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Dit is echter niet verplicht." class=""><span>Account aanmaken</span></a> </li> <li id="pt-login-2" class="user-links-collapsible-item mw-list-item user-links-collapsible-item"><a data-mw="interface" href="/w/index.php?title=Speciaal:Aanmelden&returnto=Ferroceen" title="U wordt van harte uitgenodigd om aan te melden, maar dit is niet verplicht [o]" accesskey="o" class=""><span>Aanmelden</span></a> </li> </ul> </div> </div> </div> <div id="vector-user-links-dropdown" class="vector-dropdown vector-user-menu vector-button-flush-right vector-user-menu-logged-out" title="Meer opties" > <input type="checkbox" id="vector-user-links-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-user-links-dropdown" class="vector-dropdown-checkbox " aria-label="Persoonlijke hulpmiddelen" > <label id="vector-user-links-dropdown-label" for="vector-user-links-dropdown-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-ellipsis mw-ui-icon-wikimedia-ellipsis"></span> <span class="vector-dropdown-label-text">Persoonlijke hulpmiddelen</span> </label> <div class="vector-dropdown-content"> <div id="p-personal" class="vector-menu mw-portlet mw-portlet-personal user-links-collapsible-item" title="Gebruikersmenu" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="pt-sitesupport" class="user-links-collapsible-item mw-list-item"><a href="//donate.wikimedia.org/wiki/Special:FundraiserRedirector?utm_source=donate&utm_medium=sidebar&utm_campaign=C13_nl.wikipedia.org&uselang=nl"><span>Doneren</span></a></li><li id="pt-createaccount" class="user-links-collapsible-item mw-list-item"><a href="/w/index.php?title=Speciaal:GebruikerAanmaken&returnto=Ferroceen" title="Registreer u vooral en meld u aan. Dit is echter niet verplicht."><span class="vector-icon mw-ui-icon-userAdd mw-ui-icon-wikimedia-userAdd"></span> <span>Account aanmaken</span></a></li><li id="pt-login" class="user-links-collapsible-item mw-list-item"><a href="/w/index.php?title=Speciaal:Aanmelden&returnto=Ferroceen" title="U wordt van harte uitgenodigd om aan te melden, maar dit is niet verplicht [o]" accesskey="o"><span class="vector-icon mw-ui-icon-logIn mw-ui-icon-wikimedia-logIn"></span> <span>Aanmelden</span></a></li> </ul> </div> </div> <div id="p-user-menu-anon-editor" class="vector-menu mw-portlet mw-portlet-user-menu-anon-editor" > <div class="vector-menu-heading"> Pagina's voor uitgelogde redacteuren <a href="/wiki/Help:Inleiding" aria-label="Meer leren over bewerken"><span>meer lezen</span></a> </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="pt-anoncontribs" class="mw-list-item"><a href="/wiki/Speciaal:MijnBijdragen" title="Bijdragen IP-adres [y]" accesskey="y"><span>Bijdragen</span></a></li><li id="pt-anontalk" class="mw-list-item"><a href="/wiki/Speciaal:MijnOverleg" title="Overlegpagina van de anonieme gebruiker van dit IP-adres [n]" accesskey="n"><span>Overleg</span></a></li> </ul> </div> </div> </div> </div> </nav> </div> </header> </div> <div class="mw-page-container"> <div class="mw-page-container-inner"> <div class="vector-sitenotice-container"> <div id="siteNotice"></div> </div> <div class="vector-column-start"> <div class="vector-main-menu-container"> <div id="mw-navigation"> <nav id="mw-panel" class="vector-main-menu-landmark" aria-label="Site"> <div id="vector-main-menu-pinned-container" class="vector-pinned-container"> </div> </nav> </div> </div> <div class="vector-sticky-pinned-container"> <nav id="mw-panel-toc" aria-label="Inhoud" data-event-name="ui.sidebar-toc" class="mw-table-of-contents-container vector-toc-landmark"> <div id="vector-toc-pinned-container" class="vector-pinned-container"> <div id="vector-toc" class="vector-toc vector-pinnable-element"> <div class="vector-pinnable-header vector-toc-pinnable-header vector-pinnable-header-pinned" data-feature-name="toc-pinned" data-pinnable-element-id="vector-toc" > <h2 class="vector-pinnable-header-label">Inhoud</h2> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-toc.pin">naar zijbalk verplaatsen</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-toc.unpin">verbergen</button> </div> <ul class="vector-toc-contents" id="mw-panel-toc-list"> <li id="toc-mw-content-text" class="vector-toc-list-item vector-toc-level-1"> <a href="#" class="vector-toc-link"> <div class="vector-toc-text">Top</div> </a> </li> <li id="toc-Geschiedenis" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Geschiedenis"> <div class="vector-toc-text"> <span class="vector-toc-numb">1</span> <span>Geschiedenis</span> </div> </a> <ul id="toc-Geschiedenis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Synthese" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Synthese"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Synthese</span> </div> </a> <ul id="toc-Synthese-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Structuur" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Structuur"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Structuur</span> </div> </a> <ul id="toc-Structuur-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Eigenschappen" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Eigenschappen"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Eigenschappen</span> </div> </a> <ul