitamin_B12" title="Vitamin B12">vitamin B<sub>12</sub></a>, the first biomolecule found to contain a metal-carbon bond, see <a href="/wiki/Bioorganometallic_chemistry" title="Bioorganometallic chemistry">bioorganometallic chemistry</a></li> <li>1963 <a href="/wiki/Nobel_Prize_in_Chemistry" title="Nobel Prize in Chemistry">Nobel prize</a> for <a href="/wiki/Karl_Ziegler" title="Karl Ziegler">Karl Ziegler</a> and <a href="/wiki/Giulio_Natta" title="Giulio Natta">Giulio Natta</a> on <a href="/wiki/Ziegler%E2%80%93Natta_catalyst" title="Ziegler–Natta catalyst">Ziegler–Natta catalyst</a></li> <li>1973 <a href="/wiki/Nobel_Prize_in_Chemistry" title="Nobel Prize in Chemistry">Nobel prize</a> <a href="/wiki/Geoffrey_Wilkinson" title="Geoffrey Wilkinson">Geoffrey Wilkinson</a> and <a href="/wiki/Ernst_Otto_Fischer" title="Ernst Otto Fischer">Ernst Otto Fischer</a> on <a href="/wiki/Sandwich_compound" title="Sandwich compound">sandwich compounds</a></li> <li>1981 <a href="/wiki/Nobel_Prize_in_Chemistry" title="Nobel Prize in Chemistry">Nobel prize</a> <a href="/wiki/Roald_Hoffmann" title="Roald Hoffmann">Roald Hoffmann</a> and <a href="/wiki/Kenichi_Fukui" title="Kenichi Fukui">Kenichi Fukui</a> for creation of the Woodward-Hoffman Rules</li> <li>2001 <a href="/wiki/Nobel_Prize_in_Chemistry" title="Nobel Prize in Chemistry">Nobel prize</a> <a href="/wiki/W._S._Knowles" class="mw-redirect" title="W. S. Knowles">W. S. Knowles</a>, <a href="/wiki/R._Noyori" class="mw-redirect" title="R. Noyori">R. Noyori</a> and <a href="/wiki/Karl_Barry_Sharpless" title="Karl Barry Sharpless">Karl Barry Sharpless</a> for asymmetric hydrogenation</li> <li>2005 <a href="/wiki/Nobel_Prize_in_Chemistry" title="Nobel Prize in Chemistry">Nobel prize</a> <a href="/wiki/Yves_Chauvin" title="Yves Chauvin">Yves Chauvin</a>, <a href="/wiki/Robert_Grubbs" class="mw-redirect" title="Robert Grubbs">Robert Grubbs</a>, and <a href="/wiki/Richard_Schrock" class="mw-redirect" title="Richard Schrock">Richard Schrock</a> on metal-catalyzed <a href="/wiki/Olefin_metathesis" title="Olefin metathesis">alkene metathesis</a></li> <li>2010 <a href="/wiki/Nobel_Prize_in_Chemistry" title="Nobel Prize in Chemistry">Nobel prize</a> <a href="/wiki/Richard_F._Heck" title="Richard F. Heck">Richard F. Heck</a>, <a href="/wiki/Ei-ichi_Negishi" title="Ei-ichi Negishi">Ei-ichi Negishi</a>, <a href="/wiki/Akira_Suzuki_(chemist)" class="mw-redirect" title="Akira Suzuki (chemist)">Akira Suzuki</a> for palladium catalyzed cross coupling reactions</li></ul> <div class="mw-heading mw-heading2"><h2 id="Scope">Scope</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organometallic_chemistry&action=edit&section=7" title="Edit section: Scope"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Subspecialty areas of organometallic chemistry include: </p> <ul><li><a href="/wiki/Period_2_element" title="Period 2 element">Period 2 elements</a>: <a href="/wiki/Organolithium_chemistry" class="mw-redirect" title="Organolithium chemistry">organolithium chemistry</a>, <a href="/wiki/Organoberyllium_chemistry" title="Organoberyllium chemistry">organoberyllium chemistry</a>, <a href="/wiki/Organoborane_chemistry" class="mw-redirect" title="Organoborane chemistry">organoborane chemistry</a></li> <li><a href="/wiki/Period_3_element" title="Period 3 element">Period 3 elements</a>: <a href="/wiki/Organosodium_chemistry" title="Organosodium chemistry">organosodium chemistry</a>, <a href="/wiki/Organomagnesium_chemistry" class="mw-redirect" title="Organomagnesium chemistry">organomagnesium chemistry</a>, <a href="/wiki/Organoaluminium_chemistry" title="Organoaluminium chemistry">organoaluminium chemistry</a>, <a href="/wiki/Organosilicon" class="mw-redirect" title="Organosilicon">organosilicon chemistry</a></li> <li><a href="/wiki/Period_4_element" title="Period 4 element">Period 4 elements</a>: <a href="/wiki/Organocalcium_chemistry" class="mw-redirect" title="Organocalcium chemistry">organocalcium chemistry</a>, <a href="/wiki/Organoscandium_chemistry" title="Organoscandium chemistry">organoscandium chemistry</a>, <a href="/wiki/Organotitanium_chemistry" title="Organotitanium chemistry">organotitanium chemistry</a>, <a href="/wiki/Organovanadium_chemistry" title="Organovanadium chemistry">organovanadium chemistry</a>, <a href="/wiki/Organochromium_chemistry" title="Organochromium chemistry">organochromium chemistry</a>, <a href="/wiki/Organomanganese_chemistry" title="Organomanganese chemistry">organomanganese chemistry</a>, <a href="/wiki/Organoiron_chemistry" title="Organoiron chemistry">organoiron chemistry</a>, <a href="/wiki/Organocobalt_chemistry" title="Organocobalt chemistry">organocobalt chemistry</a>, <a href="/wiki/Organonickel_chemistry" title="Organonickel chemistry">organonickel chemistry</a>, <a href="/wiki/Organocopper_chemistry" title="Organocopper chemistry">organocopper chemistry</a>, <a href="/wiki/Organozinc_chemistry" title="Organozinc chemistry">organozinc chemistry</a>, <a href="/wiki/Organogallium_chemistry" title="Organogallium chemistry">organogallium chemistry</a>, <a href="/wiki/Organogermanium_chemistry" title="Organogermanium chemistry">organogermanium chemistry</a>, <a href="/wiki/Organoarsenic_chemistry" title="Organoarsenic chemistry">organoarsenic chemistry</a>, <a href="/wiki/Organoselenium_chemistry" title="Organoselenium chemistry">organoselenium chemistry</a></li> <li><a href="/wiki/Period_5_element" title="Period 5 element">Period 5 elements</a>: <a href="/wiki/Organoyttrium_chemistry" title="Organoyttrium chemistry">organoyttrium chemistry</a>, <a href="/wiki/Organozirconium_chemistry" class="mw-redirect" title="Organozirconium chemistry">organozirconium chemistry</a>, <a href="/wiki/Organoniobium_chemistry" title="Organoniobium chemistry">organoniobium chemistry</a>, <a href="/wiki/Organomolybdenum_chemistry" title="Organomolybdenum chemistry">organomolybdenum chemistry</a>, <a href="/wiki/Organotechnetium_chemistry" title="Organotechnetium chemistry">organotechnetium chemistry</a>, <a href="/wiki/Organoruthenium_chemistry" title="Organoruthenium chemistry">organoruthenium chemistry</a>, <a href="/wiki/Organorhodium_chemistry" title="Organorhodium chemistry">organorhodium chemistry</a>, <a href="/wiki/Organopalladium_chemistry" title="Organopalladium chemistry">organopalladium chemistry</a>, <a href="/wiki/Organosilver_chemistry" title="Organosilver chemistry">organosilver chemistry</a>, <a href="/wiki/Organocadmium_chemistry" title="Organocadmium chemistry">organocadmium chemistry</a>, <a href="/wiki/Organoindium_chemistry" title="Organoindium chemistry">organoindium chemistry</a>, <a href="/wiki/Organotin_chemistry" title="Organotin chemistry">organotin chemistry</a>, <a href="/wiki/Organoantimony_chemistry" title="Organoantimony chemistry">organoantimony chemistry</a>, <a href="/wiki/Organotellurium_chemistry" title="Organotellurium chemistry">organotellurium chemistry</a></li> <li><a href="/wiki/Period_6_element" title="Period 6 element">Period 6 elements</a>: <a href="/wiki/Organolanthanide_chemistry" title="Organolanthanide chemistry">organolanthanide chemistry</a>, <a href="/wiki/Organocerium_chemistry" title="Organocerium chemistry">organocerium chemistry</a>, <a href="/wiki/Organotantalum_chemistry" title="Organotantalum chemistry">organotantalum chemistry</a>, <a href="/wiki/Organotungsten_chemistry" class="mw-redirect" title="Organotungsten chemistry">organotungsten chemistry</a>, <a href="/wiki/Organorhenium_chemistry" title="Organorhenium chemistry">organorhenium chemistry</a>, <a href="/wiki/Organoosmium_chemistry" class="mw-redirect" title="Organoosmium chemistry">organoosmium chemistry</a>, <a href="/wiki/Organoiridium_chemistry" title="Organoiridium chemistry">organoiridium chemistry</a>, <a href="/wiki/Organoplatinum_chemistry" title="Organoplatinum chemistry">organoplatinum chemistry</a>, <a href="/wiki/Organogold_chemistry" title="Organogold chemistry">organogold chemistry</a>, <a href="/wiki/Organomercury" class="mw-redirect" title="Organomercury">organomercury chemistry</a>, <a href="/wiki/Organothallium_chemistry" title="Organothallium chemistry">organothallium chemistry</a>, <a href="/wiki/Organolead_chemistry" title="Organolead chemistry">organolead chemistry</a>, <a href="/wiki/Organobismuth_chemistry" title="Organobismuth chemistry">organobismuth chemistry</a>, <a href="/wiki/Organopolonium_chemistry" title="Organopolonium chemistry">organopolonium chemistry</a></li> <li><a href="/wiki/Period_7_element" title="Period 7 element">Period 7 elements</a>: <a href="/wiki/Organoactinide_chemistry" title="Organoactinide chemistry">organoactinide chemistry</a>, <a href="/wiki/Organothorium_chemistry" title="Organothorium chemistry">organothorium chemistry</a>, <a href="/wiki/Organouranium_chemistry" title="Organouranium chemistry">organouranium chemistry</a>, <a href="/wiki/Organoneptunium_chemistry" title="Organoneptunium chemistry">organoneptunium chemistry</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="Industrial_applications">Industrial applications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organometallic_chemistry&action=edit&section=8" title="Edit section: Industrial applications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Organometallic compounds find wide use in commercial reactions, both as <a href="/wiki/Homogeneous_catalysis" title="Homogeneous catalysis">homogenous catalysts</a> and as <a href="/wiki/Stoichiometry" title="Stoichiometry">stoichiometric reagents</a>. For instance, <a href="/wiki/Organolithium_compound" class="mw-redirect" title="Organolithium compound">organolithium</a>, <a href="/wiki/Organomagnesium" class="mw-redirect" title="Organomagnesium">organomagnesium</a>, and <a href="/wiki/Organoaluminium_compound" class="mw-redirect" title="Organoaluminium compound">organoaluminium compounds</a>, examples of which are highly basic and highly reducing, are useful stoichiometrically but also catalyze many polymerization reactions.<sup id="cite_ref-FOOTNOTEElschenbroich2016[[Category:Wikipedia_articles_needing_page_number_citations_from_October_2021]]<sup_class="noprint_Inline-Template_"_style="white-space:nowrap;">&#91;<i>[[Wikipedia:Citing_sources|<span_title="This_citation_requires_a_reference_to_the_specific_page_or_range_of_pages_in_which_the_material_appears.&#32;(October_2021)">page&nbsp;needed</span>]]</i>&#93;</sup>_14-0" class="reference"><a href="#cite_note-FOOTNOTEElschenbroich2016[[Category:Wikipedia_articles_needing_page_number_citations_from_October_2021]]<sup_class="noprint_Inline-Template_"_style="white-space:nowrap;">&#91;<i>[[Wikipedia:Citing_sources|<span_title="This_citation_requires_a_reference_to_the_specific_page_or_range_of_pages_in_which_the_material_appears.