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六甲苯 - 维基百科,自由的百科全书

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href="/w/index.php?title=Special:%E5%88%9B%E5%BB%BA%E8%B4%A6%E6%88%B7&amp;returnto=%E5%85%AD%E7%94%B2%E8%8B%AF" title="我们推荐您创建账号并登录,但这不是强制性的"><span class="vector-icon mw-ui-icon-userAdd mw-ui-icon-wikimedia-userAdd"></span> <span>创建账号</span></a></li><li id="pt-login" class="user-links-collapsible-item mw-list-item"><a href="/w/index.php?title=Special:%E7%94%A8%E6%88%B7%E7%99%BB%E5%BD%95&amp;returnto=%E5%85%AD%E7%94%B2%E8%8B%AF" title="建议你登录,尽管并非必须。​[o]" accesskey="o"><span class="vector-icon mw-ui-icon-logIn mw-ui-icon-wikimedia-logIn"></span> <span>登录</span></a></li> </ul> </div> </div> <div id="p-user-menu-anon-editor" class="vector-menu mw-portlet mw-portlet-user-menu-anon-editor" > <div class="vector-menu-heading"> 未登录编辑者的页面 <a href="/wiki/Help:%E6%96%B0%E6%89%8B%E5%85%A5%E9%97%A8" aria-label="了解有关编辑的更多信息"><span>了解详情</span></a> </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="pt-anoncontribs" class="mw-list-item"><a href="/wiki/Special:%E6%88%91%E7%9A%84%E8%B4%A1%E7%8C%AE" title="来自此IP地址的编辑列表​[y]" accesskey="y"><span>贡献</span></a></li><li id="pt-anontalk" class="mw-list-item"><a href="/wiki/Special:%E6%88%91%E7%9A%84%E8%AE%A8%E8%AE%BA%E9%A1%B5" title="对于来自此IP地址编辑的讨论​[n]" accesskey="n"><span>讨论</span></a></li> </ul> </div> </div> </div> </div> </nav> </div> </header> </div> <div class="mw-page-container"> <div class="mw-page-container-inner"> <div class="vector-sitenotice-container"> <div id="siteNotice"><!-- CentralNotice --></div> </div> <div class="vector-column-start"> <div class="vector-main-menu-container"> <div id="mw-navigation"> <nav id="mw-panel" class="vector-main-menu-landmark" aria-label="站点"> <div id="vector-main-menu-pinned-container" class="vector-pinned-container"> </div> </nav> </div> </div> <div class="vector-sticky-pinned-container"> <nav id="mw-panel-toc" aria-label="目录" data-event-name="ui.sidebar-toc" class="mw-table-of-contents-container vector-toc-landmark"> <div id="vector-toc-pinned-container" class="vector-pinned-container"> <div id="vector-toc" class="vector-toc vector-pinnable-element"> <div class="vector-pinnable-header vector-toc-pinnable-header vector-pinnable-header-pinned" data-feature-name="toc-pinned" data-pinnable-element-id="vector-toc" > <h2 class="vector-pinnable-header-label">目录</h2> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-toc.pin">移至侧栏</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-toc.unpin">隐藏</button> </div> <ul class="vector-toc-contents" id="mw-panel-toc-list"> <li id="toc-mw-content-text" class="vector-toc-list-item vector-toc-level-1"> <a href="#" class="vector-toc-link"> <div class="vector-toc-text">序言</div> </a> </li> <li id="toc-性质" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#性质"> <div class="vector-toc-text"> <span class="vector-toc-numb">1</span> <span>性质</span> </div> </a> <button aria-controls="toc-性质-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>开关性质子章节</span> </button> <ul id="toc-性质-sublist" class="vector-toc-list"> <li id="toc-结构" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#结构"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.1</span> <span>结构</span> </div> </a> <ul id="toc-结构-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-制备" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#制备"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>制备</span> </div> </a> <ul id="toc-制备-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-用处" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#用处"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>用处</span> </div> </a> <ul id="toc-用处-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-反应" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#反应"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>反应</span> </div> </a> <button aria-controls="toc-反应-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>开关反应子章节</span> </button> <ul id="toc-反应-sublist" class="vector-toc-list"> <li id="toc-双阳离子" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#双阳离子"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>双阳离子</span> </div> </a> <ul id="toc-双阳离子-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-参考资料" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#参考资料"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>参考资料</span> </div> </a> <ul id="toc-参考资料-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="目录" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" title="目录" > <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="开关目录" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">开关目录</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">六甲苯</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="前往另一种语言写成的文章。