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<span>Definition</span> </div> </a> <ul id="toc-Definition-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Classification" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Classification"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Classification</span> </div> </a> <ul id="toc-Classification-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Synthesis" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Synthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Synthesis</span> </div> </a> <button aria-controls="toc-Synthesis-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Synthesis subsection</span> </button> <ul id="toc-Synthesis-sublist" class="vector-toc-list"> <li id="toc-Using_a_metal_salt_and_cyclopentadienyl_reagents" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Using_a_metal_salt_and_cyclopentadienyl_reagents"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>Using a metal salt and cyclopentadienyl reagents</span> </div> </a> <ul id="toc-Using_a_metal_salt_and_cyclopentadienyl_reagents-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Using_a_metal_and_cyclopentadiene" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Using_a_metal_and_cyclopentadiene"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2</span> <span>Using a metal and cyclopentadiene</span> </div> </a> <ul id="toc-Using_a_metal_and_cyclopentadiene-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Using_cyclopentadienyl_reagents" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Using_cyclopentadienyl_reagents"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.3</span> <span>Using cyclopentadienyl reagents</span> </div> </a> <ul id="toc-Using_cyclopentadienyl_reagents-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Structure" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Structure"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Structure</span> </div> </a> <ul id="toc-Structure-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Spectroscopic_properties[8]" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Spectroscopic_properties[8]"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Spectroscopic properties<sup><span>[</span>8<span>]</span></sup></span> </div> </a> <button aria-controls="toc-Spectroscopic_properties[8]-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 Spectroscopic properties<sup><span>[</span>8<span>]</span></sup> subsection</span> </button> <ul id="toc-Spectroscopic_properties[8]-sublist" class="vector-toc-list"> <li id="toc-Vibrational_(infrared_and_Raman)_spectroscopy_of_metallocenes" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Vibrational_(infrared_and_Raman)_spectroscopy_of_metallocenes"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.1</span> <span>Vibrational (infrared and Raman) spectroscopy of metallocenes</span> </div> </a> <ul id="toc-Vibrational_(infrared_and_Raman)_spectroscopy_of_metallocenes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-NMR_(1H_and_13C)_spectroscopy_of_metallocenes" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#NMR_(1H_and_13C)_spectroscopy_of_metallocenes"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.2</span> <span>NMR (<sup>1</sup>H and <sup>13</sup>C) spectroscopy of metallocenes</span> </div> </a> <ul id="toc-NMR_(1H_and_13C)_spectroscopy_of_metallocenes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Mass_spectrometry_of_metallocenes" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Mass_spectrometry_of_metallocenes"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.3</span> <span>Mass spectrometry of metallocenes</span> </div> </a> <ul id="toc-Mass_spectrometry_of_metallocenes-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Derivatives" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Derivatives"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Derivatives</span> </div> </a> <button aria-controls="toc-Derivatives-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 Derivatives subsection</span> </button> <ul id="toc-Derivatives-sublist" class="vector-toc-list"> <li id="toc-Metallocenophanes" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Metallocenophanes"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.1</span> <span>Metallocenophanes</span> </div> </a> <ul id="toc-Metallocenophanes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Polynuclear_and_heterobimetallic_metallocenes" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Polynuclear_and_heterobimetallic_metallocenes"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.2</span> <span>Polynuclear and heterobimetallic metallocenes</span> </div> </a> <ul id="toc-Polynuclear_and_heterobimetallic_metallocenes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Multi-decker_sandwich_compounds" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Multi-decker_sandwich_compounds"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.3</span> <span>Multi-decker sandwich compounds</span> </div> </a> <ul id="toc-Multi-decker_sandwich_compounds-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Metallocenium_ions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Metallocenium_ions"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.4</span> <span>Metallocenium ions</span> </div> </a> <ul id="toc-Metallocenium_ions-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Applications" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Applications"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>Applications</span> </div> </a> <button aria-controls="toc-Applications-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Applications subsection</span> </button> <ul id="toc-Applications-sublist" class="vector-toc-list"> <li id="toc-Potential_applications" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Potential_applications"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.1</span> <span>Potential applications</span> </div> </a> <ul id="toc-Potential_applications-sublist" class="vector-toc-list"> </ul> </li> </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> <button aria-controls="toc-References-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 References subsection</span> </button> <ul id="toc-References-sublist" class="vector-toc-list"> <li id="toc-Additional_references" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Additional_references"> <div class="vector-toc-text"> <span class="vector-toc-numb">10.1</span> <span>Additional references</span> </div> </a> <ul id="toc-Additional_references-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> 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</div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Metallocene</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 23 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-23" 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">23 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-als mw-list-item"><a href="https://als.wikipedia.org/wiki/Metallocen" title="Metallocen – Alemannic" lang="gsw" hreflang="gsw" data-title="Metallocen" data-language-autonym="Alemannisch" data-language-local-name="Alemannic" class="interlanguage-link-target"><span>Alemannisch</span></a></li><li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D9%85%D9%8A%D8%AA%D8%A7%D9%84%D9%88%D8%B3%D9%8A%D9%86" title="ميتالوسين – Arabic" lang="ar" hreflang="ar" data-title="ميتالوسين" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Metalosenl%C9%99r" title="Metalosenlər – Azerbaijani" lang="az" hreflang="az" data-title="Metalosenlər" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Metal%C2%B7loc%C3%A8" title="Metal·locè – Catalan" lang="ca" hreflang="ca" data-title="Metal·locè" 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/Metaloceny" title="Metaloceny – Czech" lang="cs" hreflang="cs" data-title="Metaloceny" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-de badge-Q17437798 badge-goodarticle mw-list-item" title="good article badge"><a href="https://de.wikipedia.org/wiki/Metallocene" title="Metallocene – German" lang="de" hreflang="de" data-title="Metallocene" 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/Metaloceno" title="Metaloceno – Spanish" lang="es" hreflang="es" data-title="Metaloceno" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D9%85%D8%AA%D8%A7%D9%84%D9%88%D8%B3%D9%86" title="متالوسن – Persian" lang="fa" hreflang="fa" data-title="متالوسن" 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/M%C3%A9talloc%C3%A8ne" title="Métallocène – French" lang="fr" hreflang="fr" data-title="Métallocène" 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/%EB%A9%94%ED%83%88%EB%A1%9C%EC%84%BC" title="메탈로센 – Korean" lang="ko" hreflang="ko" data-title="메탈로센" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Metalosena" title="Metalosena – Indonesian" lang="id" hreflang="id" data-title="Metalosena" 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/Metallocene" title="Metallocene – Italian" lang="it" hreflang="it" data-title="Metallocene" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Metalloc%C3%A9n" title="Metallocén – Hungarian" lang="hu" hreflang="hu" data-title="Metallocén" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Metalloceen" title="Metalloceen – Dutch" lang="nl" hreflang="nl" data-title="Metalloceen" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%A1%E3%82%BF%E3%83%AD%E3%82%BB%E3%83%B3" title="メタロセン – Japanese" lang="ja" hreflang="ja" data-title="メタロセン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Metaloceno" title="Metaloceno – Portuguese" lang="pt" hreflang="pt" data-title="Metaloceno" 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/Metalocen" title="Metalocen – Romanian" lang="ro" hreflang="ro" data-title="Metalocen" 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%D1%86%D0%B5%D0%BD%D1%8B" title="Металлоцены – Russian" lang="ru" hreflang="ru" data-title="Металлоцены" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Metalocen" title="Metalocen – Serbian" lang="sr" hreflang="sr" data-title="Metalocen" 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-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Metalloseenit" title="Metalloseenit – Finnish" lang="fi" hreflang="fi" data-title="Metalloseenit" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Metallocen" title="Metallocen – Swedish" lang="sv" hreflang="sv" data-title="Metallocen" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%9C%D0%B5%D1%82%D0%B0%D0%BB%D0%BE%D1%86%D0%B5%D0%BD%D0%B8" title="Металоцени – Ukrainian" lang="uk" hreflang="uk" data-title="Металоцени" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E8%8C%82%E9%87%91%E5%B1%9E" title="茂金属 – Chinese" lang="zh" hreflang="zh" data-title="茂金属" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q413676#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> </div> </header> <div class="vector-page-toolbar"> <div class="vector-page-toolbar-container"> <div id="left-navigation"> <nav aria-label="Namespaces"> <div id="p-associated-pages" class="vector-menu vector-menu-tabs mw-portlet mw-portlet-associated-pages" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li 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<div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="cdx-message cdx-message--block cdx-message--warning"><span class="cdx-message__icon"></span><div class="cdx-message__content">The printable version is no longer supported and may have rendering errors. Please update your browser bookmarks and please use the default browser print function instead.</div></div><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Type of compound having a metal center</div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Metallocene.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e4/Metallocene.svg/150px-Metallocene.svg.png" decoding="async" width="150" height="214" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e4/Metallocene.svg/225px-Metallocene.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e4/Metallocene.svg/300px-Metallocene.svg.png 2x" data-file-width="132" data-file-height="188" /></a><figcaption>General <a href="/wiki/Chemical_structure" title="Chemical structure">chemical structure</a> of a <b>metallocene</b> compound, where <b>M</b> is a <a href="/wiki/Metallic_element" class="mw-redirect" title="Metallic element">metal</a> cation</figcaption></figure> <p>A <b>metallocene</b> is a compound typically consisting of two <a href="/wiki/Cyclopentadienyl_anion" title="Cyclopentadienyl anion">cyclopentadienyl anions</a> (<span class="chemf nowrap">C<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">5</sub></span></span>H<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">5</sub></span></span></span>, abbreviated Cp) bound to a <a href="/wiki/Metallic_element" class="mw-redirect" title="Metallic element">metal</a> center (M) in the <a href="/wiki/Oxidation_state" title="Oxidation state">oxidation state</a> II, with the resulting general formula <span class="nowrap">(C<sub>5</sub>H<sub>5</sub>)<sub>2</sub>M.</span> Closely related to the metallocenes are the metallocene derivatives, e.g. <a href="/wiki/Titanocene_dichloride" title="Titanocene dichloride">titanocene dichloride</a> or <a href="/wiki/Vanadocene_dichloride" title="Vanadocene dichloride">vanadocene dichloride</a>. Certain metallocenes and their derivatives exhibit <a href="/wiki/Catalysis" title="Catalysis">catalytic</a> properties, although metallocenes are rarely used industrially. Cationic group 4 metallocene derivatives related to [Cp<sub>2</sub>ZrCH<sub>3</sub>]<sup>+</sup> catalyze <a href="/wiki/Ziegler%E2%80%93Natta_catalyst" title="Ziegler–Natta catalyst">olefin polymerization</a>. </p><p>Some metallocenes consist of metal plus two <a href="/wiki/Cyclooctatetraenide_anion" title="Cyclooctatetraenide anion">cyclooctatetraenide anions</a> (<span class="chemf nowrap">C<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">8</sub></span></span>H<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">2−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">8</sub></span></span></span>, abbreviated cot<sup>2−</sup>), namely the lanthanocenes and the <a href="/wiki/Actinocene" title="Actinocene">actinocenes</a> (<a href="/wiki/Uranocene" title="Uranocene">uranocene</a> and others). </p><p>Metallocenes are a subset of a broader class of compounds called <a href="/wiki/Sandwich_compound" title="Sandwich compound">sandwich compounds</a>.<sup id="cite_ref-Wilkinson_G._1-0" class="reference"><a href="#cite_note-Wilkinson_G.-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> In the structure shown at right, the two pentagons are the cyclopentadienyl anions with circles inside them indicating they are <a href="/wiki/Aromaticity" title="Aromaticity">aromatically</a> stabilized. Here they are shown in a <a href="/wiki/Staggered_conformation" title="Staggered conformation">staggered conformation</a>. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="History">History</h2></div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Ferrocene.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e9/Ferrocene.svg/120px-Ferrocene.svg.png" decoding="async" width="120" height="203" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e9/Ferrocene.svg/180px-Ferrocene.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e9/Ferrocene.svg/240px-Ferrocene.svg.png 2x" data-file-width="103" data-file-height="174" /></a><figcaption>Ferrocene</figcaption></figure> <p>The first metallocene to be classified was <a href="/wiki/Ferrocene" title="Ferrocene">ferrocene</a>, and was discovered simultaneously in 1951 by Kealy and Pauson,<sup id="cite_ref-Pauson_Kealy_2-0" class="reference"><a href="#cite_note-Pauson_Kealy-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> and Miller et al.<sup id="cite_ref-Miller_S.A._3-0" class="reference"><a href="#cite_note-Miller_S.A.-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Kealy and Pauson were attempting to synthesize <a href="/wiki/Fulvalene" title="Fulvalene">fulvalene</a> through the oxidation of a <a href="/wiki/Cyclopentadienyl_anion" title="Cyclopentadienyl anion">cyclopentadienyl</a> salt with anhydrous FeCl<sub>3</sub> but obtained instead the substance C<sub>10</sub>H<sub>10</sub>Fe<sup id="cite_ref-Pauson_Kealy_2-1" class="reference"><a href="#cite_note-Pauson_Kealy-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> At the same time, Miller <i>et al</i> reported the same iron product from a reaction of <a href="/wiki/Cyclopentadiene" title="Cyclopentadiene">cyclopentadiene</a> with iron in the presence of aluminum, potassium, or molybdenum oxides.<sup id="cite_ref-Miller_S.A._3-1" class="reference"><a href="#cite_note-Miller_S.A.-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> The structure of "C<sub>10</sub>H<sub>10</sub>Fe" was determined by <a href="/wiki/Geoffrey_Wilkinson" title="Geoffrey Wilkinson">Geoffrey Wilkinson</a> et al.<sup id="cite_ref-Wilkinson_G._1-1" class="reference"><a href="#cite_note-Wilkinson_G.-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> and by <a href="/wiki/Ernst_Otto_Fischer" title="Ernst Otto Fischer">Ernst Otto Fischer</a> et al.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> These two were awarded the <a href="/wiki/Nobel_Prize_in_Chemistry" title="Nobel Prize in Chemistry">Nobel Prize in Chemistry</a> in 1973 for their work on sandwich compounds, including the structural determination of ferrocene.