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class="vector-toc-numb">2</span> <span>Reactivity</span> </div> </a> <button aria-controls="toc-Reactivity-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Reactivity subsection</span> </button> <ul id="toc-Reactivity-sublist" class="vector-toc-list"> <li id="toc-Rearrangements" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Rearrangements"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1</span> <span>Rearrangements</span> </div> </a> <ul id="toc-Rearrangements-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-As_electrophiles" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#As_electrophiles"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.2</span> <span>As electrophiles</span> </div> </a> <ul id="toc-As_electrophiles-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Types_of_carbenium_ions" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Types_of_carbenium_ions"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Types of carbenium ions</span> </div> </a> <button aria-controls="toc-Types_of_carbenium_ions-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Types of carbenium ions subsection</span> </button> <ul id="toc-Types_of_carbenium_ions-sublist" class="vector-toc-list"> <li id="toc-Stability" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Stability"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Stability</span> </div> </a> <ul id="toc-Stability-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Alkylium_ions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Alkylium_ions"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Alkylium ions</span> </div> </a> <ul id="toc-Alkylium_ions-sublist" class="vector-toc-list"> <li id="toc-Extra_stabilizing_effects" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Extra_stabilizing_effects"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2.1</span> <span>Extra stabilizing effects</span> </div> </a> <ul id="toc-Extra_stabilizing_effects-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Aromatic_carbenium_ions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Aromatic_carbenium_ions"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.3</span> <span>Aromatic carbenium ions</span> </div> </a> <ul id="toc-Aromatic_carbenium_ions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Arenium_ions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Arenium_ions"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.4</span> <span>Arenium ions</span> </div> </a> <ul id="toc-Arenium_ions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Acylium_ions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Acylium_ions"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.5</span> <span>Acylium ions</span> </div> </a> <ul id="toc-Acylium_ions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Vinyl_and_alkynyl_carbenium_ions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Vinyl_and_alkynyl_carbenium_ions"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.6</span> <span>Vinyl and alkynyl carbenium ions</span> </div> </a> <ul id="toc-Vinyl_and_alkynyl_carbenium_ions-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Selected_applications" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Selected_applications"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Selected applications</span> </div> </a> <ul id="toc-Selected_applications-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">5</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">6</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> 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href="https://de.wikipedia.org/wiki/Carbeniumion" title="Carbeniumion – German" lang="de" hreflang="de" data-title="Carbeniumion" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Carb%C3%A9nium" title="Carbénium – French" lang="fr" hreflang="fr" data-title="Carbénium" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Carbeniumion" title="Carbeniumion – Dutch" lang="nl" hreflang="nl" data-title="Carbeniumion" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Carb%C3%AAnium" title="Carbênium – Portuguese" lang="pt" hreflang="pt" data-title="Carbênium" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Karbenijum_jon" title="Karbenijum jon – Serbian" lang="sr" hreflang="sr" data-title="Karbenijum jon" 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/Karbenijum_jon" title="Karbenijum jon – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Karbenijum jon" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / 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<div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Class of ions</div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Tert-butyl_cation_resonance_(cropped).svg" class="mw-file-description"><img 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>carbenium ion</b> is a <a href="/wiki/Cation" class="mw-redirect" title="Cation">positive ion</a> with the structure RR′R″C<sup>+</sup>, that is, a <a href="/wiki/Chemical_species" title="Chemical species">chemical species</a> with carbon atom having three covalent bonds, and it bears a +1 <a href="/wiki/Formal_charge" title="Formal charge">formal charge</a>. Carbenium ions are a major subset of <a href="/wiki/Carbocation" title="Carbocation">carbocations</a>, which is a general term for diamagnetic carbon-based cations. In parallel with carbenium ions is another subset of carbocations, the <a href="/wiki/Carbonium_ion" title="Carbonium ion">carbonium ions</a> with the formula R<sub>5</sub><sup>+</sup>. In carbenium ions charge is localized. They are isoelectronic with mono<a href="/wiki/Borane" title="Borane">boranes</a> such as B(CH<sub>3</sub>)<sub>3</sub>.