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</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"> 5 References </div> </a> <ul id="toc-References-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 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href="https://azb.wikipedia.org/wiki/%D9%87%D9%82%D8%B2%D8%A7%D9%85%D8%AA%DB%8C%D9%84%E2%80%8C%D8%A8%D9%86%D8%B2%D9%86" title="هقزامتیل‌بنزن – South Azerbaijani" lang="azb" hreflang="azb" data-title="هقزامتیل‌بنزن" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target">تۆرکجه</a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Hexamethylbenzol" title="Hexamethylbenzol – German" lang="de" hreflang="de" data-title="Hexamethylbenzol" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target">Deutsch</a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Heksametilbenzeno" title="Heksametilbenzeno – Esperanto" lang="eo" hreflang="eo" data-title="Heksametilbenzeno" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target">Esperanto</a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D9%87%DA%AF%D8%B2%D8%A7%D9%85%D8%AA%DB%8C%D9%84%E2%80%8C%D8%A8%D9%86%D8%B2%D9%86" title="هگزامتیل‌بنزن – Persian" lang="fa" hreflang="fa" data-title="هگزامتیل‌بنزن" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target">فارسی</a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Hexam%C3%A9thylbenz%C3%A8ne" title="Hexaméthylbenzène – French" lang="fr" hreflang="fr" data-title="Hexaméthylbenzène" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target">Français</a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Heksametilbenzena" title="Heksametilbenzena – Indonesian" lang="id" hreflang="id" data-title="Heksametilbenzena" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target">Bahasa Indonesia</a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Esametilbenzene" title="Esametilbenzene – Italian" lang="it" hreflang="it" data-title="Esametilbenzene" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target">Italiano</a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Hexamethylbenzeen" title="Hexamethylbenzeen – Dutch" lang="nl" hreflang="nl" data-title="Hexamethylbenzeen" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target">Nederlands</a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%98%E3%82%AD%E3%82%B5%E3%83%A1%E3%83%81%E3%83%AB%E3%83%99%E3%83%B3%E3%82%BC%E3%83%B3" title="ヘキサメチルベンゼン – Japanese" lang="ja" hreflang="ja" data-title="ヘキサメチルベンゼン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target">日本語</a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Hexametilbenzen" title="Hexametilbenzen – Romanian" lang="ro" hreflang="ro" data-title="Hexametilbenzen" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target">Română</a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%93%D0%B5%D0%BA%D1%81%D0%B0%D0%BC%D0%B5%D1%82%D0%B8%D0%BB%D0%B1%D0%B5%D0%BD%D0%B7%D0%BE%D0%BB" title="Гексаметилбензол – Russian" lang="ru" hreflang="ru" data-title="Гексаметилбензол" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target">Русский</a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Heksametilbenzen" title="Heksametilbenzen – Serbian" lang="sr" hreflang="sr" 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Click here for more information."><img alt="This is a good article. Click here for more information." src="//upload.wikimedia.org/wikipedia/en/thumb/9/94/Symbol_support_vote.svg/19px-Symbol_support_vote.svg.png" decoding="async" width="19" height="20" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/94/Symbol_support_vote.svg/29px-Symbol_support_vote.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/94/Symbol_support_vote.svg/39px-Symbol_support_vote.svg.png 2x" data-file-width="180" data-file-height="185" /></a></div></div> </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">Chemical compound</div> <style data-mw-deduplicate="TemplateStyles:r1084375498">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}</style> <table class="infobox ib-chembox"> <caption>Hexamethylbenzene </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><a href="/wiki/File:Hexamethylbenzene.svg" class="mw-file-description"><img alt="Structural formula of hexamethylbenzene" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/33/Hexamethylbenzene.svg/130px-Hexamethylbenzene.svg.png" decoding="async" width="130" height="115" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/33/Hexamethylbenzene.svg/195px-Hexamethylbenzene.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/33/Hexamethylbenzene.svg/260px-Hexamethylbenzene.svg.png 2x" data-file-width="620" data-file-height="547" /></a> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><a href="/wiki/File:Hexamethylbenzene_3D_ball.png" class="mw-file-description"><img alt="Ball-and-stick model of the hexamethylbenzene molecule" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5f/Hexamethylbenzene_3D_ball.png/130px-Hexamethylbenzene_3D_ball.png" decoding="async" width="130" height="131" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5f/Hexamethylbenzene_3D_ball.png/195px-Hexamethylbenzene_3D_ball.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5f/Hexamethylbenzene_3D_ball.png/260px-Hexamethylbenzene_3D_ball.png 2x" data-file-width="1991" data-file-height="2000" /></a> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><a href="/wiki/File:HMB2wBottle.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/74/HMB2wBottle.jpg/220px-HMB2wBottle.jpg" decoding="async" width="220" height="96" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/74/HMB2wBottle.jpg/330px-HMB2wBottle.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/74/HMB2wBottle.jpg/440px-HMB2wBottle.jpg 2x" data-file-width="2620" data-file-height="1143" /></a> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Preferred_IUPAC_name" title="Preferred IUPAC name">Preferred IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">Hexamethylbenzene</div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;">Other names <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">1,2,3,4,5,6-Hexamethylbenzene Mellitene</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=87-85-4">87-85-4</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=c1%28c%28c%28c%28c%28c1C%29C%29C%29C%29C%29C">Interactive image</a></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=39001">CHEBI:39001</a> <img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" />N</li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.6642.html">6642</a> <img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" />N</li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard">ECHA InfoCard</a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.001.616">100.001.616</a> <a href="https://www.wikidata.org/wiki/Q413592#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/6908">6908</a></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/J8SD5741V8">J8SD5741V8</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> (<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID3058957">DTXSID3058957</a> <a href="https://www.wikidata.org/wiki/Q413592#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C12H18/c1-7-8(2)10(4)12(6)11(5)9(7)3/h1-6H3 <img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" />N</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: YUWFEBAXEOLKSG-UHFFFAOYSA-N <img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" />N</div></div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1/C12H18/c1-7-8(2)10(4)12(6)11(5)9(7)3/h1-6H3</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: YUWFEBAXEOLKSG-UHFFFAOYAF</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">c1(c(c(c(c(c1C)C)C)C)C)C</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td>C12H18 </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td>162.276 g·mol−1 </td></tr> <tr> <td>Appearance </td> <td>White crystalline powder </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>1.0630 g cm−3 </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>165.6 ± 0.7 °C </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>265.2 °C (509.4 °F; 538.3 K) </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Aqueous_solution" title="Aqueous solution">Solubility in water</a></div> </td> <td>insoluble </td></tr> <tr> <td><a href="/wiki/Solubility" title="Solubility">Solubility</a> </td> <td><a href="/wiki/Acetic_acid" title="Acetic acid">acetic acid</a>, <a href="/wiki/Acetone" title="Acetone">acetone</a>, <a href="/wiki/Benzene" title="Benzene">benzene</a>, <a href="/wiki/Chloroform" title="Chloroform">chloroform</a>, <a href="/wiki/Diethyl_ether" title="Diethyl ether">diethyl ether</a>, <a href="/wiki/Ethanol" title="Ethanol">ethanol</a> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/12px-X_mark.svg.png" decoding="async" width="12" height="14" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/18px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/24px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" />N <a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=431181841&page2=Hexamethylbenzene">verify</a> (<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">what is</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y<img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" />N ?) </div></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> Hexamethylbenzene, also known as mellitene, is a <a href="/wiki/Hydrocarbon" title="Hydrocarbon">hydrocarbon</a> with the <a href="/wiki/Molecular_formula" class="mw-redirect" title="Molecular formula">molecular formula</a> C12H18 and the <a href="/wiki/Structural_formula#Condensed_formulas" title="Structural formula">condensed structural formula</a> C6(CH3)6. It is an <a href="/wiki/Aromatic_compound" title="Aromatic compound">aromatic compound</a> and a <a href="/wiki/Derivative_(chemistry)" title="Derivative (chemistry)">derivative</a> of <a href="/wiki/Benzene" title="Benzene">benzene</a>, where benzene's six hydrogen atoms have each been replaced by a <a href="/wiki/Methyl_group" title="Methyl group">methyl group</a>. In 1929, <a href="/wiki/Kathleen_Lonsdale" title="Kathleen Lonsdale">Kathleen Lonsdale</a> reported the <a href="/wiki/Crystal_structure" title="Crystal structure">crystal structure</a> of hexamethylbenzene, demonstrating that the central ring is hexagonal and flat<a href="#cite_note-Lonsdale-1">[1]</a> and thereby ending an ongoing debate about the physical parameters of the benzene system. This was a historically significant result, both for the field of <a href="/wiki/X-ray_crystallography" title="X-ray crystallography">X-ray crystallography</a> and for understanding <a href="/wiki/Aromaticity" title="Aromaticity">aromaticity</a>.<a href="#cite_note-Lydon1-2">[2]</a><a href="#cite_note-Lydon2-3">[3]</a> Hexamethylbenzene can be oxidised to <a href="/wiki/Mellitic_acid" title="Mellitic acid">mellitic acid</a>,<a href="#cite_note-HMBoxidation-4">[4]</a> which is found in nature as its aluminium <a href="/wiki/Salt_(chemistry)" title="Salt (chemistry)">salt</a> in the rare mineral <a href="/wiki/Mellite" title="Mellite">mellite</a>.<a href="#cite_note-mellite-5">[5]</a> Hexamethylbenzene can be used as a <a href="/wiki/Ligand" title="Ligand">ligand</a> in <a href="/wiki/Organometallic_compound" class="mw-redirect" title="Organometallic compound">organometallic compounds</a>.<a href="#cite_note-AreneReview-6">[6]</a> An example from <a href="/wiki/Organoruthenium_chemistry" title="Organoruthenium chemistry">organoruthenium chemistry</a> shows structural change in the ligand associated with changes in the <a href="/wiki/Oxidation_state" title="Oxidation state">oxidation state</a> of the metal centre,<a href="#cite_note-Fe-7">[7]</a><a href="#cite_note-RuHMB2-8">[8]</a> though the same change is not observed in the <a href="/wiki/Analogue_(chemistry)" class="mw-redirect" title="Analogue (chemistry)">analogous</a> <a href="/wiki/Organoiron_chemistry" title="Organoiron chemistry">organoiron</a> system.<a href="#cite_note-Fe-7">[7]</a> In 2016 the crystal structure of the hexamethylbenzene <a href="/wiki/Dication" title="Dication">dication</a> C 6(CH 3)2+ 6 was reported in <a href="/wiki/Angewandte_Chemie_International_Edition" class="mw-redirect" title="Angewandte Chemie International Edition">Angewandte Chemie International Edition</a>,<a href="#cite_note-PyramidalAngewChem-9">[9]</a> showing a pyramidal structure in which a single carbon atom has a bonding interaction with six other carbon atoms.<a href="#cite_note-PyramidalNewSci-10">[10]</a><a href="#cite_note-PyramidalC&ENews-11">[11]</a> This structure was "unprecedented",<a href="#cite_note-PyramidalAngewChem-9">[9]</a> as the usual maximum <a href="/wiki/Valence_(chemistry)" title="Valence (chemistry)">valence</a> of <a href="/wiki/Carbon" title="Carbon">carbon</a> is four, and it attracted attention from <a href="/wiki/New_Scientist" title="New Scientist">New Scientist</a>,<a href="#cite_note-PyramidalNewSci-10">[10]</a> <a href="/wiki/Chemical_%26_Engineering_News" title="Chemical & Engineering News">Chemical & Engineering News</a>,<a href="#cite_note-PyramidalC&ENews-11">[11]</a> and <a href="/wiki/Science_News" title="Science News">Science News</a>.<a href="#cite_note-PyramidalSciNews-12">[12]</a> The structure does not violate the <a href="/wiki/Octet_rule" title="Octet rule">octet rule</a> since the carbon–carbon bonds formed are not two-electron bonds, and is <a href="/wiki/Pedagogy" title="Pedagogy">pedagogically</a> valuable for illustrating that a carbon atom "can [directly bond] with more than four atoms".<a href="#cite_note-PyramidalSciNews-12">[12]</a> <a href="/wiki/Steven_Bachrach" title="Steven Bachrach">Steven Bachrach</a> has demonstrated that the compound is hypercoordinated but not <a href="/wiki/Hypervalent" class="mw-redirect" title="Hypervalent">hypervalent</a>, and also explained its aromaticity.<a href="#cite_note-Bachrach-13">[13]</a> The idea of describing the chemical bonding in compounds and <a href="/wiki/Chemical_species" title="Chemical species">chemical species</a> in this way through the lens of <a href="/wiki/Organometallic_chemistry" title="Organometallic chemistry">organometallic chemistry</a> was proposed in 1975,<a href="#cite_note-HMBviaOMetChem-14">[14]</a> soon after the dication C 6(CH 3)2+ 6 was first observed.<a href="#cite_note-HMBcatObs1-15">[15]</a><a href="#cite_note-HMBcatObs2-16">[16]</a><a href="#cite_note-HMBcatObs3-17">[17]</a> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Nomenclature_and_properties">Nomenclature and properties</h2>[<a href="/w/index.php?title=Hexamethylbenzene&action=edit&section=1" title="Edit section: Nomenclature and properties">edit</a>]</div> The complete <a href="/wiki/IUPAC_nomenclature_of_organic_chemistry" title="IUPAC nomenclature of organic chemistry">IUPAC name</a> for this compound is 1,2,3,4,5,6-hexamethylbenzene.<a href="#cite_note-18">[18]</a> The <a href="/wiki/Locant" title="Locant">locants</a> (the numbers in front of the name) are superfluous, however, as the name hexamethylbenzene uniquely identifies a single substance and thus is the formal IUPAC name for the compound.<a href="#cite_note-19">[19]</a> It is an <a href="/wiki/Aromatic_compound" title="Aromatic compound">aromatic compound</a>, with six π electrons (satisfying <a href="/wiki/H%C3%BCckel%27s_rule" title="Hückel's rule">Hückel's rule</a>) delocalised over a <a href="/wiki/Aromatic_hydrocarbon#Benzene_ring_model" class="mw-redirect" title="Aromatic hydrocarbon">cyclic planar system</a>; each of the six ring carbon atoms is sp2 <a href="/wiki/Orbital_hybridisation" title="Orbital hybridisation">hybridised</a> and displays <a href="/wiki/Trigonal_planar_molecular_geometry" title="Trigonal planar molecular geometry">trigonal planar</a> <a href="/wiki/Molecular_geometry" title="Molecular geometry">geometry</a>, while each methyl carbon is <a href="/wiki/Tetrahedral_molecular_geometry" title="Tetrahedral molecular geometry">tetrahedral</a> with sp3 hybridisation, consistent with the empirical description of its structure.<a href="#cite_note-Lonsdale-1">[1]</a> Solid hexamethylbenzene occurs as colourless to white crystalline <a href="/wiki/Orthorhombic_crystal_system" title="Orthorhombic crystal system">orthorhombic</a> prisms or needles<a href="#cite_note-CRC-20">[20]</a> with a <a href="/wiki/Melting_point" title="Melting point">melting point</a> of 165–166 °C,<a href="#cite_note-HMBOrgSynth-21">[21]</a> a <a href="/wiki/Boiling_point" title="Boiling point">boiling point</a> of 268 °C, and a <a href="/wiki/Density" title="Density">density</a> of 1.0630 g cm−3.