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id="toc-Carbenium_ions-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-History" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#History"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>History</span> </div> </a> <ul id="toc-History-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</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">5</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>External links</span> </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Carbocation</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 35 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-35" 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">35 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D9%83%D8%A7%D8%AA%D9%8A%D9%88%D9%86_%D9%83%D8%B1%D8%A8%D9%88%D9%86%D9%8A" title="كاتيون كربوني – Arabic" lang="ar" hreflang="ar" data-title="كاتيون كربوني" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Carbocati%C3%B3" title="Carbocatió – Catalan" lang="ca" hreflang="ca" data-title="Carbocatió" 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/Karbokation" title="Karbokation – Czech" lang="cs" hreflang="cs" data-title="Karbokation" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Carbokation" title="Carbokation – Danish" lang="da" hreflang="da" data-title="Carbokation" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Carbokation" title="Carbokation – German" lang="de" hreflang="de" data-title="Carbokation" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Karbokatioonid" title="Karbokatioonid – Estonian" lang="et" hreflang="et" data-title="Karbokatioonid" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%9A%CE%B1%CF%81%CE%B2%CE%BF%CE%BA%CE%B1%CF%84%CE%B9%CF%8C%CE%BD" title="Καρβοκατιόν – Greek" lang="el" hreflang="el" data-title="Καρβοκατιόν" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Carbocati%C3%B3n" title="Carbocatión – Spanish" lang="es" hreflang="es" data-title="Carbocatión" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Karbokatioi" title="Karbokatioi – Basque" lang="eu" hreflang="eu" data-title="Karbokatioi" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%DA%A9%D8%B1%D8%A8%D9%88%DA%A9%D8%A7%D8%AA%DB%8C%D9%88%D9%86" title="کربوکاتیون – Persian" lang="fa" hreflang="fa" data-title="کربوکاتیون" 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/Carbocation" title="Carbocation – French" lang="fr" hreflang="fr" data-title="Carbocation" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Carbocati%C3%B3n" title="Carbocatión – Galician" lang="gl" hreflang="gl" data-title="Carbocatión" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%ED%83%84%EC%86%8C_%EC%96%91%EC%9D%B4%EC%98%A8" title="탄소 양이온 – Korean" lang="ko" hreflang="ko" data-title="탄소 양이온" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D4%BF%D5%A1%D6%80%D5%A2%D5%B8%D5%B6%D5%AB%D5%B8%D6%82%D5%B4%D5%AB_%D5%AB%D5%B8%D5%B6%D5%B6%D5%A5%D6%80" title="Կարբոնիումի իոններ – Armenian" lang="hy" hreflang="hy" data-title="Կարբոնիումի իոններ" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Karbokation" title="Karbokation – Indonesian" lang="id" hreflang="id" data-title="Karbokation" 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/Carbocatione" title="Carbocatione – Italian" lang="it" hreflang="it" data-title="Carbocatione" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%A7%D7%A8%D7%91%D7%95%D7%A7%D7%98%D7%99%D7%95%D7%9F" title="קרבוקטיון – Hebrew" lang="he" hreflang="he" data-title="קרבוקטיון" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%9A%D0%B0%D1%80%D0%B1%D0%BE%D0%BA%D0%B0%D1%82%D1%98%D0%BE%D0%BD" title="Карбокатјон – Macedonian" lang="mk" hreflang="mk" data-title="Карбокатјон" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Karbokation" title="Karbokation – Malay" lang="ms" hreflang="ms" data-title="Karbokation" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Carbokation" title="Carbokation – Dutch" lang="nl" hreflang="nl" data-title="Carbokation" 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%82%AB%E3%83%AB%E3%83%9C%E3%82%AB%E3%83%81%E3%82%AA%E3%83%B3" title="カルボカチオン – Japanese" lang="ja" hreflang="ja" data-title="カルボカチオン" 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-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Karbokation" title="Karbokation – Polish" lang="pl" hreflang="pl" data-title="Karbokation" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Carboc%C3%A1tion" title="Carbocátion – Portuguese" lang="pt" hreflang="pt" data-title="Carbocátion" 