<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> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Nomenclature">Nomenclature</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbenium_ion&action=edit&section=1" title="Edit section: Nomenclature"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Carbocations" class="mw-redirect" title="Carbocations">carbocations</a></div> <div class="mw-heading mw-heading2"><h2 id="Reactivity">Reactivity</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbenium_ion&action=edit&section=2" title="Edit section: Reactivity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Carbenium ions are generally highly reactive due to having an incomplete <a href="/wiki/Octet_rule" title="Octet rule">octet</a> of electrons; however, certain carbenium ions, such as the <a href="/wiki/Tropylium_cation" title="Tropylium cation">tropylium</a> ion, are relatively stable due to the positive charge being delocalised between the carbon atoms. </p> <div class="mw-heading mw-heading3"><h3 id="Rearrangements">Rearrangements</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbenium_ion&action=edit&section=3" title="Edit section: Rearrangements"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Carbenium ions sometimes <a href="/wiki/Rearrangement_reaction" title="Rearrangement reaction">rearranges</a> readily. For example, when pentan-3-ol is heated with aqueous HCl, the initially formed 3-pentyl carbocation rearranges to a mixture of the 3-pentyl and 2-pentyl. These cations react with chloride ion to produce 3-chloropentane and 2-chloropentane in a ratio of approximately 1:2. <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><sup class="noprint Inline-Template" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citing_sources#What_information_to_include" title="Wikipedia:Citing sources"><span title="A complete citation is needed. (October 2024)">full citation needed</span></a></i>]</sup> Migration of an alkyl group to form a new carbocationic center is also observed.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> This often occurs with <a href="/wiki/Rate_constant" class="mw-redirect" title="Rate constant">rate constants</a> in excess of 10<sup>10</sup> s<sup>−1</sup> at ambient temperature and still takes place rapidly (compared to the NMR timescale) at temperatures as low as −120 °C (<i>see <a href="/wiki/Wagner%E2%80%93Meerwein_rearrangement" title="Wagner–Meerwein rearrangement">Wagner-Meerwein shift</a></i>). In especially favorable cases like the 2-norbornyl cation, hydrogen shifts may still take place at rates fast enough to interfere with X-ray crystallography at 86 K (−187 °C).<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> Typically, carbocations will rearrange to give a tertiary isomer. For instance, all isomers of <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">C<sub class="template-chem2-sub">6</sub>H<span class="template-chem2-su"><span>+</span><span>11</span></span></span> rapidly rearrange to give the 1-methyl-1-cyclopentyl cation. This fact often complicates synthetic pathways. For example, when 3-pentanol is heated with aqueous HCl, the initially formed 3-pentyl carbocation rearranges to a statistical mixture of the 3-pentyl and 2-pentyl. These cations react with chloride ion to produce about one third 3-chloropentane and two thirds 2-chloropentane. The <a href="/wiki/Friedel%E2%80%93Crafts_alkylation" class="mw-redirect" title="Friedel–Crafts alkylation">Friedel–Crafts alkylation</a> suffers from this limitation; for this reason, the <a href="/wiki/Friedel-Crafts_acylation" class="mw-redirect" title="Friedel-Crafts acylation">acylation</a> (followed by <a href="/wiki/Wolff%E2%80%93Kishner_reduction" title="Wolff–Kishner reduction">Wolff–Kishner</a> or <a href="/wiki/Clemmensen_reduction" title="Clemmensen reduction">Clemmensen reduction</a> to give the alkylated product) is more frequently applied. </p> <div class="mw-heading mw-heading3"><h3 id="As_electrophiles">As electrophiles</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbenium_ion&action=edit&section=4" title="Edit section: As electrophiles"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Carbocations are susceptible to attack by <a href="/wiki/Nucleophile" title="Nucleophile">nucleophiles</a>, like water, alcohols, carboxylates, azide, and halide ions, to form the addition product. Strongly basic nucleophiles, especially hindered ones, favor elimination over addition. Because even weak nucleophiles will react with carbocations, most can only be directly observed or isolated in non-nucleophilic media like <a href="/wiki/Superacid" title="Superacid">superacids</a>.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Relative_formation_energy_of_carbocations.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/45/Relative_formation_energy_of_carbocations.png/220px-Relative_formation_energy_of_carbocations.png" decoding="async" width="220" height="125" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/45/Relative_formation_energy_of_carbocations.png/330px-Relative_formation_energy_of_carbocations.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/45/Relative_formation_energy_of_carbocations.png/440px-Relative_formation_energy_of_carbocations.png 2x" data-file-width="901" data-file-height="511" /></a><figcaption>Relative formation energy of carbocations from computational calculation</figcaption></figure> <div class="mw-heading mw-heading2"><h2 id="Types_of_carbenium_ions">Types of carbenium ions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbenium_ion&action=edit&section=5" title="Edit section: Types of carbenium ions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Stability">Stability</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbenium_ion&action=edit&section=6" title="Edit section: Stability"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The stability order of carbocations, from most stable to least stable as reflected by hydride ion affinity (HIA) values, are as follows (HIA values in kcal/mol in parentheses): </p> <table class="wikitable"> <caption>Hydride ion affinity (HIA) as a measure of carbocation stability </caption> <tbody><tr> <th><b>Carbocation</b> </th> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap"><i>c</i>-C<sub class="template-chem2-sub">7</sub>H<span class="template-chem2-su"><span>+</span><span>7</span></span></span> <i>(most stable)</i> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>)<sub class="template-chem2-sub">3</sub>C<sup class="template-chem2-sup">+</sup></span> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap"><i>c</i>-C<sub class="template-chem2-sub">3</sub>H<span class="template-chem2-su"><span>+</span><span>3</span></span></span> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>)<sub class="template-chem2-sub">2</sub>CH<sup class="template-chem2-sup">+</sup></span> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">2-norbornyl<sup class="template-chem2-sup">+</sup></span> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap"><i>t</i>-C<sub class="template-chem2-sub">4</sub>H<span class="template-chem2-su"><span>+</span><span>9</span></span></span> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>CH<span class="template-chem2-su"><span>+</span><span>2</span></span></span> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap"><i>i</i>-C<sub class="template-chem2-sub">3</sub>H<span class="template-chem2-su"><span>+</span><span>7</span></span></span> </td></tr> <tr> <th><b>HIA (kcal/mol)</b> </th> <td>201 </td> <td>215 </td> <td>221 </td> <td>222 </td> <td>231 </td> <td>231 </td> <td>234 </td> <td>246 </td></tr> <tr> <th><b>Carbocation</b> </th> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap"><i>c</i>-C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>CH<span class="template-chem2-su"><span>+</span><span>2</span></span></span> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">2</sub>=CH−CH<span class="template-chem2-su"><span>+</span><span>2</span></span></span> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap"><i>c</i>-C<sub class="template-chem2-sub">5</sub>H<span class="template-chem2-su"><span>+</span><span>5</span></span></span> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH≡C−CH<span class="template-chem2-su"><span>+</span><span>2</span></span></span> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">2</sub>H<span class="template-chem2-su"><span>+</span><span>5</span></span></span> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">2</sub>H<span class="template-chem2-su"><span>+</span><span>3</span></span></span> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<span class="template-chem2-su"><span>+</span><span>5</span></span></span> </td> <td><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> <i>(least stable)</i> </td></tr> <tr> <th><b>HIA (kcal/mol)</b> </th> <td>249 </td> <td>256 </td> <td>258 </td> <td>270 </td> <td>273 </td> <td>287 </td> <td>298 </td> <td>312 </td></tr></tbody></table> <p>Since carbenium ions can be highly reactive, a major consideration is their stability. The stability of carbenium ions correlates with the electron-donating properties of the substituents. Trialkylcarbenium ions, such as <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">3</sub>C<sup class="template-chem2-sup">+</sup></span>, are isolable as salts, but <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">H<sub class="template-chem2-sub">3</sub>C<sup class="template-chem2-sup">+</sup></span> cannot. An analogous situation applies to triarylcarbenium ions: salts of triphenylcarbenium <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(C<sub class="template-chem2-sub">5</sub>H<sub class="template-chem2-sub">5</sub>)<sub class="template-chem2-sub">3</sub>C<sup class="template-chem2-sup">+</sup></span> are readily isolable (see <a href="/wiki/Trityl" class="mw-redirect" title="Trityl">trityl</a>), and those with amine substituents so robust that they are used as dyes, e.g. <a href="/wiki/Crystal_violet" title="Crystal violet">crystal violet</a>. Carbenium ions can also be stabilized by conjugation to double bonds giving allyl cations, which enjoy some <a href="/wiki/Resonance_stabilization" class="mw-redirect" title="Resonance stabilization">resonance stabilization</a>. This situation is illustrated by the isolation of protonated benzene.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> Lone-pair bearing <a href="/wiki/Heteroatom" title="Heteroatom">heteroatoms</a> also stabilize carbenium ions.<sup id="cite_ref-Gruetz_8-0" class="reference"><a href="#cite_note-Gruetz-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Alkylium_ions">Alkylium ions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbenium_ion&action=edit&section=7" title="Edit section: Alkylium ions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Stabilization_of_t-butyl_cation(2).png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/29/Stabilization_of_t-butyl_cation%282%29.png/400px-Stabilization_of_t-butyl_cation%282%29.png" decoding="async" width="400" height="108" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/29/Stabilization_of_t-butyl_cation%282%29.png/600px-Stabilization_of_t-butyl_cation%282%29.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/29/Stabilization_of_t-butyl_cation%282%29.png/800px-Stabilization_of_t-butyl_cation%282%29.png 2x" data-file-width="13686" data-file-height="3683" /></a><figcaption>Hyperconjugation by neighboring alkyl groups stabilizes the <i>t</i>-butyl cation. The stabilizing interaction can be depicted as an orbital interaction or by resonance structures involving "no-bond" resonance forms. (For clarity, a dashed line is used to show that the hydrogen atom is still attached, although the formal C–H bond order in the hyperconjugative structure is zero.)</figcaption></figure> <p>The stability of alkyl-substituted carbocations follows the order <span class="nowrap">3° > 2° > 1° > methyl</span>. This trend can be inferred by the hydride ion affinity values (231, 246, 273, and 312 kcal/mol for <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">3</sub>C<sup class="template-chem2-sup">+</sup></span>, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub>CH<sup class="template-chem2-sup">+</sup></span>, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>CH<span class="template-chem2-su"><span>+</span><span>2</span></span></span>, and <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>).<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> The effect of alkyl substitution is a strong one: </p> <ul><li>tertiary cations are stable and many are directly observable in superacid media. The stabilization by alkyl groups is explained by <a href="/wiki/Hyperconjugation" title="Hyperconjugation">hyperconjugation</a>.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> The donation of electron density from a β C-H or C-C bond into the unoccupied p orbital of the carbocation (a σ<sub>CH/CC</sub> → p interaction) allows the positive charge to be delocalized.</li> <li>Secondary cations are usually transient. Only the isopropyl, <i>s</i>-butyl, and cyclopentyl cations have been observed in solution.<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></li> <li>Primary carbocations in the solution phase, even as transient intermediates (the ethyl cation has been proposed for reactions in 99.9% sulfuric acid and in <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">FSO<sub class="template-chem2-sub">2</sub>OH·SbF<sub class="template-chem2-sub">5</sub></span>),<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> and methyl cation has only been unambiguously identified in the gas phase. In most, if not all cases, the ground state of alleged primary carbenium ions consist of bridged structures in which positive charge is shared by two or more carbon atoms and are better described as side-protonated alkenes, edge-protonated cyclopropanes, or corner-protonated cyclopropanes rather than true primary cations.<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><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> The simple ethyl cation, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">2</sub>H<span class="template-chem2-su"><span>+</span><span>5</span></span></span> has been demonstrated experimentally and computationally to be bridged<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> and can be thought of as a symmetrically protonated ethylene molecule. The same is true for higher homologues like 1-propyl and 1-butyl cations.