18种语言可用" > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-18" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">18种语言</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%B3%D8%AF%D8%A7%D8%B3%D9%8A_%D9%85%D9%8A%D8%AB%D9%8A%D9%84_%D8%A7%D9%84%D8%A8%D9%86%D8%B2%D9%8A%D9%86" title="سداسي ميثيل البنزين – 阿拉伯语" lang="ar" hreflang="ar" data-title="سداسي ميثيل البنزين" data-language-autonym="العربية" data-language-local-name="阿拉伯语" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D9%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"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Hexamethylbenzol" title="Hexamethylbenzol – 德语" lang="de" hreflang="de" data-title="Hexamethylbenzol" data-language-autonym="Deutsch" data-language-local-name="德语" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-en badge-Q17437798 badge-goodarticle mw-list-item" title="优良条目"><a href="https://en.wikipedia.org/wiki/Hexamethylbenzene" title="Hexamethylbenzene – 英语" lang="en" hreflang="en" data-title="Hexamethylbenzene" data-language-autonym="English" data-language-local-name="英语" class="interlanguage-link-target"><span>English</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Heksametilbenzeno" title="Heksametilbenzeno – 世界语" lang="eo" hreflang="eo" data-title="Heksametilbenzeno" data-language-autonym="Esperanto" data-language-local-name="世界语" class="interlanguage-link-target"><span>Esperanto</span></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 – 波斯语" lang="fa" hreflang="fa" data-title="هگزامتیل‌بنزن" data-language-autonym="فارسی" data-language-local-name="波斯语" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Heksametyylibentseeni" title="Heksametyylibentseeni – 芬兰语" lang="fi" hreflang="fi" data-title="Heksametyylibentseeni" data-language-autonym="Suomi" data-language-local-name="芬兰语" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Hexam%C3%A9thylbenz%C3%A8ne" title="Hexaméthylbenzène – 法语" lang="fr" hreflang="fr" data-title="Hexaméthylbenzène" data-language-autonym="Français" data-language-local-name="法语" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Heksametilbenzena" title="Heksametilbenzena – 印度尼西亚语" lang="id" hreflang="id" data-title="Heksametilbenzena" data-language-autonym="Bahasa Indonesia" data-language-local-name="印度尼西亚语" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Esametilbenzene" title="Esametilbenzene – 意大利语" lang="it" hreflang="it" data-title="Esametilbenzene" data-language-autonym="Italiano" data-language-local-name="意大利语" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%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 – 日语" 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="日语" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Hexamethylbenzeen" title="Hexamethylbenzeen – 荷兰语" lang="nl" hreflang="nl" data-title="Hexamethylbenzeen" data-language-autonym="Nederlands" data-language-local-name="荷兰语" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Hexametilbenzen" title="Hexametilbenzen – 罗马尼亚语" lang="ro" hreflang="ro" data-title="Hexametilbenzen" data-language-autonym="Română" data-language-local-name="罗马尼亚语" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%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 – 俄语" lang="ru" hreflang="ru" data-title="Гексаметилбензол" data-language-autonym="Русский" data-language-local-name="俄语" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Heksametilbenzen" title="Heksametilbenzen – 塞尔维亚-克罗地亚语" lang="sh" hreflang="sh" data-title="Heksametilbenzen" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="塞尔维亚-克罗地亚语" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Heksametilbenzen" title="Heksametilbenzen – 塞尔维亚语" lang="sr" hreflang="sr" data-title="Heksametilbenzen" data-language-autonym="Српски / srpski" data-language-local-name="塞尔维亚语" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.