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/Carbocation" title="Carbocation – Romanian" lang="ro" hreflang="ro" data-title="Carbocation" 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%9A%D0%B0%D1%80%D0%B1%D0%BA%D0%B0%D1%82%D0%B8%D0%BE%D0%BD" title="Карбкатион – Russian" lang="ru" hreflang="ru" data-title="Карбкатион" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Carbocation" title="Carbocation – Simple English" lang="en-simple" hreflang="en-simple" data-title="Carbocation" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target"><span>Simple English</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Karbokation" title="Karbokation – Slovenian" lang="sl" hreflang="sl" data-title="Karbokation" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Karbokatjon" title="Karbokatjon – Serbian" lang="sr" hreflang="sr" data-title="Karbokatjon" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Karbokatjon" title="Karbokatjon – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Karbokatjon" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Karbokationi" title="Karbokationi – Finnish" lang="fi" hreflang="fi" data-title="Karbokationi" 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/Karbokatjon" title="Karbokatjon – Swedish" lang="sv" hreflang="sv" data-title="Karbokatjon" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Karbokatyon" title="Karbokatyon – Turkish" lang="tr" hreflang="tr" data-title="Karbokatyon" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%9A%D0%B0%D1%80%D0%B1%D0%BE%D0%BA%D0%B0%D1%82%D1%96%D0%BE%D0%BD" title="Карбокатіон – Ukrainian" lang="uk" hreflang="uk" data-title="Карбокатіон" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link 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</div> </nav> </div> </div> </div> <div class="vector-column-end"> <div class="vector-sticky-pinned-container"> <nav class="vector-page-tools-landmark" aria-label="Page tools"> <div id="vector-page-tools-pinned-container" class="vector-pinned-container"> </div> </nav> <nav class="vector-appearance-landmark" aria-label="Appearance"> <div id="vector-appearance-pinned-container" class="vector-pinned-container"> <div id="vector-appearance" class="vector-appearance vector-pinnable-element"> <div class="vector-pinnable-header vector-appearance-pinnable-header vector-pinnable-header-pinned" data-feature-name="appearance-pinned" data-pinnable-element-id="vector-appearance" data-pinned-container-id="vector-appearance-pinned-container" data-unpinned-container-id="vector-appearance-unpinned-container" > <div class="vector-pinnable-header-label">Appearance</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" 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src="//upload.wikimedia.org/wikipedia/commons/thumb/8/82/Tert-butyl_cation_resonance_%28cropped%29.svg/120px-Tert-butyl_cation_resonance_%28cropped%29.svg.png" decoding="async" width="120" height="78" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/82/Tert-butyl_cation_resonance_%28cropped%29.svg/180px-Tert-butyl_cation_resonance_%28cropped%29.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/82/Tert-butyl_cation_resonance_%28cropped%29.svg/240px-Tert-butyl_cation_resonance_%28cropped%29.svg.png 2x" data-file-width="250" data-file-height="162" /></a><figcaption>The <i>tert</i>-butyl cation is a relatively stable carbenium ion.<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></figcaption></figure> <p>A <b>carbocation</b> is an <a href="/wiki/Ion" title="Ion">ion</a> with a positively charged <a href="/wiki/Carbon" title="Carbon">carbon</a> <a href="/wiki/Atom" title="Atom">atom</a>. Among the simplest examples are the <a href="/wiki/Methenium" title="Methenium">methenium</a> <span class="chemf nowrap">CH<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">3</sub></span></span></span>, <a href="/wiki/Methanium" title="Methanium">methanium</a> <span class="chemf nowrap">CH<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>, <a href="/wiki/Acylium_ions" title="Acylium ions">acylium ions</a> <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">RCO<sup class="template-chem2-sup">+</sup></span>, and <a href="/wiki/Vinyl_cation" title="Vinyl cation">vinyl</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">2</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">3</sub></span></span></span> cations.<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>Until the early 1970s, carbocations were called <i>carbonium ions</i>.