id="toc-Eigenschappen-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Reactiviteit" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Reactiviteit"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Reactiviteit</span> </div> </a> <ul id="toc-Reactiviteit-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Toepassingen" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Toepassingen"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Toepassingen</span> </div> </a> <ul id="toc-Toepassingen-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Zie_ook" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Zie_ook"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Zie ook</span> </div> </a> <ul id="toc-Zie_ook-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Externe_link" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Externe_link"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>Externe link</span> </div> </a> <ul id="toc-Externe_link-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Inhoud" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Inhoudsopgave omschakelen" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Inhoudsopgave omschakelen</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Ferroceen</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="Ga naar een artikel in een andere taal. Beschikbaar in 31 talen" > <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-31" 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">31 talen</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-af mw-list-item"><a href="https://af.wikipedia.org/wiki/Ferroseen" title="Ferroseen – Afrikaans" lang="af" hreflang="af" data-title="Ferroseen" data-language-autonym="Afrikaans" data-language-local-name="Afrikaans" class="interlanguage-link-target"><span>Afrikaans</span></a></li><li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D9%81%D8%B1%D9%88%D8%B3%D9%8A%D9%86" title="فروسين – Arabisch" lang="ar" hreflang="ar" data-title="فروسين" data-language-autonym="العربية" data-language-local-name="Arabisch" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D9%81%D8%B1%D9%88%D8%B3%D9%86" title="فروسن – South Azerbaijani" lang="azb" hreflang="azb" data-title="فروسن" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%AB%E0%A7%87%E0%A6%B0%E0%A7%8B%E0%A6%B8%E0%A6%BF%E0%A6%A8" title="ফেরোসিন – Bengaals" lang="bn" hreflang="bn" data-title="ফেরোসিন" data-language-autonym="বাংলা" data-language-local-name="Bengaals" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Ferroc%C3%A8" title="Ferrocè – Catalaans" lang="ca" hreflang="ca" data-title="Ferrocè" data-language-autonym="Català" data-language-local-name="Catalaans" 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/Ferrocen" title="Ferrocen – Tsjechisch" lang="cs" hreflang="cs" data-title="Ferrocen" data-language-autonym="Čeština" data-language-local-name="Tsjechisch" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-de badge-Q17437798 badge-goodarticle mw-list-item" title="goed artikel"><a href="https://de.wikipedia.org/wiki/Ferrocen" title="Ferrocen – Duits" lang="de" hreflang="de" data-title="Ferrocen" data-language-autonym="Deutsch" data-language-local-name="Duits" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-en mw-list-item"><a href="https://en.wikipedia.org/wiki/Ferrocene" title="Ferrocene – Engels" lang="en" hreflang="en" data-title="Ferrocene" data-language-autonym="English" data-language-local-name="Engels" class="interlanguage-link-target"><span>English</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Ferroceno" title="Ferroceno – Spaans" lang="es" hreflang="es" data-title="Ferroceno" data-language-autonym="Español" data-language-local-name="Spaans" 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%81%D8%B1%D9%88%D8%B3%D9%86" title="فروسن – Perzisch" lang="fa" hreflang="fa" data-title="فروسن" data-language-autonym="فارسی" data-language-local-name="Perzisch" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Ferroseeni" title="Ferroseeni – Fins" lang="fi" hreflang="fi" data-title="Ferroseeni" data-language-autonym="Suomi" data-language-local-name="Fins" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Ferroc%C3%A8ne" title="Ferrocène – Frans" lang="fr" hreflang="fr" data-title="Ferrocène" data-language-autonym="Français" data-language-local-name="Frans" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ga mw-list-item"><a href="https://ga.wikipedia.org/wiki/Fear%C3%B3ic%C3%A9in" title="Fearóicéin – Iers" lang="ga" hreflang="ga" data-title="Fearóicéin" data-language-autonym="Gaeilge" data-language-local-name="Iers" class="interlanguage-link-target"><span>Gaeilge</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Ferroc%C3%A9n" title="Ferrocén – Hongaars" lang="hu" hreflang="hu" data-title="Ferrocén" data-language-autonym="Magyar" data-language-local-name="Hongaars" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Ferosena" title="Ferosena – Indonesisch" lang="id" hreflang="id" data-title="Ferosena" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesisch" 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/Ferrocene" title="Ferrocene – Italiaans" lang="it" hreflang="it" data-title="Ferrocene" data-language-autonym="Italiano" data-language-local-name="Italiaans" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%95%E3%82%A7%E3%83%AD%E3%82%BB%E3%83%B3" title="フェロセン – Japans" lang="ja" hreflang="ja" data-title="フェロセン" data-language-autonym="日本語" data-language-local-name="Japans" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%ED%8E%98%EB%A1%9C%EC%84%BC" title="페로센 – Koreaans" lang="ko" hreflang="ko" data-title="페로센" data-language-autonym="한국어" data-language-local-name="Koreaans" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-ky mw-list-item"><a href="https://ky.wikipedia.org/wiki/%D0%A4%D0%B5%D1%80%D1%80%D0%BE%D1%86%D0%B5%D0%BD" title="Ферроцен – Kirgizisch" lang="ky" hreflang="ky" data-title="Ферроцен" data-language-autonym="Кыргызча" data-language-local-name="Kirgizisch" class="interlanguage-link-target"><span>Кыргызча</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Ferrocen" title="Ferrocen – Pools" lang="pl" hreflang="pl" data-title="Ferrocen" data-language-autonym="Polski" data-language-local-name="Pools" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Ferroceno" title="Ferroceno – Portugees" lang="pt" hreflang="pt" data-title="Ferroceno" data-language-autonym="Português" data-language-local-name="Portugees" 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/Ferocen" title="Ferocen – Roemeens" lang="ro" hreflang="ro" data-title="Ferocen" data-language-autonym="Română" data-language-local-name="Roemeens" 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%A4%D0%B5%D1%80%D1%80%D0%BE%D1%86%D0%B5%D0%BD" title="Ферроцен – Russisch" lang="ru" hreflang="ru" data-title="Ферроцен" data-language-autonym="Русский" data-language-local-name="Russisch" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Ferocen" title="Ferocen – Servo-Kroatisch" lang="sh" hreflang="sh" data-title="Ferocen" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Servo-Kroatisch" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Ferocen" title="Ferocen – Sloveens" lang="sl" hreflang="sl" data-title="Ferocen" data-language-autonym="Slovenščina" data-language-local-name="Sloveens" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Ferocen" title="Ferocen – Servisch" lang="sr" hreflang="sr" data-title="Ferocen" data-language-autonym="Српски / srpski" data-language-local-name="Servisch" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Ferrocen" title="Ferrocen – Zweeds" lang="sv" hreflang="sv" data-title="Ferrocen" data-language-autonym="Svenska" data-language-local-name="Zweeds" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B9%80%E0%B8%9F%E0%B8%AD%E0%B8%A3%E0%B9%8C%E0%B9%82%E0%B8%A3%E0%B8%8B%E0%B8%B5%E0%B8%99" title="เฟอร์โรซีน – Thai" lang="th" hreflang="th" data-title="เฟอร์โรซีน" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Ferrosen" title="Ferrosen – Turks" lang="tr" hreflang="tr" data-title="Ferrosen" data-language-autonym="Türkçe" data-language-local-name="Turks" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%A4%D0%B5%D1%80%D0%BE%D1%86%D0%B5%D0%BD" title="Фероцен – Oekraïens" lang="uk" hreflang="uk" data-title="Фероцен" data-language-autonym="Українська" data-language-local-name="Oekraïens" 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/%E4%BA%8C%E8%8C%82%E9%93%81" title="二茂铁 – Chinees" lang="zh" hreflang="zh" data-title="二茂铁" data-language-autonym="中文" data-language-local-name="Chinees" 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/Q211972#sitelinks-wikipedia" title="Taalkoppelingen bewerken" class="wbc-editpage">Koppelingen bewerken</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="Naamruimten"> <div id="p-associated-pages" class="vector-menu vector-menu-tabs mw-portlet mw-portlet-associated-pages" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="ca-nstab-main" class="selected vector-tab-noicon mw-list-item"><a href="/wiki/Ferroceen" title="Inhoudspagina bekijken [c]" accesskey="c"><span>Artikel</span></a></li><li id="ca-talk" class="new vector-tab-noicon mw-list-item"><a href="/w/index.php?title=Overleg:Ferroceen&action=edit&redlink=1" rel="discussion" class="new" title="Overleg over deze pagina (de pagina bestaat niet) [t]" accesskey="t"><span>Overleg</span></a></li> </ul> </div> </div> <div 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cellspacing="1"> <tbody><tr> <th class="infobox-kop notheme" style="background-color:#DDEEFF; color:inherit; text-align:center; font-size:120%;" colspan="3">Ferroceen </th></tr> <tr> <th class="infobox-kop notheme" style="background-color:#DDEEFF; color:inherit; text-align:center;" colspan="3">Structuurformule en molecuulmodel </th></tr> <tr> <td style="text-align:center; padding:0;" colspan="3"><span typeof="mw:File"><a href="/wiki/Bestand:Ferroceen.png" class="mw-file-description"><img alt="Structuurformule van ferroceen" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f9/Ferroceen.png/110px-Ferroceen.png" decoding="async" width="110" height="149" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f9/Ferroceen.png/165px-Ferroceen.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f9/Ferroceen.png/220px-Ferroceen.png 2x" data-file-width="267" data-file-height="362" /></a></span> </td></tr> <tr> <td style="text-align:center;" colspan="3"><div style="font-size:90%"><a href="/wiki/Structuurformule" title="Structuurformule">Structuurformule</a> van ferroceen</div> </td></tr> <tr> <td style="text-align:center; padding:0;" colspan="3"><span typeof="mw:File"><a href="/wiki/Bestand:Ferrocenecrystals.jpg" class="mw-file-description"><img alt="Ferroceenkristallen" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5f/Ferrocenecrystals.jpg/266px-Ferrocenecrystals.jpg" decoding="async" width="266" height="443" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5f/Ferrocenecrystals.jpg/399px-Ferrocenecrystals.