&#32;(October_2021)">page&nbsp;needed</span>]]</i>&#93;</sup>-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p><p>Almost all processes involving carbon monoxide rely on catalysts, notable examples being described as <a href="/wiki/Carbonylation" title="Carbonylation">carbonylations</a>.<sup id="cite_ref-Ullmann_15-0" class="reference"><a href="#cite_note-Ullmann-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> The production of acetic acid from methanol and carbon monoxide is catalyzed via <a href="/wiki/Metal_carbonyl_complex" class="mw-redirect" title="Metal carbonyl complex">metal carbonyl complexes</a> in the <a href="/wiki/Monsanto_process" title="Monsanto process">Monsanto process</a> and <a href="/wiki/Cativa_process" title="Cativa process">Cativa process</a>. Most synthetic aldehydes are produced via <a href="/wiki/Hydroformylation" title="Hydroformylation">hydroformylation</a>. The bulk of the synthetic alcohols, at least those larger than ethanol, are produced by <a href="/wiki/Hydrogenation" title="Hydrogenation">hydrogenation</a> of hydroformylation-derived aldehydes. Similarly, the <a href="/wiki/Wacker_process" title="Wacker process">Wacker process</a> is used in the oxidation of <a href="/wiki/Ethylene" title="Ethylene">ethylene</a> to <a href="/wiki/Acetaldehyde" title="Acetaldehyde">acetaldehyde</a>.<sup id="cite_ref-FOOTNOTELeeuwen2005[[Category:Wikipedia_articles_needing_page_number_citations_from_October_2021]]<sup_class="noprint_Inline-Template_"_style="white-space:nowrap;">&#91;<i>[[Wikipedia:Citing_sources|<span_title="This_citation_requires_a_reference_to_the_specific_page_or_range_of_pages_in_which_the_material_appears.&#32;(October_2021)">page&nbsp;needed</span>]]</i>&#93;</sup>_16-0" class="reference"><a href="#cite_note-FOOTNOTELeeuwen2005[[Category:Wikipedia_articles_needing_page_number_citations_from_October_2021]]<sup_class="noprint_Inline-Template_"_style="white-space:nowrap;">&#91;<i>[[Wikipedia:Citing_sources|<span_title="This_citation_requires_a_reference_to_the_specific_page_or_range_of_pages_in_which_the_material_appears.&#32;(October_2021)">page&nbsp;needed</span>]]</i>&#93;</sup>-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p> <figure typeof="mw:File/Thumb"><a href="/wiki/File:ConstrainedGeomCmpx.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/22/ConstrainedGeomCmpx.png/120px-ConstrainedGeomCmpx.png" decoding="async" width="120" height="117" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/22/ConstrainedGeomCmpx.png/180px-ConstrainedGeomCmpx.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/22/ConstrainedGeomCmpx.png/240px-ConstrainedGeomCmpx.png 2x" data-file-width="862" data-file-height="837" /></a><figcaption>A constrained geometry organotitanium complex is a precatalyst for olefin polymerization.</figcaption></figure> <p>Almost all industrial processes involving <a href="/wiki/Alkene" title="Alkene">alkene</a>-derived polymers rely on organometallic catalysts. The world's polyethylene and polypropylene are produced via both <a href="/wiki/Heterogeneous_catalysis" title="Heterogeneous catalysis">heterogeneously</a> via <a href="/wiki/Ziegler%E2%80%93Natta" class="mw-redirect" title="Ziegler–Natta">Ziegler–Natta</a> catalysis and homogeneously, e.g., via <a href="/wiki/Constrained_geometry_catalyst" class="mw-redirect" title="Constrained geometry catalyst">constrained geometry catalysts</a>.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p><p>Most processes involving hydrogen rely on metal-based catalysts. Whereas bulk <a href="/wiki/Hydrogenation" title="Hydrogenation">hydrogenations</a> (e.g., margarine production) rely on heterogeneous catalysts, for the production of fine chemicals such hydrogenations rely on soluble (homogenous) organometallic complexes or involve organometallic intermediates.<sup id="cite_ref-Rylander_18-0" class="reference"><a href="#cite_note-Rylander-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> Organometallic complexes allow these hydrogenations to be effected asymmetrically. </p><p>Many <a href="/wiki/III-V_semiconductor" class="mw-redirect" title="III-V semiconductor">semiconductors</a> are produced from <a href="/wiki/Trimethylgallium" title="Trimethylgallium">trimethylgallium</a>, <a href="/wiki/Trimethylindium" title="Trimethylindium">trimethylindium</a>, <a href="/wiki/Trimethylaluminium" title="Trimethylaluminium">trimethylaluminium</a>, and <a href="/wiki/Trimethylantimony" class="mw-redirect" title="Trimethylantimony">trimethylantimony</a>. These volatile compounds are decomposed along with <a href="/wiki/Ammonia" title="Ammonia">ammonia</a>, <a href="/wiki/Arsine" title="Arsine">arsine</a>, <a href="/wiki/Phosphine" title="Phosphine">phosphine</a> and related hydrides on a heated substrate via <a href="/wiki/Metalorganic_vapor_phase_epitaxy" class="mw-redirect" title="Metalorganic vapor phase epitaxy">metalorganic vapor phase epitaxy</a> (MOVPE) process in the production of <a href="/wiki/Light-emitting_diode" title="Light-emitting diode">light-emitting diodes</a> (LEDs). </p> <div class="mw-heading mw-heading2"><h2 id="Organometallic_reactions">Organometallic reactions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organometallic_chemistry&action=edit&section=9" title="Edit section: Organometallic reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Organometallic compounds undergo several important reactions: </p> <ul><li><a href="/wiki/Associative_substitution" title="Associative substitution">associative</a> and <a href="/wiki/Dissociative_substitution" title="Dissociative substitution">dissociative substitution</a></li> <li><a href="/wiki/Oxidative_addition" title="Oxidative addition">oxidative addition</a> and <a href="/wiki/Reductive_elimination" title="Reductive elimination">reductive elimination</a></li> <li><a href="/wiki/Transmetalation" title="Transmetalation">transmetalation</a></li> <li><a href="/wiki/Migratory_insertion" title="Migratory insertion">migratory insertion</a></li> <li><a href="/wiki/Beta-hydride_elimination" class="mw-redirect" title="Beta-hydride elimination">β-hydride elimination</a></li> <li><a href="/wiki/Electron_transfer" title="Electron transfer">electron transfer</a></li> <li><a href="/wiki/Carbon-hydrogen_bond_activation" class="mw-redirect" title="Carbon-hydrogen bond activation">carbon-hydrogen bond activation</a></li> <li><a href="/wiki/Carbometalation" title="Carbometalation">carbometalation</a></li> <li><a href="/wiki/Hydrometalation" title="Hydrometalation">hydrometalation</a></li> <li><a href="/wiki/Cyclometalation" class="mw-redirect" title="Cyclometalation">cyclometalation</a></li> <li><a href="/wiki/Nucleophilic_abstraction" title="Nucleophilic abstraction">nucleophilic abstraction</a></li></ul> <p>The synthesis of many organic molecules are facilitated by organometallic complexes. <a href="/wiki/Sigma-bond_metathesis" title="Sigma-bond metathesis">Sigma-bond metathesis</a> is a synthetic method for forming new carbon-carbon <a href="/wiki/Sigma_bond" title="Sigma bond">sigma bonds</a>. Sigma-bond metathesis is typically used with early transition-metal complexes that are in their highest oxidation state.<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> Using transition-metals that are in their highest oxidation state prevents other reactions from occurring, such as <a href="/wiki/Oxidative_addition" title="Oxidative addition">oxidative addition</a>. In addition to sigma-bond metathesis, <a href="/wiki/Olefin_metathesis" title="Olefin metathesis">olefin metathesis</a> is used to synthesize various carbon-carbon <a href="/wiki/Pi_bond" title="Pi bond">pi bonds</a>. Neither sigma-bond metathesis or olefin metathesis change the oxidation state of the metal.<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><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> Many other methods are used to form new carbon-carbon bonds, including <a href="/wiki/Beta-Hydride_elimination" class="mw-redirect" title="Beta-Hydride elimination">beta-hydride elimination</a> and <a href="/wiki/Insertion_reaction" title="Insertion reaction">insertion reactions</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Catalysis">Catalysis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organometallic_chemistry&action=edit&section=10" title="Edit section: Catalysis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Organometallic complexes are commonly used in catalysis. Major industrial processes include <a href="/wiki/Hydrogenation" title="Hydrogenation">hydrogenation</a>, <a href="/wiki/Hydrosilylation" title="Hydrosilylation">hydrosilylation</a>, <a href="/wiki/Hydrocyanation" title="Hydrocyanation">hydrocyanation</a>, <a href="/wiki/Olefin_metathesis" title="Olefin metathesis">olefin metathesis</a>, <a href="/wiki/Alkene_polymerization" class="mw-redirect" title="Alkene polymerization">alkene polymerization</a>, <a href="/wiki/Shell_higher_olefin_process" title="Shell higher olefin process">alkene oligomerization</a>, <a href="/wiki/Hydrocarboxylation" class="mw-redirect" title="Hydrocarboxylation">hydrocarboxylation</a>, <a href="/wiki/Methanol_carbonylation" class="mw-redirect" title="Methanol carbonylation">methanol carbonylation</a>, and <a href="/wiki/Hydroformylation" title="Hydroformylation">hydroformylation</a>.<sup id="cite_ref-FOOTNOTELeeuwen2005[[Category:Wikipedia_articles_needing_page_number_citations_from_October_2021]]<sup_class="noprint_Inline-Template_"_style="white-space:nowrap;">&#91;<i>[[Wikipedia:Citing_sources|<span_title="This_citation_requires_a_reference_to_the_specific_page_or_range_of_pages_in_which_the_material_appears.&#32;(October_2021)">page&nbsp;needed</span>]]</i>&#93;</sup>_16-1" class="reference"><a href="#cite_note-FOOTNOTELeeuwen2005[[Category:Wikipedia_articles_needing_page_number_citations_from_October_2021]]<sup_class="noprint_Inline-Template_"_style="white-space:nowrap;">&#91;<i>[[Wikipedia:Citing_sources|<span_title="This_citation_requires_a_reference_to_the_specific_page_or_range_of_pages_in_which_the_material_appears.