<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> In the present-day definition given by the IUPAC, a carbocation is any even-electron cation with significant partial positive charge on a carbon atom. They are further classified in two main categories according to the <a href="/wiki/Coordination_number" title="Coordination number">coordination number</a> of the charged carbon: three in the <a href="/wiki/Carbenium_ion" title="Carbenium ion">carbenium ions</a> and five in the <a href="/wiki/Carbonium_ion" title="Carbonium ion">carbonium ions</a>. This nomenclature was proposed by <a href="/wiki/George_Andrew_Olah" title="George Andrew Olah">G. A. Olah</a>.<sup id="cite_ref-OlahCXVIII_4-0" class="reference"><a href="#cite_note-OlahCXVIII-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Carbonium ions, as originally defined by Olah, are characterized by a <a href="/wiki/Three-center_two-electron_bond" title="Three-center two-electron bond">three-center two-electron</a> delocalized bonding scheme and are essentially synonymous with so-called '<a href="/wiki/Non-classical_carbocation" class="mw-redirect" title="Non-classical carbocation">non-classical carbocations</a>', which are carbocations that contain bridging C–C or C–H σ-bonds. However, others have more narrowly defined the term 'carbonium ion' as formally protonated or alkylated alkanes (<span class="chemf nowrap">CR<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>, where R is H or alkyl), to the exclusion of non-classical carbocations like the <a href="/wiki/Norbornyl_cation" class="mw-redirect" title="Norbornyl cation">2-norbornyl cation</a>.<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> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Definitions">Definitions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbocation&action=edit&section=1" title="Edit section: Definitions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>According to the <a href="/wiki/International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">IUPAC</a>, a <i>carbocation</i> is any cation containing an even number of electrons in which a significant portion of the positive charge resides on a carbon atom.<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> Prior to the observation of five-coordinate carbocations by Olah and coworkers, <i>carbocation</i> and <i>carbonium ion</i> were used interchangeably. Olah proposed a redefinition of <i>carbonium ion</i> as a carbocation featuring any type of three-center two-electron bonding, while a <i>carbenium ion</i> was newly coined to refer to a carbocation containing only two-center two-electron bonds with a three-coordinate positive carbon. Subsequently, others have used the term <i>carbonium ion</i> more narrowly to refer to species that are derived (at least formally) from electrophilic attack of H<sup>+</sup> or R<sup>+</sup> on an alkane, in analogy to other main group <a href="/wiki/Onium_compound" class="mw-redirect" title="Onium compound">onium</a> species, while a carbocation that contains any type of three-centered bonding is referred to as a <i>non-classical carbocation</i>. In this usage, 2-norbornyl cation is not a carbonium ion, because it is formally derived from protonation of an alkene (norbornene) rather than an alkane, although it is a non-classical carbocation due to its bridged structure. The IUPAC acknowledges the three divergent definitions of carbonium ion and urges care in the usage of this term. For the remainder of this article, the term <i>carbonium ion</i> will be used in this latter restricted sense, while <i>non-classical carbocation</i> will be used to refer to any carbocation with C–C and/or C–H σ-bonds delocalized by bridging. </p><p><br /> </p> <div class="mw-heading mw-heading2"><h2 id="Structure_and_properties">Structure and properties</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbocation&action=edit&section=2" title="Edit section: Structure and properties"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Carbonium_ions">Carbonium ions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbocation&action=edit&section=3" title="Edit section: Carbonium ions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:CSD_CIF_HIGNAOhires.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f9/CSD_CIF_HIGNAOhires.png/220px-CSD_CIF_HIGNAOhires.png" decoding="async" width="220" height="243" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f9/CSD_CIF_HIGNAOhires.png/330px-CSD_CIF_HIGNAOhires.