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5f/Ferrocenecrystals.jpg/532px-Ferrocenecrystals.jpg 2x" data-file-width="1344" data-file-height="2240" /></a></span> </td></tr> <tr> <td style="text-align:center;" colspan="3"><div style="font-size:90%">Ferroceenkristallen</div> </td></tr> <tr> <th class="infobox-kop notheme" style="background-color:#DDEEFF; color:inherit; text-align:center;" colspan="3">Algemeen </th></tr> <tr> <th><a href="/wiki/Molecuulformule" title="Molecuulformule">Molecuulformule</a> </th> <td colspan="2">C<sub>10</sub>H<sub>10</sub>Fe </td></tr> <tr> <th><a href="/wiki/IUPAC-nomenclatuur" title="IUPAC-nomenclatuur">IUPAC-naam</a> </th> <td colspan="2">bis(η<sup>5</sup>-cyclopentadienyl)ijzer(II) </td></tr> <tr> <th><a href="/wiki/Nomenclatuur" title="Nomenclatuur">Andere namen</a> </th> <td colspan="2">di(cyclopentadienyl)ijzer </td></tr> <tr> <th><a href="/wiki/Molaire_massa" title="Molaire massa">Molmassa</a> </th> <td colspan="2">186,04 <a href="/wiki/Gram_(eenheid)" title="Gram (eenheid)">g</a>/<a href="/wiki/Mol_(eenheid)" title="Mol (eenheid)">mol</a> </td></tr> <tr> <th><a href="/wiki/CAS-nummer" title="CAS-nummer">CAS-nummer</a> </th> <td colspan="2"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=102-54-5">102-54-5</a> </td></tr> <tr> <th><a href="/wiki/EG-nummer" title="EG-nummer">EG-nummer</a> </th> <td colspan="2"><a rel="nofollow" class="external text" href="http://echa.europa.eu/web/guest/information-on-chemicals/cl-inventory-database/-/cl-inventory/search-clinventory-by-other-identifier/203-039-3">203-039-3</a> </td></tr> <tr> <th><a href="/wiki/PubChem" title="PubChem">PubChem</a> </th> <td colspan="2"><a rel="nofollow" class="external text" href="http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=11985121">11985121</a> </td></tr> <tr> <th><a href="/wiki/Wikidata" title="Wikidata">Wikidata</a> </th> <td colspan="2"><a href="https://www.wikidata.org/wiki/Q211972" class="extiw" title="d:Q211972">Q211972</a> </td></tr> <tr> <th>Beschrijving </th> <td colspan="2">Oranje stof met kamfergeur<sup id="cite_ref-BGIA_GESTIS_1-0" class="reference"><a href="#cite_note-BGIA_GESTIS-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <th>Vergelijkbaar met </th> <td colspan="2"><a href="/wiki/Nikkeloceen" title="Nikkeloceen">nikkeloceen</a>, <a href="/wiki/Kobaltoceen" title="Kobaltoceen">kobaltoceen</a> </td></tr> <tr> <th class="infobox-kop notheme" style="background-color:#DDEEFF; color:inherit;" colspan="3">Waarschuwingen en veiligheidsmaatregelen </th></tr> <tr> <td class="ta-center" colspan="3"><table align="center" style="border-style:none;"><tbody><tr><td style="margin-left:auto;margin-right:auto;vertical-align:top;text-align:center;border-style:none;cell-padding:2px"><span typeof="mw:File"><a href="/wiki/Bestand:GHS-pictogram-flamme.svg" class="mw-file-description" title="Ontvlambaar"><img alt="Ontvlambaar" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/GHS-pictogram-flamme.svg/60px-GHS-pictogram-flamme.svg.png" decoding="async" width="60" height="60" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/GHS-pictogram-flamme.svg/90px-GHS-pictogram-flamme.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6d/GHS-pictogram-flamme.svg/120px-GHS-pictogram-flamme.svg.png 2x" data-file-width="512" data-file-height="512" /></a></span></td><td style="margin-left:auto;margin-right:auto;vertical-align:top;text-align:center;border-style:none;cell-padding:2px"><span typeof="mw:File"><a href="/wiki/Bestand:GHS-pictogram-exclam.svg" class="mw-file-description" title="Schadelijk"><img alt="Schadelijk" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/60px-GHS-pictogram-exclam.svg.png" decoding="async" width="60" height="60" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/90px-GHS-pictogram-exclam.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/120px-GHS-pictogram-exclam.svg.png 2x" data-file-width="512" data-file-height="512" /></a></span></td></tr></tbody></table><b>Gevaar</b> </td></tr> <tr> <th><a href="/wiki/H-_en_P-zinnen" title="H- en P-zinnen">H-zinnen</a> </th> <td colspan="2"><abbr title="Ontvlambare vaste stof.">H228</abbr> - <abbr title="Schadelijk bij inslikken.">H302</abbr> </td></tr> <tr> <th><span class="nowrap"><a href="/wiki/H-_en_P-zinnen" title="H- en P-zinnen">EUH-zinnen</a></span> </th> <td colspan="2"><i>geen</i> </td></tr> <tr> <th><a href="/wiki/H-_en_P-zinnen" title="H- en P-zinnen">P-zinnen</a> </th> <td colspan="2"><abbr title="Verwijderd houden van warmte/vonken/open vuur/hete oppervlakken. Niet roken.">P210</abbr> </td></tr> <tr> <th><a href="/wiki/Stofidentificatienummer" title="Stofidentificatienummer">VN-nummer</a> </th> <td colspan="2">1325 </td></tr> <tr> <th class="infobox-kop notheme" style="background-color:#DDEEFF; color:inherit;" colspan="3">Fysische eigenschappen </th></tr> <tr> <th><a href="/wiki/Aggregatietoestand" title="Aggregatietoestand">Aggregatietoestand</a> </th> <td colspan="2">vast<sup id="cite_ref-BGIA_GESTIS_1-1" class="reference"><a href="#cite_note-BGIA_GESTIS-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <th><a href="/wiki/Kleur_(hoofdbetekenis)" class="mw-redirect" title="Kleur (hoofdbetekenis)">Kleur</a> </th> <td