&#32;(October_2021)">page&nbsp;needed</span>]]</i>&#93;</sup>-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> Organometallic intermediates are also invoked in many <a href="/wiki/Heterogeneous_catalysis" title="Heterogeneous catalysis">heterogeneous catalysis</a> processes, analogous to those listed above. Additionally, organometallic intermediates are assumed for <a href="/wiki/Fischer%E2%80%93Tropsch_process" title="Fischer–Tropsch process">Fischer–Tropsch process</a>. </p><p>Organometallic complexes are commonly used in small-scale fine chemical synthesis as well, especially in <a href="/wiki/Cross-coupling_reaction" title="Cross-coupling reaction">cross-coupling reactions</a><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> that form carbon-carbon bonds, e.g. <a href="/wiki/Suzuki-Miyaura_coupling" class="mw-redirect" title="Suzuki-Miyaura coupling">Suzuki-Miyaura coupling</a>,<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> <a href="/wiki/Buchwald-Hartwig_amination" class="mw-redirect" title="Buchwald-Hartwig amination">Buchwald-Hartwig amination</a> for producing aryl amines from aryl halides,<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> and <a href="/wiki/Sonogashira_coupling" title="Sonogashira coupling">Sonogashira coupling</a>, etc. </p> <div class="mw-heading mw-heading2"><h2 id="Environmental_concerns">Environmental concerns</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organometallic_chemistry&action=edit&section=11" title="Edit section: Environmental concerns"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Roxarsone.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/20/Roxarsone.png/120px-Roxarsone.png" decoding="async" width="120" height="141" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/20/Roxarsone.png/180px-Roxarsone.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/20/Roxarsone.png/240px-Roxarsone.png 2x" data-file-width="1250" data-file-height="1468" /></a><figcaption><a href="/wiki/Roxarsone" title="Roxarsone">Roxarsone</a> is an organoarsenic compound used as an animal feed.</figcaption></figure> <p>Natural and contaminant organometallic compounds are found in the environment. Some that are remnants of human use, such as organolead and organomercury compounds, are toxicity hazards. <a href="/wiki/Tetraethyllead" title="Tetraethyllead">Tetraethyllead</a> was prepared for use as a <a href="/wiki/Gasoline" title="Gasoline">gasoline</a> additive but has fallen into disuse because of lead's toxicity. Its replacements are other organometallic compounds, such as <a href="/wiki/Ferrocene" title="Ferrocene">ferrocene</a> and <a href="/wiki/Methylcyclopentadienyl_manganese_tricarbonyl" title="Methylcyclopentadienyl manganese tricarbonyl">methylcyclopentadienyl manganese tricarbonyl</a> (MMT).<sup id="cite_ref-Seyferth_25-0" class="reference"><a href="#cite_note-Seyferth-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/Organoarsenic_compound" class="mw-redirect" title="Organoarsenic compound">organoarsenic compound</a> roxarsone is a controversial animal feed additive. In 2006, approximately one million kilograms of it were produced in the U.S alone.<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> <a href="/wiki/Organotin_compounds" class="mw-redirect" title="Organotin compounds">Organotin compounds</a> were once widely used in <a href="/wiki/Anti-fouling_paint" title="Anti-fouling paint">anti-fouling paints</a> but have since been banned due to environmental concerns.<sup id="cite_ref-27" class="reference"><a href="#cite_note-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organometallic_chemistry&action=edit&section=12" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Bioorganometallic_chemistry" title="Bioorganometallic chemistry">Bioorganometallic chemistry</a></li> <li><a href="/wiki/Metal_carbon_dioxide_complex" title="Metal carbon dioxide complex">Metal carbon dioxide complex</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organometallic_chemistry&action=edit&section=13" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-FOOTNOTECrabtree2009[[Category:Wikipedia_articles_needing_page_number_citations_from_October_2021]]<sup_class="noprint_Inline-Template_"_style="white-space:nowrap;">&#91;<i>[[Wikipedia:Citing_sources|<span_title="This_citation_requires_a_reference_to_the_specific_page_or_range_of_pages_in_which_the_material_appears.&#32;(October_2021)">page&nbsp;needed</span>]]</i>&#93;</sup>-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-FOOTNOTECrabtree2009[[Category:Wikipedia_articles_needing_page_number_citations_from_October_2021]]<sup_class="noprint_Inline-Template_"_style="white-space:nowrap;">&#91;<i>[[Wikipedia:Citing_sources|<span_title="This_citation_requires_a_reference_to_the_specific_page_or_range_of_pages_in_which_the_material_appears.&#32;(October_2021)">page&nbsp;needed</span>]]</i>&#93;</sup>_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-FOOTNOTECrabtree2009[[Category:Wikipedia_articles_needing_page_number_citations_from_October_2021]]<sup_class="noprint_Inline-Template_"_style="white-space:nowrap;">&#91;<i>[[Wikipedia:Citing_sources|<span_title="This_citation_requires_a_reference_to_the_specific_page_or_range_of_pages_in_which_the_material_appears.&#32;(October_2021)">page&nbsp;needed</span>]]</i>&#93;</sup>_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-FOOTNOTECrabtree2009[[Category:Wikipedia_articles_needing_page_number_citations_from_October_2021]]<sup_class="noprint_Inline-Template_"_style="white-space:nowrap;">&#91;<i>[[Wikipedia:Citing_sources|<span_title="This_citation_requires_a_reference_to_the_specific_page_or_range_of_pages_in_which_the_material_appears.&#32;(October_2021)">page&nbsp;needed</span>]]</i>&#93;</sup>_1-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-FOOTNOTECrabtree2009[[Category:Wikipedia_articles_needing_page_number_citations_from_October_2021]]<sup_class="noprint_Inline-Template_"_style="white-space:nowrap;">&#91;<i>[[Wikipedia:Citing_sources|<span_title="This_citation_requires_a_reference_to_the_specific_page_or_range_of_pages_in_which_the_material_appears.&#32;(October_2021)">page&nbsp;needed</span>]]</i>&#93;</sup>_1-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-FOOTNOTECrabtree2009[[Category:Wikipedia_articles_needing_page_number_citations_from_October_2021]]<sup_class="noprint_Inline-Template_"_style="white-space:nowrap;">&#91;<i>[[Wikipedia:Citing_sources|<span_title="This_citation_requires_a_reference_to_the_specific_page_or_range_of_pages_in_which_the_material_appears.&#32;(October_2021)">page&nbsp;needed</span>]]</i>&#93;</sup>_1-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-FOOTNOTECrabtree2009[[Category:Wikipedia_articles_needing_page_number_citations_from_October_2021]]<sup_class="noprint_Inline-Template_"_style="white-space:nowrap;">&#91;<i>[[Wikipedia:Citing_sources|<span_title="This_citation_requires_a_reference_to_the_specific_page_or_range_of_pages_in_which_the_material_appears.&#32;(October_2021)">page&nbsp;needed</span>]]</i>&#93;</sup>_1-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-FOOTNOTECrabtree2009[[Category:Wikipedia_articles_needing_page_number_citations_from_October_2021]]<sup_class="noprint_Inline-Template_"_style="white-space:nowrap;">&#91;<i>[[Wikipedia:Citing_sources|<span_title="This_citation_requires_a_reference_to_the_specific_page_or_range_of_pages_in_which_the_material_appears.&#32;(October_2021)">page&nbsp;needed</span>]]</i>&#93;</sup>_1-6"><sup><i><b>g</b></i></sup></a> <a href="#cite_ref-FOOTNOTECrabtree2009[[Category:Wikipedia_articles_needing_page_number_citations_from_October_2021]]<sup_class="noprint_Inline-Template_"_style="white-space:nowrap;">&#91;<i>[[Wikipedia:Citing_sources|<span_title="This_citation_requires_a_reference_to_the_specific_page_or_range_of_pages_in_which_the_material_appears.&#32;(October_2021)">page&nbsp;needed</span>]]</i>&#93;</sup>_1-7"><sup><i><b>h</b></i></sup></a> <a href="#cite_ref-FOOTNOTECrabtree2009[[Category:Wikipedia_articles_needing_page_number_citations_from_October_2021]]<sup_class="noprint_Inline-Template_"_style="white-space:nowrap;">&#91;<i>[[Wikipedia:Citing_sources|<span_title="This_citation_requires_a_reference_to_the_specific_page_or_range_of_pages_in_which_the_material_appears.&#32;(October_2021)">page&nbsp;needed</span>]]</i>&#93;</sup>_1-8"><sup><i><b>i</b></i></sup></a> <a href="#cite_ref-FOOTNOTECrabtree2009[[Category:Wikipedia_articles_needing_page_number_citations_from_October_2021]]<sup_class="noprint_Inline-Template_"_style="white-space:nowrap;">&#91;<i>[[Wikipedia:Citing_sources|<span_title="This_citation_requires_a_reference_to_the_specific_page_or_range_of_pages_in_which_the_material_appears.&#32;(October_2021)">page&nbsp;needed</span>]]</i>&#93;</sup>_1-9"><sup><i><b>j</b></i></sup></a></span> <span class="reference-text"><a href="#CITEREFCrabtree2009">Crabtree 2009</a>, p. <sup class="noprint Inline-Template" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citing_sources" title="Wikipedia:Citing sources"><span title="This citation requires a reference to the specific page or range of pages in which the material appears. (October 2021)">page needed</span></a></i>]</sup>.</span> </li> <li id="cite_note-:0-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-:0_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-:0_2-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-:0_2-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-:0_2-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><a href="/wiki/International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">IUPAC</a>, <i><a href="/wiki/IUPAC_books#Gold_Book" class="mw-redirect" title="IUPAC books">Compendium of Chemical Terminology</a></i>, 2nd ed. (the "Gold Book") (1997). 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(October 2021)">page needed</span></a></i>]</sup>.</span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRodríguez-ReyesSilva-Quiñones2018" class="citation book cs1">Rodríguez-Reyes, J.C.F.; Silva-Quiñones, D. (2018). "Metalorganic Functionalization in Vacuum". <i>Encyclopedia of Interfacial Chemistry</i>. pp. 761–768. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FB978-0-12-409547-2.13135-X">10.1016/B978-0-12-409547-2.13135-X</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-12-809894-3" title="Special:BookSources/978-0-12-809894-3"><bdi>978-0-12-809894-3</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Metalorganic+Functionalization+in+Vacuum&rft.btitle=Encyclopedia+of+Interfacial+Chemistry&rft.pages=761-768&rft.date=2018&rft_id=info%3Adoi%2F10.1016%2FB978-0-12-409547-2.13135-X&rft.isbn=978-0-12-809894-3&rft.aulast=Rodr%C3%ADguez-Reyes&rft.aufirst=J.C.F.&rft.au=Silva-Qui%C3%B1ones%2C+D.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AOrganometallic+chemistry" class="Z3988"></span></span> </li> <li id="cite_note-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-6">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20220125201058/https://www.chemblink.com/MSDS/MSDSFiles/97-93-8_Sigma-Aldrich.pdf">"Triethylaluminium – SDS"</a> <span class="cs1-format">(PDF)</span>. <i>chemBlink</i>. 24 May 2016. 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Retrieved <span class="nowrap">3 January</span> 2021</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=chemBlink&rft.atitle=Triethylaluminium+%E2%80%93+SDS&rft.date=2016-05-24&rft_id=https%3A%2F%2Fwww.chemblink.com%2FMSDS%2FMSDSFiles%2F97-93-8_Sigma-Aldrich.