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f9/CSD_CIF_HIGNAOhires.png/440px-CSD_CIF_HIGNAOhires.png 2x" data-file-width="2131" data-file-height="2349" /></a><figcaption>Structure of the 2-norbornyl carbonium ion. All other C-C bond lengths are normal (ca. 1.5 Å).<sup id="cite_ref-:0_7-0" class="reference"><a href="#cite_note-:0-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </figcaption></figure> <p>Carbonium ions can be thought of as protonated or alkylated alkanes. They feature delocalized 3c-2e bonds. For this reason, they are often referred to as non-classical ions. A well studied example, albeit of no practical value, is the <a href="/wiki/2-Norbornyl_cation" title="2-Norbornyl cation">2-norbornyl cation</a>. Like carbenium ions, carbonium ions are often invoked as intermediates in the upgrading of hydrocarbons in refineries. </p> <div class="mw-heading mw-heading3"><h3 id="Carbenium_ions">Carbenium ions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbocation&action=edit&section=4" title="Edit section: Carbenium ions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>At least in a formal sense, carbenium ions are derived from the protonation (addition of <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">H<sup class="template-chem2-sup">+</sup></span>) or alkylation (addition of <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R<sup class="template-chem2-sup">+</sup></span>) of a <a href="/wiki/Carbene" title="Carbene">carbene</a> or <a href="/wiki/Alkene" title="Alkene">alkene</a>. Thus, in at least one of their <a href="/wiki/Resonance_(chemistry)" title="Resonance (chemistry)">resonance</a> depictions, they possess a carbon atom bearing a formal positive charge that is surrounded by a sextet of electrons (six <a href="/wiki/Valence_electron" title="Valence electron">valence electrons</a>) instead of the usual octet required to fill the valence shell of carbon (<a href="/wiki/Octet_rule" title="Octet rule">octet rule</a>). Therefore, carbenium ions (and carbocations in general) are often reactive, seeking to fill the octet of valence electrons as well as regain a neutral <a href="/wiki/Electric_charge" title="Electric charge">charge</a>. In accord with <a href="/wiki/VSEPR_theory" title="VSEPR theory">VSEPR</a> and <a href="/wiki/Bent%27s_rule" title="Bent's rule">Bent's rule</a>, unless geometrically constrained to be pyramidal (e.g., 1-adamantyl cation), 3-coordinate carbon in carbenium ions are usually trigonal planar, with a pure p character empty orbital as its lowest unoccupied molecular orbital (LUMO) and CH/CC bonds formed from C(sp<sup>2</sup>) orbitals. A prototypical example is the methyl cation, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<span class="template-chem2-su"><span>+</span><span>3</span></span></span>. </p> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbocation&action=edit&section=5" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The history of carbocations dates back to 1891 when G. Merling<sup id="cite_ref-Merling1891_8-0" class="reference"><a href="#cite_note-Merling1891-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> reported that he added bromine to tropylidene (<a href="/wiki/Cycloheptatriene" title="Cycloheptatriene">cycloheptatriene</a>) and then heated the product to obtain a crystalline, water-soluble material, <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">7</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">7</sub></span></span>Br</span>. He did not suggest a structure for it; however, <a href="/wiki/William_von_Eggers_Doering" title="William von Eggers Doering">Doering</a> and Knox<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> convincingly showed that it was <a href="/wiki/Tropylium_cation" title="Tropylium cation">tropylium</a> (cycloheptatrienylium) bromide. This ion is predicted to be <a href="/wiki/Aromatic" class="mw-redirect" title="Aromatic">aromatic</a> by <a href="/wiki/H%C3%BCckel%27s_rule" title="Hückel's rule">Hückel's rule</a>. </p><p>In 1902, Norris and Kehrman independently discovered that colorless <a href="/wiki/Triphenylmethanol" title="Triphenylmethanol">triphenylmethanol</a> gives deep-yellow solutions in concentrated <a href="/wiki/Sulfuric_acid" title="Sulfuric acid">sulfuric acid</a>. <a href="/wiki/Triphenylmethyl_chloride" title="Triphenylmethyl chloride">Triphenylmethyl chloride</a> similarly formed orange complexes when treated with aluminium and tin chlorides. In 1902, <a href="/wiki/Adolf_von_Baeyer" title="Adolf von Baeyer">Adolf von Baeyer</a> recognized the salt-like character of the compounds formed. He dubbed the relationship between color and salt formation <b>halochromy</b>, of which <a href="/wiki/Malachite_green" title="Malachite green">malachite green</a> is a prime example. The <a href="/wiki/Triphenylcarbenium" title="Triphenylcarbenium">trityl carbocation</a> (shown below) is indeed a stable carbocationic system, for example in the form of <a href="/wiki/Triphenylmethyl_hexafluorophosphate" title="Triphenylmethyl hexafluorophosphate">trityl hexafluorophosphate</a>.