<sup id="cite_ref-Wilkinson_G._1-2" class="reference"><a href="#cite_note-Wilkinson_G.-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> They determined that the carbon atoms of the cyclopentadienyl (Cp) <a href="/wiki/Ligand" title="Ligand">ligand</a> contributed equally to the bonding and that bonding occurred due to the metal <span class="nowrap"><a href="/wiki/D-orbital" class="mw-redirect" title="D-orbital">d-orbitals</a></span> and the <span class="nowrap">π-<a href="/wiki/Electron" title="Electron">electrons</a></span> in the <span class="nowrap"><a href="/wiki/P-orbital" class="mw-redirect" title="P-orbital">p-orbitals</a></span> of the Cp ligands. This complex is now known as ferrocene, and the group of <a href="/wiki/Transition_metal" title="Transition metal">transition metal</a> dicyclopentadienyl compounds is known as metallocenes. Metallocenes have the general formula <span class="nowrap">[(<i>η</i><sup>5</sup>-C<sub>5</sub>H<sub>5</sub>)<sub>2</sub>M].</span> Fischer et al. first prepared the ferrocene derivatives involving Co and Ni. Often derived from substituted derivatives of <a href="/wiki/Cyclopentadienide" class="mw-redirect" title="Cyclopentadienide">cyclopentadienide</a>, metallocenes of many elements have been prepared.<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>One of the very earliest commercial manufacturers of metallocenes was Arapahoe Chemicals in Boulder, Colorado<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="Definition">Definition</h2></div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Ferrocene-from-xtal-3D-balls.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7a/Ferrocene-from-xtal-3D-balls.png/150px-Ferrocene-from-xtal-3D-balls.png" decoding="async" width="150" height="165" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/7a/Ferrocene-from-xtal-3D-balls.png/225px-Ferrocene-from-xtal-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/7a/Ferrocene-from-xtal-3D-balls.png/300px-Ferrocene-from-xtal-3D-balls.png 2x" data-file-width="1002" data-file-height="1100" /></a><figcaption><a href="/wiki/Ball-and-stick_model" title="Ball-and-stick model">Ball-and-stick model</a> of a metallocene <a href="/wiki/Molecule" title="Molecule">molecule</a> where the cyclopentadienyl anions are in a <a href="/wiki/Staggered_conformation" title="Staggered conformation">staggered conformation</a>. The purple ball in the middle represents the metal cation.</figcaption></figure> <p>The general name metallocene is derived from <a href="/wiki/Ferrocene" title="Ferrocene">ferrocene</a>, (C<sub>5</sub>H<sub>5</sub>)<sub>2</sub>Fe or Cp<sub>2</sub>Fe, systematically named <span class="nowrap">bis(<i>η</i><sup>5</sup>-<a href="/wiki/Cyclopentadienyl_complex" title="Cyclopentadienyl complex">cyclopentadienyl</a>)iron(II).</span> According to the <a href="/wiki/International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">International Union of Pure and Applied Chemistry</a> definition, a metallocene contains a <a href="/wiki/Transition_metal" title="Transition metal">transition metal</a> and two cyclopentadienyl ligands coordinated in a sandwich structure, i.e., the two cyclopentadienyl anions are on parallel <a href="/wiki/Plane_(geometry)" class="mw-redirect" title="Plane (geometry)">planes</a> with equal <a href="/wiki/Bond_length" title="Bond length">bond lengths</a> and strengths. Using the nomenclature of "<a href="/wiki/Hapticity" title="Hapticity">hapticity</a>", the equivalent bonding of all 5 carbon atoms of a cyclopentadienyl ring is denoted as <i>η</i><sup>5</sup>, pronounced "pentahapto". There are exceptions, such as <a href="/wiki/Uranocene" title="Uranocene">uranocene</a>, which has two <a href="/wiki/Cyclooctatetraene" title="Cyclooctatetraene">cyclooctatetraene</a> rings sandwiching a <a href="/wiki/Uranium" title="Uranium">uranium</a> atom. </p><p>In metallocene names, the prefix before the <i>-ocene</i> ending indicates what <a href="/wiki/Metallic_element" class="mw-redirect" title="Metallic element">metallic element</a> is between the Cp groups. For example, in ferrocene, iron(II), ferrous iron is present. </p><p>In contrast to the more strict definition proposed by International Union of Pure and Applied Chemistry, which requires a d-block metal and a sandwich structure, the term metallocene and thus the denotation <i>-ocene</i>, is applied in the chemical literature also to non-transition metal compounds, such as <a href="/w/index.php?title=Barocene&action=edit&redlink=1" class="new" title="Barocene (page does not exist)">barocene</a> (Cp<sub>2</sub>Ba), or structures where the aromatic rings are not parallel, such as found in <a href="/wiki/Manganocene" title="Manganocene">manganocene</a> or <a href="/wiki/Titanocene_dichloride" title="Titanocene dichloride">titanocene dichloride</a> (Cp<sub>2</sub>TiCl<sub>2</sub>). </p><p>Some metallocene complexes of <a href="/wiki/Actinide" title="Actinide">actinides</a> have been reported where there are three cyclopentadienyl ligands for a monometallic complex, all three of them bound η<sup>5</sup>.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Classification">Classification</h2></div> <p>There are many (<i>η</i><sup>5</sup>-C<sub>5</sub>H<sub>5</sub>)–metal complexes and they can be classified by the following formulas:<sup id="cite_ref-Metallocenes_8-0" class="reference"><a href="#cite_note-Metallocenes-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <table class="wikitable"> <tbody><tr> <th>Formula</th> <th>Description </th></tr> <tr> <td>[(<i>η</i><sup>5</sup>-C<sub>5</sub>H<sub>5</sub>)<sub>2</sub>M]</td> <td>Symmetrical, classical 'sandwich' structure </td></tr> <tr> <td>[(<i>η</i><sup>5</sup>-C<sub>5</sub>H<sub>5</sub>)<sub>2</sub>ML<sub><i>x</i></sub>]</td> <td>Bent or tilted Cp rings with additional ligands, L </td></tr> <tr> <td>[(<i>η</i><sup>5</sup>-C<sub>5</sub>H<sub>5</sub>)ML<sub><i>x</i></sub>]</td> <td>Only one Cp ligand with additional ligands, L ('piano-stool' structure) </td></tr></tbody></table> <p>Cp-based complexes can also be classified by type:<sup id="cite_ref-Metallocenes_8-1" class="reference"><a href="#cite_note-Metallocenes-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <ol><li>Parallel</li> <li>Multi-decker</li> <li><a href="/wiki/Half-sandwich_compound" class="mw-redirect" title="Half-sandwich compound">Half-sandwich compound</a></li> <li><a href="/wiki/Bent_metallocene" title="Bent metallocene">Bent metallocene</a> or tilted</li> <li>More than two Cp ligands</li></ol> <div class="mw-heading mw-heading2"><h2 id="Synthesis">Synthesis</h2></div> <p>Three main routes are normally employed in the formation of these types of compounds:<sup id="cite_ref-Metallocenes_8-2" class="reference"><a href="#cite_note-Metallocenes-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Using_a_metal_salt_and_cyclopentadienyl_reagents">Using a metal salt and cyclopentadienyl reagents</h3></div> <p>Sodium cyclopentadienide (NaCp) is the preferred reagent for these types of reactions. It is most easily obtained by the reaction of molten sodium and dicyclopentadiene.<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> Traditionally, the starting point is the cracking of <a href="/wiki/Dicyclopentadiene" title="Dicyclopentadiene">dicyclopentadiene</a>, the dimer of cyclopentadiene. Cyclopentadiene is deprotonated by strong bases or alkali metals. </p> <dl><dd>MCl<sub>2</sub> + 2 NaC<sub>5</sub>H<sub>5</sub> → (C<sub>5</sub>H<sub>5</sub>)<sub>2</sub>M + 2 NaCl <span class="nowrap">          </span> (M = V, Cr, Mn, Fe, Co; solvent = THF, DME, NH<sub>3</sub>)</dd></dl> <dl><dd>CrCl<sub>3</sub> + 3 NaC<sub>5</sub>H<sub>5</sub> → [(C<sub>5</sub>H<sub>5</sub>)<sub>2</sub>Cr] + <style data-mw-deduplicate="TemplateStyles:r1154941027">.mw-parser-output .frac{white-space:nowrap}.mw-parser-output .frac .num,.mw-parser-output .frac .den{font-size:80%;line-height:0;vertical-align:super}.mw-parser-output .frac .den{vertical-align:sub}.mw-parser-output .sr-only{border:0;clip:rect(0,0,0,0);clip-path:polygon(0px 0px,0px 0px,0px 0px);height:1px;margin:-1px;overflow:hidden;padding:0;position:absolute;width:1px}</style><span class="frac"><span class="num">1</span>⁄<span class="den">2</span></span> "C<sub>10</sub>H<sub>10</sub>" + 3 NaCl</dd></dl> <p>NaCp acts as a reducing agent and a ligand in this reaction. </p> <div class="mw-heading mw-heading3"><h3 id="Using_a_metal_and_cyclopentadiene">Using a metal and cyclopentadiene</h3></div> <p>This technique provides using metal atoms in the gas phase rather than the solid metal. The highly reactive atoms or molecules are generated at a high temperature under vacuum and brought together with chosen reactants