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AOrganometallic+chemistry" class="Z3988"></span></span> </li> <li id="cite_note-:02-7"><span class="mw-cite-backlink">^ <a href="#cite_ref-:02_7-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-:02_7-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-:02_7-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-:02_7-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCrabtree2014" class="citation book cs1">Crabtree, Robert H. 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Hoboken, New Jersey. pp. 43, 44, 205. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-118-78824-0" title="Special:BookSources/978-1-118-78824-0"><bdi>978-1-118-78824-0</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/863383849">863383849</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+organometallic+chemistry+of+the+transition+metals&rft.place=Hoboken%2C+New+Jersey&rft.pages=43%2C+44%2C+205&rft.edition=6&rft.date=2014&rft_id=info%3Aoclcnum%2F863383849&rft.isbn=978-1-118-78824-0&rft.aulast=Crabtree&rft.aufirst=Robert+H.&rft_id=https%3A%2F%2Fwww.worldcat.org%2Foclc%2F863383849&rfr_id=info%3Asid%2Fen.wikipedia.org%3AOrganometallic+chemistry" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_book" title="Template:Cite book">cite book</a>}}</code>: CS1 maint: location missing publisher (<a href="/wiki/Category:CS1_maint:_location_missing_publisher" title="Category:CS1 maint: location missing publisher">link</a>)</span></span> </li> <li id="cite_note-FOOTNOTEShriverWellerOvertonArmstrong2014[[Category:Wikipedia_articles_needing_page_number_citations_from_October_2021]]<sup_class="noprint_Inline-Template_"_style="white-space:nowrap;">&#91;<i>[[Wikipedia:Citing_sources|<span_title="This_citation_requires_a_reference_to_the_specific_page_or_range_of_pages_in_which_the_material_appears.&#32;(October_2021)">page&nbsp;needed</span>]]</i>&#93;</sup>-8"><span class="mw-cite-backlink">^ <a href="#cite_ref-FOOTNOTEShriverWellerOvertonArmstrong2014[[Category:Wikipedia_articles_needing_page_number_citations_from_October_2021]]<sup_class="noprint_Inline-Template_"_style="white-space:nowrap;">&#91;<i>[[Wikipedia:Citing_sources|<span_title="This_citation_requires_a_reference_to_the_specific_page_or_range_of_pages_in_which_the_material_appears.&#32;(October_2021)">page&nbsp;needed</span>]]</i>&#93;</sup>_8-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-FOOTNOTEShriverWellerOvertonArmstrong2014[[Category:Wikipedia_articles_needing_page_number_citations_from_October_2021]]<sup_class="noprint_Inline-Template_"_style="white-space:nowrap;">&#91;<i>[[Wikipedia:Citing_sources|<span_title="This_citation_requires_a_reference_to_the_specific_page_or_range_of_pages_in_which_the_material_appears.&#32;(October_2021)">page&nbsp;needed</span>]]</i>&#93;</sup>_8-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-FOOTNOTEShriverWellerOvertonArmstrong2014[[Category:Wikipedia_articles_needing_page_number_citations_from_October_2021]]<sup_class="noprint_Inline-Template_"_style="white-space:nowrap;">&#91;<i>[[Wikipedia:Citing_sources|<span_title="This_citation_requires_a_reference_to_the_specific_page_or_range_of_pages_in_which_the_material_appears.&#32;(October_2021)">page&nbsp;needed</span>]]</i>&#93;</sup>_8-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-FOOTNOTEShriverWellerOvertonArmstrong2014[[Category:Wikipedia_articles_needing_page_number_citations_from_October_2021]]<sup_class="noprint_Inline-Template_"_style="white-space:nowrap;">&#91;<i>[[Wikipedia:Citing_sources|<span_title="This_citation_requires_a_reference_to_the_specific_page_or_range_of_pages_in_which_the_material_appears.&#32;(October_2021)">page&nbsp;needed</span>]]</i>&#93;</sup>_8-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><a href="#CITEREFShriverWellerOvertonArmstrong2014">Shriver et al. 2014</a>, p. <sup class="noprint Inline-Template" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citing_sources" title="Wikipedia:Citing sources"><span title="This citation requires a reference to the specific page or range of pages in which the material appears. (October 2021)">page needed</span></a></i>]</sup>.</span> </li> <li id="cite_note-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-9">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFNelsonMiller2012" class="citation journal cs1">Nelson, Ryan C.; Miller, Jeffrey T. (2012). "An introduction to X-ray absorption spectroscopy and its in situ application to organometallic compounds and homogeneous catalysts". <i>Catal. Sci. 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(2003). <a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fom030621b">"The Rise and Fall of Tetraethyllead. 2"</a>. <i><a href="/wiki/Organometallics" title="Organometallics">Organometallics</a></i>. <b>22</b> (25): 5154–5178. <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/10.1021%2Fom030621b">10.1021/om030621b</a></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Organometallics&rft.atitle=The+Rise+and+Fall+of+Tetraethyllead.+2&rft.volume=22&rft.issue=25&rft.pages=5154-5178&rft.date=2003&rft_id=info%3Adoi%2F10.1021%2Fom030621b&rft.au=Seyferth%2C+D.&rft_id=https%3A%2F%2Fdoi.org%2F10.1021%252Fom030621b&rfr_id=info%3Asid%2Fen.wikipedia.org%3AOrganometallic+chemistry" class="Z3988"></span></span> </li> <li id="cite_note-26"><span class="mw-cite-backlink"><b><a href="#cite_ref-26">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHileman2007" class="citation journal cs1">Hileman, Bette (9 April 2007). <a rel="nofollow" class="external text" href="https://cen.acs.org/articles/85/i15/Arsenic-Chicken-Production.html">"Arsenic In Chicken Production"</a>. <i>Chemical & Engineering News</i>. <b>85</b> (15): 34–35. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fcen-v085n015.p034">10.1021/cen-v085n015.p034</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chemical+%26+Engineering+News&rft.atitle=Arsenic+In+Chicken+Production&rft.volume=85&rft.issue=15&rft.pages=34-35&rft.date=2007-04-09&rft_id=info%3Adoi%2F10.1021%2Fcen-v085n015.p034&rft.aulast=Hileman&rft.aufirst=Bette&rft_id=https%3A%2F%2Fcen.acs.org%2Farticles%2F85%2Fi15%2FArsenic-Chicken-Production.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AOrganometallic+chemistry" class="Z3988"></span></span> </li> <li id="cite_note-27"><span class="mw-cite-backlink"><b><a href="#cite_ref-27">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLagerströmStrandEklundYtreberg2017" class="citation journal cs1">Lagerström, Maria; Strand, Jakob; Eklund, Britta; Ytreberg, Erik (January 2017). <a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.envpol.2016.11.001">"Total tin and organotin speciation in historic layers of antifouling paint on leisure boat hulls"</a>. <i>Environmental Pollution</i>. <b>220</b> (Pt B): 1333–1341. <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/10.1016%2Fj.envpol.2016.11.001">10.1016/j.envpol.2016.11.001</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/27836476">27836476</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Environmental+Pollution&rft.atitle=Total+tin+and+organotin+speciation+in+historic+layers+of+antifouling+paint+on+leisure+boat+hulls&rft.volume=220&rft.issue=Pt+B&rft.pages=1333-1341&rft.date=2017-01&rft_id=info%3Adoi%2F10.1016%2Fj.envpol.2016.11.001&rft_id=info%3Apmid%2F27836476&rft.aulast=Lagerstr%C3%B6m&rft.aufirst=Maria&rft.au=Strand%2C+Jakob&rft.au=Eklund%2C+Britta&rft.au=Ytreberg%2C+Erik&rft_id=https%3A%2F%2Fdoi.org%2F10.1016%252Fj.envpol.2016.11.001&rfr_id=info%3Asid%2Fen.wikipedia.org%3AOrganometallic+chemistry" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="Sources">Sources</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organometallic_chemistry&action=edit&section=14" title="Edit section: Sources"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFClaydenGreevesWarren2012" class="citation book cs1">Clayden, Jonathan; Greeves, Nick; Warren, Stuart (2012). <i>Organic Chemistry</i>. OUP Oxford. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-19-927029-3" title="Special:BookSources/978-0-19-927029-3"><bdi>978-0-19-927029-3</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Organic+Chemistry&rft.pub=OUP+Oxford&rft.date=2012&rft.isbn=978-0-19-927029-3&rft.aulast=Clayden&rft.aufirst=Jonathan&rft.au=Greeves%2C+Nick&rft.au=Warren%2C+Stuart&rfr_id=info%3Asid%2Fen.wikipedia.org%3AOrganometallic+chemistry" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCrabtree2009" class="citation book cs1">Crabtree, Robert H. (2009). <i>The Organometallic Chemistry of the Transition Metals</i>. John Wiley & Sons. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-470-25762-3" title="Special:BookSources/978-0-470-25762-3"><bdi>978-0-470-25762-3</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Organometallic+Chemistry+of+the+Transition+Metals&rft.pub=John+Wiley+%26+Sons&rft.date=2009&rft.isbn=978-0-470-25762-3&rft.aulast=Crabtree&rft.aufirst=Robert+H.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AOrganometallic+chemistry" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFElschenbroich2016" class="citation book cs1">Elschenbroich, Christoph (2016). <i>Organometallics</i>. John Wiley & Sons. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-527-80514-3" title="Special:BookSources/978-3-527-80514-3"><bdi>978-3-527-80514-3</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Organometallics&rft.pub=John+Wiley+%26+Sons&rft.date=2016&rft.isbn=978-3-527-80514-3&rft.aulast=Elschenbroich&rft.aufirst=Christoph&rfr_id=info%3Asid%2Fen.wikipedia.org%3AOrganometallic+chemistry" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGuptaElias2013" class="citation book cs1">Gupta, B. D; Elias, A J (2013). <i>Basic Organometallic Chemistry: Concepts, Syntheses, and Applications of Transition Metals</i>. Hyderabad: Universities Press. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-81-7371-709-3" title="Special:BookSources/978-81-7371-709-3"><bdi>978-81-7371-709-3</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/903314566">903314566</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Basic+Organometallic+Chemistry%3A+Concepts%2C+Syntheses%2C+and+Applications+of+Transition+Metals&rft.place=Hyderabad&rft.pub=Universities+Press&rft.date=2013&rft_id=info%3Aoclcnum%2F903314566&rft.isbn=978-81-7371-709-3&rft.aulast=Gupta&rft.aufirst=B.+D&rft.au=Elias%2C+A+J&rfr_id=info%3Asid%2Fen.wikipedia.org%3AOrganometallic+chemistry" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFJenkins1992" class="citation book cs1">Jenkins, Paul R. (1992). <a rel="nofollow" class="external text" href="https://archive.org/details/organometallicre0000jenk"><i>Organometallic Reagents in Synthesis</i></a>. Oxford University Press. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-19-855666-4" title="Special:BookSources/978-0-19-855666-4"><bdi>978-0-19-855666-4</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Organometallic+Reagents+in+Synthesis&rft.pub=Oxford+University+Press&rft.date=1992&rft.isbn=978-0-19-855666-4&rft.aulast=Jenkins&rft.aufirst=Paul+R.&rft_id=https%3A%2F%2Farchive.org%2Fdetails%2Forganometallicre0000jenk&rfr_id=info%3Asid%2Fen.wikipedia.org%3AOrganometallic+chemistry" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLeeuwen2005" class="citation book cs1">Leeuwen, Piet W. N. M. van (2005). <i>Homogeneous Catalysis: Understanding the Art</i>. Springer Science & Business Media. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4020-3176-2" title="Special:BookSources/978-1-4020-3176-2"><bdi>978-1-4020-3176-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Homogeneous+Catalysis%3A+Understanding+the+Art&rft.pub=Springer+Science+%26+Business+Media&rft.date=2005&rft.isbn=978-1-4020-3176-2&rft.aulast=Leeuwen&rft.aufirst=Piet+W.+N.+M.+van&rfr_id=info%3Asid%2Fen.wikipedia.org%3AOrganometallic+chemistry" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLippardBerg1994" class="citation book cs1">Lippard, Stephen J.; Berg, Jeremy Mark (1994). <i>Principles of Bioinorganic Chemistry</i>. University Science Books. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-935702-73-6" title="Special:BookSources/978-0-935702-73-6"><bdi>978-0-935702-73-6</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Principles+of+Bioinorganic+Chemistry&rft.pub=University+Science+Books&rft.date=1994&rft.isbn=978-0-935702-73-6&rft.aulast=Lippard&rft.aufirst=Stephen+J.&rft.au=Berg%2C+Jeremy+Mark&rfr_id=info%3Asid%2Fen.wikipedia.org%3AOrganometallic+chemistry" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPearson1985" class="citation book cs1">Pearson, Anthony J (1985). <a rel="nofollow" class="external text" href="https://archive.org/details/metalloorganicch0000pear"><i>Metallo-organic chemistry</i></a>. Wiley. <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/1200566627">1200566627</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Metallo-organic+chemistry&rft.pub=Wiley&rft.date=1985&rft_id=info%3Aoclcnum%2F1200566627&rft.aulast=Pearson&rft.aufirst=Anthony+J&rft_id=https%3A%2F%2Farchive.org%2Fdetails%2Fmetalloorganicch0000pear&rfr_id=info%3Asid%2Fen.wikipedia.org%3AOrganometallic+chemistry" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFShriverWellerOvertonArmstrong2014" class="citation book cs1">Shriver, Duward; Weller, Mark; Overton, Tina; Armstrong, Fraser; Rourke, Jonathan (2014). <i>Inorganic Chemistry</i>. W. H. Freeman. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4292-9906-0" title="Special:BookSources/978-1-4292-9906-0"><bdi>978-1-4292-9906-0</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Inorganic+Chemistry&rft.pub=W.+H.+Freeman&rft.date=2014&rft.isbn=978-1-4292-9906-0&rft.aulast=Shriver&rft.aufirst=Duward&rft.au=Weller%2C+Mark&rft.au=Overton%2C+Tina&rft.au=Armstrong%2C+Fraser&rft.au=Rourke%2C+Jonathan&rfr_id=info%3Asid%2Fen.wikipedia.org%3AOrganometallic+chemistry" class="Z3988"></span></li></ul> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organometallic_chemistry&action=edit&section=15" title="Edit section: External links"><span>edit</span></a><span 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aria-labelledby="Organometallic_chemistry" style="padding:3px"><table class="nowraplinks hlist mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><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:Organometallics" title="Template:Organometallics"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Organometallics" title="Template talk:Organometallics"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Organometallics" title="Special:EditPage/Template:Organometallics"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Organometallic_chemistry" style="font-size:114%;margin:0 4em"><a class="mw-selflink selflink">Organometallic chemistry</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Principles</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/Crystal_field_theory" title="Crystal field theory">Crystal field theory</a></li> <li><a href="/wiki/Ligand_field_theory" title="Ligand field theory">Ligand field theory</a></li> <li><a href="/wiki/18-electron_rule" title="18-electron rule">18-electron rule</a></li> <li><a href="/wiki/D_electron_count" title="D electron count">d electron count</a></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/Isolobal_principle" title="Isolobal principle">Isolobal principle</a></li> <li><a href="/wiki/Pi_backbonding" title="Pi backbonding">π backbonding</a></li> <li><a href="/wiki/Dewar%E2%80%93Chatt%E2%80%93Duncanson_model" title="Dewar–Chatt–Duncanson model">Dewar–Chatt–Duncanson model</a></li> <li><a href="/wiki/Hapticity" title="Hapticity">Hapticity</a></li> <li><a href="/wiki/Spin_states_(d_electrons)" title="Spin states (d electrons)">spin states</a></li> <li><a href="/wiki/Agostic_interaction" title="Agostic interaction">Agostic interaction</a></li> <li><a href="/wiki/Metal%E2%80%93ligand_multiple_bond" title="Metal–ligand multiple bond">Metal–ligand multiple bond</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Reactions</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/Oxidative_addition" title="Oxidative addition">Oxidative addition</a> / <a href="/wiki/Reductive_elimination" title="Reductive elimination">reductive elimination</a></li> <li><a href="/wiki/Migratory_insertion" title="Migratory insertion">Migratory insertion</a></li> <li><a href="/wiki/Beta-Hydride_elimination" class="mw-redirect" title="Beta-Hydride elimination">β-hydride elimination</a></li> <li><a href="/wiki/Transmetalation" title="Transmetalation">Transmetalation</a></li> <li><a href="/wiki/Carbometalation" title="Carbometalation">Carbometalation</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Types of compounds</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/Gilman_reagent" title="Gilman reagent">Gilman reagents</a></li> <li><a href="/wiki/Grignard_reagent" title="Grignard reagent">Grignard reagents</a></li> <li><a href="/wiki/Cyclopentadienyl_complex" title="Cyclopentadienyl complex">Cyclopentadienyl complexes</a></li> <li><a href="/wiki/Transition_metal_indenyl_complex" title="Transition metal indenyl complex">Transition metal indenyl complexes</a></li> <li><a href="/wiki/Transition_metal_fullerene_complex" title="Transition metal fullerene complex">Transition metal fullerene complexes</a></li> <li><a href="/wiki/Metallocene" title="Metallocene">Metallocenes</a></li> <li><a href="/wiki/Metal_tetranorbornyl" title="Metal tetranorbornyl">Metal tetranorbornyls</a></li> <li><a href="/wiki/Sandwich_compound" title="Sandwich compound">Sandwich compounds</a></li> <li><a href="/wiki/Half_sandwich_compound" title="Half sandwich compound">Half sandwich compounds</a></li> <li><a href="/wiki/Transition_metal_acyl_complexes" title="Transition metal acyl complexes">Transition metal acyl complexes</a></li> <li><a href="/wiki/Transition_metal_carbene_complex" title="Transition metal carbene complex">Transition metal carbene complexes</a></li> <li><a href="/wiki/Transition_metal_carbyne_complex" title="Transition metal carbyne complex">Transition metal carbyne complexes</a></li> <li><a href="/wiki/Transition_metal_alkene_complex" title="Transition metal alkene complex">Transition metal alkene complexes</a></li> <li><a href="/wiki/Transition_metal_alkyne_complex" title="Transition metal alkyne complex">Transition metal alkyne complexes</a></li> <li><a href="/wiki/Transition-metal_allyl_complex" title="Transition-metal allyl complex">Transition-metal allyl complexes</a></li> <li><a href="/wiki/Metal_carbido_complex" title="Metal carbido complex">Transition metal carbides</a></li> <li><a href="/wiki/Arene_complexes_of_univalent_gallium,_indium,_and_thallium" title="Arene complexes of univalent gallium, indium, and thallium">Arene complexes of univalent gallium, indium, and thallium</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Applications</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/Carbonylation" title="Carbonylation">Carbonylation</a></li> <li><a href="/wiki/Cativa_process" title="Cativa process">Cativa process</a></li> <li><a href="/wiki/Grignard_reaction" title="Grignard reaction">Grignard reaction</a></li> <li><a href="/wiki/Monsanto_process" title="Monsanto process">Monsanto process</a></li> <li><a href="/wiki/Olefin_metathesis" title="Olefin metathesis">Olefin metathesis</a></li> <li><a href="/wiki/Shell_higher_olefin_process" title="Shell higher olefin process">Shell higher olefin process</a></li> <li><a href="/wiki/Ziegler%E2%80%93Natta_catalyst" title="Ziegler–Natta catalyst">Ziegler–Natta process</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Related branches of <a href="/wiki/Chemistry" title="Chemistry">chemistry</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/Organic_chemistry" title="Organic chemistry">Organic chemistry</a></li> <li><a href="/wiki/Inorganic_chemistry" title="Inorganic chemistry">Inorganic chemistry</a></li> <li><a href="/wiki/Bioinorganic_chemistry" title="Bioinorganic chemistry">Bioinorganic chemistry</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <ul><li><span class="noviewer" typeof="mw:File"><span title="Category"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/16px-Symbol_category_class.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/23px-Symbol_category_class.