<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> Neopentyl derivatives are thought to ionize with concomitant migration of a methyl group (<a href="/wiki/Anchimeric_assistance" class="mw-redirect" title="Anchimeric assistance">anchimeric assistance</a>); thus, in most if not all cases, a discrete neopentyl cation is not believed to be involved.<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></li></ul> <p>Carbenium ions can be prepared directly from <a href="/wiki/Alkane" title="Alkane">alkanes</a> by removing a <a href="/wiki/Hydride" title="Hydride">hydride</a> anion, <span class="chemf nowrap">H<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:0.8em;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"></sub></span></span></span>, with a strong acid. For example, <a href="/wiki/Magic_acid" title="Magic acid">magic acid</a>, a mixture of <a href="/wiki/Antimony_pentafluoride" title="Antimony pentafluoride">antimony pentafluoride</a> (<span class="chemf nowrap">SbF<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>) and <a href="/wiki/Fluorosulfuric_acid" title="Fluorosulfuric acid">fluorosulfuric acid</a> (<span class="chemf nowrap">FSO<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>H</span>), turns <a href="/wiki/Isobutane" title="Isobutane">isobutane</a> into the trimethylcarbenium cation, <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 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>C<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:0.8em;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"></sub></span></span></span>.<sup id="cite_ref-olah_18-0" class="reference"><a href="#cite_note-olah-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:CarboCationStabilities.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/be/CarboCationStabilities.svg/220px-CarboCationStabilities.svg.png" decoding="async" width="220" height="57" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/be/CarboCationStabilities.svg/330px-CarboCationStabilities.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/be/CarboCationStabilities.svg/440px-CarboCationStabilities.svg.png 2x" data-file-width="386" data-file-height="100" /></a><figcaption>Order of stability of examples of tertiary (III), secondary (II), and primary (I) alkylcarbenium ions, as well as the methyl cation (far right).</figcaption></figure> <div class="mw-heading mw-heading4"><h4 id="Extra_stabilizing_effects">Extra stabilizing effects</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbenium_ion&action=edit&section=8" title="Edit section: Extra stabilizing effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A carbocation may be stabilized by <a href="/wiki/Resonance_(chemistry)" title="Resonance (chemistry)">resonance</a> by a carbon–carbon double bond or by the lone pair of a <a href="/wiki/Heteroatom" title="Heteroatom">heteroatom</a> adjacent to the ionized carbon. The <i><a href="/wiki/Allyl" class="mw-redirect" title="Allyl">allyl</a></i> cation <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">2</sub>=CH−CH<span class="template-chem2-su"><span>+</span><span>2</span></span></span> and <i><a href="/wiki/Benzyl" class="mw-redirect" title="Benzyl">benzyl</a></i> cation <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>−CH<span class="template-chem2-su"><span>+</span><span>2</span></span></span> are more stable than most other carbenium ions due to donation of electron density from π systems to the cationic center.<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> The doubly- and triply-benzylic carbocations, diphenylcarbenium and <a href="/wiki/Triphenylmethyl_cation" class="mw-redirect" title="Triphenylmethyl cation">triphenylcarbenium</a> (trityl) cation, are particularly stable. For the same reasons, the partial p character of strained C–C bonds in cyclopropyl groups also allows for donation of electron density<sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> and stabilizes the <i>cyclopropylmethyl</i> (cyclopropylcarbinyl) cation. </p><p><a href="/wiki/Oxocarbenium" title="Oxocarbenium">Oxocarbenium</a> and <a href="/wiki/Iminium" title="Iminium">iminium</a> ions have important secondary canonical forms (resonance structures) in which carbon bears a positive charge. As such, they are carbocations according to the IUPAC definition although some chemists do not regard them to be "true" carbocations, as their most important resonance contributors carry the formal positive charge on an oxygen or nitrogen atom, respectively. </p> <figure typeof="mw:File/Thumb"><a href="/wiki/File:5.13_final-_resonance-stabalized_carbocation.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f7/5.13_final-_resonance-stabalized_carbocation.jpg/409px-5.13_final-_resonance-stabalized_carbocation.jpg" decoding="async" width="409" height="213" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f7/5.13_final-_resonance-stabalized_carbocation.jpg/614px-5.13_final-_resonance-stabalized_carbocation.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f7/5.13_final-_resonance-stabalized_carbocation.jpg/818px-5.13_final-_resonance-stabalized_carbocation.jpg 2x" data-file-width="1020" data-file-height="532" /></a><figcaption>The sp2 lone pair of molecule A is oriented such that it forms sufficient orbital overlap with the empty p orbital of the carbonation to allow the formation of a π bond, sequestering the carbonation in a contributing resonance structure. The lone pair of molecule B is rotated 90° with respect to the empty p orbital of the carbonation, demonstrated by the Newman projection (bottom right). Without proper orbital overlap, the nitrogen lone pair cannot donate into the carbocation's empty p orbital. Thus, the carbocation in molecule B is not resonance-stabilized.</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Aromatic_carbenium_ions">Aromatic carbenium ions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbenium_ion&action=edit&section=9" title="Edit section: Aromatic carbenium ions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Tropylium_cation" title="Tropylium cation">Tropylium cation</a></div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Tropylium-ion-3D-balls.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/09/Tropylium-ion-3D-balls.png/150px-Tropylium-ion-3D-balls.png" decoding="async" width="150" height="133" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/09/Tropylium-ion-3D-balls.png/225px-Tropylium-ion-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/09/Tropylium-ion-3D-balls.png/300px-Tropylium-ion-3D-balls.png 2x" data-file-width="1100" data-file-height="973" /></a><figcaption>Ball-and-stick model of the tropylium cation</figcaption></figure> <p>The <b>tropylium ion</b> is an <a href="/wiki/Aromatic" class="mw-redirect" title="Aromatic">aromatic</a> species with the formula <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></span>.<sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> Its name derives from the molecule <a href="/wiki/Tropine" title="Tropine">tropine</a> (itself named for the molecule <a href="/wiki/Atropine" title="Atropine">atropine</a>). Salts of the tropylium cation can be stable, e.g. <a href="/wiki/Tropylium_tetrafluoroborate" title="Tropylium tetrafluoroborate">tropylium tetrafluoroborate</a>. It can be made from <a href="/wiki/Cycloheptatriene" title="Cycloheptatriene">cycloheptatriene</a> (tropylidene) and <a href="/wiki/Bromine" title="Bromine">bromine</a> or <a href="/wiki/Phosphorus_pentachloride" title="Phosphorus pentachloride">phosphorus pentachloride</a>.<sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> </p><p>It is a planar, cyclic, <a href="/wiki/Heptagon" title="Heptagon">heptagonal</a> ion; it also has 6 π-electrons (4<i>n</i> + 2, where <i>n</i> = 1), which fulfills <a href="/wiki/H%C3%BCckel%27s_rule" title="Hückel's rule">Hückel's rule</a> of aromaticity. It can coordinate as a <a href="/wiki/Ligand" title="Ligand">ligand</a> to <a href="/wiki/Metal" title="Metal">metal</a> <a href="/wiki/Atoms" class="mw-redirect" title="Atoms">atoms</a>. </p><p>The structure shown is a composite of seven <a href="/wiki/Resonance_contributor" class="mw-redirect" title="Resonance contributor">resonance contributors</a> in which each carbon carries part of the positive charge. </p><p>In 1891 G. Merling obtained a water-soluble salt from a reaction of cycloheptatriene and bromine.<sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> The structure was elucidated by <a href="/wiki/William_von_Eggers_Doering" title="William von Eggers Doering">Eggers Doering</a> and Knox in 1954.<sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> </p><p>On the other hand, the <a href="/wiki/Antiaromatic" class="mw-redirect" title="Antiaromatic">antiaromatic</a> cyclopentadienyl cation (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">5</sub>H<span class="template-chem2-su"><span>+</span><span>5</span></span></span>) is destabilized by some 40 kcal/mol. </p><p>Another aromatic carbenium ion is the cyclopropenyl or <a href="/wiki/Cyclopropenium_ion" title="Cyclopropenium ion">cyclopropenium ion</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">3</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>.<sup id="cite_ref-27" class="reference"><a href="#cite_note-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> Although less stable than the tropylium cation, this carbenium ion can also form salts at room temperature. Solutions of such salts were exhibit conventional spectroscopic and chemical properties. The cyclopropenium cation (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">3</sub>H<span class="template-chem2-su"><span>+</span><span>3</span></span></span>), although somewhat destabilized by angle strain, is still clearly stabilized by aromaticity when compared to its open-chain analog, allyl cation. </p><p>These varying cation stabilities, depending on the number of π electrons in the ring system, can furthermore be crucial factors in reaction kinetics. The formation of an aromatic carbocation is much faster than the formation of an anti-aromatic or open-chain carbocation. </p> <figure class="mw-halign-center" typeof="mw:File/Frameless"><a href="/wiki/File:Aromatic_cations.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/24/Aromatic_cations.jpg/275px-Aromatic_cations.jpg" decoding="async" width="275" height="121" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/24/Aromatic_cations.jpg/413px-Aromatic_cations.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/2/24/Aromatic_cations.jpg 2x" data-file-width="496" data-file-height="218" /></a><figcaption></figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Arenium_ions">Arenium ions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbenium_ion&action=edit&section=10" title="Edit section: Arenium ions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Arenium_ion" title="Arenium ion">Arenium ion</a></div> <p>An <b>arenium ion</b> is a cyclohexadienyl cation that appears as a reactive intermediate in <a href="/wiki/Electrophilic_aromatic_substitution" title="Electrophilic aromatic substitution">electrophilic aromatic substitution</a>.<sup id="cite_ref-Olah1972_28-0" class="reference"><a href="#cite_note-Olah1972-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> For historic reasons this complex is also called a <i>Wheland intermediate</i>,<sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> or a <i>σ-complex</i>. </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:AreniumIon.png" class="mw-file-description" title="benzenium ion"><img alt="benzenium ion" src="//upload.wikimedia.org/wikipedia/commons/thumb/9/93/AreniumIon.png/400px-AreniumIon.png" decoding="async" width="400" height="111" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/93/AreniumIon.png/600px-AreniumIon.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/93/AreniumIon.png/800px-AreniumIon.png 2x" data-file-width="946" data-file-height="262" /></a></span></dd></dl> <p>Two hydrogen atoms bonded to one carbon lie in a plane perpendicular to the benzene ring.<sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> The arenium ion is no longer an aromatic species; however it is relatively stable due to delocalization: the positive charge is delocalized over 5 carbon atoms. Also contributing to the stability of arenium ions is the energy gain resulting from the strong C-e bond (E = electrophile). </p><p>The smallest arenium ion is protonated <a href="/wiki/Benzene" title="Benzene">benzene</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">6</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></span>. The <b>benzenium ion</b> can be isolated as a stable compound when benzene is protonated by the <a href="/wiki/Carborane_superacid" class="mw-redirect" title="Carborane superacid">carborane superacid</a>, H(CB<sub>11</sub>H(CH<sub>3</sub>)<sub>5</sub>Br<sub>6</sub>).<sup id="cite_ref-31" class="reference"><a href="#cite_note-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> The benzenium salt is crystalline with thermal stability up to 150 °C. <a href="/wiki/Bond_length" title="Bond length">Bond lengths</a> deduced from <a href="/wiki/X-ray_crystallography" title="X-ray crystallography">X-ray crystallography</a> are consistent with a cyclohexadienyl cation structure. </p> <div class="mw-heading mw-heading3"><h3 id="Acylium_ions">Acylium ions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbenium_ion&action=edit&section=11" title="Edit section: Acylium ions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>An <a href="/wiki/Acylium_ion" class="mw-redirect" title="Acylium ion">acylium ion</a> is a cation with the formula RCO<sup>+</sup>.