colspan="2">oranje<sup id="cite_ref-BGIA_GESTIS_1-2" class="reference"><a href="#cite_note-BGIA_GESTIS-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <th><a href="/wiki/Massadichtheid" title="Massadichtheid">Dichtheid</a> </th> <td colspan="2">1,49<sup id="cite_ref-BGIA_GESTIS_1-3" class="reference"><a href="#cite_note-BGIA_GESTIS-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> g/cm³ </td></tr> <tr> <th><a href="/wiki/Smeltpunt" title="Smeltpunt">Smeltpunt</a> </th> <td colspan="2">173-174<sup id="cite_ref-BGIA_GESTIS_1-4" class="reference"><a href="#cite_note-BGIA_GESTIS-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> °C </td></tr> <tr> <th><a href="/wiki/Kookpunt" title="Kookpunt">Kookpunt</a> </th> <td colspan="2">249<sup id="cite_ref-BGIA_GESTIS_1-5" class="reference"><a href="#cite_note-BGIA_GESTIS-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> °C </td></tr> <tr> <th><a href="/wiki/Dampdruk" title="Dampdruk">Dampdruk</a> </th> <td colspan="2">(bij 100°C) 340<sup id="cite_ref-BGIA_GESTIS_1-6" class="reference"><a href="#cite_note-BGIA_GESTIS-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Pa </td></tr> <tr> <th><a href="/wiki/Oplosbaarheid" title="Oplosbaarheid">Oplosbaarheid</a> in <a href="/wiki/Water" title="Water">water</a> </th> <td colspan="2">< 10<sup>−4</sup> g/L </td></tr> <tr> <th>Goed oplosbaar in </th> <td colspan="2">apolaire organische oplosmiddelen </td></tr> <tr> <th>Slecht oplosbaar in </th> <td colspan="2">water </td></tr> <tr> <th><a href="/wiki/Octanol-water-partitieco%C3%ABffici%C3%ABnt" title="Octanol-water-partitiecoëfficiënt">log(<i>P</i><sub>ow</sub>)</a> </th> <td colspan="2">2,66<sup id="cite_ref-BGIA_GESTIS_1-7" class="reference"><a href="#cite_note-BGIA_GESTIS-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <th class="infobox-kop notheme" style="background-color:#DDEEFF; color:inherit;" colspan="3"><small>Tenzij anders vermeld zijn <a href="/wiki/Standaardomstandigheden" title="Standaardomstandigheden">standaardomstandigheden</a> gebruikt (298,15 <a href="/wiki/Kelvin_(eenheid)" title="Kelvin (eenheid)">K</a> of 25 <a href="/wiki/Celsius" title="Celsius">°C</a>, 1 <a href="/wiki/Bar_(druk)" title="Bar (druk)">bar</a>).</small> </th></tr> <tr> <td class="infobox-kop notheme center" style="background-color:#DDEEFF; color:inherit;" colspan="3"> <table cellspacing="0" cellpadding="0"> <tbody><tr> <td style="vertical-align:middle;"><b>Portaal</b>  <span class="noviewer" typeof="mw:File"><a href="/wiki/Bestand:Portal.svg" class="mw-file-description" title="Portaalicoon"><img alt="Portaalicoon" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c9/Portal.svg/22px-Portal.svg.png" decoding="async" width="22" height="20" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c9/Portal.svg/33px-Portal.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c9/Portal.svg/44px-Portal.svg.png 2x" data-file-width="36" data-file-height="32" /></a></span>   </td> <td class="ta-left"><b><a href="/wiki/Portaal:Scheikunde" title="Portaal:Scheikunde">Scheikunde</a> </b> </td></tr></tbody></table> </td></tr> </tbody></table> <p><b>Ferroceen</b> of <b>bis(η<sup>5</sup>-cyclopentadienyl)ijzer(II)</b> was het eerst bekende <a href="/wiki/Metalloceen" title="Metalloceen">metalloceen</a>. Ferroceen is een <a href="/wiki/Organometaalchemie" title="Organometaalchemie">organometaalverbinding</a>, meer specifiek een <a href="/wiki/Organoijzerchemie" class="mw-redirect" title="Organoijzerchemie">organoijzerverbinding</a>, waarbij het ijzeratoom is gecoördineerd tussen twee <a href="/wiki/Cyclopentadienyl" title="Cyclopentadienyl">cyclopentadienyl</a>-<a href="/wiki/Ligand" title="Ligand">liganden</a>. De stof komt voor als een oranje <a href="/wiki/Kristallijn" class="mw-redirect" title="Kristallijn">kristallijn</a> <a href="/wiki/Poeder" title="Poeder">poeder</a> met <a href="/wiki/Kamfer" title="Kamfer">kamfergeur</a>. Ferroceen is slecht oplosbaar in <a href="/wiki/Water" title="Water">water</a>. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Geschiedenis">Geschiedenis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ferroceen&veaction=edit&section=1" title="Bewerk dit kopje: Geschiedenis" class="mw-editsection-visualeditor"><span>bewerken</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Ferroceen&action=edit&section=1" title="De broncode bewerken van de sectie: Geschiedenis"><span>brontekst bewerken</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Ferroceen werd bij toeval ontdekt in <a href="/wiki/1951" title="1951">1951</a> door <a href="/w/index.php?title=T.J._Kealy&action=edit&redlink=1" class="new" title="T.J. Kealy (de pagina bestaat niet)">T.J. Kealy</a> en <a href="/w/index.php?title=P.L._Pauson&action=edit&redlink=1" class="new" title="P.L. Pauson (de pagina bestaat niet)">P.L. Pauson</a>, die <a href="/wiki/IJzer(II)chloride" title="IJzer(II)chloride">ijzer(II)chloride</a> lieten reageren met <a href="/w/index.php?title=Cyclopentadienylmagnesiumbromide&action=edit&redlink=1" class="new" title="Cyclopentadienylmagnesiumbromide (de pagina bestaat niet)">cyclopentadienylmagnesiumbromide</a> om <a href="/wiki/Fulvaleen" title="Fulvaleen">fulvaleen</a> te synthetiseren.