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/31px-Symbol_category_class.svg.png 2x" data-file-width="180" data-file-height="185" /></span></span> <b><a href="/wiki/Category:Organometallic_chemistry" title="Category:Organometallic chemistry">Category</a></b></li> <li><span class="noviewer" typeof="mw:File"><span title="Commons page"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/12px-Commons-logo.svg.png" decoding="async" width="12" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/18px-Commons-logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/24px-Commons-logo.svg.png 2x" data-file-width="1024" data-file-height="1376" /></span></span> <b><a href="https://commons.wikimedia.org/wiki/Category:Organometallic_chemistry" class="extiw" title="commons:Category:Organometallic chemistry">Commons</a></b></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Branches_of_chemistry" style="padding:3px"><table class="nowraplinks hlist mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Branches_of_chemistry" title="Template:Branches of chemistry"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Branches_of_chemistry" title="Template talk:Branches of chemistry"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Branches_of_chemistry" title="Special:EditPage/Template:Branches of chemistry"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Branches_of_chemistry" style="font-size:114%;margin:0 4em">Branches of <a href="/wiki/Chemistry" title="Chemistry">chemistry</a></div></th></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <ul><li><a href="/wiki/Glossary_of_chemical_formulae" title="Glossary of chemical formulae">Glossary of chemical formulae</a></li> <li><a href="/wiki/List_of_biomolecules" title="List of biomolecules">List of biomolecules</a></li> <li><a href="/wiki/List_of_inorganic_compounds" title="List of inorganic compounds">List of inorganic compounds</a></li> <li><a href="/wiki/Periodic_table" title="Periodic table">Periodic table</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Analytical_chemistry" title="Analytical chemistry">Analytical</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Instrumental_chemistry" title="Instrumental chemistry">Instrumental chemistry</a></li> <li><a href="/wiki/Electroanalytical_methods" title="Electroanalytical methods">Electroanalytical methods</a></li> <li><a href="/wiki/Spectroscopy" title="Spectroscopy">Spectroscopy</a> <ul><li><a href="/wiki/Infrared_spectroscopy" title="Infrared spectroscopy">IR</a></li> <li><a href="/wiki/Raman_spectroscopy" title="Raman spectroscopy">Raman</a></li> <li><a href="/wiki/Ultraviolet%E2%80%93visible_spectroscopy" title="Ultraviolet–visible spectroscopy">UV-Vis</a></li> <li><a href="/wiki/Nuclear_magnetic_resonance_spectroscopy" title="Nuclear magnetic resonance spectroscopy">NMR</a></li></ul></li> <li><a href="/wiki/Mass_spectrometry" title="Mass spectrometry">Mass spectrometry</a> <ul><li><a href="/wiki/Electron_ionization" title="Electron ionization">EI</a></li> <li><a href="/wiki/Inductively_coupled_plasma_mass_spectrometry" title="Inductively coupled plasma mass spectrometry">ICP</a></li> <li><a href="/wiki/Matrix-assisted_laser_desorption/ionization" title="Matrix-assisted laser desorption/ionization">MALDI</a></li></ul></li> <li><a href="/wiki/Separation_process" title="Separation process">Separation process</a></li> <li><a href="/wiki/Chromatography" title="Chromatography">Chromatography</a> <ul><li><a href="/wiki/Gas_chromatography" title="Gas chromatography">GC</a></li> <li><a href="/wiki/High-performance_liquid_chromatography" title="High-performance liquid chromatography">HPLC</a></li></ul></li> <li><a href="/wiki/Crystallography" title="Crystallography">Crystallography</a></li> <li><a href="/wiki/Characterization_(materials_science)" title="Characterization (materials science)">Characterization</a></li> <li><a href="/wiki/Titration" title="Titration">Titration</a></li> <li><a href="/wiki/Wet_chemistry" title="Wet chemistry">Wet chemistry</a></li> <li><a href="/wiki/Calorimetry" title="Calorimetry">Calorimetry</a></li> <li><a href="/wiki/Elemental_analysis" title="Elemental analysis">Elemental analysis</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Theoretical_chemistry" title="Theoretical chemistry">Theoretical</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Quantum_chemistry" title="Quantum chemistry">Quantum chemistry</a></li> <li><a href="/wiki/Computational_chemistry" title="Computational chemistry">Computational chemistry</a> <ul><li><a href="/wiki/Mathematical_chemistry" title="Mathematical chemistry">Mathematical chemistry</a></li></ul></li> <li><a href="/wiki/Molecular_modelling" title="Molecular modelling">Molecular modelling</a></li> <li><a href="/wiki/Molecular_mechanics" title="Molecular mechanics">Molecular mechanics</a></li> <li><a href="/wiki/Molecular_dynamics" title="Molecular dynamics">Molecular dynamics</a></li> <li><a href="/wiki/Molecular_geometry" title="Molecular geometry">Molecular geometry</a> <ul><li><a href="/wiki/VSEPR_theory" title="VSEPR theory">VSEPR theory</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Physical_chemistry" title="Physical chemistry">Physical</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Electrochemistry" title="Electrochemistry">Electrochemistry</a> <ul><li><a href="/wiki/Spectroelectrochemistry" title="Spectroelectrochemistry">Spectroelectrochemistry</a></li> <li><a href="/wiki/Photoelectrochemistry" title="Photoelectrochemistry">Photoelectrochemistry</a></li></ul></li> <li><a href="/wiki/Thermochemistry" title="Thermochemistry">Thermochemistry</a></li> <li><a href="/wiki/Chemical_thermodynamics" title="Chemical thermodynamics">Chemical thermodynamics</a></li> <li><a href="/wiki/Surface_science" title="Surface science">Surface science</a></li> <li><a href="/wiki/Interface_and_colloid_science" title="Interface and colloid science">Interface and colloid science</a> <ul><li><a href="/wiki/Micromeritics" title="Micromeritics">Micromeritics</a></li></ul></li> <li><a href="/wiki/Cryochemistry" title="Cryochemistry">Cryochemistry</a></li> <li><a href="/wiki/Sonochemistry" title="Sonochemistry">Sonochemistry</a></li> <li><a href="/wiki/Structural_chemistry" title="Structural chemistry">Structural chemistry</a></li> <li><a href="/wiki/Chemical_physics" title="Chemical physics">Chemical physics</a> <ul><li><a href="/wiki/Molecular_physics" title="Molecular physics">Molecular physics</a></li></ul></li> <li><a href="/wiki/Femtochemistry" title="Femtochemistry">Femtochemistry</a></li> <li><a href="/wiki/Chemical_kinetics" title="Chemical kinetics">Chemical kinetics</a></li> <li><a href="/wiki/Spectroscopy" title="Spectroscopy">Spectroscopy</a></li> <li><a href="/wiki/Photochemistry" title="Photochemistry">Photochemistry</a></li> <li><a href="/wiki/Spin_chemistry" title="Spin chemistry">Spin chemistry</a></li> <li><a href="/wiki/Microwave_chemistry" title="Microwave chemistry">Microwave chemistry</a></li> <li><a href="/wiki/Equilibrium_chemistry" title="Equilibrium chemistry">Equilibrium chemistry</a></li> <li><a href="/wiki/Mechanochemistry" title="Mechanochemistry">Mechanochemistry</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Inorganic_chemistry" title="Inorganic chemistry">Inorganic</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Coordination_complex" title="Coordination complex">Coordination chemistry</a></li> <li><a href="/wiki/Magnetochemistry" title="Magnetochemistry">Magnetochemistry</a></li> <li><a class="mw-selflink selflink">Organometallic chemistry</a> <ul><li><a href="/wiki/Organolanthanide_chemistry" title="Organolanthanide chemistry">Organolanthanide chemistry</a></li></ul></li> <li><a href="/wiki/Atom_cluster" class="mw-redirect" title="Atom cluster">Cluster chemistry</a></li> <li><a href="/wiki/Solid-state_chemistry" title="Solid-state chemistry">Solid-state chemistry</a></li> <li><a href="/wiki/Ceramic_chemistry" class="mw-redirect" title="Ceramic chemistry">Ceramic chemistry</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Organic_chemistry" title="Organic chemistry">Organic</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Stereochemistry" title="Stereochemistry">Stereochemistry</a> <ul><li><a href="/wiki/Alkane_stereochemistry" class="mw-redirect" title="Alkane stereochemistry">Alkane stereochemistry</a></li></ul></li> <li><a href="/wiki/Physical_organic_chemistry" title="Physical organic chemistry">Physical organic chemistry</a></li> <li><a href="/wiki/Organic_reactions" class="mw-redirect" title="Organic reactions">Organic reactions</a></li> <li><a href="/wiki/Organic_synthesis" title="Organic synthesis">Organic synthesis</a></li> <li><a href="/wiki/Retrosynthetic_analysis" title="Retrosynthetic analysis">Retrosynthetic analysis</a></li> <li><a href="/wiki/Enantioselective_synthesis" title="Enantioselective synthesis">Enantioselective synthesis</a></li> <li><a href="/wiki/Total_synthesis" title="Total synthesis">Total synthesis</a> / <a href="/wiki/Semisynthesis" title="Semisynthesis">Semisynthesis</a></li> <li><a href="/wiki/Fullerene_chemistry" title="Fullerene chemistry">Fullerene chemistry</a></li> <li><a href="/wiki/Polymer_chemistry" title="Polymer chemistry">Polymer chemistry</a></li> <li><a href="/wiki/Petrochemistry" class="mw-redirect" title="Petrochemistry">Petrochemistry</a></li> <li><a href="/wiki/Dynamic_covalent_chemistry" title="Dynamic covalent chemistry">Dynamic covalent chemistry</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Biochemistry" title="Biochemistry">Biological</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Biochemistry" title="Biochemistry">Biochemistry</a> <ul><li><a href="/wiki/Molecular_biology" title="Molecular biology">Molecular biology</a></li> <li><a href="/wiki/Cell_biology" title="Cell biology">Cell biology</a></li></ul></li> <li><a href="/wiki/Chemical_biology" title="Chemical biology">Chemical biology</a> <ul><li><a href="/wiki/Bioorthogonal_chemistry" title="Bioorthogonal chemistry">Bioorthogonal chemistry</a></li></ul></li> <li><a href="/wiki/Medicinal_chemistry" title="Medicinal chemistry">Medicinal chemistry</a> <ul><li><a href="/wiki/Pharmacology" title="Pharmacology">Pharmacology</a></li></ul></li> <li><a href="/wiki/Clinical_chemistry" title="Clinical chemistry">Clinical chemistry</a></li> <li><a href="/wiki/Neurochemistry" title="Neurochemistry">Neurochemistry</a></li> <li><a href="/wiki/Bioorganic_chemistry" title="Bioorganic chemistry">Bioorganic chemistry</a></li> <li><a href="/wiki/Bioorganometallic_chemistry" title="Bioorganometallic chemistry">Bioorganometallic chemistry</a></li> <li><a href="/wiki/Bioinorganic_chemistry" title="Bioinorganic chemistry">Bioinorganic chemistry</a></li> <li><a href="/wiki/Biophysical_chemistry" title="Biophysical chemistry">Biophysical chemistry</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Interdisciplinarity" title="Interdisciplinarity">Interdisciplinarity</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Nuclear_chemistry" title="Nuclear chemistry">Nuclear chemistry</a> <ul><li><a href="/wiki/Radiochemistry" title="Radiochemistry">Radiochemistry</a></li> <li><a href="/wiki/Radiation_chemistry" title="Radiation chemistry">Radiation chemistry</a></li> <li><a href="/wiki/Actinide_chemistry" title="Actinide chemistry">Actinide chemistry</a></li></ul></li> <li><a href="/wiki/Cosmochemistry" title="Cosmochemistry">Cosmochemistry</a> / <a href="/wiki/Astrochemistry" title="Astrochemistry">Astrochemistry</a> / <a href="/wiki/Stellar_chemistry" title="Stellar chemistry">Stellar chemistry</a></li> <li><a href="/wiki/Geochemistry" title="Geochemistry">Geochemistry</a> <ul><li><a href="/wiki/Biogeochemistry" title="Biogeochemistry">Biogeochemistry</a></li> <li><a href="/wiki/Photogeochemistry" title="Photogeochemistry">Photogeochemistry</a></li></ul></li></ul> <ul><li><a href="/wiki/Environmental_chemistry" title="Environmental chemistry">Environmental chemistry</a> <ul><li><a href="/wiki/Atmospheric_chemistry" title="Atmospheric chemistry">Atmospheric chemistry</a></li> <li><a href="/wiki/Ocean_chemistry" class="mw-redirect" title="Ocean chemistry">Ocean