<sup id="cite_ref-32" class="reference"><a href="#cite_note-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> The structure is described as R−C≡O<sup>+</sup> or R−<span class="sfrac nowrap;"><span style="display:none; display:inline-block; text-align:center;"><span style="display:block; line-height:0.8em; font-size:70%;">+</span><span style="display:block; line-height:1em;">C</span></span></span>=O. It is an acyl carbocation, but the actual structure has the oxygen and carbon linked by a triple bond. Such species are common reactive intermediates, for example, in the <a href="/w/index.php?title=Friedel%E2%88%92Crafts_acylation&action=edit&redlink=1" class="new" title="Friedel−Crafts acylation (page does not exist)">Friedel−Crafts acylations</a> also in many other <a href="/wiki/Organic_reaction" title="Organic reaction">organic reactions</a> such as the <a href="/wiki/Hayashi_rearrangement" title="Hayashi rearrangement">Hayashi rearrangement</a>. Salts containing acylium ions can be generated by removal of the halide from <a href="/wiki/Acyl_halide" title="Acyl halide">acyl halides</a>: </p> <dl><dd>RCOCl + SbCl<sub>5</sub> → RCO<sup>+</sup><span class="chemf nowrap">SbCl<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">6</sub></span></span></span></dd></dl> <p>The C–O distance in these cations is near 1.1 <a href="/wiki/%C3%85ngstr%C3%B6m" class="mw-redirect" title="Ångström">ångströms</a>, even shorter than that in <a href="/wiki/Carbon_monoxide" title="Carbon monoxide">carbon monoxide</a>.<sup id="cite_ref-33" class="reference"><a href="#cite_note-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> Acylium cations are characteristic fragments observed in EI-<a href="/wiki/Mass_spectra" class="mw-redirect" title="Mass spectra">mass spectra</a> of <a href="/wiki/Ketone" title="Ketone">ketones</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Vinyl_and_alkynyl_carbenium_ions">Vinyl and alkynyl carbenium ions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbenium_ion&action=edit&section=12" title="Edit section: Vinyl and alkynyl carbenium ions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Based on hydride ion affinity, the parent vinyl cation is less stable than even a primary sp<sup>2</sup>-hybridized carbocation, while an α alkyl-substituted vinyl cation has a stability that is comparable to the latter. Hence, vinyl cations are relatively uncommon intermediates. They can be generated by the ionization of a vinyl electrophile, provided the leaving group is sufficiently good (e.g., <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">TfO<sup><sup class="template-chem2-sup">−</sup></sup></span>, IPh, or <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">N<sub class="template-chem2-sub">2</sub></span>). They have been implicated as intermediates in some vinyl substitution reactions (designated as S<sub>N</sub>1(vinyl)) and as intermediates in the electrophilic addition reactions of arylalkynes. With the exception of the parent vinyl cation, which is believed to be a bridged species, and geometrically constrained cyclic vinyl cations, most vinyl cations take on sp hybridization and are linear. </p><p>Aryl cations are less stable than vinyl cations due to the ring-enforced distortion to a nonlinear geometry and approximately sp<sup>2</sup>-character of the unoccupied orbital. Only <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">N<sub class="template-chem2-sub">2</sub></span> in <a href="/wiki/Diazonium_compound" title="Diazonium compound">aryldiazonium</a> salts is a good enough leaving group for the chemical generation of aryl cations.<sup id="cite_ref-34" class="reference"><a href="#cite_note-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> </p><p>Alkynyl cations are extremely unstable, much less stable than even <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> (hydride ion affinity 386 kcal/mol versus 312 kcal/mol for <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>) and cannot be generated by purely chemical means. They can, however, be generated radiochemically via the <a href="/wiki/Beta_decay" title="Beta decay">beta decay</a> of <a href="/wiki/Tritium" title="Tritium">tritium</a>:<sup id="cite_ref-35" class="reference"><a href="#cite_note-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> </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 {RC#CT -> [RC#C^3 He]+ + e-}}+{\bar {\nu }}_{e}\longrightarrow {\ce {RC#C+ + ^{3}He + e-}}+{\bar {\nu }}_{e}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mtext>RC</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>≡</mo> </mrow> <mtext>CT</mtext> <mo stretchy="false">⟶</mo> <msup> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">[</mo> <mtext>RC</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>≡</mo> </mrow> <msup> <mtext>C</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> </msup> <mtext>He</mtext> <mo stretchy="false">]</mo> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mo>+</mo> </mrow> </msup> <mo>+</mo> <msup> <mtext>e</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> </msup> </mrow> <mo>+</mo> <msub> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mover> <mi>ν</mi> <mo stretchy="false">¯</mo> </mover> </mrow> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mi>e</mi> </mrow> </msub> <mo stretchy="false">⟶</mo> <mrow class="MJX-TeXAtom-ORD"> <mtext>RC</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>≡</mo> </mrow> <msup> <mtext>C</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>+</mo> </mrow> </msup> <mo>+</mo> <mmultiscripts> <mtext>He</mtext> <none /> <none /> <mprescripts /> <none /> <mn>3</mn> </mmultiscripts> <mo>+</mo> <msup> <mtext>e</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> </msup> </mrow> <mo>+</mo> <msub> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mover> <mi>ν</mi> <mo stretchy="false">¯</mo> </mover> </mrow> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mi>e</mi> </mrow> </msub> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {RC#CT -> [RC#C^3 He]+ + e-}}+{\bar {\nu }}_{e}\longrightarrow {\ce {RC#C+ + ^{3}He + e-}}+{\bar {\nu }}_{e}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/b407467d1926148009140dc78110535945708543" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -0.838ex; width:68.329ex; height:3.509ex;" alt="{\displaystyle {\ce {RC#CT -> [RC#C^3 He]+ + e-}}+{\bar {\nu }}_{e}\longrightarrow {\ce {RC#C+ + ^{3}He + e-}}+{\bar {\nu }}_{e}}"></span></dd></dl> <div class="mw-heading mw-heading2"><h2 id="Selected_applications">Selected applications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbenium_ion&action=edit&section=13" title="Edit section: Selected applications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Rosaniline_hydrochloride.