<sup id="cite_ref-Urch_10-0" class="reference"><a href="#cite_note-Urch-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-default-size mw-halign-center" typeof="mw:File"><a href="/wiki/File:TriphenylmethanolCarbocationFormation.svg" class="mw-file-description" title="reaction of triphenylmethanol with sulfuric acid"><img alt="reaction of triphenylmethanol with sulfuric acid" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/af/TriphenylmethanolCarbocationFormation.svg/411px-TriphenylmethanolCarbocationFormation.svg.png" decoding="async" width="411" height="171" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/af/TriphenylmethanolCarbocationFormation.svg/617px-TriphenylmethanolCarbocationFormation.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/af/TriphenylmethanolCarbocationFormation.svg/822px-TriphenylmethanolCarbocationFormation.svg.png 2x" data-file-width="411" data-file-height="171" /></a><figcaption>reaction of triphenylmethanol with sulfuric acid</figcaption></figure> <p>Carbocations are <a href="/wiki/Reactive_intermediates" class="mw-redirect" title="Reactive intermediates">reactive intermediates</a> in many organic reactions. This idea, first proposed by <a href="/wiki/Julius_Stieglitz" title="Julius Stieglitz">Julius Stieglitz</a> in 1899,<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> was further developed by <a href="/wiki/Hans_Meerwein" title="Hans Meerwein">Hans Meerwein</a> in his 1922 study<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><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> of the <a href="/wiki/Wagner%E2%80%93Meerwein_rearrangement" title="Wagner–Meerwein rearrangement">Wagner–Meerwein rearrangement</a>. Carbocations were also found to be involved in the <a href="/wiki/SN1_reaction" title="SN1 reaction">S<sub>N</sub>1 reaction</a>, the <a href="/wiki/Elimination_reaction" title="Elimination reaction">E1 reaction</a>, and in <a href="/wiki/Rearrangement_reaction" title="Rearrangement reaction">rearrangement reactions</a> such as the <a href="/wiki/Whitmore_1,2_shift" class="mw-redirect" title="Whitmore 1,2 shift">Whitmore 1,2 shift</a>. The chemical establishment was reluctant to accept the notion of a carbocation and for a long time the Journal of the American Chemical Society refused articles that mentioned them. </p><p>An <a href="/wiki/NMR_spectrum" class="mw-redirect" title="NMR spectrum">NMR spectrum</a> of a carbocation was first reported by Doering et al.<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> in 1958. It was the heptamethyl<a href="/wiki/Arenium_ion" title="Arenium ion">benzenium</a> ion, made by treating <a href="/wiki/Hexamethylbenzene" title="Hexamethylbenzene">hexamethylbenzene</a> with <a href="/wiki/Methyl_chloride" class="mw-redirect" title="Methyl chloride">methyl chloride</a> and <a href="/wiki/Aluminium_chloride" title="Aluminium chloride">aluminium chloride</a>. The stable 7-norbornadienyl cation was prepared by Story et al. in 1960<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> by reacting <a href="/wiki/Norbornadiene" title="Norbornadiene">norbornadienyl chloride</a> with <a href="/wiki/Silver_tetrafluoroborate" title="Silver tetrafluoroborate">silver tetrafluoroborate</a> in <a href="/wiki/Sulfur_dioxide" title="Sulfur dioxide">sulfur dioxide</a> at −80 °C. The NMR spectrum established that it was non-classically bridged (the first stable <a href="/wiki/Non-classical_ion" class="mw-redirect" title="Non-classical ion">non-classical ion</a> observed). </p><p>In 1962, <a href="/wiki/George_Andrew_Olah" title="George Andrew Olah">Olah</a> directly observed the <a href="/wiki/Tert-butyl" class="mw-redirect" title="Tert-butyl"><i>tert</i>-butyl</a> carbocation by <a href="/wiki/Nuclear_magnetic_resonance" title="Nuclear magnetic resonance">nuclear magnetic resonance</a> as a stable species on dissolving <i>tert</i>-butyl fluoride in <a href="/wiki/Magic_acid" title="Magic acid">magic acid</a>. The NMR spectrum of the norbornyl cation was reported by Schleyer et al.