chemistry</a></li></ul></li> <li><a href="/wiki/Clay_chemistry" title="Clay chemistry">Clay chemistry</a></li> <li><a href="/wiki/Carbochemistry" title="Carbochemistry">Carbochemistry</a></li> <li><a href="/wiki/Food_chemistry" title="Food chemistry">Food chemistry</a> <ul><li><a href="/wiki/Carbohydrate_chemistry" class="mw-redirect" title="Carbohydrate chemistry">Carbohydrate chemistry</a></li> <li><a href="/wiki/Food_physical_chemistry" title="Food physical chemistry">Food physical chemistry</a></li></ul></li> <li><a href="/wiki/Agricultural_chemistry" title="Agricultural chemistry">Agricultural chemistry</a> <ul><li><a href="/wiki/Soil_chemistry" title="Soil chemistry">Soil chemistry</a></li></ul></li></ul> <ul><li><a href="/wiki/Chemistry_education" title="Chemistry education">Chemistry education</a> <ul><li><a href="/wiki/Amateur_chemistry" title="Amateur chemistry">Amateur chemistry</a></li> <li><a href="/wiki/General_chemistry" title="General chemistry">General chemistry</a></li></ul></li> <li><a href="/wiki/Clandestine_chemistry" title="Clandestine chemistry">Clandestine chemistry</a></li> <li><a href="/wiki/Forensic_chemistry" title="Forensic chemistry">Forensic chemistry</a> <ul><li><a href="/wiki/Forensic_toxicology" title="Forensic toxicology">Forensic toxicology</a></li> <li><a href="/wiki/Post-mortem_chemistry" title="Post-mortem chemistry">Post-mortem chemistry</a></li></ul></li></ul> <ul><li><a href="/wiki/Nanochemistry" title="Nanochemistry">Nanochemistry</a> <ul><li><a href="/wiki/Supramolecular_chemistry" title="Supramolecular chemistry">Supramolecular chemistry</a></li></ul></li> <li><a href="/wiki/Chemical_synthesis" title="Chemical synthesis">Chemical synthesis</a> <ul><li><a href="/wiki/Green_chemistry" title="Green chemistry">Green chemistry</a></li> <li><a href="/wiki/Click_chemistry" title="Click chemistry">Click chemistry</a></li> <li><a href="/wiki/Combinatorial_chemistry" title="Combinatorial chemistry">Combinatorial chemistry</a></li> <li><a href="/wiki/Biosynthesis" title="Biosynthesis">Biosynthesis</a></li></ul></li> <li><a href="/wiki/Chemical_engineering" title="Chemical engineering">Chemical engineering</a> <ul><li><a href="/wiki/Stoichiometry" title="Stoichiometry">Stoichiometry</a></li></ul></li> <li><a href="/wiki/Materials_science" title="Materials science">Materials science</a> <ul><li><a href="/wiki/Metallurgy" title="Metallurgy">Metallurgy</a></li> <li><a href="/wiki/Ceramic_engineering" title="Ceramic engineering">Ceramic engineering</a></li> <li><a href="/wiki/Polymer_science" title="Polymer science">Polymer science</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">See also</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/History_of_chemistry" title="History of chemistry">History of chemistry</a></li> <li><a href="/wiki/Nobel_Prize_in_Chemistry" title="Nobel Prize in Chemistry">Nobel Prize in Chemistry</a></li> <li><a href="/wiki/Timeline_of_chemistry" title="Timeline of chemistry">Timeline of chemistry</a> <ul><li><a href="/wiki/Discovery_of_chemical_elements" title="Discovery of chemical elements">of element discoveries</a></li></ul></li> <li>"<a href="/wiki/The_central_science" title="The central science">The central science</a>"</li> <li><a href="/wiki/Chemical_reaction" title="Chemical reaction">Chemical reaction</a> <ul><li><a href="/wiki/Catalysis" title="Catalysis">Catalysis</a></li></ul></li> <li><a href="/wiki/Chemical_element" title="Chemical element">Chemical element</a></li> <li><a href="/wiki/Chemical_compound" title="Chemical compound">Chemical compound</a></li> <li><a href="/wiki/Atom" title="Atom">Atom</a></li> <li><a href="/wiki/Molecule" title="Molecule">Molecule</a></li> <li><a href="/wiki/Ion" title="Ion">Ion</a></li> <li><a href="/wiki/Chemical_substance" title="Chemical substance">Chemical substance</a></li> <li><a href="/wiki/Chemical_bond" title="Chemical bond">Chemical bond</a></li> <li><a href="/wiki/Alchemy" title="Alchemy">Alchemy</a></li> <li><a href="/wiki/Quantum_mechanics" title="Quantum mechanics">Quantum mechanics</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <ul><li><span class="noviewer" typeof="mw:File"><span title="Category"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/16px-Symbol_category_class.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/23px-Symbol_category_class.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/31px-Symbol_category_class.svg.png 2x" data-file-width="180" data-file-height="185" /></span></span> <b><a href="/wiki/Category:Chemistry" 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Chemistry">WikiProject</a></b></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"></div><div role="navigation" class="navbox" aria-labelledby="Compounds_of_carbon_with_other_elements_in_the_periodic_table" 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="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:ChemicalBondsToCarbon" title="Template:ChemicalBondsToCarbon"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:ChemicalBondsToCarbon" title="Template talk:ChemicalBondsToCarbon"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:ChemicalBondsToCarbon" title="Special:EditPage/Template:ChemicalBondsToCarbon"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Compounds_of_carbon_with_other_elements_in_the_periodic_table" style="font-size:114%;margin:0 4em">Compounds of <a href="/wiki/Carbon" title="Carbon">carbon</a> with other elements in the periodic table</div></th></tr><tr><td colspan="2" class="navbox-list navbox-odd wikitable" style="width:100%;padding:0"><div style="padding:0 0.25em"> <table cellpadding="3" style="margin:0 auto"> <tbody><tr> <td style="background-color:#99bbff"><a href="/wiki/Carbon%E2%80%93hydrogen_bond" title="Carbon–hydrogen bond">CH</a> </td> <td colspan="1" style="border:none"> </td> <td colspan="11" style="border:none" rowspan="3"> </td> <td colspan="5" style="border:none"> </td> <td style="background-color:#FFE4E1">He </td></tr> <tr> <td style="background-color:#99bbff"><a href="/wiki/Organolithium_reagent" title="Organolithium reagent">CLi</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoberyllium_chemistry" title="Organoberyllium chemistry">CBe</a> </td> <td style="background-color:#99bbff"><a href="/wiki/Organoboron_chemistry" title="Organoboron chemistry">CB</a> </td> <td style="background-color:#99bbff"><a href="/wiki/Carbon%E2%80%93carbon_bond" title="Carbon–carbon bond">CC</a> </td> <td style="background-color:#99bbff"><a href="/wiki/Carbon%E2%80%93nitrogen_bond" title="Carbon–nitrogen bond">CN</a> </td> <td style="background-color:#99bbff"><a href="/wiki/Carbon%E2%80%93oxygen_bond" title="Carbon–oxygen bond">CO</a> </td> <td style="background-color:#99bbff"><a href="/wiki/Organofluorine_chemistry" title="Organofluorine chemistry">CF</a> </td> <td style="background-color:#FFE4E1">Ne </td></tr> <tr> <td style="background-color:#98FF98"><a href="/wiki/Organosodium_chemistry" title="Organosodium chemistry">CNa</a> </td> <td style="background-color:#99bbff"><a href="/wiki/Organomagnesium_chemistry" class="mw-redirect" title="Organomagnesium chemistry">CMg</a> </td> <td style="background-color:#98FF98"><a href="/wiki/Organoaluminium_chemistry" title="Organoaluminium chemistry">CAl</a> </td> <td style="background-color:#99bbff"><a href="/wiki/Organosilicon_chemistry" title="Organosilicon chemistry">CSi</a> </td> <td style="background-color:#99bbff"><a href="/wiki/Organophosphorus_chemistry" title="Organophosphorus chemistry">CP</a> </td> <td style="background-color:#99bbff"><a href="/wiki/Organosulfur_chemistry" title="Organosulfur chemistry">CS</a> </td> <td style="background-color:#99bbff"><a href="/wiki/Organochlorine_chemistry" title="Organochlorine chemistry">CCl</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoargon_chemistry" class="mw-redirect" title="Organoargon chemistry">CAr</a> </td></tr> <tr> <td style="background-color:#F0DC82"><a href="/wiki/Organopotassium_chemistry" class="mw-redirect" title="Organopotassium chemistry">CK</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organocalcium_chemistry" class="mw-redirect" title="Organocalcium chemistry">CCa</a> </td> <td> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoscandium_chemistry" title="Organoscandium chemistry">CSc</a> </td> <td style="background-color:#98FF98"><a href="/wiki/Organotitanium_chemistry" title="Organotitanium chemistry">CTi</a> </td> <td style="background-color:#98FF98"><a href="/wiki/Organovanadium_chemistry" title="Organovanadium chemistry">CV</a> </td> <td style="background-color:#98FF98"><a href="/wiki/Organochromium_chemistry" title="Organochromium chemistry">CCr</a> </td> <td style="background-color:#98FF98"><a href="/wiki/Organomanganese_chemistry" title="Organomanganese chemistry">CMn</a> </td> <td style="background-color:#98FF98"><a href="/wiki/Organoiron_chemistry" title="Organoiron chemistry">CFe</a> </td> <td style="background-color:#98FF98"><a href="/wiki/Organocobalt_chemistry" title="Organocobalt chemistry">CCo</a> </td> <td style="background-color:#98FF98"><a href="/wiki/Organonickel_chemistry" title="Organonickel chemistry">CNi</a> </td> <td style="background-color:#98FF98"><a href="/wiki/Organocopper_chemistry" title="Organocopper chemistry">CCu</a> </td> <td style="background-color:#98FF98"><a href="/wiki/Organozinc_chemistry" title="Organozinc chemistry">CZn</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organogallium_chemistry" title="Organogallium chemistry">CGa</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organogermanium_chemistry" title="Organogermanium chemistry">CGe</a> </td> <td style="background-color:#98FF98"><a href="/wiki/Organoarsenic_chemistry" title="Organoarsenic chemistry">CAs</a> </td> <td style="background-color:#98FF98"><a href="/wiki/Organoselenium_chemistry" title="Organoselenium chemistry">CSe</a> </td> <td style="background-color:#99bbff"><a href="/wiki/Organobromine_chemistry" title="Organobromine chemistry">CBr</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organokrypton_chemistry" title="Organokrypton chemistry">CKr</a> </td></tr> <tr> <td style="background-color:#F0DC82"><a href="/wiki/Organorubidium_chemistry" class="mw-redirect" title="Organorubidium chemistry">CRb</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organostrontium_chemistry" class="mw-redirect" title="Organostrontium chemistry">CSr</a> </td> <td> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoyttrium_chemistry" title="Organoyttrium chemistry">CY</a> </td> <td style="background-color:#98FF98"><a href="/wiki/Organozirconium_chemistry" class="mw-redirect" title="Organozirconium chemistry">CZr</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoniobium_chemistry" title="Organoniobium chemistry">CNb</a> </td> <td style="background-color:#98FF98"><a