on a cold surface. </p> <dl><dd>M + C<sub>5</sub>H<sub>6</sub> → MC<sub>5</sub>H<sub>5</sub> + <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1154941027"><span class="frac"><span class="num">1</span>⁄<span class="den">2</span></span> H<sub>2</sub> <span class="nowrap">          </span> (M = Li, Na, K)</dd> <dd>M + 2 C<sub>5</sub>H<sub>6</sub> → [(C<sub>5</sub>H<sub>5</sub>)<sub>2</sub>M] + H<sub>2</sub> <span class="nowrap">          </span> (M = Mg, Fe)</dd></dl> <div class="mw-heading mw-heading3"><h3 id="Using_cyclopentadienyl_reagents">Using cyclopentadienyl reagents</h3></div> <p>A variety of reagents have been developed that transfer Cp to metals. Once popular was <a href="/wiki/Thallium_cyclopentadienide" class="mw-redirect" title="Thallium cyclopentadienide">thallium cyclopentadienide</a>. It reacts with metal halides to give thallium chloride, which is poorly soluble, and the <a href="/wiki/Cyclopentadienyl_complex" title="Cyclopentadienyl complex">cyclopentadienyl complex</a>. Trialkyl<a href="/wiki/Tin" title="Tin">tin</a> derivatives of Cp<sup>−</sup> have also been used. </p><p>Many other methods have been developed. <a href="/wiki/Chromocene" title="Chromocene">Chromocene</a> can be prepared from <a href="/wiki/Chromium_hexacarbonyl" title="Chromium hexacarbonyl">chromium hexacarbonyl</a> by direct reaction with cyclopentadiene in the presence of <a href="/wiki/Diethylamine" title="Diethylamine">diethylamine</a>; in this case, the formal deprotonation of the cyclopentadiene is followed by <a href="/wiki/Redox" title="Redox">reduction</a> of the resulting protons to <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a> gas, facilitating the <a href="/wiki/Oxidation" class="mw-redirect" title="Oxidation">oxidation</a> of the metal centre.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p> <dl><dd>Cr(CO)<sub>6</sub> + 2 C<sub>5</sub>H<sub>6</sub> → Cr(C<sub>5</sub>H<sub>5</sub>)<sub>2</sub> + 6 CO + H<sub>2</sub></dd></dl> <p>Metallocenes generally have high thermal stability. Ferrocene can be sublimed in air at over 100 °C with no decomposition; metallocenes are generally purified in the laboratory by vacuum <a href="/wiki/Sublimation_(chemistry)" class="mw-redirect" title="Sublimation (chemistry)">sublimation</a>. Industrially, sublimation is not practical so metallocenes are isolated by crystallization or produced as part of a hydrocarbon solution. For Group IV metallocenes, donor solvents like ether or THF are distinctly undesirable for polyolefin catalysis. Charge-neutral metallocenes are soluble in common organic solvents. Alkyl substitution on the metallocene increases the solubility in hydrocarbon solvents. </p> <div class="mw-heading mw-heading2"><h2 id="Structure">Structure</h2></div> <p>A structural trend for the series MCp<sub>2</sub> involves the variation of the M-C bonds, which elongate as the valence electron count deviates from 18.<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> </p> <table class="wikitable"> <tbody><tr> <th>M(C<sub>5</sub>H<sub>5</sub>)<sub>2</sub></th> <th><i>r</i><sub>M–C</sub> (pm)</th> <th>Valence electron count </th></tr> <tr> <td align="center">Fe</td> <td>203.3</td> <td>18 </td></tr> <tr> <td align="center">Co</td> <td>209.6</td> <td>19 </td></tr> <tr> <td align="center">Cr</td> <td>215.1</td> <td>16 </td></tr> <tr> <td align="center">Ni</td> <td>218.5</td> <td>20 </td></tr> <tr> <td align="center">V</td> <td>226</td> <td>15 </td></tr> </tbody></table> <p>In metallocenes of the type (C<sub>5</sub>R<sub>5</sub>)<sub>2</sub>M, the cyclopentadienyl rings rotate with very low barriers. Single crystal <a href="/wiki/X-ray_diffraction" title="X-ray diffraction">X-ray diffraction</a> studies reveal both <a href="/wiki/Eclipsed_conformation" title="Eclipsed conformation">eclipsed</a> or <a href="/wiki/Staggered_conformation" title="Staggered conformation">staggered</a> rotamers. For non-substituted metallocenes the energy difference between the staggered and eclipsed conformations is only a few <a href="/wiki/Kilojoule_per_mole" class="mw-redirect" title="Kilojoule per mole">kJ/mol</a>. Crystals of ferrocene and osmocene exhibit eclipsed conformations at low temperatures, whereas in the related bis(pentamethylcyclopentadienyl) complexes the rings usually crystallize in a staggered conformation, apparently to minimize <a href="/wiki/Steric_effect" class="mw-redirect" title="Steric effect">steric hindrance</a> between the <a href="/wiki/Methyl_group" title="Methyl group">methyl groups</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Spectroscopic_properties[8]"><span id="Spectroscopic_properties.5B8.5D"></span>Spectroscopic properties<sup id="cite_ref-Metallocenes_8-3" class="reference"><a href="#cite_note-Metallocenes-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup></h2></div> <div class="mw-heading mw-heading3"><h3 id="Vibrational_(infrared_and_Raman)_spectroscopy_of_metallocenes"><span id="Vibrational_.28infrared_and_Raman.29_spectroscopy_of_metallocenes"></span>Vibrational (infrared and Raman) spectroscopy of metallocenes</h3></div> <p><a href="/wiki/Infrared_spectroscopy" title="Infrared spectroscopy">Infrared</a> and <a href="/wiki/Raman_spectroscopy" title="Raman spectroscopy">Raman</a> spectroscopies have proved to be important in the analysis of cyclic polyenyl metal sandwich species, with particular use in elucidating covalent or ionic M–ring bonds and distinguishing between central and coordinated rings. Some typical spectral bands and assignments of iron group metallocenes are shown in the following table:<sup id="cite_ref-Metallocenes_8-4" class="reference"><a href="#cite_note-Metallocenes-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <table class="wikitable"> <caption>Spectral frequencies of <a href="/wiki/Group_8_element" title="Group 8 element">group 8</a> metallocenes </caption> <tbody><tr> <th></th> <th><a href="/wiki/Ferrocene" title="Ferrocene">Ferrocene</a> (cm<sup>−1</sup>)</th> <th><a href="/wiki/Ruthenocene" title="Ruthenocene">Ruthenocene</a> (cm<sup>−1</sup>)</th> <th><a href="/wiki/Osmocene" title="Osmocene">Osmocene</a> (cm<sup>−1</sup>) </th></tr> <tr> <td>C–H stretch</td> <td>3085</td> <td>3100</td> <td>3095 </td></tr> <tr> <td>C–C stretch</td> <td>1411</td> <td>1413</td> <td>1405 </td></tr> <tr> <td>Ring deformation</td> <td>1108</td> <td>1103</td> <td>1096 </td></tr> <tr> <td>C–H deformation</td> <td>1002</td> <td>1002</td> <td>995 </td></tr> <tr> <td>C–H out-of-plane bend</td> <td>811</td> <td>806</td> <td>819 </td></tr> <tr> <td>Ring tilt</td> <td>492</td> <td>528</td> <td>428 </td></tr> <tr> <td>M–ring stretch</td> <td>478</td> <td>446</td> <td>353 </td></tr> <tr> <td>M–ring bend</td> <td>170</td> <td>185</td> <td>– </td></tr></tbody></table> <div class="mw-heading mw-heading3"><h3 id="NMR_(1H_and_13C)_spectroscopy_of_metallocenes"><span id="NMR_.281H_and_13C.29_spectroscopy_of_metallocenes"></span>NMR (<sup>1</sup>H and <sup>13</sup>C) <a href="/wiki/Spectroscopy" title="Spectroscopy">spectroscopy</a> of metallocenes</h3></div> <p><a href="/wiki/Nuclear_magnetic_resonance" title="Nuclear magnetic resonance">Nuclear magnetic resonance</a> (NMR) is the most applied tool in the study of metal sandwich compounds and organometallic species, giving information on nuclear structures in solution, as liquids, gases, and in the solid state. <sup>1</sup>H NMR chemical shifts for paramagnetic organotransition-metal compounds is usually observed between 25 and 40 ppm, but this range is much more narrow for diamagnetic metallocene complexes, with chemical shifts usually observed between 3 and 7 ppm.