<a href="#cite_note-CRC-20">[20]</a> It is insoluble in water, but soluble in organic solvents including <a href="/wiki/Benzene" title="Benzene">benzene</a> and <a href="/wiki/Ethanol" title="Ethanol">ethanol</a>.<a href="#cite_note-CRC-20">[20]</a> <style data-mw-deduplicate="TemplateStyles:r1237032888/mw-parser-output/.tmulti">.mw-parser-output .tmulti .multiimageinner{display:flex;flex-direction:column}.mw-parser-output .tmulti .trow{display:flex;flex-direction:row;clear:left;flex-wrap:wrap;width:100%;box-sizing:border-box}.mw-parser-output .tmulti .tsingle{margin:1px;float:left}.mw-parser-output .tmulti .theader{clear:both;font-weight:bold;text-align:center;align-self:center;background-color:transparent;width:100%}.mw-parser-output .tmulti .thumbcaption{background-color:transparent}.mw-parser-output .tmulti .text-align-left{text-align:left}.mw-parser-output .tmulti .text-align-right{text-align:right}.mw-parser-output .tmulti .text-align-center{text-align:center}@media all and (max-width:720px){.mw-parser-output .tmulti .thumbinner{width:100%!important;box-sizing:border-box;max-width:none!important;align-items:center}.mw-parser-output .tmulti .trow{justify-content:center}.mw-parser-output .tmulti .tsingle{float:none!important;max-width:100%!important;box-sizing:border-box;text-align:center}.mw-parser-output .tmulti .tsingle .thumbcaption{text-align:left}.mw-parser-output .tmulti .trow>.thumbcaption{text-align:center}}@media screen{html.skin-theme-clientpref-night .mw-parser-output .tmulti .multiimageinner img{background-color:white}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .tmulti .multiimageinner img{background-color:white}}</style><div class="thumb tmulti tnone center"><div class="thumbinner multiimageinner" style="width:367px;max-width:367px"><div class="trow"><div class="tsingle" style="width:176px;max-width:176px"><div class="thumbimage" style="height:160px;overflow:hidden"><a href="/wiki/File:Mellite-20130.jpg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f4/Mellite-20130.jpg/174px-Mellite-20130.jpg" decoding="async" width="174" height="160" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f4/Mellite-20130.jpg/261px-Mellite-20130.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f4/Mellite-20130.jpg/348px-Mellite-20130.jpg 2x" data-file-width="400" data-file-height="368" /></a></div></div><div class="tsingle" style="width:187px;max-width:187px"><div class="thumbimage" style="height:160px;overflow:hidden"><a href="/wiki/File:Mellitic-acid.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3f/Mellitic-acid.svg/185px-Mellitic-acid.svg.png" decoding="async" width="185" height="160" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3f/Mellitic-acid.svg/278px-Mellitic-acid.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3f/Mellitic-acid.svg/370px-Mellitic-acid.svg.png 2x" data-file-width="416" data-file-height="360" /></a></div></div></div><div class="trow" style="display:flex"><div class="thumbcaption">The mineral <a href="/wiki/Mellite" title="Mellite">mellite</a> (left) is composed of a hydrated aluminium salt of <a href="/wiki/Mellitic_acid" title="Mellitic acid">mellitic acid</a> (right)</div></div></div></div> Hexamethylbenzene is sometimes called mellitene,<a href="#cite_note-CRC-20">[20]</a> a name derived from <a href="/wiki/Mellite" title="Mellite">mellite</a>, a rare honey-coloured <a href="/wiki/Mineral" title="Mineral">mineral</a> (<a href="https://en.wiktionary.org/wiki/%CE%BC%CE%AD%CE%BB%CE%B9" class="extiw" title="wikt:μέλι">μέλι</a> meli (<a href="/wiki/Genitive_case" title="Genitive case">GEN</a> μέλιτος melitos) is the Greek word for honey.<a href="#cite_note-22">[22]</a>) Mellite is composed of a <a href="/wiki/Water_of_crystallisation" class="mw-redirect" title="Water of crystallisation">hydrated</a> aluminium salt of benzenehexacarboxylic acid (mellitic acid), with formula Al 2[C 6(CO 2) 6]•16H 2O.<a href="#cite_note-mellite-5">[5]</a> Mellitic acid itself can be derived from the mineral,<a href="#cite_note-23">[23]</a> and subsequent <a href="/wiki/Organic_reduction" class="mw-redirect" title="Organic reduction">reduction</a> yields mellitene. Conversely, mellitene can be <a href="/wiki/Organic_oxidation" class="mw-redirect" title="Organic oxidation">oxidised</a> to form mellitic acid:<a href="#cite_note-HMBoxidation-4">[4]</a> <figure class="mw-halign-center" typeof="mw:File/Frameless"><a href="/wiki/File:Mellitic_redox.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8e/Mellitic_redox.png/400px-Mellitic_redox.png" decoding="async" width="400" height="118" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8e/Mellitic_redox.png/600px-Mellitic_redox.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8e/Mellitic_redox.png/800px-Mellitic_redox.png 2x" data-file-width="2456" data-file-height="726" /></a><figcaption></figcaption></figure> <div style="clear:both;" class=""></div>Treatment of hexamethylbenzene with a superelectrophilic mixture of methyl chloride and aluminum trichloride (a source of Meδ⊕Cl---δ⊖AlCl3) gives heptamethylbenzenium cation, one of the first carbocations to be directly observed. <figure class="mw-halign-center" typeof="mw:File/Frameless"><a href="/wiki/File:Heptamethylbenzenium2.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6c/Heptamethylbenzenium2.png/450px-Heptamethylbenzenium2.png" decoding="async" width="450" height="122" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6c/Heptamethylbenzenium2.png/675px-Heptamethylbenzenium2.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6c/Heptamethylbenzenium2.png/900px-Heptamethylbenzenium2.png 2x" data-file-width="8696" data-file-height="2350" /></a><figcaption></figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Structure">Structure</h3>[<a href="/w/index.php?title=Hexamethylbenzene&action=edit&section=2" title="Edit section: Structure">edit</a>]</div> In 1927 <a href="/wiki/Kathleen_Lonsdale" title="Kathleen Lonsdale">Kathleen Lonsdale</a> determined the <a href="/wiki/Crystal_structure" title="Crystal structure">solid structure</a> of hexamethylbenzene from crystals provided by <a href="/wiki/Christopher_Kelk_Ingold" title="Christopher Kelk Ingold">Christopher Kelk Ingold</a>.<a href="#cite_note-Lydon2-3">[3]</a> Her <a href="/wiki/X-ray_diffraction" title="X-ray diffraction">X-ray diffraction</a> analysis was published in <a href="/wiki/Nature_(journal)" title="Nature (journal)">Nature</a><a href="#cite_note-24">[24]</a> and was subsequently described as "remarkable ... for that early date".<a href="#cite_note-Lydon2-3">[3]</a> Lonsdale described the work in her book Crystals and X-Rays,<a href="#cite_note-25">[25]</a> explaining that she recognised that, though the <a href="/wiki/Unit_cell" title="Unit cell">unit cell</a> was <a href="/wiki/Triclinic" class="mw-redirect" title="Triclinic">triclinic</a>, the <a href="/wiki/Diffraction_pattern" class="mw-redirect" title="Diffraction pattern">diffraction pattern</a> had pseudo-hexagonal symmetry that allowed the structural possibilities to be restricted sufficiently for a trial-and-error approach to produce a model.<a href="#cite_note-Lydon2-3">[3]</a> This work definitively showed that hexamethylbenzene is flat and that the carbon-to-carbon distances within the ring are the same,<a href="#cite_note-Lydon1-2">[2]</a> providing crucial evidence in understanding the nature of <a href="/wiki/Aromaticity" title="Aromaticity">aromaticity</a>. <div class="mw-heading mw-heading2"><h2 id="Preparation">Preparation</h2>[<a href="/w/index.php?title=Hexamethylbenzene&action=edit&section=3" title="Edit section: Preparation">edit</a>]</div> The compound can be prepared by reacting <a href="/wiki/Phenol" title="Phenol">phenol</a> with <a href="/wiki/Methanol" title="Methanol">methanol</a> at elevated temperatures over a suitable solid <a href="/wiki/Catalyst" class="mw-redirect" title="Catalyst">catalyst</a> such as <a href="/wiki/Alumina" class="mw-redirect" title="Alumina">alumina</a>.<a href="#cite_note-HMBSynth-26">[26]</a><a href="#cite_note-HMBOrgSynth-21">[21]</a><a href="#cite_note-PMB-27">[27]</a> The <a href="/wiki/Reaction_mechanism" title="Reaction mechanism">mechanism</a> of the process has been studied extensively,<a href="#cite_note-Koptyug1-28">[28]</a><a href="#cite_note-Ipatiew-29">[29]</a><a href="#cite_note-Takeshi1-30">[30]</a><a href="#cite_note-Takeshi2-31">[31]</a> with several <a href="/wiki/Reaction_intermediate" title="Reaction intermediate">intermediates</a> having been identified.<a href="#cite_note-PMB-27">[27]</a><a href="#cite_note-CullinaneChard-32">[32]</a><a href="#cite_note-Koptyug2-33">[33]</a> <a href="/wiki/Alkyne_trimerisation" title="Alkyne trimerisation">Alkyne trimerisation</a> of <a href="/wiki/Dimethylacetylene" class="mw-redirect" title="Dimethylacetylene">dimethylacetylene</a> also yields hexamethylbenzene<a href="#cite_note-Trimerisation-34">[34]</a> in the presence of a suitable catalyst.<a href="#cite_note-Cr-35">[35]</a><a href="#cite_note-Ti-36">[36]</a> In 1880, <a href="/wiki/Joseph_Achille_Le_Bel" title="Joseph Achille Le Bel">Joseph Achille Le Bel</a> and William H. Greene reported<a href="#cite_note-37">[37]</a> what has been described as an "extraordinary" <a href="/wiki/Zinc_chloride" title="Zinc chloride">zinc chloride</a>-<a href="/wiki/Catalysis" title="Catalysis">catalysed</a> <a href="/wiki/One-pot_synthesis" title="One-pot synthesis">one-pot synthesis</a> of hexamethylbenzene from <a href="/wiki/Methanol" title="Methanol">methanol</a>.<a href="#cite_note-HMB-38">[38]</a> At the catalyst's melting point (283 °C), the reaction has a <a href="/wiki/Gibbs_free_energy" title="Gibbs free energy">Gibbs free energy</a> (ΔG) of −1090 kJ mol−1 and can be idealised as:<a href="#cite_note-HMB-38">[38]</a> <dl><dd>15 CH 3OH   →   C 6(CH 3) 6   +   3 CH 4   +   15 H 2O</dd></dl> Le Bel and Greene rationalised the process as involving <a href="/wiki/Aromatisation" class="mw-redirect" title="Aromatisation">aromatisation</a> by condensation of <a href="/wiki/Methylene_(compound)" title="Methylene (compound)">methylene</a> units, formed by dehydration of methanol molecules, followed by complete <a href="/wiki/Friedel%E2%80%93Crafts" class="mw-redirect" title="Friedel–Crafts">Friedel–Crafts</a> methylation of the resulting benzene ring with <a href="/wiki/Chloromethane" title="Chloromethane">chloromethane</a> generated in situ.<a href="#cite_note-HMB-38">[38]</a> The major products were a mixture of <a href="/wiki/Saturated_hydrocarbon" class="mw-redirect" title="Saturated hydrocarbon">saturated hydrocarbons</a>, with hexamethylbenzene as a minor product.<a href="#cite_note-39">[39]</a> Hexamethylbenzene is also produced as a minor product in the Friedel–Crafts alkylation synthesis of <a href="/wiki/Durene" title="Durene">durene</a> from <a href="/wiki/P-xylene" class="mw-redirect" title="P-xylene">p-xylene</a>, and can be produced by <a href="/wiki/Alkylation" title="Alkylation">alkylation</a> in good yield from durene or <a href="/wiki/Pentamethylbenzene" title="Pentamethylbenzene">pentamethylbenzene</a>.<a href="#cite_note-40">[40]</a> Hexamethylbenzene is typically prepared in the <a href="/wiki/Gas" title="Gas">gas phase</a> at elevated temperatures over solid catalysts. An early approach to preparing hexamethylbenzene involved reacting a mixture of <a href="/wiki/Acetone" title="Acetone">acetone</a> and methanol vapours over an <a href="/wiki/Alumina" class="mw-redirect" title="Alumina">alumina</a> catalyst at 400 °C.<a href="#cite_note-41">[41]</a> Combining <a href="/wiki/Phenol" title="Phenol">phenols</a> with methanol over alumina in a dry <a href="/wiki/Carbon_dioxide" title="Carbon dioxide">carbon dioxide</a> atmosphere at 410–440 °C also produces hexamethylbenzene,<a href="#cite_note-HMBSynth-26">[26]</a> though as part of a complex mixture of <a href="/wiki/Anisole" title="Anisole">anisole</a> (methoxybenzene), <a href="/wiki/Cresol" title="Cresol">cresols</a> (methylphenols), and other methylated phenols.<a href="#cite_note-CullinaneChard-32">[32]</a> An Organic Syntheses preparation, using methanol and phenol with an alumina catalyst at 530 °C, gives approximately a 66% yield,<a href="#cite_note-HMBOrgSynth-21">[21]</a> though synthesis under different conditions has also been reported.<a href="#cite_note-PMB-27">[27]</a> <figure class="mw-halign-center" typeof="mw:File/Frameless"><a href="/wiki/File:Hexamethylbenzene_synthesis.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9c/Hexamethylbenzene_synthesis.png/400px-Hexamethylbenzene_synthesis.png" decoding="async" width="400" height="145" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9c/Hexamethylbenzene_synthesis.png/600px-Hexamethylbenzene_synthesis.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9c/Hexamethylbenzene_synthesis.png/800px-Hexamethylbenzene_synthesis.png 2x" data-file-width="2002" data-file-height="727" /></a><figcaption></figcaption></figure> The mechanisms of such surface-mediated reactions have been investigated, with an eye to achieving greater control over the outcome of the reaction,<a href="#cite_note-Ipatiew-29">[29]</a><a href="#cite_note-42">[42]</a> especially in search of selective and controlled <a href="/wiki/Arene_substitution_pattern" title="Arene substitution pattern">ortho</a>-methylation.<a href="#cite_note-Takeshi1-30">[30]</a><a href="#cite_note-Takeshi2-31">[31]</a><a href="#cite_note-43">[43]</a><a href="#cite_note-44">[44]</a> Both anisole<a href="#cite_note-CullinaneChard-32">[32]</a> and pentamethylbenzene<a href="#cite_note-PMB-27">[27]</a> have been reported as intermediates in the process. <a href="/wiki/Valentin_Koptyug" title="Valentin Koptyug">Valentin Koptyug</a> and co-workers found that both hexamethylcyclohexadienone <a href="/wiki/Isomer" title="Isomer">isomers</a> (2,3,4,4,5,6- and 2,3,4,5,6,6-) are intermediates in the process, undergoing <a href="/wiki/Methyl_migration" class="mw-redirect" title="Methyl migration">methyl migration</a> to form the 1,2,3,4,5,6-hexamethylbenzene carbon skeleton.<a href="#cite_note-Koptyug1-28">[28]</a><a href="#cite_note-Koptyug2-33">[33]</a> <a href="/wiki/Alkyne_trimerisation" title="Alkyne trimerisation">Trimerisation</a> of three <a href="/wiki/2-butyne" class="mw-redirect" title="2-butyne">2-butyne</a> (dimethylacetylene) molecules yields hexamethylbenzene.<a href="#cite_note-Trimerisation-34">[34]</a> The reaction is catalyzed by triphenylchromium tri-tetrahydrofuranate<a href="#cite_note-Cr-35">[35]</a> or by a <a href="/wiki/Complex_(chemistry)" class="mw-redirect" title="Complex (chemistry)">complex</a> of <a href="/wiki/Triisobutylaluminium" title="Triisobutylaluminium">triisobutylaluminium</a> and <a href="/wiki/Titanium_tetrachloride" title="Titanium tetrachloride">titanium tetrachloride</a>.<a href="#cite_note-Ti-36">[36]</a> <figure class="mw-halign-center" typeof="mw:File/Frameless"><a href="/wiki/File:2-Butyne_cyclotrimerization.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3a/2-Butyne_cyclotrimerization.png/350px-2-Butyne_cyclotrimerization.png" decoding="async" width="350" height="129" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3a/2-Butyne_cyclotrimerization.png/525px-2-Butyne_cyclotrimerization.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3a/2-Butyne_cyclotrimerization.png/700px-2-Butyne_cyclotrimerization.png 2x" data-file-width="1680" data-file-height="617" /></a><figcaption></figcaption></figure> <div class="mw-heading mw-heading2"><h2 id="Uses">Uses</h2>[<a href="/w/index.php?title=Hexamethylbenzene&action=edit&section=4" title="Edit section: Uses">edit</a>]</div> <div class="mw-heading mw-heading3"><h3 id="Synthetic_uses">Synthetic uses</h3>[<a href="/w/index.php?title=Hexamethylbenzene&action=edit&section=5" title="Edit section: Synthetic uses">edit</a>]</div> Hexamethylbenzene can be used as a <a href="/wiki/Ligand" title="Ligand">ligand</a> in <a href="/wiki/Organometallic_compound" class="mw-redirect" title="Organometallic compound">organometallic compounds</a>. <div class="mw-heading mw-heading3"><h3 id="Other_uses">Other uses</h3>[<a href="/w/index.php?title=Hexamethylbenzene&action=edit&section=6" title="Edit section: Other uses">edit</a>]</div> Hexamethylbenzene has no commercial or widespread uses. It is exclusively of interest for chemical research. <div class="mw-heading mw-heading2"><h2 id="Reactions">Reactions</h2>[<a href="/w/index.php?title=Hexamethylbenzene&action=edit&section=7" title="Edit section: Reactions">edit</a>]</div> It forms orange-yellow 1:1 adduct with <a href="/wiki/Picryl_chloride" title="Picryl chloride">picryl chloride</a>,<a href="#cite_note-45">[45]</a> probably due to <a href="/wiki/Pi-stacking" title="Pi-stacking">π-stacking</a> of the aromatic systems. Oxidation with <a href="/wiki/Trifluoroperacetic_acid" title="Trifluoroperacetic acid">trifluoroperacetic acid</a> or <a href="/wiki/Hydrogen_peroxide" title="Hydrogen peroxide">hydrogen peroxide</a> gives 2,3,4,5,6,6-hexamethyl-2,4-cyclohexadienone:<a href="#cite_note-46">[46]</a><a href="#cite_note-Koptyug1-28">[28]</a><a href="#cite_note-Koptyug2-33">[33]</a>) <figure class="mw-halign-center" typeof="mw:File/Frameless"><a href="/wiki/File:Hexamethylbenzene_oxidation.