href="/wiki/Organomolybdenum_chemistry" title="Organomolybdenum chemistry">CMo</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organotechnetium_chemistry" title="Organotechnetium chemistry">CTc</a> </td> <td style="background-color:#98FF98"><a href="/wiki/Organoruthenium_chemistry" title="Organoruthenium chemistry">CRu</a> </td> <td style="background-color:#98FF98"><a href="/wiki/Organorhodium_chemistry" title="Organorhodium chemistry">CRh</a> </td> <td style="background-color:#99bbff"><a href="/wiki/Organopalladium_chemistry" title="Organopalladium chemistry">CPd</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organosilver_chemistry" title="Organosilver chemistry">CAg</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organocadmium_chemistry" title="Organocadmium chemistry">CCd</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoindium_chemistry" title="Organoindium chemistry">CIn</a> </td> <td style="background-color:#98FF98"><a href="/wiki/Organotin_chemistry" title="Organotin chemistry">CSn</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoantimony_chemistry" title="Organoantimony chemistry">CSb</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organotellurium_chemistry" title="Organotellurium chemistry">CTe</a> </td> <td style="background-color:#99bbff"><a href="/wiki/Organoiodine_chemistry" title="Organoiodine chemistry">CI</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoxenon_chemistry" title="Organoxenon chemistry">CXe</a> </td></tr> <tr> <td style="background-color:#F0DC82"><a href="/wiki/Organocesium_chemistry" class="mw-redirect" title="Organocesium chemistry">CCs</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organobarium_chemistry" class="mw-redirect" title="Organobarium chemistry">CBa</a> </td> <td style="text-align:center; vertical-align:middle; background:white"><span class="skin-invert-image" typeof="mw:File"><span><img alt="1 asterisk" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/49/Asterisks_one.svg/16px-Asterisks_one.svg.png" decoding="async" width="16" height="15" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/49/Asterisks_one.svg/24px-Asterisks_one.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/49/Asterisks_one.svg/32px-Asterisks_one.svg.png 2x" data-file-width="106" data-file-height="98" /></span></span> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organolanthanide_chemistry" title="Organolanthanide chemistry">CLu</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organohafnium_chemistry" class="mw-redirect" title="Organohafnium chemistry">CHf</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organotantalum_chemistry" title="Organotantalum chemistry">CTa</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organotungsten_chemistry" class="mw-redirect" title="Organotungsten chemistry">CW</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organorhenium_chemistry" title="Organorhenium chemistry">CRe</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoosmium_chemistry" class="mw-redirect" title="Organoosmium chemistry">COs</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoiridium_chemistry" title="Organoiridium chemistry">CIr</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoplatinum_chemistry" title="Organoplatinum chemistry">CPt</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organogold_chemistry" title="Organogold chemistry">CAu</a> </td> <td style="background-color:#98FF98"><a href="/wiki/Organomercury_chemistry" title="Organomercury chemistry">CHg</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organothallium_chemistry" title="Organothallium chemistry">CTl</a> </td> <td style="background-color:#98FF82"><a href="/wiki/Organolead_chemistry" title="Organolead chemistry">CPb</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organobismuth_chemistry" title="Organobismuth chemistry">CBi</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organopolonium_chemistry" title="Organopolonium chemistry">CPo</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoastatine_chemistry" title="Organoastatine chemistry">CAt</a> </td> <td style="background-color:#FFE4E1">Rn </td></tr> <tr style="background-color:#FFE4E1"> <td style="background-color:#FFE4E1">Fr </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoradium_chemistry" class="mw-redirect" title="Organoradium chemistry">CRa</a> </td> <td style="text-align:center; vertical-align:middle; background:white"><span class="skin-invert-image" typeof="mw:File"><span><img alt="2 asterisks" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3f/Asterisks_two.svg/16px-Asterisks_two.svg.png" decoding="async" width="16" height="15" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3f/Asterisks_two.svg/24px-Asterisks_two.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3f/Asterisks_two.svg/32px-Asterisks_two.svg.png 2x" data-file-width="106" data-file-height="98" /></span></span> </td> <td><a href="/wiki/Organoactinide_chemistry" title="Organoactinide chemistry">Lr</a> </td> <td>Rf </td> <td>Db </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoseaborgium_chemistry" class="mw-redirect" title="Organoseaborgium chemistry">CSg</a> </td> <td>Bh </td> <td>Hs </td> <td>Mt </td> <td>Ds </td> <td>Rg </td> <td>Cn </td> <td>Nh </td> <td>Fl </td> <td>Mc </td> <td>Lv </td> <td>Ts </td> <td>Og </td></tr> <tr> <td style="border:none; line-height:0.7em;">  </td></tr> <tr style="background-color:#F0DC82"> <td colspan="2" style="border:none; background-color:white"> </td> <td style="text-align:center; vertical-align:middle; background:white"><span class="skin-invert-image" typeof="mw:File"><span><img alt="1 asterisk" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/49/Asterisks_one.svg/16px-Asterisks_one.svg.png" decoding="async" width="16" height="15" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/49/Asterisks_one.svg/24px-Asterisks_one.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/49/Asterisks_one.svg/32px-Asterisks_one.svg.png 2x" data-file-width="106" data-file-height="98" /></span></span> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organolanthanide_chemistry" title="Organolanthanide chemistry">CLa</a> </td> <td><a href="/wiki/Organocerium_chemistry" title="Organocerium chemistry">CCe</a> </td> <td><a href="/wiki/Organolanthanide_chemistry" title="Organolanthanide chemistry">CPr</a> </td> <td><a href="/wiki/Organolanthanide_chemistry" title="Organolanthanide chemistry">CNd</a> </td> <td><a href="/wiki/Organolanthanide_chemistry" title="Organolanthanide chemistry">CPm</a> </td> <td><a href="/wiki/Organolanthanide_chemistry" title="Organolanthanide chemistry">CSm</a> </td> <td><a href="/wiki/Organolanthanide_chemistry" title="Organolanthanide chemistry">CEu</a> </td> <td><a href="/wiki/Organolanthanide_chemistry" title="Organolanthanide chemistry">CGd</a> </td> <td><a href="/wiki/Organolanthanide_chemistry" title="Organolanthanide chemistry">CTb</a> </td> <td><a href="/wiki/Organolanthanide_chemistry" title="Organolanthanide chemistry">CDy</a> </td> <td><a href="/wiki/Organolanthanide_chemistry" title="Organolanthanide chemistry">CHo</a> </td> <td><a href="/wiki/Organolanthanide_chemistry" title="Organolanthanide chemistry">CEr</a> </td> <td><a href="/wiki/Organolanthanide_chemistry" title="Organolanthanide chemistry">CTm</a> </td> <td><a href="/wiki/Organolanthanide_chemistry" title="Organolanthanide chemistry">CYb</a> </td></tr> <tr style="background-color:#FFE4E1"> <td colspan="2" style="border:none; background-color:white"> </td> <td style="text-align:center; vertical-align:middle; background:white;"><span class="skin-invert-image" typeof="mw:File"><span><img alt="2 asterisks" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3f/Asterisks_two.svg/16px-Asterisks_two.svg.png" decoding="async" width="16" height="15" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3f/Asterisks_two.svg/24px-Asterisks_two.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3f/Asterisks_two.svg/32px-Asterisks_two.svg.png 2x" data-file-width="106" data-file-height="98" /></span></span> </td> <td><a href="/wiki/Organoactinide_chemistry" title="Organoactinide chemistry">Ac</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organothorium_chemistry" title="Organothorium chemistry">CTh</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoactinide_chemistry" title="Organoactinide chemistry">CPa</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organouranium_chemistry" title="Organouranium chemistry">CU</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoneptunium_chemistry" title="Organoneptunium chemistry">CNp</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoactinide_chemistry" title="Organoactinide chemistry">CPu</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoactinide_chemistry" title="Organoactinide chemistry">CAm</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoactinide_chemistry" title="Organoactinide chemistry">CCm</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoactinide_chemistry" title="Organoactinide chemistry">CBk</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoactinide_chemistry" title="Organoactinide chemistry">CCf</a> </td> <td style="background-color:#F0DC82"><a href="/wiki/Organoactinide_chemistry" title="Organoactinide chemistry">CEs</a> </td> <td><a href="/wiki/Organoactinide_chemistry" title="Organoactinide chemistry">Fm</a> </td> <td><a href="/wiki/Organoactinide_chemistry" title="Organoactinide chemistry">Md</a> </td> <td><a href="/wiki/Organoactinide_chemistry" title="Organoactinide chemistry">No</a> </td></tr></tbody></table> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Legend</th><td class="navbox-list-with-group navbox-list navbox-even wikitable" style="width:100%;padding:0"><div style="padding:0 0.25em"><div class="hlist"><ul><li><a href="/wiki/Chemical_bond" title="Chemical bond">Chemical bonds</a> to carbon</li><li><span style="background:#99bbff; padding:3px;; display:inline-block;">Core organic chemistry</span></li><li><span style="background:#98FF98; padding:3px;; display:inline-block;">Many uses in chemistry</span></li><li><span style="background:#F0DC82; padding:3px;; display:inline-block;">Academic research, no widespread use</span></li><li><span style="background:#FFE4E1; padding:3px;; display:inline-block;">Bond unknown</span></li></ul></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"><style data-mw-deduplicate="TemplateStyles:r1038841319">.mw-parser-output .tooltip-dotted{border-bottom:1px dotted;cursor:help}</style><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1038841319"></div><div role="navigation" class="navbox authority-control" aria-label="Navbox" 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" 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