<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p><p>Onafhankelijk van dit werk, maakte de onderzoeksgroep van Miller ferroceen door ijzerpoeder onder hoge temperatuur te laten reageren met <a href="/wiki/Cyclopentadieen" title="Cyclopentadieen">cyclopentadieen</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Synthese">Synthese</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ferroceen&veaction=edit&section=2" title="Bewerk dit kopje: Synthese" class="mw-editsection-visualeditor"><span>bewerken</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Ferroceen&action=edit&section=2" title="De broncode bewerken van de sectie: Synthese"><span>brontekst bewerken</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Ferroceen kan bereid worden door <a href="/wiki/Cyclopentadieen" title="Cyclopentadieen">cyclopentadieen</a> in aanwezigheid van <a href="/wiki/Sterke_base" title="Sterke base">sterke base</a> te laten reageren met een <a href="/wiki/IJzer_(element)" title="IJzer (element)">ijzerzout</a>, zoals <a href="/wiki/IJzer(II)chloride" title="IJzer(II)chloride">ijzer(II)chloride</a>: </p> <dl><dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {2C5H6 + FeCl2 . 4H2O + 2KOH -> Fe(C5H5)2 + 2KCl + 6H2O}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> <mspace width="thinmathspace" /> <msubsup> <mtext>C</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>5</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>6</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo>+</mo> <msubsup> <mtext>FeCl</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo>⋅</mo> <mn>4</mn> <mspace width="thinmathspace" /> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>O</mtext> <mo>+</mo> <mn>2</mn> <mspace width="thinmathspace" /> <mtext>KOH</mtext> <mo stretchy="false">⟶</mo> <mtext>Fe</mtext> <msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msubsup> <mtext>C</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>5</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>5</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo stretchy="false">)</mo> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo>+</mo> <mn>2</mn> <mspace width="thinmathspace" /> <mtext>KCl</mtext> <mo>+</mo> <mn>6</mn> <mspace width="thinmathspace" /> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>O</mtext> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {2C5H6 + FeCl2 . 4H2O + 2KOH -> Fe(C5H5)2 + 2KCl + 6H2O}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/04ea365dae91f4a5c647a8d6de53e5e8b2d7b313" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:66.99ex; height:3.009ex;" alt="{\displaystyle {\ce {2C5H6 + FeCl2 . 4H2O + 2KOH -> Fe(C5H5)2 + 2KCl + 6H2O}}}"></span></dd></dl> <div class="mw-heading mw-heading2"><h2 id="Structuur">Structuur</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ferroceen&veaction=edit&section=3" title="Bewerk dit kopje: Structuur" class="mw-editsection-visualeditor"><span>bewerken</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Ferroceen&action=edit&section=3" title="De broncode bewerken van de sectie: Structuur"><span>brontekst bewerken</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>De directe structuur van de nieuwe verbinding werd niet meteen begrepen, maar al snel werden de eerste, correcte structuurvoorstellen gedaan. <a href="/wiki/Hermann_Emil_Fischer" title="Hermann Emil Fischer">Emil Fischer</a> stelde voor op basis van <a href="/wiki/R%C3%B6ntgendiffractie" class="mw-redirect" title="Röntgendiffractie">röntgendiffractie</a>, het chemische gedrag en het feit dat de verbinding <a href="/wiki/Diamagnetisme" title="Diamagnetisme">diamagnetisch</a> is, een structuur voor in de vorm van een dubbele kegel. <a href="/wiki/Geoffrey_Wilkinson" title="Geoffrey Wilkinson">Geoffrey Wilkinson</a> en <a href="/wiki/Robert_Burns_Woodward" title="Robert Burns Woodward">Robert Burns Woodward</a> kwamen tot dezelfde conclusie aan de hand van <a href="/wiki/Infraroodspectroscopie" title="Infraroodspectroscopie">infraroodspectroscopie</a>, het diamagnetisme en de afwezigheid van een <a href="/wiki/Dipoolmoment" title="Dipoolmoment">dipoolmoment</a> (hetgeen erop wees dat het molecuul symmetrisch moest zijn). Zij duidden de structuur aan als <i><a href="/wiki/Sandwichverbinding" title="Sandwichverbinding">sandwichverbinding</a></i> en noemden het ferroceen, om het aromatische karakter van de verbinding aan te geven. Deze aanduiding werd later overgenomen voor andere verbindingen en deze klasse van verbindingen wordt nu als metallocenen aangeduid. Later werd de kristalstructuur verder verfijnd door onder andere <a href="/w/index.php?title=Jack_Dunitz&action=edit&redlink=1" class="new" title="Jack Dunitz (de pagina bestaat niet)">Jack Dunitz</a>. </p><p>De structuur van ferroceen kan verklaard worden door de <a href="/wiki/18-elektronenregel" title="18-elektronenregel">18-elektronenregel</a> toe te passen. Formeel gezien bestaat ferroceen uit een ijzer(II)-kation met zes d-elektronen en twee (anionische) cyclopentadienyl-liganden met elk eveneens 6 <a href="/wiki/Elektron" title="Elektron">elektronen</a>. Het totaal aantal <a href="/wiki/Valentie-elektron" title="Valentie-elektron">valentie-elektronen</a> komt daardoor op 18, waardoor het complex elektronisch gezien lijkt op <a href="/wiki/Krypton_(element)" title="Krypton (element)">krypton</a> en waardoor het stabiel is. Een andere benadering die tot dezelfde 18-elektronconfiguratie voert, is door het ijzer als neutraal te beschouwen met 8 elektronen en