<sup id="cite_ref-Metallocenes_8-5" class="reference"><a href="#cite_note-Metallocenes-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Mass_spectrometry_of_metallocenes">Mass spectrometry of metallocenes</h3></div> <p><a href="/wiki/Mass_spectrometry" title="Mass spectrometry">Mass spectrometry</a> of metallocene complexes has been very well studied and the effect of the metal on the fragmentation of the organic moiety has received considerable attention and the identification of metal-containing fragments is often facilitated by the <a href="/wiki/Isotope" title="Isotope">isotope</a> distribution of the metal. The three major fragments observed in mass spectrometry are the molecular ion peak, [C<sub>10</sub>H<sub>10</sub>M]<sup>+</sup>, and fragment ions, [C<sub>5</sub>H<sub>5</sub>M]<sup>+</sup> and M<sup>+</sup>. </p> <div class="mw-heading mw-heading2"><h2 id="Derivatives">Derivatives</h2></div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Sandwich_compound" title="Sandwich compound">Sandwich compound</a></div> <p>After the discovery of ferrocene, the synthesis and characterization of derivatives of metallocene and other sandwich compounds attracted researchers’ interests. </p> <div class="mw-heading mw-heading3"><h3 id="Metallocenophanes">Metallocenophanes</h3></div> <p><a href="/w/index.php?title=Metallocenophanes&action=edit&redlink=1" class="new" title="Metallocenophanes (page does not exist)">Metallocenophanes</a> feature linking of the cyclopentadienyl or polyarenyl rings by the introduction of one or more heteroannular bridges. Some of these compounds undergo thermal <a href="/wiki/Ring-opening_polymerization" title="Ring-opening polymerization">ring-opening polymerizations</a> to give soluble high molecular weight polymers with transition metals in the polymer backbone. <a href="/wiki/Ansa-metallocene" title="Ansa-metallocene">Ansa-metallocenes</a> are derivatives of metallocenes with an intramolecular <a href="/wiki/Bridge_(chemical)" class="mw-redirect" title="Bridge (chemical)">bridge</a> between the two cyclopentadienyl rings. </p> <div class="mw-heading mw-heading3"><h3 id="Polynuclear_and_heterobimetallic_metallocenes">Polynuclear and heterobimetallic metallocenes</h3></div> <ul><li>Ferrocene derivatives: biferrocenophanes have been studied for their mixed <a href="/wiki/Valence_(chemistry)" title="Valence (chemistry)">valence</a> properties. Upon one-electron oxidation of a compound with two or more equivalent ferrocene moieties, the electron vacancy could be localized on one ferrocene unit or completely <a href="/wiki/Delocalized" class="mw-redirect" title="Delocalized">delocalized</a>.</li> <li><a href="/wiki/Ruthenocene" title="Ruthenocene">Ruthenocene</a> derivatives: in the solid state biruthenocene is disordered and adopts the transoid conformation with the mutual orientation of Cp rings depending on the intermolecular interactions.</li> <li><a href="/wiki/Vanadocene" title="Vanadocene">Vanadocene</a> and <a href="/wiki/Rhodocene" title="Rhodocene">rhodocene</a> derivatives: vanadocene complexes have been used as starting materials for the synthesis of heterobimetallic complexes. The 18 <a href="/wiki/Valence_electron" title="Valence electron">valence electron</a> ions [Cp<sub>2</sub>Rh]<sup>+</sup> are very stable, unlike the neutral monomers Cp<sub>2</sub>Rh which <a href="/wiki/Dimer_(chemistry)" class="mw-redirect" title="Dimer (chemistry)">dimerize</a> immediately at room temperature and they have been observed in <a href="/wiki/Matrix_isolation" title="Matrix isolation">matrix isolation</a>.</li></ul> <div class="mw-heading mw-heading3"><h3 id="Multi-decker_sandwich_compounds">Multi-decker sandwich compounds</h3></div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Ni-triple-sandwich.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/cc/Ni-triple-sandwich.png/150px-Ni-triple-sandwich.png" decoding="async" width="150" height="175" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/cc/Ni-triple-sandwich.png/225px-Ni-triple-sandwich.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/cc/Ni-triple-sandwich.png/300px-Ni-triple-sandwich.png 2x" data-file-width="366" data-file-height="427" /></a><figcaption>Nickel triple-decker sandwich complex</figcaption></figure> <p>Triple-decker complexes are composed of three Cp anions and two metal cations in alternating order. The first triple-decker sandwich complex, <style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">[Ni<sub class="template-chem2-sub">2</sub>Cp<sub class="template-chem2-sub">3</sub>]<sup>+</sup></span>, was reported in 1972.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> Many examples have been reported subsequently, often with <a href="/wiki/Carborane" title="Carborane">boron-containing rings</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="Metallocenium_ions">Metallocenium ions</h3></div> <p>The most famous example is <a href="/wiki/Ferrocenium" class="mw-redirect" title="Ferrocenium">ferrocenium</a>, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">[Fe(C<sub class="template-chem2-sub">5</sub>H<sub class="template-chem2-sub">5</sub>)<sub class="template-chem2-sub">2</sub>]<sup>+</sup></span>, the blue iron(III) complex derived from oxidation of orange iron(II) ferrocene. The lithocene anion, [Li(C<sub>5</sub>H<sub>5</sub>)<sub>2</sub>]<sup>–</sup>,<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> is the best-documented example of a metallocene anion; otherwise such ions are little known. </p> <div class="mw-heading mw-heading2"><h2 id="Applications">Applications</h2></div> <p>Many derivatives of early metal metallocenes are active catalysts for <a href="/wiki/Olefin_polymerization" class="mw-redirect" title="Olefin polymerization">olefin polymerization</a>. Unlike traditional and still dominant heterogeneous <a href="/wiki/Ziegler%E2%80%93Natta" class="mw-redirect" title="Ziegler–Natta">Ziegler–Natta</a> catalysts, metallocene catalysts are homogeneous.<sup id="cite_ref-Metallocenes_8-6" class="reference"><a href="#cite_note-Metallocenes-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> Early metal metallocene derivatives, e.g. <a href="/wiki/Tebbe%27s_reagent" title="Tebbe's reagent">Tebbe's reagent</a>, <a href="/wiki/Petasis_reagent" title="Petasis reagent">Petasis reagent</a>, and <a href="/wiki/Schwartz%27s_reagent" title="Schwartz's reagent">Schwartz's reagent</a> are useful in specialized organic synthetic operations. </p> <div class="mw-heading mw-heading3"><h3 id="Potential_applications">Potential applications</h3></div> <p>The ferrocene/<a href="/wiki/Ferrocenium" class="mw-redirect" title="Ferrocenium">ferrocenium</a> <a href="/wiki/Biosensor" title="Biosensor">biosensor</a> has been discussed for determining the levels of glucose in a sample electrochemically through a series of connected <a href="/wiki/Redox" title="Redox">redox</a> cycles.<sup id="cite_ref-Metallocenes_8-7" class="reference"><a href="#cite_note-Metallocenes-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p><p>Metallocene dihalides [Cp<sub>2</sub>MX<sub>2</sub>] (M = Ti, Mo, Nb) exhibit anti-tumor properties, although none have proceeded far in clinical trials.<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2></div> <ul><li><a href="/wiki/Jemmis_mno_rules" title="Jemmis mno rules">Jemmis <i>mno</i> rules</a></li> <li><a href="/wiki/Actinocenes" class="mw-redirect" title="Actinocenes">Actinocenes</a></li> <li><a href="/wiki/F-block_metallocene" title="F-block metallocene">f-block metallocene</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2></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-Wilkinson_G.-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-Wilkinson_G._1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Wilkinson_G._1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Wilkinson_G._1-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFWilkinsonRosenblumWhitingWoodward1952" class="citation journal cs1"><a href="/wiki/Geoffrey_Wilkinson" title="Geoffrey Wilkinson">Wilkinson, G.</a>; Rosenblum, M.; Whiting, M. 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"The Simplest Metallocene Sandwich: the Lithocene Anion". <i>Angewandte Chemie International Edition in English</i>. <b>33</b> (17): 1744-1746. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fanie.199417441">10.1002/anie.199417441</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Angewandte+Chemie+International+Edition+in+English&rft.atitle=The+Simplest+Metallocene+Sandwich%3A+the+Lithocene+Anion&rft.volume=33&rft.issue=17&rft.pages=1744-1746&rft.date=1994-09-16&rft_id=info%3Adoi%2F10.1002%2Fanie.199417441&rft.aulast=Harder&rft.aufirst=Sjoerd&rft.au=Prosenc%2C+Marc+Heinrich&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMetallocene" class="Z3988"></span></span> </li> <li id="cite_note-15"><span class="mw-cite-backlink"><b><a href="#cite_ref-15">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKuoKanatzidisSabatMarks1991" class="citation journal cs1">Kuo, L. Y.; Kanatzidis, M. G.; Sabat, M.; Marks, T. J.; Marks, Tobin J. (1991). "Metallocene antitumor agents. Solution and solid-state molybdenocene coordination chemistry of DNA constituents". <i><a href="/wiki/J._Am._Chem._Soc." class="mw-redirect" title="J. Am. Chem. Soc.">J. Am. Chem. Soc.</a></i> <b>113</b> (24): 9027–9045. <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%2Fja00024a002">10.1021/ja00024a002</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Am.+Chem.+Soc.&rft.atitle=Metallocene+antitumor+agents.+Solution+and+solid-state+molybdenocene+coordination+chemistry+of+DNA+constituents&rft.volume=113&rft.issue=24&rft.pages=9027-9045&rft.date=1991&rft_id=info%3Adoi%2F10.1021%2Fja00024a002&rft.aulast=Kuo&rft.aufirst=L.+Y.&rft.au=Kanatzidis%2C+M.+G.&rft.au=Sabat%2C+M.&rft.au=Marks%2C+T.+J.&rft.au=Marks%2C+Tobin+J.