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/79/Hexamethylbenzene_oxidation.png/400px-Hexamethylbenzene_oxidation.png" decoding="async" width="400" height="115" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/79/Hexamethylbenzene_oxidation.png/600px-Hexamethylbenzene_oxidation.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/79/Hexamethylbenzene_oxidation.png/800px-Hexamethylbenzene_oxidation.png 2x" data-file-width="2518" data-file-height="726" /></a><figcaption></figcaption></figure> It has also been used as a solvent for <a href="/wiki/Helium-3_nuclear_magnetic_resonance" title="Helium-3 nuclear magnetic resonance">3He-NMR spectroscopy</a>.<a href="#cite_note-47">[47]</a> Just as with benzene itself, the electron-rich aromatic system in hexamethylbenzene allows it to act as a <a href="/wiki/Ligand" title="Ligand">ligand</a> in <a href="/wiki/Organometallic_chemistry" title="Organometallic chemistry">organometallic chemistry</a>.<a href="#cite_note-AreneReview-6">[6]</a> The <a href="/wiki/Electron_donating_group" class="mw-redirect" title="Electron donating group">electron-donating</a> nature of the methyl groups—both that there are six of them individually and that there are six <a href="/wiki/Arene_substitution_pattern" title="Arene substitution pattern">meta</a> pairs among them—enhance the basicity of the central ring by six to seven <a href="/wiki/Orders_of_magnitude" class="mw-redirect" title="Orders of magnitude">orders of magnitude</a> relative to benzene.<a href="#cite_note-48">[48]</a> Examples of <a href="/wiki/Organometallic_complex" class="mw-redirect" title="Organometallic complex">such complexes</a> have been reported for a variety of metal centres, including cobalt,<a href="#cite_note-CoRh-49">[49]</a> chromium,<a href="#cite_note-Cr-35">[35]</a> iron,<a href="#cite_note-Fe-7">[7]</a> rhenium,<a href="#cite_note-50">[50]</a> rhodium,<a href="#cite_note-CoRh-49">[49]</a> ruthenium,<a href="#cite_note-RuHMB2-8">[8]</a> and titanium.<a href="#cite_note-Ti-36">[36]</a> Known <a href="/wiki/Cation" class="mw-redirect" title="Cation">cations</a> of <a href="/wiki/Sandwich_complex" class="mw-redirect" title="Sandwich complex">sandwich complexes</a> of cobalt and rhodium with hexamethylbenzene take the form [M(C 6(CH 3) 6) 2]n+ (M = Co, Fe, Rh, Ru; n = 1, 2), where the metal centre is bound by the π electrons of the two arene <a href="/wiki/Moiety_(chemistry)" title="Moiety (chemistry)">moieties</a>, and can easily be synthesised from appropriate metal salts by ligand exchange, for example:<a href="#cite_note-CoRh-49">[49]</a> <dl><dd>CoBr 2   +   2 AlBr 3   →   [Co(C 6(CH 3) 6) 2]2+   +   2 AlBr− 4</dd></dl> The complexes can undergo <a href="/wiki/Redox" title="Redox">redox</a> reactions. The rhodium and cobalt <a href="/wiki/Dication" title="Dication">dications</a> undergo a one-electron reduction with a suitable active metal (aluminium for the cobalt system, zinc for the rhodium), and the equations describing the reactions in the cobalt system are as follows:<a href="#cite_note-CoRh-49">[49]</a> <dl><dd>3 [Co(C 6(CH 3) 6) 2]2+   +   Al   →   3 [Co(C 6(CH 3) 6) 2]+   +   Al3+ </dd></dl> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Ru(C6H6)2redox_pi-highlight.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b9/Ru%28C6H6%292redox_pi-highlight.png/300px-Ru%28C6H6%292redox_pi-highlight.png" decoding="async" width="300" height="149" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b9/Ru%28C6H6%292redox_pi-highlight.png/450px-Ru%28C6H6%292redox_pi-highlight.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b9/Ru%28C6H6%292redox_pi-highlight.png/600px-Ru%28C6H6%292redox_pi-highlight.png 2x" data-file-width="911" data-file-height="451" /></a><figcaption>The structure of the [Ru(C6(CH3)6)2]n+ <a href="/wiki/Moiety_(chemistry)" title="Moiety (chemistry)">moiety</a> changes with the oxidation state of the metal centre<a href="#cite_note-RuHMB2-8">[8]</a> Left: n = 2, [RuII(η6-C6(CH3)6)2]2+ Right: n = 0, [Ru0(η4-C6(CH3)6)(η6-C6(CH3)6)] Methyl groups omitted for clarity. The electron-pairs involved with carbon–ruthenium bonding are in red.</figcaption></figure> In the field of <a href="/wiki/Organoruthenium_chemistry" title="Organoruthenium chemistry">organoruthenium chemistry</a>, the redox interconversion of the analogous two-electron reduction of the dication and its neutral product occurs at −1.02 V in <a href="/wiki/Acetonitrile" title="Acetonitrile">acetonitrile</a><a href="#cite_note-Fe-7">[7]</a> and is accompanied by a structural change.<a href="#cite_note-RuHMB2-8">[8]</a><a href="#cite_note-51">[51]</a> The <a href="/wiki/Hapticity" title="Hapticity">hapticity</a> of one of the hexamethylbenzene ligands changes with the <a href="/wiki/Oxidation_state" title="Oxidation state">oxidation state</a> of the ruthenium centre, the dication [Ru(η6-C6(CH3)6)2]2+ being reduced to [Ru(η4-C6(CH3)6)(η6-C6(CH3)6)],<a href="#cite_note-RuHMB2-8">[8]</a> with the structural change allowing each complex to comply with the <a href="/wiki/18-electron_rule" title="18-electron rule">18-electron rule</a> and maximise stability. The equivalent iron(II) complex undergoes a reversible one-electron reduction (at −0.48 V in aqueous ethanol), but the two-electron reduction (at −1.46 V) is irreversible,<a href="#cite_note-Fe-7">[7]</a> suggesting a change in structure different from that found in the ruthenium system. <div class="mw-heading mw-heading3"><h3 id="Dication">Dication</h3>[<a href="/w/index.php?title=Hexamethylbenzene&action=edit&section=8" title="Edit section: Dication">edit</a>]</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/Pyramidal_carbocation" title="Pyramidal carbocation">Pyramidal carbocation</a></div> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:C6(CH3)6_2%2B.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f1/C6%28CH3%296_2%2B.png/220px-C6%28CH3%296_2%2B.png" decoding="async" width="220" height="219" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f1/C6%28CH3%296_2%2B.png/330px-C6%28CH3%296_2%2B.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f1/C6%28CH3%296_2%2B.png/440px-C6%28CH3%296_2%2B.png 2x" data-file-width="838" data-file-height="836" /></a><figcaption><a href="/wiki/Pyramidal_carbocation" title="Pyramidal carbocation">Pyramidal carbocation</a> with composition C 6(CH 3)2+ 6</figcaption></figure> The isolation of an ion with composition C 6(CH 3) 6H+ was first reported from investigations of <a href="/wiki/Hexamethyl_Dewar_benzene" class="mw-redirect" title="Hexamethyl Dewar benzene">hexamethyl Dewar benzene</a> in the 1960s;<a href="#cite_note-52">[52]</a> a pyramidal structure was suggested based on <a href="/wiki/NMR" class="mw-redirect" title="NMR">NMR</a> evidence<a href="#cite_note-53">[53]</a> and subsequently supported by <a href="/wiki/Disordered_phase" class="mw-redirect" title="Disordered phase">disordered</a><a href="#cite_note-PyramidalAngewChem-9">[9]</a> crystal structure data.<a href="#cite_note-54">[54]</a> In the early 1970s theoretical work led by Hepke Hogeveen predicted the existence of a pyramidal dication C 6(CH 3)2+ 6, and the suggestion was soon supported by experimental evidence.<a href="#cite_note-HMBcatObs1-15">[15]</a><a href="#cite_note-HMBcatObs2-16">[16]</a><a href="#cite_note-HMBcatObs3-17">[17]</a> <a href="/wiki/Spectroscopy" title="Spectroscopy">Spectroscopic</a> investigation of the two-electron oxidation of benzene at very low temperatures (below 4 K) shows that a hexagonal dication forms and then rapidly rearranges into a pyramidal structure:<a href="#cite_note-55">[55]</a> <figure class="mw-halign-center" typeof="mw:File/Frameless"><a href="/wiki/File:Oxidation_of_benzene_to_its_dication.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/a/a3/Oxidation_of_benzene_to_its_dication.jpg" decoding="async" width="479" height="103" class="mw-file-element" data-file-width="479" data-file-height="103" /></a><figcaption></figcaption></figure> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:C6(CH3)6(2%2B)_3D_skeletal.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1f/C6%28CH3%296%282%2B%29_3D_skeletal.png/220px-C6%28CH3%296%282%2B%29_3D_skeletal.png" decoding="async" width="220" height="147" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1f/C6%28CH3%296%282%2B%29_3D_skeletal.png/330px-C6%28CH3%296%282%2B%29_3D_skeletal.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1f/C6%28CH3%296%282%2B%29_3D_skeletal.png/440px-C6%28CH3%296%282%2B%29_3D_skeletal.png 2x" data-file-width="768" data-file-height="512" /></a><figcaption>Three-dimensional representation of C 6(CH 3)2+ 6 having a rearranged pentagonal-pyramid framework</figcaption></figure> Two-electron oxidation of hexamethylbenzene would be expected to result in a near-identical rearrangement to a <a href="/wiki/Pyramidal_carbocation" title="Pyramidal carbocation">pyramidal carbocation</a>, but attempts to synthesise it in bulk by this method have been unsuccessful.<a href="#cite_note-PyramidalAngewChem-9">[9]</a> However, a modification of the Hogeveen approach was reported in 2016, along with a high-quality crystal structure determination of [C 6(CH 3) 6][SbF 6] 2•HSO 3F. The pyramidal core is about 1.18 <a href="/wiki/%C3%85ngstr%C3%B6m" class="mw-redirect" title="Ångström">ångströms</a> high, and each of the methyl groups on the ring is located slightly above that base plane<a href="#cite_note-PyramidalAngewChem-9">[9]</a> to give a somewhat <a href="/wiki/Inverted_tetrahedral_geometry" class="mw-redirect" title="Inverted tetrahedral geometry">inverted tetrahedral geometry</a> for the carbons of the base of the pyramid. The preparation method involved treating the <a href="/wiki/Epoxide" title="Epoxide">epoxide</a> of hexamethyl Dewar benzene with <a href="/wiki/Magic_acid" title="Magic acid">magic acid</a>, which formally abstracts an oxide anion (O2− ) to form the dication:<a href="#cite_note-PyramidalAngewChem-9">[9]</a> <figure class="mw-halign-center" typeof="mw:File/Frameless"><a href="/wiki/File:C6(CH3)6_(SbF6)2_synthesis.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/C6%28CH3%296_%28SbF6%292_synthesis.png/500px-C6%28CH3%296_%28SbF6%292_synthesis.png" decoding="async" width="500" height="97" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/C6%28CH3%296_%28SbF6%292_synthesis.png/750px-C6%28CH3%296_%28SbF6%292_synthesis.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/aa/C6%28CH3%296_%28SbF6%292_synthesis.png/1000px-C6%28CH3%296_%28SbF6%292_synthesis.png 2x" data-file-width="2441" data-file-height="473" /></a><figcaption></figcaption></figure> Though indirect spectroscopic evidence and theoretical calculations previously pointed to their existence, the isolation and structural determination of a species with a hexacoordinate carbon bound only to other carbon atoms is unprecedented,<a href="#cite_note-PyramidalAngewChem-9">[9]</a> and has attracted comment in <a href="/wiki/Chemical_%26_Engineering_News" title="Chemical & Engineering News">Chemical & Engineering News</a>,<a href="#cite_note-PyramidalC&ENews-11">[11]</a> <a href="/wiki/New_Scientist" title="New Scientist">New Scientist</a>,<a href="#cite_note-PyramidalNewSci-10">[10]</a> <a href="/wiki/Science_News" title="Science News">Science News</a>,<a href="#cite_note-PyramidalSciNews-12">[12]</a> and ZME Science.<a href="#cite_note-56">[56]</a> The carbon atom at the top of the pyramid is bonding with six other atoms, an unusual arrangement as the usual maximum <a href="/wiki/Valence_(chemistry)" title="Valence (chemistry)">valence</a> for this element is four.<a href="#cite_note-PyramidalC&ENews-11">[11]</a> The molecule is aromatic and avoids exceeding the <a href="/wiki/Octet_rule" title="Octet rule">octet</a> on carbon by having only a total of six electrons in the five bonds between the base of the pyramid and its apex. That is, each of the vertical edges of the pyramid is only a partial bond rather than a normal <a href="/wiki/Covalent_bond" title="Covalent bond">covalent bond</a> that would have two electrons shared between two atoms. Although the top carbon does bond to six others, it does so using a total of no more than eight electrons.<a href="#cite_note-HMBviaOMetChem-14">[14]</a> The dication, noting the weak bonds forming the upright edges of the pyramid, shown as dashed lines in the structure, have a Wiberg <a href="/wiki/Bond_order" title="Bond order">bond order</a> of about 0.54; it follows that the total bond order is 5 × 0.54 + 1 = 3.7 < 4, and thus the species is not <a href="/wiki/Hypervalent_molecule" title="Hypervalent molecule">hypervalent</a>, though it is hypercoordinate.<a href="#cite_note-Bachrach-13">[13]</a> The differences in bonding in the dication—the ring having aromatic character and the vertical edges being weak partial bonds—are reflected in variations of the carbon–carbon <a href="/wiki/Bond_length" title="Bond length">bond lengths</a>: the ring bonds are 1.439–1.445 Å,, the bonds to the methyl groups are 1.479–1.489 Å,, and the vertical edges are 1.694–1.715 Å.<a href="#cite_note-PyramidalAngewChem-9">[9]</a> Bachrach rationalised the three-dimensional aromaticity of the dication by considering it as comprising the ring C 5(CH 3)+ 5 as a four-electron donor and topped by the CCH+ 3 fragment, which provides two electrons, for a total of six electrons in the aromatic cage, in line with Hückel's rule for n = 1.<a href="#cite_note-Bachrach-13">[13]</a> From the perspective of organometallic chemistry, the species can be viewed as [(η5 –C 5(CH 3) 5)C(CH 3)] .<a href="#cite_note-HMBviaOMetChem-14">[14]</a> This satisfies the octet rule by binding a carbon(IV) centre (C4+ ) to an aromatic η5–<a href="/wiki/Pentamethylcyclopentadienyl" class="mw-redirect" title="Pentamethylcyclopentadienyl">pentamethylcyclopentadienyl</a> anion (six-electron donor) and methyl anion (two-electron donor), analogous to the way the gas-phase <a href="/wiki/Organozinc_compound" class="mw-redirect" title="Organozinc compound">organozinc</a> monomer [(η5 –C 5(CH 3) 5)Zn(CH 3)], having the same ligands bound to a zinc(II) centre (Zn2+ ) satisfies the <a href="/wiki/18_electron_rule" class="mw-redirect" title="18 electron rule">18 electron rule</a> on the metal.<a href="#cite_note-Cp*ZnMe-57">[57]</a><a href="#cite_note-58">[58]</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1237032888/mw-parser-output/.tmulti"><div class="thumb tmulti tnone center"><div class="thumbinner multiimageinner" style="width:442px;max-width:442px"><div class="trow"><div class="tsingle" style="width:234px;max-width:234px"><div class="thumbimage" style="height:161px;overflow:hidden"><a href="/wiki/File:Bachrach_image_of_hexamethylbenzene_dication.png" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/79/Bachrach_image_of_hexamethylbenzene_dication.png/232px-Bachrach_image_of_hexamethylbenzene_dication.png" decoding="async" width="232" height="162" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/79/Bachrach_image_of_hexamethylbenzene_dication.png/348px-Bachrach_image_of_hexamethylbenzene_dication.png 1.5x, //upload.wikimedia.org/wikipedia/commons/7/79/Bachrach_image_of_hexamethylbenzene_dication.png 2x" data-file-width="359" data-file-height="250" /></a></div></div><div class="tsingle" style="width:204px;max-width:204px"><div class="thumbimage" style="height:161px;overflow:hidden"><a href="/wiki/File:Structure_of_organometallic_zinc_complex_(C5Me5)Zn(Me).png" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/ef/Structure_of_organometallic_zinc_complex_%28C5Me5%29Zn%28Me%29.png/202px-Structure_of_organometallic_zinc_complex_%28C5Me5%29Zn%28Me%29.png" decoding="async" width="202" height="149" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/ef/Structure_of_organometallic_zinc_complex_%28C5Me5%29Zn%28Me%29.png/303px-Structure_of_organometallic_zinc_complex_%28C5Me5%29Zn%28Me%29.