de cyclopentadieenliganden met elk 5 elektronen in het pi-systeem als <a href="/wiki/Radicaal_(scheikunde)" title="Radicaal (scheikunde)">radicaal</a> aan te nemen. </p> <div class="mw-heading mw-heading2"><h2 id="Eigenschappen">Eigenschappen</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ferroceen&veaction=edit&section=4" title="Bewerk dit kopje: Eigenschappen" class="mw-editsection-visualeditor"><span>bewerken</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Ferroceen&action=edit&section=4" title="De broncode bewerken van de sectie: Eigenschappen"><span>brontekst bewerken</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Ferroceen is in <a href="/wiki/Apolaire_verbinding" title="Apolaire verbinding">apolaire</a> <a href="/wiki/Organisch_oplosmiddel" title="Organisch oplosmiddel">organische oplosmiddelen</a> zoals <a href="/wiki/Tetrahydrofuraan" title="Tetrahydrofuraan">tetrahydrofuraan</a>, <a href="/wiki/Tolueen" title="Tolueen">tolueen</a> en <a href="/wiki/N-hexaan" title="N-hexaan">n-hexaan</a> goed oplosbaar. Het is onoplosbaar in water. De stof is thermisch en chemisch stabiel en wordt gebruikt als uitgangsstof voor de synthese van vele derivaten. </p><p>In de vaste toestand is de structuur van ferroceen temperatuurafhankelijk. Bij kamertemperatuur zijn de kristallen <a href="/wiki/Monoklien_kristalstelsel" title="Monoklien kristalstelsel">monoklien</a>, bij een temperatuur lager dan −164 °C <a href="/wiki/Triklien_kristalstelsel" title="Triklien kristalstelsel">triklien</a> en bij een temperatuur lager dan −110 °C <a href="/wiki/Orthorombisch_kristalstelsel" title="Orthorombisch kristalstelsel">orthorombisch</a>. De twee cyclopentadienylringen bevinden zich in het kristal veelal in een <a href="/wiki/Ge%C3%ABclipseerde_conformatie" title="Geëclipseerde conformatie">geëclipseerde conformatie</a>. In het monokliene kristal is de superpositie van de twee ringen exact geëclipseerd (met een D<sub>5</sub>-symmetrie), in het trikliene kristal heeft het een kleine afwijking van 9°. Dit in tegenstelling tot bijvoorbeeld <a href="/wiki/Nikkeloceen" title="Nikkeloceen">nikkeloceen</a> of <a href="/wiki/Kobaltoceen" title="Kobaltoceen">kobaltoceen</a>. </p><p>De afstand tussen beide cyclopentadienylliganden bedraagt 332 <a href="/wiki/Picometer" title="Picometer">pm</a>, wat overeenkomt met de <a href="/wiki/Vanderwaalsafstand" class="mw-redirect" title="Vanderwaalsafstand">vanderwaalsafstand</a> van twee aromatische pi-systemen. In de gasfase en in oplossing nemen de twee cyclopentadienylringen eveneens een geëclipseerde conformatie aan, hoewel de rotatiebarrière erg laag is en de ringen in feite vrij kunnen roteren ten opzichte van elkaar. </p> <div class="mw-heading mw-heading2"><h2 id="Reactiviteit">Reactiviteit</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ferroceen&veaction=edit&section=5" title="Bewerk dit kopje: Reactiviteit" class="mw-editsection-visualeditor"><span>bewerken</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Ferroceen&action=edit&section=5" title="De broncode bewerken van de sectie: Reactiviteit"><span>brontekst bewerken</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>De chemie van ferroceen is zeer divers door de stabiliteit van de verbinding. Voorbeelden van reactie aan ferroceen zijn bijvoorbeeld <a href="/wiki/Friedel-Crafts-acylering" class="mw-redirect" title="Friedel-Crafts-acylering">Friedel-Crafts-acylering</a> en de bis-lithiëring met <a href="/wiki/N-butyllithium" title="N-butyllithium"><i>n</i>-butyllithium</a> en <a href="/wiki/Tetramethylethyleendiamine" title="Tetramethylethyleendiamine">TMEDA</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Toepassingen">Toepassingen</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ferroceen&veaction=edit&section=6" title="Bewerk dit kopje: Toepassingen" class="mw-editsection-visualeditor"><span>bewerken</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Ferroceen&action=edit&section=6" title="De broncode bewerken van de sectie: Toepassingen"><span>brontekst bewerken</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Ferroceen is uitgangsstof voor vele <a href="/wiki/Derivaat_(scheikunde)" title="Derivaat (scheikunde)">derivaten</a>, die onder andere toepassing vinden als <a href="/wiki/Ligand" title="Ligand">ligand</a> in de <a href="/wiki/Asymmetrische_synthese" title="Asymmetrische synthese">asymmetrische synthese</a>. Het wordt ook gebruikt als <a href="/wiki/Klopvastheid" title="Klopvastheid">antiklopmiddel</a> in brandstoffen. </p><p>In de <a href="/wiki/Cyclovoltammetrie" title="Cyclovoltammetrie">cyclovoltammetrie</a> wordt ferroceen wegens zijn reversibele <a href="/wiki/Oxidatie" title="Oxidatie">oxidatie</a> tot het <a href="/w/index.php?title=Ferrocenium&action=edit&redlink=1" class="new" title="Ferrocenium (de pagina bestaat niet)">ferrocenium</a>-<a href="/wiki/Ion_(deeltje)" title="Ion (deeltje)">ion</a> vaak als referentie gebruikt in niet-waterige oplossingen. </p><p>Een andere toepassing is de één-staps-synthese van <a href="/wiki/Nanobuis" title="Nanobuis">nanobuisjes</a> uit ferroceen.