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMetallocene" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading3"><h3 id="Additional_references">Additional references</h3></div> <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSalzer1999" class="citation journal cs1">Salzer, A. (1999). <a rel="nofollow" class="external text" href="https://doi.org/10.1351%2Fpac199971081557">"Nomenclature of Organometallic Compounds of the Transition Elements"</a>. <i><a href="/wiki/Pure_Appl._Chem." class="mw-redirect" title="Pure Appl. Chem.">Pure Appl. Chem.</a></i> <b>71</b> (8): 1557–1585. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1351%2Fpac199971081557">10.1351/pac199971081557</a></span>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:14367196">14367196</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Pure+Appl.+Chem.&rft.atitle=Nomenclature+of+Organometallic+Compounds+of+the+Transition+Elements&rft.volume=71&rft.issue=8&rft.pages=1557-1585&rft.date=1999&rft_id=info%3Adoi%2F10.1351%2Fpac199971081557&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A14367196%23id-name%3DS2CID&rft.aulast=Salzer&rft.aufirst=A.&rft_id=https%3A%2F%2Fdoi.org%2F10.1351%252Fpac199971081557&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMetallocene" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCrabtree2005" class="citation book cs1"><a href="/wiki/Robert_H._Crabtree" title="Robert H. Crabtree">Crabtree, Robert H.</a> (2005). <i>The Organometallic Chemistry of the Transition Metals</i> (4th ed.). Wiley-Interscience.</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.edition=4th&rft.pub=Wiley-Interscience&rft.date=2005&rft.aulast=Crabtree&rft.aufirst=Robert+H.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMetallocene" class="Z3988"></span><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0470257628" title="Special:BookSources/0470257628">0470257628</a></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMiesslerTarr2004" class="citation book cs1">Miessler, Gary L.; Tarr, Donald A. (2004). <span class="id-lock-registration" title="Free registration required"><a rel="nofollow" class="external text" href="https://archive.org/details/inorganicchemist03edmies"><i>Inorganic Chemistry</i></a></span>. Upper Saddle River, NJ: Pearson Education. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-13-035471-6" title="Special:BookSources/978-0-13-035471-6"><bdi>978-0-13-035471-6</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Inorganic+Chemistry&rft.place=Upper+Saddle+River%2C+NJ&rft.pub=Pearson+Education&rft.date=2004&rft.isbn=978-0-13-035471-6&rft.aulast=Miessler&rft.aufirst=Gary+L.&rft.au=Tarr%2C+Donald+A.&rft_id=https%3A%2F%2Farchive.org%2Fdetails%2Finorganicchemist03edmies&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMetallocene" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCottonWilkinson1988" class="citation book cs1"><a href="/wiki/F._Albert_Cotton" title="F. Albert Cotton">Cotton, F. A.</a>; <a href="/wiki/Geoffrey_Wilkinson" title="Geoffrey Wilkinson">Wilkinson, G.</a> (1988). <i>Inorganic Chemistry</i> (5th ed.). Wiley. pp. 626–7.</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.pages=626-7&rft.edition=5th&rft.pub=Wiley&rft.date=1988&rft.aulast=Cotton&rft.aufirst=F.+A.&rft.au=Wilkinson%2C+G.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMetallocene" class="Z3988"></span><sup class="noprint Inline-Template" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citing_sources" title="Wikipedia:Citing sources"><span title="Please supply an ISBN for this book.">ISBN missing</span></a></i>]</sup></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFTogniHalterman1998" class="citation book cs1">Togni, A.; Halterman, R. L. (1998). <i>Metallocenes</i>. Wiley-VCH.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Metallocenes&rft.pub=Wiley-VCH&rft.date=1998&rft.aulast=Togni&rft.aufirst=A.&rft.au=Halterman%2C+R.+L.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMetallocene" class="Z3988"></span><sup class="noprint Inline-Template" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citing_sources" title="Wikipedia:Citing sources"><span title="Please supply an ISBN for this book.">ISBN missing</span></a></i>]</sup></li></ul> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl 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.navbox-image img{max-width:none!important}@media print{body.ns-0 .mw-parser-output .navbox{display:none!important}}</style></div><div role="navigation" class="navbox" aria-labelledby="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 href="/wiki/Organometallic_chemistry" title="Organometallic chemistry">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 class="mw-selflink selflink">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="Coordination_complexes" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Coordination_complexes" title="Template:Coordination complexes"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Coordination_complexes" title="Template talk:Coordination complexes"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Coordination_complexes" title="Special:EditPage/Template:Coordination complexes"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Coordination_complexes" style="font-size:114%;margin:0 4em"><a href="/wiki/Coordination_complex" title="Coordination complex">Coordination complexes</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">H donors:</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Transition_metal_hydride" title="Transition metal hydride">H<sup>−</sup></a></li> <li><a href="/wiki/Dihydrogen_complex" title="Dihydrogen complex">H<sub>2</sub></a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">B donors:</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Transition_metal_boryl_complex" title="Transition metal boryl complex">BR<sub>2</sub><sup>−</sup></a></li> <li><a href="/wiki/Metallaborane" title="Metallaborane">B<sub>m</sub>H<sub>n</sub></a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">C donors:</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Transition_metal_alkyl_complexes" title="Transition metal alkyl complexes">R<sup>−</sup></a></li> <li><a href="/wiki/Transition_metal_acyl_complexes" title="Transition metal acyl complexes">RC(O)<sup>−</sup></a></li> <li><a href="/wiki/Transition_metal_formyl_complex" title="Transition metal formyl complex">HC(O)<sup>−</sup></a></li> <li><a href="/wiki/Transition-metal_allyl_complex" title="Transition-metal allyl complex">CH<sub>2</sub>＝CH-CH<sub>2</sub><sup>−</sup></a></li> <li><a href="/wiki/Trimethylenemethane_complexes" title="Trimethylenemethane complexes">C(CH<sub>2</sub>)<sub>3</sub></a></li> <li><a href="/wiki/Transition_metal_alkene_complex" title="Transition metal alkene complex">CH<sub>2</sub>＝CH<sub>2</sub></a></li> <li><a href="/wiki/Transition_metal_alkyne_complex" title="Transition metal alkyne complex">RC<sub>2</sub>R</a></li> <li><a href="/wiki/Transition_metal_benzyne_complex" title="Transition metal benzyne complex">C<sub>6</sub>H<sub>4</sub></a></li> <li><a href="/wiki/Cyanometalate" title="Cyanometalate">CN<sup>−</sup></a></li> <li><a href="/wiki/Metal_carbonyl" title="Metal carbonyl">CO</a></li> <li><a href="/wiki/Metal_carbon_dioxide_complex" title="Metal carbon dioxide complex">CO<sub>2</sub></a></li> <li><a href="/wiki/Transition_metal_carbide" class="mw-redirect" title="Transition metal carbide">C<sup>4-</sup></a></li> <li><a href="/wiki/Transition_metal_arene_complex" title="Transition metal arene complex">C<sub>6</sub>R<sub>6</sub></a></li> <li><a href="/wiki/Transition_metal_fullerene_complex" title="Transition metal fullerene complex">C<sub>60</sub> & C<sub>70</sub></a></li> <li><a href="/wiki/Transition_metal_isocyanide_complexes" title="Transition metal isocyanide complexes">RNC</a></li> <li><a href="/wiki/Transition_metal_carbene_complex" title="Transition metal carbene complex">=CR<sub>2</sub></a></li> <li><a href="/wiki/Transition_metal_carbyne_complex" title="Transition metal carbyne complex">≡CR</a></li> <li><a class="mw-selflink selflink">C<sub>5</sub>H<sub>5</sub><sup>−</sup></a></li> <li><a href="/wiki/Transition_metal_indenyl_complex" title="Transition metal indenyl complex">C<sub>9</sub>H<sub>7</sub><sup>−</sup></a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Si donors:</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Transition_metal_silane_complexes" class="mw-redirect" title="Transition metal silane complexes">H<sub>n</sub>SiR<sub>4−n</sub></a></li> <li><a href="/wiki/Transition_metal_silyl_complexes" title="Transition metal silyl complexes">R<sub>3</sub>Si<sup>−</sup></a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">N