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d7/Rosaniline_hydrochloride.svg/122px-Rosaniline_hydrochloride.svg.png" decoding="async" width="122" height="93" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d7/Rosaniline_hydrochloride.svg/183px-Rosaniline_hydrochloride.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d7/Rosaniline_hydrochloride.svg/244px-Rosaniline_hydrochloride.svg.png 2x" data-file-width="1515" data-file-height="1150" /></a><figcaption><a href="/wiki/Fuchsine" title="Fuchsine">Fuchsine</a> (hydrochloride salt), a commercial dye that contains a carbenium ion.</figcaption></figure> <p>Carbenium ions are so integrated into organic chemistry that a full inventory of their commercially useful reactions would be long. For example, <a href="/wiki/Catalytic_cracking" class="mw-redirect" title="Catalytic cracking">catalytic cracking</a>, a major step in <a href="/wiki/Petroleum_refining" class="mw-redirect" title="Petroleum refining">petroleum refining</a> involves carbenium ion intermediates.<sup id="cite_ref-36" class="reference"><a href="#cite_note-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> </p><p>The <a href="/wiki/Alkylation" title="Alkylation">alkylation</a> of benzene with <a href="/wiki/Alpha-olefin" class="mw-redirect" title="Alpha-olefin">alpha-olefins</a> to give <a href="/wiki/Linear_alkylbenzene" title="Linear alkylbenzene">linear alkylbenzene</a> (LABs) illustrates the behaviour of secondary carbenium ions. The alkylation is initiated by strong acids. LABs are a key precursor to <a href="/wiki/Detergent" title="Detergent">detergents</a>. </p><p>Derivatives of the <a href="/wiki/Triphenylcarbenium" title="Triphenylcarbenium">triphenylcarbenium</a> are the <a href="/wiki/Triarylmethane_dye" title="Triarylmethane dye">triarylmethane dyes</a>.<sup id="cite_ref-Ull_37-0" class="reference"><a href="#cite_note-Ull-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> </p><p>Acylium ions are intermediates in <a href="/wiki/Friedel-Crafts_acylation" class="mw-redirect" title="Friedel-Crafts acylation">Friedel-Crafts acylations</a> and <a href="/wiki/Koch_reaction" title="Koch reaction">Koch reactions</a>. </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=Carbenium_ion&action=edit&section=14" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Borenium_ion" class="mw-redirect" title="Borenium ion">Borenium ion</a></li> <li><a href="/wiki/Nitrenium_ion" title="Nitrenium ion">Nitrenium ion</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=Carbenium_ion&action=edit&section=15" 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). "Superacidic or Not…︁? Synthesis, Characterisation, and Acidity of the Room-Temperature Ionic Liquid [C(CH<sub>3</sub>)<sub>3</sub>]<sup>+</sup> [Al<sub>2</sub>Br<sub>7</sub>]<sup>−</sup>". <i>Chemistry – A European Journal</i>. <b>19</b> (1): 109–116. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fchem.201203260">10.1002/chem.201203260</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/23180742">23180742</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chemistry+%E2%80%93+A+European+Journal&rft.atitle=Superacidic+or+Not%E2%80%A6%EF%B8%81%3F+Synthesis%2C+Characterisation%2C+and+Acidity+of+the+Room-Temperature+Ionic+Liquid+%26%2391%3BC%28CH%3Csub%3E3%3C%2Fsub%3E%29%3Csub%3E3%3C%2Fsub%3E%26%2393%3B%3Csup%3E%2B%3C%2Fsup%3E+%26%2391%3BAl%3Csub%3E2%3C%2Fsub%3EBr%3Csub%3E7%3C%2Fsub%3E%26%2393%3B%3Csup%3E%E2%88%92%3C%2Fsup%3E&rft.volume=19&rft.issue=1&rft.pages=109-116&rft.date=2013&rft_id=info%3Adoi%2F10.1002%2Fchem.201203260&rft_id=info%3Apmid%2F23180742&rft.aulast=Scholz&rft.aufirst=Franziska&rft.au=Himmel%2C+Daniel&rft.au=Scherer%2C+Harald&rft.au=Krossing%2C+Ingo&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACarbenium+ion" class="Z3988"></span></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFThomas_H._LoweryKathleen_Schueller_Richardson1981" class="citation book cs1">Thomas H. Lowery; Kathleen Schueller Richardson (1981). <i>Mechanism and Theory in Organic Chemistry, Second Edition</i>. Harper and Rowe. p. 396. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0-06-044083-X" title="Special:BookSources/0-06-044083-X"><bdi>0-06-044083-X</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Mechanism+and+Theory+in+Organic+Chemistry%2C+Second+Edition&rft.pages=396&rft.pub=Harper+and+Rowe&rft.date=1981&rft.isbn=0-06-044083-X&rft.au=Thomas+H.+Lowery&rft.au=Kathleen+Schueller+Richardson&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACarbenium+ion" class="Z3988"></span></span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text">March</span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCarey2007" class="citation book cs1">Carey, Francis A. (2007). <i>Advanced Organic Chemistry: Part A: Structure and Mechanisms</i>. Sundberg, Richard J. (5th ed.). New York: Springer. p. 440. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780387448978" title="Special:BookSources/9780387448978"><bdi>9780387448978</bdi></a>. <a href="/wiki/OCLC_(identifier)" class="mw-redirect" title="OCLC (identifier)">OCLC</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/oclc/154040953">154040953</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Advanced+Organic+Chemistry%3A+Part+A%3A+Structure+and+Mechanisms&rft.place=New+York&rft.pages=440&rft.edition=5th&rft.pub=Springer&rft.date=2007&rft_id=info%3Aoclcnum%2F154040953&rft.isbn=9780387448978&rft.aulast=Carey&rft.aufirst=Francis+A.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACarbenium+ion" class="Z3988"></span></span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFScholzHimmelHeinemannSchleyer2013" class="citation journal cs1">Scholz, F.; Himmel, D.; Heinemann, F. W.; Schleyer, P. v R.; Meyer, K.; Krossing, I. (2013-07-05). "Crystal Structure Determination of the Nonclassical 2-Norbornyl Cation". <i>Science</i>. <b>341</b> (6141): 62–64. <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/2013Sci...341...62S">2013Sci...341...62S</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1126%2Fscience.1238849">10.1126/science.1238849</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0036-8075">0036-8075</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/23828938">23828938</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:206549219">206549219</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Science&rft.atitle=Crystal+Structure+Determination+of+the+Nonclassical+2-Norbornyl+Cation&rft.volume=341&rft.issue=6141&rft.pages=62-64&rft.date=2013-07-05&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A206549219%23id-name%3DS2CID&rft_id=info%3Abibcode%2F2013Sci...341...62S&rft.issn=0036-8075&rft_id=info%3Adoi%2F10.1126%2Fscience.1238849&rft_id=info%3Apmid%2F23828938&rft.aulast=Scholz&rft.aufirst=F.