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/ef/Structure_of_organometallic_zinc_complex_%28C5Me5%29Zn%28Me%29.png/404px-Structure_of_organometallic_zinc_complex_%28C5Me5%29Zn%28Me%29.png 2x" data-file-width="897" data-file-height="662" /></a></div></div></div><div class="trow" style="display:flex"><div class="thumbcaption">Left: Structure of C 6(CH 3)2+ 6, as drawn by <a href="/wiki/Steven_Bachrach" title="Steven Bachrach">Steven Bachrach</a><a href="#cite_note-Bachrach-13">[13]</a> Right: The analogous organometallic complex [(η5 –C 5(CH 3) 5)Zn(CH 3)]<a href="#cite_note-Cp*ZnMe-57">[57]</a></div></div></div></div> It has been commented that "[i]t's super important that people realize that, although we're taught carbon can only have four friends, carbon can be associated with more than four atoms" and added that the "carbon isn't making six bonds in the sense that we usually think of a carbon-carbon bond as a two-electron bond."<a href="#cite_note-PyramidalSciNews-12">[12]</a> "It is all about the challenge and the possibility to astonish chemists about what can be possible."<a href="#cite_note-PyramidalNewSci-10">[10]</a> <div class="mw-heading mw-heading2"><h2 id="References">References</h2>[<a href="/w/index.php?title=Hexamethylbenzene&action=edit&section=9" title="Edit section: References">edit</a>]</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 reflist-columns references-column-width" style="column-width: 30em;"> <ol class="references"> <li id="cite_note-Lonsdale-1">^ <a href="#cite_ref-Lonsdale_1-0">a</a> <a href="#cite_ref-Lonsdale_1-1">b</a> <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="CITEREFLonsdale1929" class="citation journal cs1"><a href="/wiki/Kathleen_Lonsdale" title="Kathleen Lonsdale">Lonsdale, Kathleen</a> (1929). <a rel="nofollow" class="external text" href="https://doi.org/10.1098%2Frspa.1929.0081">"The Structure of the Benzene Ring in Hexamethylbenzene"</a>. <a href="/wiki/Proc._R._Soc._A" class="mw-redirect" title="Proc. R. Soc. A">Proc. R. Soc. A</a>. 123 (792): 494–515. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1098%2Frspa.1929.0081">10.1098/rspa.1929.0081</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Proc.+R.+Soc.+A&rft.atitle=The+Structure+of+the+Benzene+Ring+in+Hexamethylbenzene&rft.volume=123&rft.issue=792&rft.pages=494-515&rft.date=1929&rft_id=info%3Adoi%2F10.1098%2Frspa.1929.0081&rft.aulast=Lonsdale&rft.aufirst=Kathleen&rft_id=https%3A%2F%2Fdoi.org%2F10.1098%252Frspa.1929.0081&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexamethylbenzene" class="Z3988"> </li> <li id="cite_note-Lydon1-2">^ <a href="#cite_ref-Lydon1_2-0">a</a> <a href="#cite_ref-Lydon1_2-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLydon2006" class="citation journal cs1">Lydon, John (January 2006). <a rel="nofollow" class="external text" href="https://www.iop.org/activity/groups/subject/hp/newsletter/archive/file_66399.pdf">"A Welcome to Leeds"</a> (PDF). Newsletter of the History of Physics Group (19): 8–11.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Newsletter+of+the+History+of+Physics+Group&rft.atitle=A+Welcome+to+Leeds&rft.issue=19&rft.pages=8-11&rft.date=2006-01&rft.aulast=Lydon&rft.aufirst=John&rft_id=https%3A%2F%2Fwww.iop.org%2Factivity%2Fgroups%2Fsubject%2Fhp%2Fnewsletter%2Farchive%2Ffile_66399.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexamethylbenzene" class="Z3988"> </li> <li id="cite_note-Lydon2-3">^ <a href="#cite_ref-Lydon2_3-0">a</a> <a href="#cite_ref-Lydon2_3-1">b</a> <a href="#cite_ref-Lydon2_3-2">c</a> <a href="#cite_ref-Lydon2_3-3">d</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLydon2006" class="citation journal cs1">Lydon, John (July 2006). <a rel="nofollow" class="external text" href="https://www.iop.org/activity/groups/subject/hp/newsletter/archive/file_66191.pdf">"Letters"</a> (PDF). Newsletter of the History of Physics Group (20): 34–35.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Newsletter+of+the+History+of+Physics+Group&rft.atitle=Letters&rft.issue=20&rft.pages=34-35&rft.date=2006-07&rft.aulast=Lydon&rft.aufirst=John&rft_id=https%3A%2F%2Fwww.iop.org%2Factivity%2Fgroups%2Fsubject%2Fhp%2Fnewsletter%2Farchive%2Ffile_66191.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexamethylbenzene" class="Z3988"> </li> <li id="cite_note-HMBoxidation-4">^ <a href="#cite_ref-HMBoxidation_4-0">a</a> <a href="#cite_ref-HMBoxidation_4-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWibautOverhoffJonkerGratama1941" class="citation journal cs1">Wibaut, J. P.; Overhoff, J.; Jonker, E. W.; Gratama, K. (1941). "On the preparation of mellitic acid from hexa-methylbenzene and on the hexachloride of mellitic acid". <a href="/wiki/Recl._Trav._Chim._Pays-Bas" class="mw-redirect" title="Recl. Trav. Chim. Pays-Bas">Recl. Trav. Chim. Pays-Bas</a>. 60 (10): 742–746. <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%2Frecl.19410601005">10.1002/recl.19410601005</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Recl.+Trav.+Chim.+Pays-Bas&rft.atitle=On+the+preparation+of+mellitic+acid+from+hexa-methylbenzene+and+on+the+hexachloride+of+mellitic+acid&rft.volume=60&rft.issue=10&rft.pages=742-746&rft.date=1941&rft_id=info%3Adoi%2F10.1002%2Frecl.19410601005&rft.aulast=Wibaut&rft.aufirst=J.+P.&rft.au=Overhoff%2C+J.&rft.au=Jonker%2C+E.+W.&rft.au=Gratama%2C+K.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexamethylbenzene" class="Z3988"> </li> <li id="cite_note-mellite-5">^ <a href="#cite_ref-mellite_5-0">a</a> <a href="#cite_ref-mellite_5-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWenkBulakh2016" class="citation book cs1">Wenk, Hans-Rudolf; Bulakh, Andrey (2016). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=TMaSDQAAQBAJ&pg=PT1361">"Organic Minerals"</a>. Minerals – Their Constitution and Origin (2nd ed.). <a href="/wiki/Cambridge_University_Press" title="Cambridge University Press">Cambridge University Press</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9781316423684" title="Special:BookSources/9781316423684"><bdi>9781316423684</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Organic+Minerals&rft.btitle=Minerals+%E2%80%93+Their+Constitution+and+Origin&rft.edition=2nd&rft.pub=Cambridge+University+Press&rft.date=2016&rft.isbn=9781316423684&rft.aulast=Wenk&rft.aufirst=Hans-Rudolf&rft.au=Bulakh%2C+Andrey&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DTMaSDQAAQBAJ%26pg%3DPT1361&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexamethylbenzene" class="Z3988"> </li> <li id="cite_note-AreneReview-6">^ <a href="#cite_ref-AreneReview_6-0">a</a> <a href="#cite_ref-AreneReview_6-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPampaloni2010" class="citation journal cs1">Pampaloni, Guido (2010). "Aromatic hydrocarbons as ligands. Recent advances in the synthesis, the reactivity and the applications of bis(η6-arene) complexes". <a href="/wiki/Coord._Chem._Rev." class="mw-redirect" title="Coord. Chem. Rev.">Coord. Chem. Rev.</a> 254 (5–6): 402–419. <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%2Fj.ccr.2009.05.014">10.1016/j.ccr.2009.05.014</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Coord.+Chem.+Rev.&rft.atitle=Aromatic+hydrocarbons+as+ligands.+Recent+advances+in+the+synthesis%2C+the+reactivity+and+the+applications+of+bis%28%CE%B7%3Csup%3E6%3C%2Fsup%3E-arene%29+complexes&rft.volume=254&rft.issue=5%E2%80%936&rft.pages=402-419&rft.date=2010&rft_id=info%3Adoi%2F10.1016%2Fj.ccr.2009.05.014&rft.aulast=Pampaloni&rft.aufirst=Guido&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexamethylbenzene" class="Z3988"> </li> <li id="cite_note-Fe-7">^ <a href="#cite_ref-Fe_7-0">a</a> <a href="#cite_ref-Fe_7-1">b</a> <a href="#cite_ref-Fe_7-2">c</a> <a href="#cite_ref-Fe_7-3">d</a> <a href="#cite_ref-Fe_7-4">e</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKotz1986" class="citation book cs1">Kotz, John C. (1986). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=zgUHCAAAQBAJ&pg=PA110">"The Electrochemistry of Transition Metal Organometallic Compounds"</a>. In Fry, Albert J.; Britton, Wayne E. (eds.). Topics in Organic Electrochemistry. <a href="/wiki/Springer_Science_%26_Business_Media" class="mw-redirect" title="Springer Science & Business Media">Springer Science & Business Media</a>. pp. 83–176. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9781489920348" title="Special:BookSources/9781489920348"><bdi>9781489920348</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=The+Electrochemistry+of+Transition+Metal+Organometallic+Compounds&rft.btitle=Topics+in+Organic+Electrochemistry&rft.pages=83-176&rft.pub=Springer+Science+%26+Business+Media&rft.date=1986&rft.isbn=9781489920348&rft.aulast=Kotz&rft.aufirst=John+C.&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DzgUHCAAAQBAJ%26pg%3DPA110&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexamethylbenzene" class="Z3988"> </li> <li id="cite_note-RuHMB2-8">^ <a href="#cite_ref-RuHMB2_8-0">a</a> <a href="#cite_ref-RuHMB2_8-1">b</a> <a href="#cite_ref-RuHMB2_8-2">c</a> <a href="#cite_ref-RuHMB2_8-3">d</a> <a href="#cite_ref-RuHMB2_8-4">e</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHuttnerLangeFischer1971" class="citation journal cs1">Huttner, Gottfried; Lange, Siegfried; <a href="/wiki/Ernst_Otto_Fischer" title="Ernst Otto Fischer">Fischer, Ernst O.</a> (1971). "Molecular Structure of Bis(Hexamethylbenzene)Ruthenium(0)". <a href="/wiki/Angew._Chem._Int._Ed._Engl." class="mw-redirect" title="Angew. Chem. Int. Ed. Engl.">Angew. Chem. Int. Ed. Engl.</a> 10 (8): 556–557. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fanie.197105561">10.1002/anie.197105561</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Angew.+Chem.+Int.+Ed.+Engl.&rft.atitle=Molecular+Structure+of+Bis%28Hexamethylbenzene%29Ruthenium%280%29&rft.volume=10&rft.issue=8&rft.pages=556-557&rft.date=1971&rft_id=info%3Adoi%2F10.1002%2Fanie.197105561&rft.aulast=Huttner&rft.aufirst=Gottfried&rft.au=Lange%2C+Siegfried&rft.au=Fischer%2C+Ernst+O.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexamethylbenzene" class="Z3988"> </li> <li id="cite_note-PyramidalAngewChem-9">^ <a href="#cite_ref-PyramidalAngewChem_9-0">a</a> <a href="#cite_ref-PyramidalAngewChem_9-1">b</a> <a href="#cite_ref-PyramidalAngewChem_9-2">c</a> <a href="#cite_ref-PyramidalAngewChem_9-3">d</a> <a href="#cite_ref-PyramidalAngewChem_9-4">e</a> <a href="#cite_ref-PyramidalAngewChem_9-5">f</a> <a href="#cite_ref-PyramidalAngewChem_9-6">g</a> <a href="#cite_ref-PyramidalAngewChem_9-7">h</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMalischewskiSeppelt2017" class="citation journal cs1">Malischewski, Moritz; <a href="/wiki/Konrad_Seppelt" title="Konrad Seppelt">Seppelt, Konrad</a> (2017). "Crystal Structure Determination of the Pentagonal-Pyramidal Hexamethylbenzene Dication C6(CH3)62+". <a href="/wiki/Angew._Chem._Int._Ed." class="mw-redirect" title="Angew. Chem. Int. Ed.">Angew. Chem. Int. Ed.</a> 56 (1): 368–370. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fanie.201608795">10.1002/anie.201608795</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/27885766">27885766</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Angew.+Chem.+Int.+Ed.&rft.atitle=Crystal+Structure+Determination+of+the+Pentagonal-Pyramidal+Hexamethylbenzene+Dication+C%3Csub%3E6%3C%2Fsub%3E%28CH%3Csub%3E3%3C%2Fsub%3E%29%3Csub%3E6%3C%2Fsub%3E%3Csup%3E2%2B%3C%2Fsup%3E&rft.volume=56&rft.issue=1&rft.pages=368-370&rft.date=2017&rft_id=info%3Adoi%2F10.1002%2Fanie.201608795&rft_id=info%3Apmid%2F27885766&rft.aulast=Malischewski&rft.aufirst=Moritz&rft.au=Seppelt%2C+Konrad&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexamethylbenzene" class="Z3988"> </li> <li id="cite_note-PyramidalNewSci-10">^ <a href="#cite_ref-PyramidalNewSci_10-0">a</a> <a href="#cite_ref-PyramidalNewSci_10-1">b</a> <a href="#cite_ref-PyramidalNewSci_10-2">c</a> <a href="#cite_ref-PyramidalNewSci_10-3">d</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBoyle2017" class="citation journal cs1">Boyle, Rebecca (14 January 2017). <a rel="nofollow" class="external text" href="https://www.newscientist.com/article/mg23331084-900-carbon-seen-bonding-with-six-other-atoms-for-the-first-time/">"Carbon seen bonding with six other atoms for the first time"</a>. <a href="/wiki/New_Scientist" title="New Scientist">New Scientist</a> (3108). <a rel="nofollow" class="external text" href="https://web.archive.org/web/20170116183924/https://www.newscientist.com/article/mg23331084-900-carbon-seen-bonding-with-six-other-atoms-for-the-first-time/">Archived</a> from the original on 16 January 2017. Retrieved 14 January 2017.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=New+Scientist&rft.atitle=Carbon+seen+bonding+with+six+other+atoms+for+the+first+time&rft.issue=3108&rft.date=2017-01-14&rft.aulast=Boyle&rft.aufirst=Rebecca&rft_id=https%3A%2F%2Fwww.newscientist.com%2Farticle%2Fmg23331084-900-carbon-seen-bonding-with-six-other-atoms-for-the-first-time%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexamethylbenzene" class="Z3988"> </li> <li id="cite_note-PyramidalC&ENews-11">^ <a href="#cite_ref-PyramidalC&ENews_11-0">a</a> <a href="#cite_ref-PyramidalC&ENews_11-1">b</a> <a href="#cite_ref-PyramidalC&ENews_11-2">c</a> <a href="#cite_ref-PyramidalC&ENews_11-3">d</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRitter2016" class="citation journal cs1">Ritter, Stephen K. (19 December 2016). <a rel="nofollow" class="external text" href="http://cen.acs.org/articles/94/i49/Six-bonds-carbon-Confirmed.html">"Six bonds to carbon: Confirmed"</a>. <a href="/wiki/Chem._Eng._News" class="mw-redirect" title="Chem. Eng. News">Chem. Eng. News</a>. 94 (49): 13. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fcen-09449-scicon007">10.1021/cen-09449-scicon007</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20170109183800/http://cen.acs.org/articles/94/i49/Six-bonds-carbon-Confirmed.html?type=paidArticleContent">Archived</a> from the original on 9 January 2017.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chem.+Eng.+News&rft.atitle=Six+bonds+to+carbon%3A+Confirmed&rft.volume=94&rft.issue=49&rft.pages=13&rft.date=2016-12-19&rft_id=info%3Adoi%2F10.1021%2Fcen-09449-scicon007&rft.aulast=Ritter&rft.aufirst=Stephen+K.&rft_id=http%3A%2F%2Fcen.acs.org%2Farticles%2F94%2Fi49%2FSix-bonds-carbon-Confirmed.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexamethylbenzene" class="Z3988"> </li> <li id="cite_note-PyramidalSciNews-12">^ <a href="#cite_ref-PyramidalSciNews_12-0">a</a> <a href="#cite_ref-PyramidalSciNews_12-1">b</a> <a href="#cite_ref-PyramidalSciNews_12-2">c</a> <a href="#cite_ref-PyramidalSciNews_12-3">d</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHamers2016" class="citation journal cs1">Hamers, Laurel (24 December 2016). <a rel="nofollow" class="external text" href="https://www.sciencenews.org/article/carbon-can-exceed-four-bond-limit">"Carbon can exceed four-bond limit"</a>. <a href="/wiki/Science_News" title="Science News">Science News</a>. 190 (13): 17. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20170203045239/https://www.sciencenews.org/article/carbon-can-exceed-four-bond-limit">Archived</a> from the original on 3 February 2017.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Science+News&rft.atitle=Carbon+can+exceed+four-bond+limit&rft.volume=190&rft.issue=13&rft.pages=17&rft.date=2016-12-24&rft.aulast=Hamers&rft.aufirst=Laurel&rft_id=https%3A%2F%2Fwww.sciencenews.org%2Farticle%2Fcarbon-can-exceed-four-bond-limit&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexamethylbenzene" class="Z3988"> </li> <li id="cite_note-Bachrach-13">^ <a href="#cite_ref-Bachrach_13-0">a</a> <a href="#cite_ref-Bachrach_13-1">b</a> <a href="#cite_ref-Bachrach_13-2">c</a> <a href="#cite_ref-Bachrach_13-3">d</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBachrach2017" class="citation web cs1"><a href="/wiki/Steven_Bachrach" title="Steven Bachrach">Bachrach, Steven M.</a> (17 January 2017). <a rel="nofollow" class="external text" href="http://comporgchem.com/blog/?page_id=3929">"A six-coordinate carbon atom"</a>. comporgchem.com. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20170119050221/http://comporgchem.com/blog/?p=3929">Archived</a> from the original on 19 January 2017. Retrieved 18 January 2017.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=comporgchem.com&rft.atitle=A+six-coordinate+carbon+atom&rft.date=2017-01-17&rft.aulast=Bachrach&rft.aufirst=Steven+M.