donors:</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Metal_ammine_complex" title="Metal ammine complex">NH<sub>3</sub></a></li> <li><a href="/wiki/Transition_metal_azide_complex" title="Transition metal azide complex">N<sub>3</sub><sup>−</sup></a></li> <li><a href="/wiki/Transition_metal_imidazole_complex" title="Transition metal imidazole complex">imidazole</a></li> <li><a href="/wiki/Metal_nitrosyl_complex" title="Metal nitrosyl complex">NO</a></li> <li><a href="/wiki/Transition_metal_nitroso_complexes" title="Transition metal nitroso complexes">RNO</a></li> <li><a href="/wiki/Transition_metal_nitrite_complex#Bonding_modes" title="Transition metal nitrite complex">NO<sub>2</sub><sup>−</sup></a></li> <li><a href="/wiki/Transition_metal_pyridine_complexes" title="Transition metal pyridine complexes">py</a></li> <li><a href="/wiki/Transition_metal_amino_acid_complexes" title="Transition metal amino acid complexes">amino acid</a></li> <li><a href="/wiki/Metal_nitrido_complex" title="Metal nitrido complex">N<sup>3-</sup></a></li> <li><a href="/wiki/Transition_metal_imido_complex" title="Transition metal imido complex">RN<sup>2-</sup></a></li> <li><a href="/wiki/Transition_metal_nitrile_complexes" title="Transition metal nitrile complexes">RCN</a></li> <li><a href="/wiki/Transition_metal_complexes_of_2,2%27-bipyridine" title="Transition metal complexes of 2,2'-bipyridine">bipy</a></li> <li><a href="/wiki/Transition_metal_complexes_of_1,10-phenanthroline" title="Transition metal complexes of 1,10-phenanthroline">phen</a></li> <li><a href="/wiki/Transition_metal_porphyrin_complexes" title="Transition metal porphyrin complexes">porphyrin</a></li> <li><a href="/wiki/Metal_bis(trimethylsilyl)amides" title="Metal bis(trimethylsilyl)amides">(Me<sub>3</sub>Si)<sub>2</sub>N<sup>−</sup></a></li> <li><a href="/wiki/Transition_metal_dinitrogen_complex" title="Transition metal dinitrogen complex">N<sub>2</sub></a></li> <li><a href="/wiki/Transition_metal_complexes_of_thiocyanate" title="Transition metal complexes of thiocyanate"><i>N</i>CS<sup>-</sup></a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">P donors:</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Metal_phosphine_complex" class="mw-redirect" title="Metal phosphine complex">PR<sub>3</sub></a></li> <li><a href="/wiki/Transition_metal_phosphido_complexes" title="Transition metal phosphido complexes">PR<sub>2</sub><sup>−</sup></a></li> <li><a href="/wiki/Transition_metal_complexes_of_phosphine_oxides#Secondary_phosphine_oxides_as_ligands" title="Transition metal complexes of phosphine oxides">PR<sub>2</sub>OH</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">O donors:</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Metal_aquo_complex" title="Metal aquo complex">H<sub>2</sub>O</a></li> <li><a href="/wiki/Transition_metal_ether_complex" title="Transition metal ether complex">R<sub>2</sub>O</a></li> <li><a href="/wiki/Metal_alkoxide" class="mw-redirect" title="Metal alkoxide">RO<sup>−</sup></a></li> <li><a href="/wiki/Transition_metal_oxo_complex" title="Transition metal oxo complex">O<sup>2-</sup></a></li> <li><a href="/wiki/Transition_metal_dioxygen_complex" title="Transition metal dioxygen complex">O<sub>2</sub></a></li> <li><a href="/wiki/Transition_metal_carbonate_and_bicarbonate_complexes" title="Transition metal carbonate and bicarbonate complexes">CO<sub>3</sub><sup>2-</sup>/HCO<sub>3</sub><sup>-</sup></a></li> <li><a href="/wiki/Transition_metal_oxalate_complex" title="Transition metal oxalate complex">C<sub>2</sub>O<sub>4</sub><sup>2-</sup></a></li> <li><a href="/wiki/Transition_metal_carboxylate_complex" title="Transition metal carboxylate complex">RCO<sub>2</sub><sup>−</sup></a></li> <li><a href="/wiki/Metal_acetylacetonates" title="Metal acetylacetonates">acac</a></li> <li><a href="/wiki/Transition_metal_complexes_of_aldehydes_and_ketones" title="Transition metal complexes of aldehydes and ketones">R<sub>2</sub>CO</a></li> <li><a href="/wiki/Transition_metal_nitrite_complex" title="Transition metal nitrite complex">ONO<sup>−</sup></a></li> <li><a href="/wiki/Transition_metal_nitrate_complex" title="Transition metal nitrate complex">NO<sub>3</sub><sup>−</sup></a></li> <li><a href="/wiki/Transition_metal_perchlorate_complexes" title="Transition metal perchlorate complexes">ClO<sub>4</sub><sup>-</sup></a></li> <li><a href="/wiki/Transition_metal_complexes_of_pyridine-N-oxides" title="Transition metal complexes of pyridine-N-oxides">C<sub>5</sub>H<sub>5</sub>NO</a></li> <li><a href="/wiki/Transition_metal_sulfoxide_complex" title="Transition metal sulfoxide complex">OSR<sub>2</sub></a></li> <li><a href="/wiki/Transition_metal_sulfate_complex" title="Transition metal sulfate complex">SO<sub>4</sub><sup>2-</sup></a></li> <li><a href="/wiki/Transition_metal_phosphate_complex" title="Transition metal phosphate complex">PO<sub>4</sub><sup>3-</sup></a></li> <li><a href="/wiki/Transition_metal_complexes_of_phosphine_oxides" title="Transition metal complexes of phosphine oxides">OPR<sub>3</sub></a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">S donors:</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Transition_metal_dithiocarbamate_complexes" title="Transition metal dithiocarbamate complexes">R<sub>2</sub>NCS<sub>2</sub><sup>−</sup></a></li> <li><a href="/wiki/Transition_metal_thiolate_complex" title="Transition metal thiolate complex">RS<sup>−</sup></a></li> <li><a href="/wiki/Transition_metal_thioether_complex" title="Transition metal thioether complex">R<sub>2</sub>S</a></li> <li><a href="/wiki/Metal_dithiolene_complex" title="Metal dithiolene complex">R<sub>2</sub>C<sub>2</sub>S<sub>2</sub><sup>2-</sup></a></li> <li><a href="/wiki/Metal_sulfur_dioxide_complex" title="Metal sulfur dioxide complex">SO<sub>2</sub></a></li> <li><a href="/wiki/Transition_metal_thiosulfate_complex" title="Transition metal thiosulfate complex">S<sub>2</sub>O<sub>3</sub><sup>2-</sup></a></li> <li><a href="/wiki/Transition_metal_sulfoxide_complex" title="Transition metal sulfoxide complex">SR<sub>2</sub>O</a></li> <li><a href="/wiki/Transition_metal_complexes_of_thiocyanate" title="Transition metal complexes of thiocyanate">NC<i>S</i><sup>-</sup></a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Halide donors:</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=Fluoro_complex&action=edit&redlink=1" class="new" title="Fluoro complex (page does not exist)">F<sup>−</sup></a></li> <li><a href="/wiki/Difluorine_complex" title="Difluorine complex">F<sub>2</sub></a></li> <li><a href="/wiki/Transition_metal_chloride_complex" title="Transition metal chloride complex">Cl<sup>−</sup></a></li> <li><a href="/w/index.php?title=Bromo_complex&action=edit&redlink=1" class="new" title="Bromo complex (page does not exist)">Br<sup>−</sup></a></li> <li><a href="/w/index.php?title=Iodo_complex&action=edit&redlink=1" class="new" title="Iodo complex (page does not exist)">I<sup>−</sup></a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Salts_and_covalent_derivatives_of_the_cyclopentadienide_ion" style="display:table;;padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit;table-layout:fixed;"><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:Cyclopentadienide_complexes" title="Template:Cyclopentadienide complexes"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Cyclopentadienide_complexes" title="Template talk:Cyclopentadienide complexes"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Cyclopentadienide_complexes" title="Special:EditPage/Template:Cyclopentadienide complexes"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Salts_and_covalent_derivatives_of_the_cyclopentadienide_ion" style="font-size:114%;margin:0 4em">Salts and covalent derivatives of the <a href="/wiki/Cyclopentadienide" class="mw-redirect" title="Cyclopentadienide">cyclopentadienide</a> ion</div></th></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0;border-width:0;"><div style="padding:0"><div class="mw-collapsible-content" style="overflow-x:auto"> <table class="center"> <tbody><tr style="background-color:mistyrose"> <td><a href="/wiki/Cyclopentadiene" title="Cyclopentadiene">CpH</a> </td> <td style="background-color:white;border:none"> </td> <td style="background-color:white;border:none" colspan="11" rowspan="3"> </td> <td style="background-color:white;border:none" colspan="5"> </td> <td>He </td></tr> <tr style="background-color:mistyrose"> <td><a href="/wiki/Lithium_cyclopentadienide" title="Lithium cyclopentadienide">LiCp</a> </td> <td>Be </td> <td>B </td> <td><a href="/wiki/Methylcyclopentadiene" title="Methylcyclopentadiene">CpMe</a> </td> <td>N </td> <td><a href="/wiki/Cyclopentadienone" title="Cyclopentadienone">C<sub>5</sub>H<sub>4</sub>O</a> </td> <td>F </td> <td>Ne </td></tr> <tr