<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Ferroceen wordt hiervoor in een <a href="/wiki/Autoclaaf_(laboratorium)" title="Autoclaaf (laboratorium)">autoclaaf</a> gedurende 20 uur verhit bij een <a href="/wiki/Temperatuur" title="Temperatuur">temperatuur</a> van 700 °C. </p> <div class="mw-heading mw-heading2"><h2 id="Zie_ook">Zie ook</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ferroceen&veaction=edit&section=7" title="Bewerk dit kopje: Zie ook" class="mw-editsection-visualeditor"><span>bewerken</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Ferroceen&action=edit&section=7" title="De broncode bewerken van de sectie: Zie ook"><span>brontekst bewerken</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Chromoceen" title="Chromoceen">Chromoceen</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="Externe_link">Externe link</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ferroceen&veaction=edit&section=8" title="Bewerk dit kopje: Externe link" class="mw-editsection-visualeditor"><span>bewerken</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Ferroceen&action=edit&section=8" title="De broncode bewerken van de sectie: Externe link"><span>brontekst bewerken</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><style data-mw-deduplicate="TemplateStyles:r67679320">.mw-parser-output .taalaanduiding{font-family:sans-serif;font-size:85%;cursor:help;color:var(--color-subtle,#555)}.mw-parser-output .taalaanduiding span{border-bottom:1px dotted var(--color-subtle,#555)}</style><span class="taalaanduiding" title="Taal: Engels">(<span>en</span>) </span> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20160307114406/http://www.sciencelab.com/msds.php?msdsId=9924047">MSDS van <i>ferroceen</i></a></li></ul> <div class="toccolours appendix" role="presentation" style="font-size:90%; margin:1em 0 -0.5em; clear:both;"> <div><span style="font-weight:bold">Bronnen, noten en/of referenties</span></div> <div class="reflist" style="list-style-type: decimal;"><div class="mw-references-wrap"><ol class="references"> <li id="cite_note-BGIA_GESTIS-1"><span class="mw-cite-backlink">↑ <a href="#cite_ref-BGIA_GESTIS_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-BGIA_GESTIS_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-BGIA_GESTIS_1-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-BGIA_GESTIS_1-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-BGIA_GESTIS_1-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-BGIA_GESTIS_1-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-BGIA_GESTIS_1-6"><sup><i><b>g</b></i></sup></a> <a href="#cite_ref-BGIA_GESTIS_1-7"><sup><i><b>h</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r67679320"><span class="taalaanduiding" title="Taal: Engels">(<span>en</span>) </span> <a rel="nofollow" class="external text" href="https://gestis.dguv.de/data?name=492633&lang=en">Gegevens van <i>ferroceen</i></a> in de GESTIS-stoffendatabank van het IFA <small>(geraadpleegd op 2 december 2008)</small></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><a href="#cite_ref-2">↑</a></span> <span class="reference-text"><span class="citation" id="CITEREFT._J._Kealy,_P._L._Pauson1951"><span style="font-variant:small-caps;">T. J. Kealy, P. L. Pauson</span> (1951). <cite>A New Type of Organo-Iron Compound</cite>. <i>Nature</i> <b>168</b>: 1039. <a href="/wiki/Digital_object_identifier" title="Digital object identifier">DOI</a>: <a rel="nofollow" class="external text" href="https://doi.org/10.1038/1681039b0">10.1038/1681039b0</a>. </span></span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><a href="#cite_ref-3">↑</a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r67679320"><span class="taalaanduiding" title="Taal: Engels">(<span>en</span>) </span> <span style="font-variant:small-caps;">T. Cheng, Z. Fang, G. Zou, Q. Hu, B. Hu, X. Yang & Y. Zhang</span> (2006) - <a rel="nofollow" class="external text" href="http://www.ias.ac.in/matersci/bmsdec2006/701.pdf"><i>A one-step single source route to carbon nanotubes</i></a>, Bull. Mater. Sci., <b>29</b> (7), pp. 701–704</span> </li> </ol></div></div> </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="">Overgenomen van "<a dir="ltr" href="https://nl.wikipedia.org/w/index.php?title=Ferroceen&oldid=65814289">https://nl.wikipedia.org/w/index.php?title=Ferroceen&oldid=65814289</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Categorie:Alles" title="Categorie:Alles">Categorieën</a>: <ul><li><a href="/wiki/Categorie:Verbinding_van_ijzer" title="Categorie:Verbinding van ijzer">Verbinding van ijzer</a></li><li><a href="/wiki/Categorie:Cyclopentadienylcomplex" title="Categorie:Cyclopentadienylcomplex">Cyclopentadienylcomplex</a></li><li><a href="/wiki/Categorie:Ontvlambare_stof" title="Categorie:Ontvlambare stof">Ontvlambare stof</a></li></ul></div><div id="mw-hidden-catlinks" class="mw-hidden-catlinks mw-hidden-cats-hidden">Verborgen categorie: <ul><li><a href="/wiki/Categorie:Wikipedia:GHS_aanwezig" title="Categorie:Wikipedia:GHS aanwezig">Wikipedia:GHS aanwezig</a></li></ul></div></div> </div> </main> </div> <div class="mw-footer-container"> <footer id="footer" class="mw-footer" > <ul id="footer-info"> <li id="footer-info-lastmod"> Deze pagina is voor het laatst bewerkt op 10 sep 2023 om 15:24.</li> <li id="footer-info-copyright">De tekst is beschikbaar onder de licentie <a rel="nofollow" class="external text" href="//creativecommons.org/licenses/by-sa/4.0/deed.nl">Creative Commons Naamsvermelding/Gelijk delen</a>, er kunnen aanvullende voorwaarden van toepassing zijn. 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