&rft.au=Himmel%2C+D.&rft.au=Heinemann%2C+F.+W.&rft.au=Schleyer%2C+P.+v+R.&rft.au=Meyer%2C+K.&rft.au=Krossing%2C+I.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACarbenium+ion" class="Z3988"></span></span> </li> <li id="cite_note-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-6">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCarey2007" class="citation book cs1">Carey, Francis A. (2007). <i>Advanced Organic Chemistry: Part A: Structure and Mechanisms</i>. Sundberg, Richard J. (5th ed.). New York: Springer. p. 436. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780387448978" title="Special:BookSources/9780387448978"><bdi>9780387448978</bdi></a>. <a href="/wiki/OCLC_(identifier)" class="mw-redirect" title="OCLC (identifier)">OCLC</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/oclc/154040953">154040953</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Advanced+Organic+Chemistry%3A+Part+A%3A+Structure+and+Mechanisms&rft.place=New+York&rft.pages=436&rft.edition=5th&rft.pub=Springer&rft.date=2007&rft_id=info%3Aoclcnum%2F154040953&rft.isbn=9780387448978&rft.aulast=Carey&rft.aufirst=Francis+A.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACarbenium+ion" class="Z3988"></span></span> </li> <li id="cite_note-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-7">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSmith,_Michael_B.March,_Jerry2007" class="citation cs2">Smith, Michael B.; <a href="/wiki/Jerry_March" title="Jerry March">March, Jerry</a> (2007), <a rel="nofollow" class="external text" href="https://books.google.com/books?id=JDR-nZpojeEC&printsec=frontcover"><i>Advanced Organic Chemistry: Reactions, Mechanisms, and Structure</i></a> (6th ed.), New York: Wiley-Interscience, p. 239, <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-471-72091-1" title="Special:BookSources/978-0-471-72091-1"><bdi>978-0-471-72091-1</bdi></a></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Advanced+Organic+Chemistry%3A+Reactions%2C+Mechanisms%2C+and+Structure&rft.place=New+York&rft.pages=239&rft.edition=6th&rft.pub=Wiley-Interscience&rft.date=2007&rft.isbn=978-0-471-72091-1&rft.au=Smith%2C+Michael+B.&rft.au=March%2C+Jerry&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DJDR-nZpojeEC%26printsec%3Dfrontcover&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACarbenium+ion" class="Z3988"></span></span> </li> <li id="cite_note-Gruetz-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-Gruetz_8-0">^</a></b></span> <span class="reference-text">Hansjörg Grützmacher, Christina M. 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New York: Springer. pp. 300–301. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780387448978" title="Special:BookSources/9780387448978"><bdi>9780387448978</bdi></a>. <a href="/wiki/OCLC_(identifier)" class="mw-redirect" title="OCLC (identifier)">OCLC</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/oclc/154040953">154040953</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Advanced+Organic+Chemistry%3A+Part+A%3A+Structure+and+Mechanisms&rft.place=New+York&rft.pages=300-301&rft.edition=5th&rft.pub=Springer&rft.date=2007&rft_id=info%3Aoclcnum%2F154040953&rft.isbn=9780387448978&rft.aulast=Carey&rft.aufirst=Francis+A.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACarbenium+ion" class="Z3988"></span></span> </li> <li id="cite_note-21"><span class="mw-cite-backlink"><b><a href="#cite_ref-21">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCarey2007" class="citation book cs1">Carey, Francis A. 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Weinheim: Wiley-VCH. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F14356007.a27_179">10.1002/14356007.a27_179</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3527306732" title="Special:BookSources/978-3527306732"><bdi>978-3527306732</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Triarylmethane+and+Diarylmethane+Dyes&rft.btitle=Ullmann%27s+Encyclopedia+of+Industrial+Chemistry&rft.place=Weinheim&rft.pub=Wiley-VCH&rft.date=2000&rft_id=info%3Adoi%2F10.1002%2F14356007.a27_179&rft.isbn=978-3527306732&rft.aulast=Gessner&rft.aufirst=Thomas&rft.au=Mayer%2C+Udo&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACarbenium+ion" class="Z3988"></span></span> </li> </ol></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="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Carbenium_ion&oldid=1256315687">https://en.wikipedia.org/w/index.php?title=Carbenium_ion&oldid=1256315687</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Categories</a>: <ul><li><a href="/wiki/Category:Cations" title="Category:Cations">Cations</a></li><li><a href="/wiki/Category:Reactive_intermediates" title="Category:Reactive intermediates">Reactive intermediates</a></li><li><a href="/wiki/Category:Carbocations" title="Category:Carbocations">Carbocations</a></li></ul></div><div id="mw-hidden-catlinks" class="mw-hidden-catlinks mw-hidden-cats-hidden">Hidden categories: <ul><li><a href="/wiki/Category:Webarchive_template_wayback_links" title="Category:Webarchive template wayback links">Webarchive template wayback links</a></li><li><a href="/wiki/Category:Articles_with_short_description" title="Category:Articles with short description">Articles with short description</a></li><li><a href="/wiki/Category:Short_description_matches_Wikidata" title="Category:Short description matches Wikidata">Short description matches Wikidata</a></li><li><a href="/wiki/Category:All_articles_with_incomplete_citations" title="Category:All articles with incomplete citations">All articles with incomplete citations</a></li><li><a href="/wiki/Category:Articles_with_incomplete_citations_from_October_2024" title="Category:Articles with incomplete citations from October 2024">Articles with incomplete citations from October 2024</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"> This page was last edited on 9 November 2024, at 09:14<span class="anonymous-show"> (UTC)</span>.</li> <li id="footer-info-copyright">Text is available under the <a href="/wiki/Wikipedia:Text_of_the_Creative_Commons_Attribution-ShareAlike_4.0_International_License" title="Wikipedia:Text of the Creative Commons Attribution-ShareAlike 4.0 International License">Creative Commons Attribution-ShareAlike 4.0 License</a>; additional terms may apply. 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