style="background-color:mistyrose"> <td><a href="/wiki/Sodium_cyclopentadienide" title="Sodium cyclopentadienide">NaCp</a> </td> <td><a href="/wiki/Magnesocene" title="Magnesocene">MgCp<sub>2</sub></a><br /> <p><a href="/wiki/Cyclopentadienyl_magnesium_bromide" title="Cyclopentadienyl magnesium bromide">MgCpBr</a> </p> </td> <td>Al </td> <td>Si </td> <td>P </td> <td>S </td> <td>Cl </td> <td>Ar </td></tr> <tr style="background-color:mistyrose"> <td>K </td> <td><a href="/wiki/Calcium_cyclopentadienylide" class="mw-redirect" title="Calcium cyclopentadienylide">CaCp<sub>2</sub></a> </td> <td style="background-color:white;border:none"> </td> <td><a href="/wiki/Scandocene" title="Scandocene">ScCp<sub>3</sub></a> </td> <td><a href="/wiki/Titanocene_dichloride" title="Titanocene dichloride">TiCp<sub>2</sub>Cl<sub>2</sub></a><br /> <p><a href="/wiki/Nugent-RajanBabu_reagent" class="mw-redirect" title="Nugent-RajanBabu reagent">(TiCp<sub>2</sub>Cl)<sub>2</sub></a><br /> <a href="/wiki/(Cyclopentadienyl)titanium_trichloride" title="(Cyclopentadienyl)titanium trichloride">TiCpCl<sub>3</sub></a><br /> <a href="/wiki/Titanocene_pentasulfide" title="Titanocene pentasulfide">TiCp<sub>2</sub>S<sub>5</sub></a><br /> <a href="/wiki/Titanocene_dicarbonyl" title="Titanocene dicarbonyl">TiCp<sub>2</sub>(CO)<sub>2</sub></a><br /> <a href="/wiki/Petasis_reagent" title="Petasis reagent">TiCp<sub>2</sub>Me<sub>2</sub></a> </p> </td> <td><a href="/wiki/Vanadocene" title="Vanadocene">VCp<sub>2</sub></a><br /> <p><a href="/wiki/(Cycloheptatrienyl)(cyclopentadienyl)vanadium" title="(Cycloheptatrienyl)(cyclopentadienyl)vanadium">VCpCh</a><br /> <a href="/wiki/Vanadocene_dichloride" title="Vanadocene dichloride">VCp<sub>2</sub>Cl<sub>2</sub></a><br /> <a href="/wiki/Cyclopentadienylvanadium_tetracarbonyl" title="Cyclopentadienylvanadium tetracarbonyl">VCp(CO)<sub>4</sub></a> </p> </td> <td><a href="/wiki/Chromocene" title="Chromocene">CrCp<sub>2</sub></a><br /> <p><a href="/wiki/Cyclopentadienylchromium_tricarbonyl_dimer" title="Cyclopentadienylchromium tricarbonyl dimer">(CrCp(CO)<sub>3</sub>)<sub>2</sub></a> </p> </td> <td><a href="/wiki/Manganocene" title="Manganocene">MnCp<sub>2</sub></a> </td> <td><a href="/wiki/Ferrocene" title="Ferrocene">FeCp<sub>2</sub></a><br /> <p><a href="/wiki/1,1%27-Dilithioferrocene" title="1,1'-Dilithioferrocene">Fe(η<sup>5</sup>-C<sub>5</sub>H<sub>4</sub>Li)<sub>2</sub></a><br /> <a href="/wiki/Biferrocene" title="Biferrocene">((C<sub>5</sub>H<sub>5</sub>)Fe(C<sub>5</sub>H<sub>4</sub>))<sub>2</sub></a><br /> <a href="/wiki/Bis(fulvalene)diiron" title="Bis(fulvalene)diiron">(C<sub>5</sub>H<sub>4</sub>-C<sub>5</sub>H<sub>4</sub>)<sub>2</sub>Fe<sub>2</sub></a><br /> <a href="/wiki/Ferrocenium_hexafluorophosphate" title="Ferrocenium hexafluorophosphate">FeCp<sub>2</sub>PF<sub>6</sub></a><br /> <a href="/wiki/Cyclopentadienyliron_dicarbonyl_iodide" title="Cyclopentadienyliron dicarbonyl iodide">FeCp(CO)<sub>2</sub>I</a> </p> </td> <td><a href="/wiki/Cobaltocene" title="Cobaltocene">CoCp<sub>2</sub></a><br /> <p><a href="/wiki/Cyclopentadienylcobalt_dicarbonyl" title="Cyclopentadienylcobalt dicarbonyl">CoCp(CO)<sub>2</sub></a> </p> </td> <td><a href="/wiki/Nickelocene" title="Nickelocene">NiCp<sub>2</sub></a><br /> <p><a href="/wiki/Cyclopentadienyl_nickel_nitrosyl" title="Cyclopentadienyl nickel nitrosyl">NiCpNO</a> </p> </td> <td>Cu </td> <td>Zn </td> <td>Ga </td> <td>Ge </td> <td>As </td> <td>Se </td> <td>Br </td> <td>Kr </td></tr> <tr style="background-color:mistyrose"> <td>Rb </td> <td>Sr </td> <td style="background-color:white;border:none"> </td> <td><a href="/wiki/Yttrocene" title="Yttrocene">Y(C<sub>5</sub>H<sub>5</sub>)<sub>3</sub></a> </td> <td><a href="/wiki/Zirconocene_dichloride" title="Zirconocene dichloride">ZrCp<sub>2</sub>Cl<sub>2</sub></a><br /> <p><a href="/wiki/Schwartz%27s_reagent" title="Schwartz's reagent">ZrCp<sub>2</sub>ClH</a> </p> </td> <td><a href="/wiki/Niobocene_dichloride" title="Niobocene dichloride">NbCp<sub>2</sub>Cl<sub>2</sub></a> </td> <td><a href="/wiki/Molybdocene_dihydride" title="Molybdocene dihydride">MoCp<sub>2</sub>H<sub>2</sub></a><br /> <p><a href="/wiki/Molybdocene_dichloride" title="Molybdocene dichloride">MoCp<sub>2</sub>Cl<sub>2</sub></a><br /> <a href="/wiki/Cyclopentadienylmolybdenum_tricarbonyl_dimer" title="Cyclopentadienylmolybdenum tricarbonyl dimer">(MoCp(CO)<sub>3</sub>)<sub>2</sub></a> </p> </td> <td>Tc </td> <td><a href="/wiki/Ruthenocene" title="Ruthenocene">RuCp<sub>2</sub></a><br /> <p><a href="/wiki/Chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium" title="Chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium">RuCp(PPh<sub>3</sub>)<sub>2</sub>Cl</a><br /> <a href="/wiki/Tris(acetonitrile)cyclopentadienylruthenium_hexafluorophosphate" title="Tris(acetonitrile)cyclopentadienylruthenium hexafluorophosphate">RuCp(MeCN)<sub>3</sub>PF<sub>6</sub></a> </p> </td> <td><a href="/wiki/Rhodocene" title="Rhodocene">RhCp<sub>2</sub></a> </td> <td><a href="/wiki/Cyclopentadienyl_allyl_palladium" title="Cyclopentadienyl allyl palladium">PdCp(C<sub>3</sub>H<sub>5</sub>)</a> </td> <td>Ag </td> <td>Cd </td> <td><a href="/wiki/Cyclopentadienylindium(I)" title="Cyclopentadienylindium(I)">InCp</a> </td> <td><a href="/wiki/Stannocene" title="Stannocene">SnCp<sub>2</sub></a> </td> <td>Sb </td> <td>Te </td> <td>I </td> <td>Xe </td></tr> <tr style="background-color:mistyrose"> <td>Cs </td> <td>Ba </td> <td style="background-color:white;border:none">* </td> <td><a href="/wiki/Lanthanocene" title="Lanthanocene">LuCp<sub>3</sub></a> </td> <td><a href="/wiki/Hafnocene_dichloride" title="Hafnocene dichloride">HfCp<sub>2</sub>Cl<sub>2</sub></a> </td> <td>Ta </td> <td><a href="/wiki/Cyclopentadienyltungsten_tricarbonyl_dimer" title="Cyclopentadienyltungsten tricarbonyl dimer">(WCp(CO)<sub>3</sub>)<sub>2</sub></a> </td> <td><a href="/wiki/Rhenocene" class="mw-redirect" title="Rhenocene">ReCp<sub>2</sub>H</a> </td> <td><a href="/wiki/Osmocene" title="Osmocene">OsCp<sub>2</sub></a> </td> <td><a href="/wiki/Iridocene" class="mw-redirect" title="Iridocene">IrCp<sub>2</sub></a> </td> <td>Pt </td> <td>Au </td> <td>Hg </td> <td><a href="/wiki/Cyclopentadienylthallium" title="Cyclopentadienylthallium">TlCp</a> </td> <td><a href="/wiki/Plumbocene" title="Plumbocene">PbCp<sub>2</sub></a> </td> <td>Bi </td> <td>Po </td> <td>At </td> <td>Rn </td></tr> <tr style="background-color:mistyrose"> <td>Fr </td> <td>Ra </td> <td style="background-color:white;border:none">** </td> <td>Lr </td> <td>Rf </td> <td>Db </td> <td>Sg </td> <td>Bh </td> <td><a href="/wiki/Hassocene" class="mw-redirect" title="Hassocene">HsCp<sub>2</sub></a> </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="background-color:white;border:none" colspan="2" rowspan="3"> </td> <td style="background-color:white;border:none" colspan="20">  </td></tr> <tr style="background-color:mistyrose"> <td style="background-color:white;border:none">* </td> <td><a href="/wiki/Lanthanocene" title="Lanthanocene">LaCp<sub>3</sub></a> </td> <td><a href="/wiki/Cerocene" title="Cerocene">CeCp<sub>3</sub></a> </td> <td><a href="/wiki/Lanthanocene" title="Lanthanocene">PrCp<sub>3</sub></a> </td> <td><a href="/wiki/Lanthanocene" title="Lanthanocene">NdCp<sub>3</sub></a> </td> <td><a href="/wiki/Promethocene" title="Promethocene">PmCp<sub>3</sub></a> </td> <td><a href="/wiki/Lanthanocene" title="Lanthanocene">SmCp<sub>3</sub></a> </td> <td>Eu </td> <td>Gd </td> <td>Tb </td> <td><a href="/wiki/Lanthanocene" title="Lanthanocene">DyCp<sub>3</sub></a> </td> <td>Ho </td> <td><a href="/wiki/Lanthanocene" title="Lanthanocene">ErCp<sub>3</sub></a> </td> <td><a href="/wiki/Lanthanocene" title="Lanthanocene">TmCp<sub>3</sub></a> </td> <td><a href="/wiki/Lanthanocene" title="Lanthanocene">YbCp<sub>3</sub></a> </td></tr> <tr style="background-color:mistyrose"> <td style="background-color:white;border:none">** </td> <td>Ac </td> <td><a href="/wiki/Thorium#Organothorium_compounds" title="Thorium">ThCp<sub>3</sub><br />ThCp<sub>4</sub></a> </td> <td>Pa </td> <td><a href="/wiki/Tetrakis(cyclopentadienyl)uranium(IV)" title="Tetrakis(cyclopentadienyl)uranium(IV)">UCp<sub>4</sub></a> </td> <td>Np </td> <td>Pu </td> <td>Am </td> <td>Cm </td> <td>Bk </td> <td>Cf </td> <td>Es </td> <td>Fm </td> <td>Md </td> <td>No </td></tr></tbody></table></div> </div></td></tr></tbody></table></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Metallocene&oldid=1246419401">https://en.wikipedia.org/w/index.php?title=Metallocene&oldid=1246419401</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Category</a>: <ul><li><a href="/wiki/Category:Metallocenes" title="Category:Metallocenes">Metallocenes</a></li></ul></div><div 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