&rft_id=http%3A%2F%2Fcomporgchem.com%2Fblog%2F%3Fpage_id%3D3929&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexamethylbenzene" class="Z3988"> </li> <li id="cite_note-HMBviaOMetChem-14">^ <a href="#cite_ref-HMBviaOMetChem_14-0">a</a> <a href="#cite_ref-HMBviaOMetChem_14-1">b</a> <a href="#cite_ref-HMBviaOMetChem_14-2">c</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHogeveenKwant1975" class="citation journal cs1">Hogeveen, Hepke; Kwant, Peter W. (1975). "Pyramidal mono- and dications. Bridge between organic and organometallic chemistry". <a href="/wiki/Acc._Chem._Res." class="mw-redirect" title="Acc. Chem. Res.">Acc. Chem. Res.</a> 8 (12): 413–420. <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%2Far50096a004">10.1021/ar50096a004</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Acc.+Chem.+Res.&rft.atitle=Pyramidal+mono-+and+dications.+Bridge+between+organic+and+organometallic+chemistry&rft.volume=8&rft.issue=12&rft.pages=413-420&rft.date=1975&rft_id=info%3Adoi%2F10.1021%2Far50096a004&rft.aulast=Hogeveen&rft.aufirst=Hepke&rft.au=Kwant%2C+Peter+W.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexamethylbenzene" class="Z3988"> </li> <li id="cite_note-HMBcatObs1-15">^ <a href="#cite_ref-HMBcatObs1_15-0">a</a> <a href="#cite_ref-HMBcatObs1_15-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHogeveenKwant1973" class="citation journal cs1">Hogeveen, Hepke; Kwant, Peter W. (1973). "Direct observation of a remarkably stable dication of unusual structure: (CCH3)62⊕". <a href="/wiki/Tetrahedron_Lett." class="mw-redirect" title="Tetrahedron Lett.">Tetrahedron Lett.</a> 14 (19): 1665–1670. <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%2FS0040-4039%2801%2996023-X">10.1016/S0040-4039(01)96023-X</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Tetrahedron+Lett.&rft.atitle=Direct+observation+of+a+remarkably+stable+dication+of+unusual+structure%3A+%28CCH%3Csub%3E3%3C%2Fsub%3E%29%3Csub%3E6%3C%2Fsub%3E%3Csup%3E2%E2%8A%95%3C%2Fsup%3E&rft.volume=14&rft.issue=19&rft.pages=1665-1670&rft.date=1973&rft_id=info%3Adoi%2F10.1016%2FS0040-4039%2801%2996023-X&rft.aulast=Hogeveen&rft.aufirst=Hepke&rft.au=Kwant%2C+Peter+W.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexamethylbenzene" class="Z3988"> </li> <li id="cite_note-HMBcatObs2-16">^ <a href="#cite_ref-HMBcatObs2_16-0">a</a> <a href="#cite_ref-HMBcatObs2_16-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHogeveenKwantPostmavan_Duynen1974" class="citation journal cs1">Hogeveen, Hepke; Kwant, Peter W.; Postma, J.; van Duynen, P. Th. (1974). "Electronic spectra of pyramidal dications, (CCH3)62+ and (CCH)62+". <a href="/wiki/Tetrahedron_Lett." class="mw-redirect" title="Tetrahedron Lett.">Tetrahedron Lett.</a> 15 (49–50): 4351–4354. <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%2FS0040-4039%2801%2992161-6">10.1016/S0040-4039(01)92161-6</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Tetrahedron+Lett.&rft.atitle=Electronic+spectra+of+pyramidal+dications%2C+%28CCH%3Csub%3E3%3C%2Fsub%3E%29%3Csub%3E6%3C%2Fsub%3E%3Csup%3E2%2B%3C%2Fsup%3E+and+%28CCH%29%3Csub%3E6%3C%2Fsub%3E%3Csup%3E2%2B%3C%2Fsup%3E&rft.volume=15&rft.issue=49%E2%80%9350&rft.pages=4351-4354&rft.date=1974&rft_id=info%3Adoi%2F10.1016%2FS0040-4039%2801%2992161-6&rft.aulast=Hogeveen&rft.aufirst=Hepke&rft.au=Kwant%2C+Peter+W.&rft.au=Postma%2C+J.&rft.au=van+Duynen%2C+P.+Th.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexamethylbenzene" class="Z3988"> </li> <li id="cite_note-HMBcatObs3-17">^ <a href="#cite_ref-HMBcatObs3_17-0">a</a> <a href="#cite_ref-HMBcatObs3_17-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHogeveenKwant1974" class="citation journal cs1">Hogeveen, Hepke; Kwant, Peter W. (1974). "Chemistry and spectroscopy in strongly acidic solutions. XL. (CCH3)62+, an unusual dication". <a href="/wiki/J._Am._Chem._Soc." class="mw-redirect" title="J. Am. Chem. Soc.">J. Am. Chem. Soc.</a> 96 (7): 2208–2214. <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%2Fja00814a034">10.1021/ja00814a034</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Am.+Chem.+Soc.&rft.atitle=Chemistry+and+spectroscopy+in+strongly+acidic+solutions.+XL.+%28CCH%3Csub%3E3%3C%2Fsub%3E%29%3Csub%3E6%3C%2Fsub%3E%3Csup%3E2%2B%3C%2Fsup%3E%2C+an+unusual+dication&rft.volume=96&rft.issue=7&rft.pages=2208-2214&rft.date=1974&rft_id=info%3Adoi%2F10.1021%2Fja00814a034&rft.aulast=Hogeveen&rft.aufirst=Hepke&rft.au=Kwant%2C+Peter+W.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexamethylbenzene" class="Z3988"> </li> <li id="cite_note-18"><a href="#cite_ref-18">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPubChem" class="citation web cs1">PubChem. <a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/6908">"Hexamethylbenzene"</a>. pubchem.ncbi.nlm.nih.gov. Retrieved 5 May 2024.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=pubchem.ncbi.nlm.nih.gov&rft.atitle=Hexamethylbenzene&rft.au=PubChem&rft_id=https%3A%2F%2Fpubchem.ncbi.nlm.nih.gov%2Fcompound%2F6908&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexamethylbenzene" class="Z3988"> </li> <li id="cite_note-19"><a href="#cite_ref-19">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFavrePowell2013" class="citation book cs1">Favre, Henri A.; Powell, Warren H. (2013). Nomenclature of Organic Chemistry. IUPAC Recommendations and Preferred Name 2013. <a href="/wiki/Royal_Society_of_Chemistry" title="Royal Society of Chemistry">Royal Society of Chemistry</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780854041824" title="Special:BookSources/9780854041824"><bdi>9780854041824</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Nomenclature+of+Organic+Chemistry.+IUPAC+Recommendations+and+Preferred+Name+2013&rft.pub=Royal+Society+of+Chemistry&rft.date=2013&rft.isbn=9780854041824&rft.aulast=Favre&rft.aufirst=Henri+A.&rft.au=Powell%2C+Warren+H.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexamethylbenzene" class="Z3988"> </li> <li id="cite_note-CRC-20">^ <a href="#cite_ref-CRC_20-0">a</a> <a href="#cite_ref-CRC_20-1">b</a> <a href="#cite_ref-CRC_20-2">c</a> <a href="#cite_ref-CRC_20-3">d</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHaynes2016" class="citation book cs1">Haynes, William M., ed. (2016). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=c1rNBQAAQBAJ&pg=SA3-PA296">CRC Handbook of Chemistry and Physics</a> (93rd ed.). <a href="/wiki/CRC_Press" title="CRC Press">CRC Press</a>. p. 3-296. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9781439880500" title="Special:BookSources/9781439880500"><bdi>9781439880500</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=CRC+Handbook+of+Chemistry+and+Physics&rft.pages=p.-3-296&rft.edition=93rd&rft.pub=CRC+Press&rft.date=2016&rft.isbn=9781439880500&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dc1rNBQAAQBAJ%26pg%3DSA3-PA296&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexamethylbenzene" class="Z3988"> </li> <li id="cite_note-HMBOrgSynth-21">^ <a href="#cite_ref-HMBOrgSynth_21-0">a</a> <a href="#cite_ref-HMBOrgSynth_21-1">b</a> <a href="#cite_ref-HMBOrgSynth_21-2">c</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCullinaneChardDawkins1955" class="citation journal cs1">Cullinane, N. M.; Chard, S. J.; Dawkins, C. W. C. (1955). <a rel="nofollow" class="external text" href="http://www.orgsyn.org/demo.aspx?prep=cv4p0520">"Hexamethylbenzene"</a>. <a href="/wiki/Organic_Syntheses" title="Organic Syntheses">Organic Syntheses</a>. 35: 73. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.15227%2Forgsyn.035.0073">10.15227/orgsyn.035.0073</a></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Organic+Syntheses&rft.atitle=Hexamethylbenzene&rft.volume=35&rft.pages=73&rft.date=1955&rft_id=info%3Adoi%2F10.15227%2Forgsyn.035.0073&rft.aulast=Cullinane&rft.aufirst=N.+M.&rft.au=Chard%2C+S.+J.&rft.au=Dawkins%2C+C.+W.+C.&rft_id=http%3A%2F%2Fwww.orgsyn.org%2Fdemo.aspx%3Fprep%3Dcv4p0520&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexamethylbenzene" class="Z3988">; <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation cs2">Collected Volumes, vol. 4, p. 520</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Collected+Volumes&rft.pages=520&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexamethylbenzene" class="Z3988">. </li> <li id="cite_note-22"><a href="#cite_ref-22">^</a> <a rel="nofollow" class="external text" href="https://www.perseus.tufts.edu/hopper/text?doc=Perseus:text:1999.04.0057:entry=me/li^">μέλι</a> in <a href="/wiki/Henry_Liddell" title="Henry Liddell">Liddell, Henry George</a>; <a href="/wiki/Robert_Scott_(philologist)" title="Robert Scott (philologist)">Scott, Robert</a> (1940) A Greek–English Lexicon, revised and augmented throughout by <a href="/wiki/Henry_Stuart_Jones" title="Henry Stuart Jones">Jones, Sir Henry Stuart</a>, with the assistance of McKenzie, Roderick. Oxford: Clarendon Press. In the <a href="/wiki/Perseus_Project" class="mw-redirect" title="Perseus Project">Perseus Digital Library</a>, Tufts University.. </li> <li id="cite_note-23"><a href="#cite_ref-23">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLiebig1844" class="citation journal cs1">Liebig, Justus (1844). <a rel="nofollow" class="external text" href="https://zenodo.org/record/1762488">"Lectures on organic chemistry: delivered during the winter session, 1844, in the University of Giessen"</a>. The Lancet. 2 (1106): 190–192. <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%2Fs0140-6736%2802%2964759-2">10.1016/s0140-6736(02)64759-2</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Lancet&rft.atitle=Lectures+on+organic+chemistry%3A+delivered+during+the+winter+session%2C+1844%2C+in+the+University+of+Giessen&rft.volume=2&rft.issue=1106&rft.pages=190-192&rft.date=1844&rft_id=info%3Adoi%2F10.1016%2Fs0140-6736%2802%2964759-2&rft.aulast=Liebig&rft.aufirst=Justus&rft_id=https%3A%2F%2Fzenodo.org%2Frecord%2F1762488&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexamethylbenzene" class="Z3988"> </li> <li id="cite_note-24"><a href="#cite_ref-24">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLonsdale1928" class="citation journal cs1"><a href="/wiki/Kathleen_Lonsdale" title="Kathleen Lonsdale">Lonsdale, Kathleen</a> (1928). <a rel="nofollow" class="external text" href="https://doi.org/10.1038%2F122810c0">"The Structure of the Benzene Ring"</a>. <a href="/wiki/Nature_(journal)" title="Nature (journal)">Nature</a>. 122 (810): 810. <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/1928Natur.122..810L">1928Natur.122..810L</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1038%2F122810c0">10.1038/122810c0</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:4105837">4105837</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Nature&rft.atitle=The+Structure+of+the+Benzene+Ring&rft.volume=122&rft.issue=810&rft.pages=810&rft.date=1928&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A4105837%23id-name%3DS2CID&rft_id=info%3Adoi%2F10.1038%2F122810c0&rft_id=info%3Abibcode%2F1928Natur.122..810L&rft.aulast=Lonsdale&rft.aufirst=Kathleen&rft_id=https%3A%2F%2Fdoi.org%2F10.1038%252F122810c0&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexamethylbenzene" class="Z3988"> </li> <li id="cite_note-25"><a href="#cite_ref-25">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLonsdale1948" class="citation book cs1"><a href="/wiki/Kathleen_Lonsdale" title="Kathleen Lonsdale">Lonsdale, Kathleen</a> (1948). Crystals and X-Rays. <a href="/wiki/George_Bell_%26_Sons" title="George Bell & Sons">George Bell & Sons</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Crystals+and+X-Rays&rft.pub=George+Bell+%26+Sons&rft.date=1948&rft.aulast=Lonsdale&rft.aufirst=Kathleen&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexamethylbenzene" class="Z3988"> </li> <li id="cite_note-HMBSynth-26">^ <a href="#cite_ref-HMBSynth_26-0">a</a> <a href="#cite_ref-HMBSynth_26-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBrinerPlüssPaillard1924" class="citation journal cs1 cs1-prop-foreign-lang-source">Briner, E.; Plüss, W.; Paillard, H. (1924). "Recherches sur la déshydration catalytique des systèmes phénols-alcools" [Research on the catalytic dehydration of phenol-alcohol systems]. <a href="/wiki/Helv._Chim._Acta" class="mw-redirect" title="Helv. Chim. Acta">Helv. Chim. Acta</a> (in French). 7 (1): 1046–1056. <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%2Fhlca.192400701132">10.1002/hlca.192400701132</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Helv.+Chim.+Acta&rft.atitle=Recherches+sur+la+d%C3%A9shydration+catalytique+des+syst%C3%A8mes+ph%C3%A9nols-alcools&rft.volume=7&rft.issue=1&rft.pages=1046-1056&rft.date=1924&rft_id=info%3Adoi%2F10.1002%2Fhlca.192400701132&rft.aulast=Briner&rft.aufirst=E.&rft.au=Pl%C3%BCss%2C+W.&rft.au=Paillard%2C+H.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexamethylbenzene" class="Z3988"> </li> <li id="cite_note-PMB-27">^ <a href="#cite_ref-PMB_27-0">a</a> <a href="#cite_ref-PMB_27-1">b</a> <a href="#cite_ref-PMB_27-2">c</a> <a href="#cite_ref-PMB_27-3">d</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLandisHaag1963" class="citation journal cs1">Landis, Phillip S.; Haag, Werner O. (1963). "Formation of Hexamethylbenzene from Phenol and Methanol". <a href="/wiki/J._Org._Chem." class="mw-redirect" title="J. Org. Chem.">J. Org. Chem.</a> 28 (2): 585. <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%2Fjo01037a517">10.1021/jo01037a517</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Org.+Chem.&rft.atitle=Formation+of+Hexamethylbenzene+from+Phenol+and+Methanol&rft.volume=28&rft.issue=2&rft.pages=585&rft.date=1963&rft_id=info%3Adoi%2F10.1021%2Fjo01037a517&rft.aulast=Landis&rft.aufirst=Phillip+S.&rft.au=Haag%2C+Werner+O.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexamethylbenzene" class="Z3988"> </li> <li id="cite_note-Koptyug1-28">^ <a href="#cite_ref-Koptyug1_28-0">a</a> <a href="#cite_ref-Koptyug1_28-1">b</a> <a href="#cite_ref-Koptyug1_28-2">c</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKrysinKoptyug1969" class="citation journal cs1">Krysin, A. P.; <a href="/wiki/Valentin_Koptyug" title="Valentin Koptyug">Koptyug, V. A.</a> (1969). "Reaction of phenols with alcohols on aluminum oxide II. The mechanism of hexamethylbenzene formation from phenol and methyl alcohol". <a href="/w/index.php?title=Russ._Chem._Bull.&action=edit&redlink=1" class="new" title="Russ. Chem. Bull. (page does not exist)">Russ. Chem. Bull.</a> 18 (7): 1479–1482. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2FBF00908756">10.1007/BF00908756</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Russ.+Chem.+Bull.&rft.atitle=Reaction+of+phenols+with+alcohols+on+aluminum+oxide+II.+The+mechanism+of+hexamethylbenzene+formation+from+phenol+and+methyl+alcohol&rft.volume=18&rft.issue=7&rft.pages=1479-1482&rft.date=1969&rft_id=info%3Adoi%2F10.1007%2FBF00908756&rft.aulast=Krysin&rft.aufirst=A.+P.&rft.au=Koptyug%2C+V.+A.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexamethylbenzene" class="Z3988"> </li> <li id="cite_note-Ipatiew-29">^ <a href="#cite_ref-Ipatiew_29-0">a</a> <a href="#cite_ref-Ipatiew_29-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFIpatiewPetrow1926" class="citation journal cs1 cs1-prop-foreign-lang-source">Ipatiew, W.; Petrow, A. D. (1926). "Über die katalytische Kondensation von Aceton bei hohen Temperaturen und Drucken. (I. Mitteilung)" [On the catalytic condensation of acetone at high temperatures and pressures. (I. Communication)]. <a href="/wiki/Ber._Dtsch._Chem._Ges._A/B" class="mw-redirect" title="Ber. Dtsch. Chem. Ges. A/B">Ber. Dtsch. Chem. Ges. A/B</a> (in German). 59 (8): 2035–2038. <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%2Fcber.19260590859">10.1002/cber.19260590859</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Ber.+Dtsch.+Chem.+Ges.+A%2FB&rft.atitle=%C3%9Cber+die+katalytische+Kondensation+von+Aceton+bei+hohen+Temperaturen+und+Drucken.+%28I.+Mitteilung%29&rft.volume=59&rft.issue=8&rft.pages=2035-2038&rft.date=1926&rft_id=info%3Adoi%2F10.1002%2Fcber.19260590859&rft.aulast=Ipatiew&rft.aufirst=W.&rft.au=Petrow%2C+A.+D.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexamethylbenzene" class="Z3988"> </li> <li id="cite_note-Takeshi1-30">^ <a href="#cite_ref-Takeshi1_30-0">a</a> <a href="#cite_ref-Takeshi1_30-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKotanigawaYamamotoShimokawaYoshida1971" class="citation journal cs1">Kotanigawa, Takeshi; Yamamoto, Mitsuyoshi; Shimokawa, Katsuyoshi; Yoshida, Yuji (1971). <a rel="nofollow" class="external text" href="https://doi.org/10.1246%2Fbcsj.44.1961">"Methylation of Phenol over Metallic Oxides"</a>. Bulletin of the Chemical Society of Japan. 44 (7): 1961–1964. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1246%2Fbcsj.44.1961">10.1246/bcsj.44.1961</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Bulletin+of+the+Chemical+Society+of+Japan&rft.atitle=Methylation+of+Phenol+over+Metallic+Oxides&rft.volume=44&rft.issue=7&rft.pages=1961-1964&rft.date=1971&rft_id=info%3Adoi%2F10.1246%2Fbcsj.44.1961&rft.aulast=Kotanigawa&rft.aufirst=Takeshi&rft.au=Yamamoto%2C+Mitsuyoshi&rft.au=Shimokawa%2C+Katsuyoshi&rft.au=Yoshida%2C+Yuji&rft_id=https%3A%2F%2Fdoi.org%2F10.1246%252Fbcsj.44.1961&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexamethylbenzene" class="Z3988"> </li> <li id="cite_note-Takeshi2-31">^ <a href="#cite_ref-Takeshi2_31-0">a</a> <a href="#cite_ref-Takeshi2_31-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKotanigawa1974" class="citation journal cs1">Kotanigawa, Takeshi (1974). <a rel="nofollow" class="external text" href="https://doi.org/10.1246%2Fbcsj.47.950">"Mechanisms for the Reaction of Phenol with Methanol over the ZnO–Fe2O3 Catalyst"</a>. <a href="/wiki/Bull._Chem._Soc._Jpn." class="mw-redirect" title="Bull. Chem. Soc. Jpn.">Bull. Chem. Soc. Jpn.</a> 47 (4): 950–953. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1246%2Fbcsj.47.950">10.1246/bcsj.47.950</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Bull.+Chem.+Soc.+Jpn.&rft.atitle=Mechanisms+for+the+Reaction+of+Phenol+with+Methanol+over+the+ZnO%E2%80%93Fe%3Csub%3E2%3C%2Fsub%3EO%3Csub%3E3%3C%2Fsub%3E+Catalyst&rft.volume=47&rft.issue=4&rft.pages=950-953&rft.date=1974&rft_id=info%3Adoi%2F10.1246%2Fbcsj.47.950&rft.aulast=Kotanigawa&rft.aufirst=Takeshi&rft_id=https%3A%2F%2Fdoi.org%2F10.1246%252Fbcsj.47.950&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexamethylbenzene" class="Z3988"> </li> <li id="cite_note-CullinaneChard-32">^ <a href="#cite_ref-CullinaneChard_32-0">a</a> <a href="#cite_ref-CullinaneChard_32-1">b</a> <a href="#cite_ref-CullinaneChard_32-2">c</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCullinaneChard1945" class="citation journal cs1">Cullinane, N. M.; Chard, S. J. (1945). "215. The action of methanol on phenol in the presence of alumina. Formation of anisole, methylated phenols, and hexamethylbenzene". <a href="/wiki/J._Chem._Soc." class="mw-redirect" title="J. Chem. Soc.">J. Chem. Soc.</a>: 821–823. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2FJR9450000821">10.1039/JR9450000821</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/21008356">21008356</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Chem.+Soc.&rft.atitle=215.+The+action+of+methanol+on+phenol+in+the+presence+of+alumina.+Formation+of+anisole%2C+methylated+phenols%2C+and+hexamethylbenzene&rft.pages=821-823&rft.date=1945&rft_id=info%3Adoi%2F10.1039%2FJR9450000821&rft_id=info%3Apmid%2F21008356&rft.aulast=Cullinane&rft.aufirst=N.+M.&rft.au=Chard%2C+S.+J.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexamethylbenzene" class="Z3988"> </li> <li id="cite_note-Koptyug2-33">^ <a href="#cite_ref-Koptyug2_33-0">a</a> <a href="#cite_ref-Koptyug2_33-1">b</a> <a href="#cite_ref-Koptyug2_33-2">c</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFShubinChzhuKorobeinichevaRezvukhin1970" class="citation journal cs1">Shubin, V. G.; Chzhu, V. P.; Korobeinicheva, I. K.; Rezvukhin, A. I.; <a href="/wiki/Valentin_Koptyug" title="Valentin Koptyug">Koptyug, V. A.</a> (1970). "UV, IR, AND PMR spectra of hydroxyhexamethylbenzenonium ions". <a href="/w/index.php?title=Russ._Chem._Bull.&action=edit&redlink=1" class="new" title="Russ. Chem. Bull. (page does not exist)">Russ. Chem. Bull.</a> 19 (8): 1643–1648. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2FBF00996497">10.1007/BF00996497</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Russ.+Chem.+Bull.&rft.atitle=UV%2C+IR%2C+AND+PMR+spectra+of+hydroxyhexamethylbenzenonium+ions&rft.volume=19&rft.issue=8&rft.pages=1643-1648&rft.date=1970&rft_id=info%3Adoi%2F10.1007%2FBF00996497&rft.aulast=Shubin&rft.aufirst=V.+G.&rft.au=Chzhu%2C+V.+P.&rft.au=Korobeinicheva%2C+I.+K.&rft.au=Rezvukhin%2C+A.+I.&rft.au=Koptyug%2C+V.+A.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexamethylbenzene" class="Z3988"> </li> <li id="cite_note-Trimerisation-34">^ <a href="#cite_ref-Trimerisation_34-0">a</a> <a href="#cite_ref-Trimerisation_34-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWeberBrintzinger1977" class="citation journal cs1">Weber, S. R.; Brintzinger, H. H. (1977). <a rel="nofollow" class="external text" href="http://nbn-resolving.de/urn:nbn:de:bsz:352-238659">"Reactions of Bis(hexamethylbenzene)iron(0) with Carbon Monoxide and with Unsaturated Hydrocarbons"</a>. <a href="/wiki/J._Organomet._Chem." class="mw-redirect" title="J. Organomet. Chem.">J. Organomet. Chem.</a> 127 (1): 45–54. <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%2FS0022-328X%2800%2984196-0">10.1016/S0022-328X(00)84196-0</a>. <a href="/wiki/Hdl_(identifier)" class="mw-redirect" title="Hdl (identifier)">hdl</a>:<a rel="nofollow" class="external text" href="https://hdl.handle.net/2027.42%2F22975">2027.42/22975</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Organomet.+Chem.&rft.atitle=Reactions+of+Bis%28hexamethylbenzene%29iron%280%29+with+Carbon+Monoxide+and+with+Unsaturated+Hydrocarbons&rft.volume=127&rft.issue=1&rft.pages=45-54&rft.date=1977&rft_id=info%3Ahdl%2F2027.42%2F22975&rft_id=info%3Adoi%2F10.1016%2FS0022-328X%2800%2984196-0&rft.aulast=Weber&rft.aufirst=S.+R.&rft.au=Brintzinger%2C+H.+H.&rft_id=http%3A%2F%2Fnbn-resolving.de%2Furn%3Anbn%3Ade%3Absz%3A352-238659&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexamethylbenzene" class="Z3988"> </li> <li id="cite_note-Cr-35">^ <a href="#cite_ref-Cr_35-0">a</a> <a href="#cite_ref-Cr_35-1">b</a> <a href="#cite_ref-Cr_35-2">c</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFZeissHerwig1958" class="citation journal cs1">Zeiss, H. H.; Herwig, W. (1958). "Acetylenic π-complexes of chromium in organic synthesis". <a href="/wiki/J._Am._Chem._Soc." class="mw-redirect" title="J. Am. Chem. Soc.">J. Am. Chem. Soc.</a> 80 (11): 2913. <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%2Fja01544a091">10.1021/ja01544a091</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Am.+Chem.+Soc.&rft.atitle=Acetylenic+%CF%80-complexes+of+chromium+in+organic+synthesis&rft.volume=80&rft.issue=11&rft.pages=2913&rft.date=1958&rft_id=info%3Adoi%2F10.1021%2Fja01544a091&rft.aulast=Zeiss&rft.aufirst=H.+H.&rft.au=Herwig%2C+W.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexamethylbenzene" class="Z3988"> </li> <li id="cite_note-Ti-36">^ <a href="#cite_ref-Ti_36-0">a</a> <a href="#cite_ref-Ti_36-1">b</a> <a href="#cite_ref-Ti_36-2">c</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFranzusCanterinoWickliffe1959" class="citation journal cs1">Franzus, B.; Canterino, P. J.; Wickliffe, R. A. (1959). "Titanium tetrachloride–trialkylaluminum complex—A cyclizing catalyst for acetylenic compounds". <a href="/wiki/J._Am._Chem._Soc." class="mw-redirect" title="J. Am. Chem. Soc.">J. Am. Chem. Soc.</a> 81 (6): 1514. <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%2Fja01515a061">10.1021/ja01515a061</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Am.+Chem.+Soc.&rft.atitle=Titanium+tetrachloride%E2%80%93trialkylaluminum+complex%E2%80%94A+cyclizing+catalyst+for+acetylenic+compounds&rft.volume=81&rft.issue=6&rft.pages=1514&rft.date=1959&rft_id=info%3Adoi%2F10.1021%2Fja01515a061&rft.aulast=Franzus&rft.aufirst=B.&rft.au=Canterino%2C+P.+J.&rft.au=Wickliffe%2C+R.+A.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexamethylbenzene" class="Z3988"> </li> <li id="cite_note-37"><a href="#cite_ref-37">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLe_BelGreene1880" class="citation journal cs1"><a href="/wiki/Joseph_Achille_Le_Bel" title="Joseph Achille Le Bel">Le Bel, Joseph Achille</a>; Greene, William H. (1880). "On the decomposition of alcohols, etc., by zinc chloride at high temperatures". American Chemical Journal. 2: 20–26.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=American+Chemical+Journal&rft.atitle=On+the+decomposition+of+alcohols%2C+etc.%2C+by+zinc+chloride+at+high+temperatures&rft.volume=2&rft.pages=20-26&rft.date=1880&rft.aulast=Le+Bel&rft.aufirst=Joseph+Achille&rft.au=Greene%2C+William+H.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexamethylbenzene" class="Z3988"> </li> <li id="cite_note-HMB-38">^ <a href="#cite_ref-HMB_38-0">a</a> <a href="#cite_ref-HMB_38-1">b</a> <a href="#cite_ref-HMB_38-2">c</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFChang1983" class="citation journal cs1">Chang, Clarence D. (1983). "Hydrocarbons from Methanol". <a href="/w/index.php?title=Catal._Rev._-_Sci._Eng.&action=edit&redlink=1" class="new" title="Catal. Rev. - Sci. Eng. (page does not exist)">Catal. Rev. - Sci. Eng.</a> 25 (1): 1–118. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1080%2F01614948308078874">10.1080/01614948308078874</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Catal.+Rev.+-+Sci.+Eng.&rft.atitle=Hydrocarbons+from+Methanol&rft.volume=25&rft.issue=1&rft.pages=1-118&rft.date=1983&rft_id=info%3Adoi%2F10.1080%2F01614948308078874&rft.aulast=Chang&rft.aufirst=Clarence+D.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexamethylbenzene" class="Z3988"> </li> <li id="cite_note-39"><a href="#cite_ref-39">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFOlahDoggweilerFelbergFrohlich1984" class="citation journal cs1">Olah, George A.; Doggweiler, Hans; Felberg, Jeff D.; Frohlich, Stephan; Grdina, Mary Jo; Karpeles, Richard; Keumi, Takashi; Inaba, Shin-ichi; Ip, Wai M.; Lammertsma, Koop; Salem, George; Tabor, Derrick (1984). "Onium Ylide chemistry. 1. Bifunctional acid-base-catalyzed conversion of heterosubstituted methanes into ethylene and derived hydrocarbons. The onium ylide mechanism of the C1→C2 conversion". <a href="/wiki/J._Am._Chem._Soc." class="mw-redirect" title="J. Am. Chem. Soc.">J. Am. Chem. Soc.</a> 106 (7): 2143–2149. <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%2Fja00319a039">10.1021/ja00319a039</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Am.+Chem.+Soc.&rft.atitle=Onium+Ylide+chemistry.+1.+Bifunctional+acid-base-catalyzed+conversion+of+heterosubstituted+methanes+into+ethylene+and+derived+hydrocarbons.+The+onium+ylide+mechanism+of+the+C%3Csub%3E1%3C%2Fsub%3E%E2%86%92C%3Csub%3E2%3C%2Fsub%3E+conversion&rft.volume=106&rft.issue=7&rft.pages=2143-2149&rft.date=1984&rft_id=info%3Adoi%2F10.1021%2Fja00319a039&rft.aulast=Olah&rft.aufirst=George+A.&rft.au=Doggweiler%2C+Hans&rft.au=Felberg%2C+Jeff+D.&rft.au=Frohlich%2C+Stephan&rft.au=Grdina%2C+Mary+Jo&rft.au=Karpeles%2C+Richard&rft.au=Keumi%2C+Takashi&rft.au=Inaba%2C+Shin-ichi&rft.au=Ip%2C+Wai+M.&rft.au=Lammertsma%2C+Koop&rft.au=Salem%2C+George&rft.au=Tabor%2C+Derrick&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexamethylbenzene" class="Z3988"> </li> <li id="cite_note-40"><a href="#cite_ref-40">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSmith1930" class="citation journal cs1">Smith, Lee Irvin (1930). <a rel="nofollow" class="external text" href="http://www.orgsyn.org/demo.aspx?prep=cv2p0248">"Durene"</a>. <a href="/wiki/Organic_Syntheses" title="Organic Syntheses">Organic Syntheses</a>. 10: 32. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.15227%2Forgsyn.010.0032">10.15227/orgsyn.010.0032</a></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Organic+Syntheses&rft.atitle=Durene&rft.volume=10&rft.pages=32&rft.date=1930&rft_id=info%3Adoi%2F10.15227%2Forgsyn.010.0032&rft.aulast=Smith&rft.aufirst=Lee+Irvin&rft_id=http%3A%2F%2Fwww.orgsyn.org%2Fdemo.aspx%3Fprep%3Dcv2p0248&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexamethylbenzene" class="Z3988">; <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation cs2">Collected Volumes, vol. 2, p. 248</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Collected+Volumes&rft.pages=248&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexamethylbenzene" class="Z3988">. </li> <li id="cite_note-41"><a href="#cite_ref-41">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRecklebenScheiber1913" class="citation journal cs1 cs1-prop-foreign-lang-source">Reckleben, Hans; Scheiber, Johannes (1913). <a rel="nofollow" class="external text" href="https://zenodo.org/record/1426519">"Über eine einfache Darstellung des Hexamethyl-benzols"</a> [A simple representation of hexamethylbenzene]. <a href="/wiki/Ber._Dtsch._Chem._Ges." class="mw-redirect" title="Ber. Dtsch. Chem. Ges.">Ber. Dtsch. Chem. Ges.</a> (in German). 46 (2): 2363–2365. <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%2Fcber.191304602168">10.1002/cber.191304602168</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Ber.+Dtsch.+Chem.+Ges.&rft.atitle=%C3%9Cber+eine+einfache+Darstellung+des+Hexamethyl-benzols&rft.volume=46&rft.issue=2&rft.pages=2363-2365&rft.date=1913&rft_id=info%3Adoi%2F10.1002%2Fcber.191304602168&rft.aulast=Reckleben&rft.aufirst=Hans&rft.au=Scheiber%2C+Johannes&rft_id=https%3A%2F%2Fzenodo.org%2Frecord%2F1426519&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexamethylbenzene" class="Z3988"> </li> <li id="cite_note-42"><a href="#cite_ref-42">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFIpatiewPetrow1927" class="citation journal cs1 cs1-prop-foreign-lang-source">Ipatiew, W. N.; Petrow, A. D. (1927). "Über die katalytische Kondensation des Acetons bei hohen Temperaturen und Drucken (II. Mitteilung)" [On the catalytic condensation of acetone at high temperatures and pressures (II. Communication)]. <a href="/wiki/Ber._Dtsch._Chem._Ges._A/B" class="mw-redirect" title="Ber. Dtsch. Chem. Ges. A/B">Ber. Dtsch. Chem. Ges. A/B</a> (in German). 60 (3): 753–755. <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%2Fcber.19270600328">10.1002/cber.19270600328</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Ber.+Dtsch.+Chem.+Ges.+A%2FB&rft.atitle=%C3%9Cber+die+katalytische+Kondensation+des+Acetons+bei+hohen+Temperaturen+und+Drucken+%28II.+Mitteilung%29&rft.volume=60&rft.issue=3&rft.pages=753-755&rft.date=1927&rft_id=info%3Adoi%2F10.1002%2Fcber.19270600328&rft.aulast=Ipatiew&rft.aufirst=W.+N.&rft.au=Petrow%2C+A.+D.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexamethylbenzene" class="Z3988"> </li> <li id="cite_note-43"><a href="#cite_ref-43">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKotanigawaShimokawa1974" class="citation journal cs1">Kotanigawa, Takeshi; Shimokawa, Katsuyoshi (1974). <a rel="nofollow" class="external text" href="https://doi.org/10.1246%2Fbcsj.47.1535">"The Alkylation of Phenol over the ZnO–Fe2O3 Catalyst"</a>. <a href="/wiki/Bull._Chem._Soc._Jpn." class="mw-redirect" title="Bull. Chem. Soc. Jpn.">Bull. Chem. Soc. Jpn.</a> 47 (6): 1535–1536. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1246%2Fbcsj.47.1535">10.1246/bcsj.47.1535</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Bull.+Chem.+Soc.+Jpn.&rft.atitle=The+Alkylation+of+Phenol+over+the+ZnO%E2%80%93Fe%3Csub%3E2%3C%2Fsub%3EO%3Csub%3E3%3C%2Fsub%3E+Catalyst&rft.volume=47&rft.issue=6&rft.pages=1535-1536&rft.date=1974&rft_id=info%3Adoi%2F10.1246%2Fbcsj.47.1535&rft.aulast=Kotanigawa&rft.aufirst=Takeshi&rft.au=Shimokawa%2C+Katsuyoshi&rft_id=https%3A%2F%2Fdoi.org%2F10.1246%252Fbcsj.47.1535&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexamethylbenzene" class="Z3988"> </li> <li id="cite_note-44"><a href="#cite_ref-44">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKotanigawa1974" class="citation journal cs1">Kotanigawa, Takeshi (1974). <a rel="nofollow" class="external text" href="https://doi.org/10.1246%2Fbcsj.47.2466">"The Methylation of Phenol and the Decomposition of Methanol on ZnO–Fe2O3 Catalyst"</a>. <a href="/wiki/Bull._Chem._Soc._Jpn." class="mw-redirect" title="Bull. Chem. Soc. Jpn.">Bull. Chem. Soc. Jpn.</a> 47 (10): 2466–2468. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1246%2Fbcsj.47.2466">10.1246/bcsj.47.2466</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Bull.+Chem.+Soc.+Jpn.&rft.atitle=The+Methylation+of+Phenol+and+the+Decomposition+of+Methanol+on+ZnO%E2%80%93Fe%3Csub%3E2%3C%2Fsub%3EO%3Csub%3E3%3C%2Fsub%3E+Catalyst&rft.volume=47&rft.issue=10&rft.pages=2466-2468&rft.date=1974&rft_id=info%3Adoi%2F10.1246%2Fbcsj.47.2466&rft.aulast=Kotanigawa&rft.aufirst=Takeshi&rft_id=https%3A%2F%2Fdoi.org%2F10.1246%252Fbcsj.47.2466&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexamethylbenzene" class="Z3988"> </li> <li id="cite_note-45"><a href="#cite_ref-45">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRossBassinFinkelsteinLeach1954" class="citation journal cs1">Ross, Sidney D.; Bassin, Morton; Finkelstein, Manuel; Leach, William A. (1954). "Molecular Compounds. I. Picryl Chloride-Hexamethylbenzene in Chloroform Solution". <a href="/wiki/J._Am._Chem._Soc." class="mw-redirect" title="J. Am. Chem. Soc.">J. Am. Chem. Soc.