<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> It was shown to rapidly undergo proton-scrambling .<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbocation&action=edit&section=6" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Armilenium" title="Armilenium">Armilenium</a></li> <li><a href="/wiki/Carbanion" title="Carbanion">Carbanion</a></li> <li><a href="/wiki/Carbene" title="Carbene">Carbene</a></li> <li><a href="/wiki/Oxocarbenium" title="Oxocarbenium">Oxocarbenium</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbocation&action=edit&section=7" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFScholzHimmelSchererKrossing2013" class="citation journal cs1">Scholz, Franziska; Himmel, Daniel; Scherer, Harald; Krossing, Ingo (2013). 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"Racemization of Isobornyl Chloride via Carbocations: A Nonclassical Look at a Classic Mechanism". <i>Journal of Chemical Education</i>. <b>87</b> (2): 221. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2010JChEd..87..221R">2010JChEd..87..221R</a>. <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%2Fed800058c">10.1021/ed800058c</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Chemical+Education&rft.atitle=Racemization+of+Isobornyl+Chloride+via+Carbocations%3A+A+Nonclassical+Look+at+a+Classic+Mechanism&rft.volume=87&rft.issue=2&rft.pages=221&rft.date=2010&rft_id=info%3Adoi%2F10.1021%2Fed800058c&rft_id=info%3Abibcode%2F2010JChEd..87..221R&rft.aulast=Rzepa&rft.aufirst=H.+S.&rft.au=Allan%2C+C.+S.+M.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACarbocation" class="Z3988"></span></span> </li> <li id="cite_note-14"><span class="mw-cite-backlink"><b><a href="#cite_ref-14">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDoeringSaundersBoytonEarhart1958" class="citation journal cs1">Doering, W. von E.; Saunders, M.; Boyton, H. G.; Earhart, H. W.; Wadley, E. F.; Edwards, W. R.; Laber, G. (1958). "The 1,1,2,3,4,5,6-heptamethylbenzenonium ion". <i>Tetrahedron</i>. <b>4</b> (1–2): 178–185. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0040-4020%2858%2988016-3">10.1016/0040-4020(58)88016-3</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Tetrahedron&rft.atitle=The+1%2C1%2C2%2C3%2C4%2C5%2C6-heptamethylbenzenonium+ion&rft.volume=4&rft.issue=1%E2%80%932&rft.pages=178-185&rft.date=1958&rft_id=info%3Adoi%2F10.1016%2F0040-4020%2858%2988016-3&rft.aulast=Doering&rft.aufirst=W.+von+E.&rft.au=Saunders%2C+M.&rft.au=Boyton%2C+H.+G.&rft.au=Earhart%2C+H.+W.&rft.au=Wadley%2C+E.+F.&rft.au=Edwards%2C+W.+R.&rft.au=Laber%2C+G.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACarbocation" 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="CITEREFStorySaunders1960" class="citation journal cs1">Story, Paul R.; Saunders, Martin (1960). 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(1964). "Stable Carbonium Ions. XI.1 The Rate of Hydride Shifts in the 2-Norbornyl Cation". <i><a href="/wiki/Journal_of_the_American_Chemical_Society" title="Journal of the American Chemical Society">Journal of the American Chemical Society</a></i>. <b>86</b> (24): 5680–5681. <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%2Fja01078a057">10.1021/ja01078a057</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+the+American+Chemical+Society&rft.atitle=Stable+Carbonium+Ions.+XI.1+The+Rate+of+Hydride+Shifts+in+the+2-Norbornyl+Cation&rft.volume=86&rft.issue=24&rft.pages=5680-5681&rft.date=1964&rft_id=info%3Adoi%2F10.1021%2Fja01078a057&rft.aulast=Saunders&rft.aufirst=Martin&rft.au=Schleyer%2C+Paul+von+R.&rft.au=Olah%2C+George+A.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACarbocation" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbocation&action=edit&section=8" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><span class="noviewer" typeof="mw:File"><a href="/wiki/File:Commons-logo.svg" class="mw-file-description"><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" /></a></span> Media related to <a href="https://commons.wikimedia.org/wiki/Category:Carbocations" class="extiw" title="commons:Category:Carbocations">Carbocations</a> at Wikimedia Commons</li> <li><a rel="nofollow" class="external text" href="http://nobelprize.org/nobel_prizes/chemistry/laureates/1994/press.html?print=1">Press Release</a> The 1994 Nobel Prize in Chemistry". 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