</a> 76 (1): 69–74. <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%2Fja01630a018">10.1021/ja01630a018</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Am.+Chem.+Soc.&rft.atitle=Molecular+Compounds.+I.+Picryl+Chloride-Hexamethylbenzene+in+Chloroform+Solution&rft.volume=76&rft.issue=1&rft.pages=69-74&rft.date=1954&rft_id=info%3Adoi%2F10.1021%2Fja01630a018&rft.aulast=Ross&rft.aufirst=Sidney+D.&rft.au=Bassin%2C+Morton&rft.au=Finkelstein%2C+Manuel&rft.au=Leach%2C+William+A.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexamethylbenzene" class="Z3988"> </li> <li id="cite_note-46"><a href="#cite_ref-46">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHartLangeCollins1968" class="citation journal cs1">Hart, Harold; Lange, Richard M.; Collins, Peter M. (1968). <a rel="nofollow" class="external text" href="http://www.orgsyn.org/demo.aspx?prep=cv5p0598">"2,3,4,5,6,6-Hexamethyl-2,4-cyclohexadien-1-one"</a>. <a href="/wiki/Organic_Syntheses" title="Organic Syntheses">Organic Syntheses</a>. 48: 87. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.15227%2Forgsyn.048.0087">10.15227/orgsyn.048.0087</a></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Organic+Syntheses&rft.atitle=2%2C3%2C4%2C5%2C6%2C6-Hexamethyl-2%2C4-cyclohexadien-1-one&rft.volume=48&rft.pages=87&rft.date=1968&rft_id=info%3Adoi%2F10.15227%2Forgsyn.048.0087&rft.aulast=Hart&rft.aufirst=Harold&rft.au=Lange%2C+Richard+M.&rft.au=Collins%2C+Peter+M.&rft_id=http%3A%2F%2Fwww.orgsyn.org%2Fdemo.aspx%3Fprep%3Dcv5p0598&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexamethylbenzene" class="Z3988">; <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation cs2">Collected Volumes, vol. 5, p. 598</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Collected+Volumes&rft.pages=598&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexamethylbenzene" class="Z3988">. </li> <li id="cite_note-47"><a href="#cite_ref-47">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSaundersJiménez-VázquezKhong1996" class="citation journal cs1">Saunders, Martin; Jiménez-Vázquez, Hugo A.; Khong, Anthony (1996). "NMR of 3He Dissolved in Organic Solids". <a href="/wiki/J._Phys._Chem." class="mw-redirect" title="J. Phys. Chem.">J. Phys. Chem.</a> 100 (39): 15968–15971. <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%2Fjp9617783">10.1021/jp9617783</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Phys.+Chem.&rft.atitle=NMR+of+%3Csup%3E3%3C%2Fsup%3EHe+Dissolved+in+Organic+Solids&rft.volume=100&rft.issue=39&rft.pages=15968-15971&rft.date=1996&rft_id=info%3Adoi%2F10.1021%2Fjp9617783&rft.aulast=Saunders&rft.aufirst=Martin&rft.au=Jim%C3%A9nez-V%C3%A1zquez%2C+Hugo+A.&rft.au=Khong%2C+Anthony&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexamethylbenzene" class="Z3988"> </li> <li id="cite_note-48"><a href="#cite_ref-48">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFEarhartKomin2000" class="citation cs1">Earhart, H. W.; Komin, Andrew P. (2000). "Polymethylbenzenes". Kirk-Othmer Encyclopedia of Chemical Technology. New York: John Wiley. <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%2F0471238961.1615122505011808.a01">10.1002/0471238961.1615122505011808.a01</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780471238966" title="Special:BookSources/9780471238966"><bdi>9780471238966</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Polymethylbenzenes&rft.btitle=Kirk-Othmer+Encyclopedia+of+Chemical+Technology&rft.place=New+York&rft.pub=John+Wiley&rft.date=2000&rft_id=info%3Adoi%2F10.1002%2F0471238961.1615122505011808.a01&rft.isbn=9780471238966&rft.aulast=Earhart&rft.aufirst=H.+W.&rft.au=Komin%2C+Andrew+P.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexamethylbenzene" class="Z3988"> </li> <li id="cite_note-CoRh-49">^ <a href="#cite_ref-CoRh_49-0">a</a> <a href="#cite_ref-CoRh_49-1">b</a> <a href="#cite_ref-CoRh_49-2">c</a> <a href="#cite_ref-CoRh_49-3">d</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFischerLindner1964" class="citation journal cs1 cs1-prop-foreign-lang-source"><a href="/wiki/Ernst_Otto_Fischer" title="Ernst Otto Fischer">Fischer, Ernst Otto</a>; Lindner, Hans Hasso (1964). "Über Aromatenkomplexe von Metallen. LXXVI. Di-hexamethylbenzol-metall-π-komplexe des ein- und zweiwertigen Kobalts und Rhodiums" [About Aromatic Complexes of Metals. LXXVI. Di-hexamethylbenzene metal-π-complexes of mono- and bivalent cobalt and rhodium]. <a href="/wiki/J._Organomet._Chem." class="mw-redirect" title="J. Organomet. Chem.">J. Organomet. Chem.</a> (in German). 1 (4): 307–317. <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%2FS0022-328X%2800%2980056-X">10.1016/S0022-328X(00)80056-X</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Organomet.+Chem.&rft.atitle=%C3%9Cber+Aromatenkomplexe+von+Metallen.+LXXVI.+Di-hexamethylbenzol-metall-%CF%80-komplexe+des+ein-+und+zweiwertigen+Kobalts+und+Rhodiums&rft.volume=1&rft.issue=4&rft.pages=307-317&rft.date=1964&rft_id=info%3Adoi%2F10.1016%2FS0022-328X%2800%2980056-X&rft.aulast=Fischer&rft.aufirst=Ernst+Otto&rft.au=Lindner%2C+Hans+Hasso&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexamethylbenzene" class="Z3988"> </li> <li id="cite_note-50"><a href="#cite_ref-50">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFischerSchmidt1966" class="citation journal cs1"><a href="/wiki/Ernst_Otto_Fischer" title="Ernst Otto Fischer">Fischer, Ernst Otto</a>; Schmidt, Manfred W. (1966). "Über Aromatenkomplexe von Metallen, XCI. Über monomeres und dimeres Bis-hexamethylbenzol-rhenium". <a href="/wiki/Chem._Ber." class="mw-redirect" title="Chem. Ber.">Chem. Ber.</a> 99 (7): 2206–2212. <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%2Fcber.19660990719">10.1002/cber.19660990719</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chem.+Ber.&rft.atitle=%C3%9Cber+Aromatenkomplexe+von+Metallen%2C+XCI.+%C3%9Cber+monomeres+und+dimeres+Bis-hexamethylbenzol-rhenium&rft.volume=99&rft.issue=7&rft.pages=2206-2212&rft.date=1966&rft_id=info%3Adoi%2F10.1002%2Fcber.19660990719&rft.aulast=Fischer&rft.aufirst=Ernst+Otto&rft.au=Schmidt%2C+Manfred+W.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexamethylbenzene" class="Z3988"> </li> <li id="cite_note-51"><a href="#cite_ref-51">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBennettHuangMathesonSmith1982" class="citation book cs1"><a href="/wiki/Martin_A._Bennett" title="Martin A. Bennett">Bennett, Martin A.</a>; Huang, T.-N.; Matheson, T. W.; Smith, A. K. (1982). 16. (η6-Hexamethylbenzene)Ruthenium Complexes. Vol. 21. pp. 74–78. <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%2F9780470132524.ch16">10.1002/9780470132524.ch16</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780470132524" title="Special:BookSources/9780470132524"><bdi>9780470132524</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=16.+%28%CE%B7%3Csup%3E6%3C%2Fsup%3E-Hexamethylbenzene%29Ruthenium+Complexes&rft.pages=74-78&rft.date=1982&rft_id=info%3Adoi%2F10.1002%2F9780470132524.ch16&rft.isbn=9780470132524&rft.aulast=Bennett&rft.aufirst=Martin+A.&rft.au=Huang%2C+T.-N.&rft.au=Matheson%2C+T.+W.&rft.au=Smith%2C+A.+K.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexamethylbenzene" class="Z3988"> <code class="cs1-code">{{<a href="/wiki/Template:Cite_book" title="Template:Cite book">cite book</a>}}</code>: <code class="cs1-code">|journal=</code> ignored (<a href="/wiki/Help:CS1_errors#periodical_ignored" title="Help:CS1 errors">help</a>) </li> <li id="cite_note-52"><a href="#cite_ref-52">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSchäferHellmann1967" class="citation journal cs1">Schäfer, W.; Hellmann, H. (1967). "Hexamethyl(Dewar Benzene) (Hexamethylbicyclo[2.2.0]hexa-2,5-diene)". <a href="/wiki/Angew._Chem._Int._Ed._Engl." class="mw-redirect" title="Angew. Chem. Int. Ed. Engl.">Angew. Chem. Int. Ed. Engl.</a> 6 (6): 518–525. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fanie.196705181">10.1002/anie.196705181</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Angew.+Chem.+Int.+Ed.+Engl.&rft.atitle=Hexamethyl%28Dewar+Benzene%29+%28Hexamethylbicyclo%5B2.2.0%5Dhexa-2%2C5-diene%29&rft.volume=6&rft.issue=6&rft.pages=518-525&rft.date=1967&rft_id=info%3Adoi%2F10.1002%2Fanie.196705181&rft.aulast=Sch%C3%A4fer&rft.aufirst=W.&rft.au=Hellmann%2C+H.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexamethylbenzene" class="Z3988"> </li> <li id="cite_note-53"><a href="#cite_ref-53">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPaquetteKrowBollingerOlah1968" class="citation journal cs1"><a href="/wiki/Leo_Paquette" title="Leo Paquette">Paquette, Leo A.</a>; Krow, Grant R.; Bollinger, J. Martin; Olah, George A. (1968). "Protonation of hexamethyl Dewar benzene and hexamethylprismane in fluorosulfuric acid – antimony pentafluoride – sulfur dioxide". <a href="/wiki/J._Am._Chem._Soc." class="mw-redirect" title="J. Am. Chem. Soc.">J. Am. Chem. Soc.</a> 90 (25): 7147–7149. <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%2Fja01027a060">10.1021/ja01027a060</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Am.+Chem.+Soc.&rft.atitle=Protonation+of+hexamethyl+Dewar+benzene+and+hexamethylprismane+in+fluorosulfuric+acid+%E2%80%93+antimony+pentafluoride+%E2%80%93+sulfur+dioxide&rft.volume=90&rft.issue=25&rft.pages=7147-7149&rft.date=1968&rft_id=info%3Adoi%2F10.1021%2Fja01027a060&rft.aulast=Paquette&rft.aufirst=Leo+A.&rft.au=Krow%2C+Grant+R.&rft.au=Bollinger%2C+J.+Martin&rft.au=Olah%2C+George+A.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexamethylbenzene" class="Z3988"> </li> <li id="cite_note-54"><a href="#cite_ref-54">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLaubeLohse1994" class="citation journal cs1">Laube, Thomas; Lohse, Christian (1994). "X-ray Crystal Structures of Two (deloc-2,3,5)-1,2,3,4,5,6- Hexamethylbicyclo[2.1.1]hex-2-en-5-ylium Ions". <a href="/wiki/J._Am._Chem._Soc." class="mw-redirect" title="J. Am. Chem. Soc.">J. Am. Chem. Soc.</a> 116 (20): 9001–9008. <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%2Fja00099a018">10.1021/ja00099a018</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Am.+Chem.+Soc.&rft.atitle=X-ray+Crystal+Structures+of+Two+%28deloc-2%2C3%2C5%29-1%2C2%2C3%2C4%2C5%2C6-+Hexamethylbicyclo%5B2.1.1%5Dhex-2-en-5-ylium+Ions&rft.volume=116&rft.issue=20&rft.pages=9001-9008&rft.date=1994&rft_id=info%3Adoi%2F10.1021%2Fja00099a018&rft.aulast=Laube&rft.aufirst=Thomas&rft.au=Lohse%2C+Christian&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexamethylbenzene" class="Z3988"> </li> <li id="cite_note-55"><a href="#cite_ref-55">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFJašíkGerlichRoithová2014" class="citation journal cs1">Jašík, Juraj; Gerlich, Dieter; Roithová, Jana (2014). "Probing Isomers of the Benzene Dication in a Low-Temperature Trap". <a href="/wiki/J._Am._Chem._Soc." class="mw-redirect" title="J. Am. Chem. Soc.">J. Am. Chem. Soc.</a> 136 (8): 2960–2962. <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%2Fja412109h">10.1021/ja412109h</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/24528384">24528384</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Am.+Chem.+Soc.&rft.atitle=Probing+Isomers+of+the+Benzene+Dication+in+a+Low-Temperature+Trap&rft.volume=136&rft.issue=8&rft.pages=2960-2962&rft.date=2014&rft_id=info%3Adoi%2F10.1021%2Fja412109h&rft_id=info%3Apmid%2F24528384&rft.aulast=Ja%C5%A1%C3%ADk&rft.aufirst=Juraj&rft.au=Gerlich%2C+Dieter&rft.au=Roithov%C3%A1%2C+Jana&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexamethylbenzene" class="Z3988"> </li> <li id="cite_note-56"><a href="#cite_ref-56">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPuiu2017" class="citation web cs1">Puiu, Tibi (5 January 2017). <a rel="nofollow" class="external text" href="http://www.zmescience.com/science/news-science/carbon-six-bond-molecule/">"Exotic carbon molecule has six bonds, breaking the four-bond limit"</a>. zmescience.com. <a href="/w/index.php?title=ZME_Science&action=edit&redlink=1" class="new" title="ZME Science (page does not exist)">ZME Science</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20170116174936/http://www.zmescience.com/science/news-science/carbon-six-bond-molecule/">Archived</a> from the original on 16 January 2017. Retrieved 14 January 2017.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=zmescience.com&rft.atitle=Exotic+carbon+molecule+has+six+bonds%2C+breaking+the+four-bond+limit&rft.date=2017-01-05&rft.aulast=Puiu&rft.aufirst=Tibi&rft_id=http%3A%2F%2Fwww.zmescience.com%2Fscience%2Fnews-science%2Fcarbon-six-bond-molecule%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexamethylbenzene" class="Z3988"> </li> <li id="cite_note-Cp*ZnMe-57">^ <a href="#cite_ref-Cp*ZnMe_57-0">a</a> <a href="#cite_ref-Cp*ZnMe_57-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHaalandSamdalSeip1978" class="citation journal cs1"><a href="/wiki/Arne_Haaland" title="Arne Haaland">Haaland, Arne</a>; Samdal, Svein; Seip, Ragnhild (1978). "The molecular structure of monomeric methyl(cyclopentadienyl)zinc, (CH3)Zn(η-C5H5), determined by gas phase electron diffraction". <a href="/wiki/J._Organomet._Chem." class="mw-redirect" title="J. Organomet. Chem.">J. Organomet. Chem.</a> 153 (2): 187–192. <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%2FS0022-328X%2800%2985041-X">10.1016/S0022-328X(00)85041-X</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Organomet.+Chem.&rft.atitle=The+molecular+structure+of+monomeric+methyl%28cyclopentadienyl%29zinc%2C+%28CH%3Csub%3E3%3C%2Fsub%3E%29Zn%28%CE%B7-C%3Csub%3E5%3C%2Fsub%3EH%3Csub%3E5%3C%2Fsub%3E%29%2C+determined+by+gas+phase+electron+diffraction&rft.volume=153&rft.issue=2&rft.pages=187-192&rft.date=1978&rft_id=info%3Adoi%2F10.1016%2FS0022-328X%2800%2985041-X&rft.aulast=Haaland&rft.aufirst=Arne&rft.au=Samdal%2C+Svein&rft.au=Seip%2C+Ragnhild&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexamethylbenzene" class="Z3988"> </li> <li id="cite_note-58"><a href="#cite_ref-58">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFElschenbroich2006" class="citation book cs1">Elschenbroich, Christoph (2006). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=B_-OCwAAQBAJ&pg=PA74">"Organometallic Compounds of Groups 2 and 12"</a>. Organometallics (3rd ed.). <a href="/wiki/John_Wiley_%26_Sons" class="mw-redirect" title="John Wiley & Sons">John Wiley & Sons</a>. pp. 59–85. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9783527805143" title="Special:BookSources/9783527805143"><bdi>9783527805143</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Organometallic+Compounds+of+Groups+2+and+12&rft.btitle=Organometallics&rft.pages=59-85&rft.edition=3rd&rft.pub=John+Wiley+%26+Sons&rft.date=2006&rft.isbn=9783527805143&rft.aulast=Elschenbroich&rft.aufirst=Christoph&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DB_-OCwAAQBAJ%26pg%3DPA74&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexamethylbenzene" class="Z3988"> </li> </ol></div> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist 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style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="AlkanesCnH2n_+_2" scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Alkane" title="Alkane">Alkanes</a> CnH2n + 2</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em">Linear alkanes</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Methane" title="Methane">Methane</a></li> <li><a href="/wiki/Ethane" title="Ethane">Ethane</a></li> <li><a href="/wiki/Propane" title="Propane">Propane</a></li> <li><a href="/wiki/Butane" title="Butane">Butane</a></li> <li><a href="/wiki/Pentane" title="Pentane">Pentane</a></li> <li><a href="/wiki/Hexane" title="Hexane">Hexane</a></li> <li><a href="/wiki/Heptane" title="Heptane">Heptane</a></li> <li><a href="/wiki/Octane" title="Octane">Octane</a></li> <li><a href="/wiki/Nonane" title="Nonane">Nonane</a></li> <li><a href="/wiki/Decane" title="Decane">Decane</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Branched alkanes</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Isobutane" title="Isobutane">Isobutane</a></li> <li><a href="/wiki/Isopentane" title="Isopentane">Isopentane</a></li> <li><a href="/wiki/3-Methylpentane" title="3-Methylpentane">3-Methylpentane</a></li> <li><a href="/wiki/Neopentane" title="Neopentane">Neopentane</a></li> <li><a href="/wiki/2-Methylpentane" title="2-Methylpentane">Isohexane</a></li> <li><a href="/wiki/2-Methylhexane" title="2-Methylhexane">Isoheptane</a></li> <li><a href="/wiki/2,2,4-Trimethylpentane" title="2,2,4-Trimethylpentane">Isooctane</a></li> <li><a href="/wiki/2-Methyloctane" title="2-Methyloctane">Isononane</a></li> <li><a href="/w/index.php?title=Isodecane&action=edit&redlink=1" class="new" title="Isodecane (page does not exist)">Isodecane</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Cycloalkane" title="Cycloalkane">Cycloalkanes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cyclopropane" title="Cyclopropane">Cyclopropane</a></li> <li><a href="/wiki/Cyclobutane" title="Cyclobutane">Cyclobutane</a></li> <li><a href="/wiki/Cyclopentane" title="Cyclopentane">Cyclopentane</a></li> <li><a href="/wiki/Cyclohexane" title="Cyclohexane">Cyclohexane</a></li> <li><a href="/wiki/Cycloheptane" title="Cycloheptane">Cycloheptane</a></li> <li><a href="/wiki/Cyclooctane" title="Cyclooctane">Cyclooctane</a></li> <li><a href="/wiki/Cyclononane" title="Cyclononane">Cyclononane</a></li> <li><a href="/wiki/Cyclodecane" title="Cyclodecane">Cyclodecane</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/w/index.php?title=Alkylcycloalkane&action=edit&redlink=1" class="new" title="Alkylcycloalkane (page does not exist)">Alkylcycloalkanes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Methylcyclopropane" title="Methylcyclopropane">Methylcyclopropane</a></li> <li><a href="/w/index.php?title=Methylcyclobutane&action=edit&redlink=1" class="new" title="Methylcyclobutane (page does not exist)">Methylcyclobutane</a></li> <li><a href="/wiki/Methylcyclopentane" title="Methylcyclopentane">Methylcyclopentane</a></li> <li><a href="/wiki/Methylcyclohexane" title="Methylcyclohexane">Methylcyclohexane</a></li> <li><a href="/w/index.php?title=Isopropylcyclohexane&action=edit&redlink=1" class="new" title="Isopropylcyclohexane (page does not exist)">Isopropylcyclohexane</a></li> <li class="mw-empty-elt"></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/w/index.php?title=Bicycloalkane&action=edit&redlink=1" class="new" title="Bicycloalkane (page does not exist)">Bicycloalkanes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Housane" title="Housane">Housane</a> (bicyclo[2.1.0]pentane)</li> <li><a href="/wiki/Norbornane" title="Norbornane">Norbornane</a> (bicyclo[2.2.1]heptane)</li> <li><a href="/wiki/Decalin" title="Decalin">Decalin</a> (bicyclo[4.4.0]decane)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/w/index.php?title=Polycycloalkane&action=edit&redlink=1" class="new" title="Polycycloalkane (page does not exist)">Polycycloalkanes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Adamantane" title="Adamantane">Adamantane</a></li> <li><a href="/wiki/Diamondoid" title="Diamondoid">Diamondoid</a></li> <li><a href="/w/index.php?title=Perhydrophenanthrene&action=edit&redlink=1" class="new" title="Perhydrophenanthrene (page does not exist)">Perhydrophenanthrene</a></li> <li><a href="/wiki/Sterane" title="Sterane">Sterane</a></li> <li><a href="/wiki/Cubane" title="Cubane">Cubane</a></li> <li><a href="/wiki/Prismane" title="Prismane">Prismane</a></li> <li><a href="/wiki/Dodecahedrane" title="Dodecahedrane">Dodecahedrane</a></li> <li><a href="/wiki/Basketane" title="Basketane">Basketane</a></li> <li><a href="/wiki/Churchane" title="Churchane">Churchane</a></li> <li><a href="/wiki/Pagodane" title="Pagodane">Pagodane</a></li> <li><a href="/wiki/Twistane" title="Twistane">Twistane</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=Spiroalkane&action=edit&redlink=1" class="new" title="Spiroalkane (page does not exist)">Spiroalkanes</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:azzurro;"><a href="/wiki/Unsaturated_hydrocarbon" class="mw-redirect" title="Unsaturated hydrocarbon">Unsaturated</a> aliphatic hydrocarbons</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Alkene" title="Alkene">Alkenes</a> CnH2n</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em">Linear alkenes</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ethylene" title="Ethylene">Ethene</a></li> <li><a href="/wiki/Propene" class="mw-redirect" title="Propene">Propene</a></li> <li><a href="/wiki/Butene" title="Butene">Butene</a></li> <li><a href="/wiki/Pentene" title="Pentene">Pentene</a></li> <li><a href="/wiki/Hexene" title="Hexene">Hexene</a></li> <li><a href="/wiki/Heptene" title="Heptene">Heptene</a></li> <li><a href="/wiki/Octene" title="Octene">Octene</a></li> <li><a href="/wiki/Nonene" title="Nonene">Nonene</a></li> <li><a href="/wiki/Decene" title="Decene">Decene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Branched alkenes</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Isobutylene" title="Isobutylene">Isobutene</a></li> <li><a href="/wiki/Isopentene" class="mw-redirect" title="Isopentene">Isopentene</a></li> <li><a href="/w/index.php?title=Isohexene&action=edit&redlink=1" class="new" title="Isohexene (page does not exist)">Isohexene</a></li> <li><a href="/w/index.php?title=Isoheptene&action=edit&redlink=1" class="new" title="Isoheptene (page does not exist)">Isoheptene</a></li> <li><a href="/w/index.php?title=Isooctene&action=edit&redlink=1" class="new" title="Isooctene (page does not exist)">Isooctene</a></li> <li><a href="/w/index.php?title=Isononene&action=edit&redlink=1" class="new" title="Isononene (page does not exist)">Isononene</a></li> <li><a href="/w/index.php?title=Isodecene&action=edit&redlink=1" class="new" title="Isodecene (page does not exist)">Isodecene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Alkyne" title="Alkyne">Alkynes</a> CnH2n − 2</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em">Linear alkynes</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetylene" title="Acetylene">Ethyne</a></li> <li><a href="/wiki/Propyne" title="Propyne">Propyne</a></li> <li><a href="/wiki/Butyne" title="Butyne">Butyne</a></li> <li><a href="/wiki/Pentyne" title="Pentyne">Pentyne</a></li> <li><a href="/wiki/3-Hexyne" title="3-Hexyne">Hexyne</a></li> <li><a href="/wiki/Heptyne" title="Heptyne">Heptyne</a></li> <li><a href="/wiki/Octyne" title="Octyne">Octyne</a></li> <li><a href="/wiki/Nonyne" title="Nonyne">Nonyne</a></li> <li><a href="/wiki/1-Decyne" title="1-Decyne">Decyne</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Branched alkynes</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=Isopentyne&action=edit&redlink=1" class="new" title="Isopentyne (page does not exist)">Isopentyne</a></li> <li><a href="/w/index.php?title=Isohexyne&action=edit&redlink=1" class="new" title="Isohexyne (page does not exist)">Isohexyne</a></li> <li><a href="/w/index.php?title=Isoheptyne&action=edit&redlink=1" class="new" title="Isoheptyne (page does not exist)">Isoheptyne</a></li> <li><a href="/w/index.php?title=Isooctyne&action=edit&redlink=1" class="new" title="Isooctyne (page does not exist)">Isooctyne</a></li> <li><a href="/w/index.php?title=Isononyne&action=edit&redlink=1" class="new" title="Isononyne (page does not exist)">Isononyne</a></li> <li><a href="/w/index.php?title=Isodecyne&action=edit&redlink=1" class="new" title="Isodecyne (page does not exist)">Isodecyne</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Cycloalkene" title="Cycloalkene">Cycloalkenes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cyclopropene" title="Cyclopropene">Cyclopropene</a></li> <li><a href="/wiki/Cyclobutene" title="Cyclobutene">Cyclobutene</a></li> <li><a href="/wiki/Cyclopentene" title="Cyclopentene">Cyclopentene</a></li> <li><a href="/wiki/Cyclohexene" title="Cyclohexene">Cyclohexene</a></li> <li><a href="/wiki/Cycloheptene" title="Cycloheptene">Cycloheptene</a></li> <li><a href="/wiki/Cyclooctene" title="Cyclooctene">Cyclooctene</a></li> <li><a href="/wiki/Cyclononene" title="Cyclononene">Cyclononene</a></li> <li><a href="/wiki/Cyclodecene" title="Cyclodecene">Cyclodecene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/w/index.php?title=Alkylcycloalkene&action=edit&redlink=1" class="new" title="Alkylcycloalkene (page does not exist)">Alkylcycloalkenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/1-Methylcyclopropene" title="1-Methylcyclopropene">Methylcyclopropene</a></li> <li><a href="/w/index.php?title=Methylcyclobutene&action=edit&redlink=1" class="new" title="Methylcyclobutene (page does not exist)">Methylcyclobutene</a></li> <li><a href="/w/index.php?title=Methylcyclopentene&action=edit&redlink=1" class="new" title="Methylcyclopentene (page does not exist)">Methylcyclopentene</a></li> <li><a href="/wiki/Methylcyclohexene" title="Methylcyclohexene">Methylcyclohexene</a></li> <li><a href="/w/index.php?title=Isopropylcyclohexene&action=edit&redlink=1" class="new" title="Isopropylcyclohexene (page does not exist)">Isopropylcyclohexene</a></li> <li class="mw-empty-elt"></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/w/index.php?title=Bicycloalkene&action=edit&redlink=1" class="new" title="Bicycloalkene (page does not exist)">Bicycloalkenes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Norbornene" title="Norbornene">Norbornene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Cycloalkyne" title="Cycloalkyne">Cycloalkynes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cyclopropyne" class="mw-redirect" title="Cyclopropyne">Cyclopropyne</a></li> <li><a href="/wiki/Cyclobutyne" title="Cyclobutyne">Cyclobutyne</a></li> <li><a href="/wiki/Cyclopentyne" title="Cyclopentyne">Cyclopentyne</a></li> <li><a href="/w/index.php?title=Cyclohexyne&action=edit&redlink=1" class="new" title="Cyclohexyne (page does not exist)">Cyclohexyne</a></li> <li><a href="/w/index.php?title=Cycloheptyne&action=edit&redlink=1" class="new" title="Cycloheptyne (page does not exist)">Cycloheptyne</a></li> <li><a href="/wiki/Cyclooctyne" title="Cyclooctyne">Cyclooctyne</a></li> <li><a href="/w/index.php?title=Cyclononyne&action=edit&redlink=1" class="new" title="Cyclononyne (page does not exist)">Cyclononyne</a></li> <li><a href="/w/index.php?title=Cyclodecyne&action=edit&redlink=1" class="new" title="Cyclodecyne (page does not exist)">Cyclodecyne</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Diene" title="Diene">Dienes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Propadiene" title="Propadiene">Propadiene</a></li> <li><a href="/wiki/Butadiene" title="Butadiene">Butadiene</a></li> <li><a href="/wiki/Piperylene" title="Piperylene">Pentadiene</a></li> <li><a href="/wiki/1,5-Hexadiene" title="1,5-Hexadiene">Hexadiene</a></li> <li><a href="/w/index.php?title=Heptadiene&action=edit&redlink=1" class="new" title="Heptadiene (page does not exist)">Heptadiene</a></li> <li><a href="/wiki/1,7-Octadiene" title="1,7-Octadiene">Octadiene</a></li> <li><a href="/w/index.php?title=Nonadiene&action=edit&redlink=1" class="new" title="Nonadiene (page does not exist)">Nonadiene</a></li> <li><a href="/w/index.php?title=Decadiene&action=edit&redlink=1" class="new" title="Decadiene (page does not exist)">Decadiene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=Alkatriene&action=edit&redlink=1" class="new" title="Alkatriene (page does not exist)">Alkatriene</a></li> <li><a href="/w/index.php?title=Alkadiyne&action=edit&redlink=1" class="new" title="Alkadiyne (page does not exist)">Alkadiyne</a></li> <li><a href="/wiki/Cumulene" title="Cumulene">Cumulene</a></li> <li><a href="/wiki/Cyclooctatetraene" title="Cyclooctatetraene">Cyclooctatetraene</a></li> <li><a href="/wiki/Cyclododecatriene" title="Cyclododecatriene">Cyclododecatriene</a></li> <li><a href="/wiki/Enyne" title="Enyne">Enyne</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:azzurro;"><a href="/wiki/Aromatic_hydrocarbon" class="mw-redirect" title="Aromatic hydrocarbon">Aromatic hydrocarbons</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Polycyclic_aromatic_hydrocarbon" title="Polycyclic aromatic hydrocarbon">PAHs</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Acene" title="Acene">Acenes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Naphthalene" title="Naphthalene">Naphthalene</a></li> <li><a href="/wiki/Anthracene" title="Anthracene">Anthracene</a></li> <li><a href="/wiki/Tetracene" title="Tetracene">Tetracene</a></li> <li><a href="/wiki/Pentacene" title="Pentacene">Pentacene</a></li> <li><a href="/wiki/Hexacene" title="Hexacene">Hexacene</a></li> <li><a href="/wiki/Heptacene" title="Heptacene">Heptacene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Azulene" title="Azulene">Azulene</a></li> <li><a href="/wiki/Fluorene" title="Fluorene">Fluorene</a></li> <li><a href="/wiki/Helicene" title="Helicene">Helicenes</a></li> <li><a href="/wiki/Circulene" title="Circulene">Circulenes</a></li> <li><a href="/wiki/Butalene" title="Butalene">Butalene</a></li> <li><a href="/wiki/Phenanthrene" title="Phenanthrene">Phenanthrene</a></li> <li><a href="/wiki/Chrysene" title="Chrysene">Chrysene</a></li> <li><a href="/wiki/Pyrene" title="Pyrene">Pyrene</a></li> <li><a href="/wiki/Corannulene" title="Corannulene">Corannulene</a></li> <li><a href="/wiki/Kekulene" title="Kekulene">Kekulene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Alkylbenzenes" class="mw-redirect" title="Alkylbenzenes">Alkylbenzenes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Toluene" title="Toluene">Toluene</a></li></ul> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/C2-Benzenes" title="C2-Benzenes">C2-Benzenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Xylene" title="Xylene">Xylenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/O-Xylene" title="O-Xylene">o-Xylene</a></li> <li><a href="/wiki/M-Xylene" title="M-Xylene">m-Xylene</a></li> <li><a href="/wiki/P-Xylene" title="P-Xylene">p-Xylene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ethylbenzene" title="Ethylbenzene">Ethylbenzene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/C3-Benzenes" title="C3-Benzenes">C3-Benzenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Trimethylbenzenes" class="mw-redirect" title="Trimethylbenzenes">Trimethylbenzenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Mesitylene" title="Mesitylene">Mesitylene</a></li> <li><a href="/wiki/Pseudocumene" class="mw-redirect" title="Pseudocumene">Pseudocumene</a></li> <li><a href="/wiki/Hemellitene" class="mw-redirect" title="Hemellitene">Hemellitene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cumene" title="Cumene">Cumene</a></li> <li><a href="/wiki/N-Propylbenzene" title="N-Propylbenzene">n-Propylbenzene</a></li> <li><a href="/wiki/4-Ethyltoluene" title="4-Ethyltoluene">4-Ethyltoluene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/C4-Benzenes" title="C4-Benzenes">C4-Benzenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Cymenes" class="mw-redirect" title="Cymenes">Cymenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/O-Cymene" title="O-Cymene">o-Cymene</a></li> <li><a href="/wiki/M-Cymene" title="M-Cymene">m-Cymene</a></li> <li><a href="/wiki/P-Cymene" title="P-Cymene">p-Cymene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Tetramethylbenzenes" class="mw-redirect" title="Tetramethylbenzenes">Tetramethylbenzenes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Durene" title="Durene">Durene</a></li> <li><a href="/wiki/Prehnitene" title="Prehnitene">Prehnitene</a></li> <li><a href="/wiki/Isodurene" title="Isodurene">Isodurene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/N-Butylbenzene" title="N-Butylbenzene">n-Butylbenzene</a></li> <li><a href="/wiki/Sec-Butylbenzene" title="Sec-Butylbenzene">sec-Butylbenzene</a></li> <li><a href="/wiki/Tert-Butylbenzene" title="Tert-Butylbenzene">tert-Butylbenzene</a></li> <li><a href="/wiki/Isobutylbenzene" title="Isobutylbenzene">Isobutylbenzene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a class="mw-selflink selflink">Hexamethylbenzene</a></li> <li><a href="/wiki/2-Phenylhexane" title="2-Phenylhexane">2-Phenylhexane</a></li> <li><a href="/wiki/1,3,5-Triethylbenzene" title="1,3,5-Triethylbenzene">1,3,5-Triethylbenzene</a></li> <li><a href="/wiki/1,3,5-Triheptylbenzene" title="1,3,5-Triheptylbenzene">1,3,5-Triheptylbenzene</a></li></ul> </div></td></tr></tbody></table><div> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Vinylbenzenes</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Styrene" title="Styrene">Styrene</a></li> <li><a href="/wiki/Divinylbenzene" title="Divinylbenzene">Divinylbenzene</a></li> <li><a href="/wiki/4-Vinyltoluene" title="4-Vinyltoluene">4-Vinyltoluene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Benzene" title="Benzene">Benzene</a></li> <li><a href="/wiki/Cyclopropenylidene" title="Cyclopropenylidene">Cyclopropenylidene</a></li> <li><a href="/wiki/Phenylacetylene" title="Phenylacetylene">Phenylacetylene</a></li> <li><a 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