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 – 乌克兰语" lang="uk" hreflang="uk" data-title="Гексаметилбензол" data-language-autonym="Українська" data-language-local-name="乌克兰语" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Hexamethylbenzen" title="Hexamethylbenzen – 越南语" lang="vi" hreflang="vi" data-title="Hexamethylbenzen" data-language-autonym="Tiếng Việt" data-language-local-name="越南语" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q413592#sitelinks-wikipedia" title="编辑跨语言链接" class="wbc-editpage">编辑链接</a></span></div> </div> </div> </div> </header> <div class="vector-page-toolbar"> <div class="vector-page-toolbar-container"> <div id="left-navigation"> <nav aria-label="命名空间"> <div id="p-associated-pages" class="vector-menu vector-menu-tabs mw-portlet mw-portlet-associated-pages" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="ca-nstab-main" class="selected vector-tab-noicon mw-list-item"><a href="/wiki/%E5%85%AD%E7%94%B2%E8%8B%AF" title="浏览条目正文​[c]" accesskey="c"><span>条目</span></a></li><li id="ca-talk" class="vector-tab-noicon mw-list-item"><a href="/wiki/Talk:%E5%85%AD%E7%94%B2%E8%8B%AF" 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class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="zh" dir="ltr"><style data-mw-deduplicate="TemplateStyles:r84001320">.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 nounderlines" cellspacing="0" cellpadding="3" rules="all" style="background-color:#f0f0f0; float:right; margin: 0 0 1em 1em; border-color: #aaaaaa; border-style:solid; border:1px; border-collapse:collapse; empty-cells:show; width:305px; font-size:90%;"> <tbody><tr> <th colspan="2" style="font-size:120%; text-align:center; background:#d6e0dc;">六甲苯 </th></tr> <tr> <td colspan="2" style="background:#ffffff; text-align:center;"><span typeof="mw:File"><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></span> </td></tr> <tr> <td colspan="2" style="background:#ffffff; text-align:center;"><span typeof="mw:File"><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></span> </td></tr> <tr> <td colspan="2" style="background:#ffffff; text-align:center;"><span typeof="mw:File"><a href="/wiki/File:HMB2wBottle.jpg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/74/HMB2wBottle.jpg/200px-HMB2wBottle.jpg" decoding="async" width="200" height="87" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/74/HMB2wBottle.jpg/300px-HMB2wBottle.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/74/HMB2wBottle.jpg/400px-HMB2wBottle.jpg 2x" data-file-width="2620" data-file-height="1143" /></a></span> </td></tr> <tr> <td colspan="2" style="max-width:305px; word-wrap: break-word; text-align: center;"><a href="/wiki/IUPAC%E5%91%BD%E5%90%8D%E6%B3%95" title="IUPAC命名法">IUPAC名</a><br />Hexamethylbenzene </td></tr> <tr> <td>别名 </td> <td>1,2,3,4,5,6-六甲基苯<br />六甲基苯 </td></tr> <tr> <th style="background:#D6E0DC; text-align:center;" colspan="2">识别 </th></tr> <tr> <td><a href="/wiki/CAS%E5%8F%B7" title="CAS号">CAS号</a> </td> <td><span class="reflink plainlinks nourlexpansion"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=87-85-4">87-85-4</a></span> <sup>&#160;<span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/commons/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/commons/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup> </td></tr> <tr> <td><a href="/wiki/PubChem" title="PubChem">PubChem</a> </td> <td><span class="reflink plainlinks nourlexpansion"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/6908">6908</a></span> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><span class="reflink plainlinks nourlexpansion"><a rel="nofollow" class="external text" href="http://www.chemspider.com/6642">6642</a></span> </td></tr> <tr> <td><a href="/wiki/SMILES" class="mw-redirect" title="SMILES">SMILES</a> </td> <td><div style="word-break:break-all;"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div>&#160;</div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0;"><li style="line-height: inherit; margin: 0"><span lang="en">c1(c(c(c(c(c1C)C)C)C)C)C</span></li></ul> </div></div> </td></tr> <tr> <td><a href="/wiki/%E5%9B%BD%E9%99%85%E5%8C%96%E5%90%88%E7%89%A9%E6%A0%87%E8%AF%86" title="国际化合物标识">InChI</a> </td> <td><div style="word-break:break-all;"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div>&#160;</div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0;"><li style="line-height: inherit; margin: 0">1/C12H18/c1-7-8(2)10(4)12(6)11(5)9(7)3/h1-6H3</li></ul> </div></div> </td></tr> <tr> <td><a href="/wiki/%E5%9B%BD%E9%99%85%E5%8C%96%E5%90%88%E7%89%A9%E6%A0%87%E8%AF%86" title="国际化合物标识">InChIKey</a> </td> <td><small>YUWFEBAXEOLKSG-UHFFFAOYAF</small> </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><span class="reflink plainlinks nourlexpansion"><a rel="nofollow" class="external text" href="http://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:39001">39001</a></span> </td></tr> <tr> <th style="background:#D6E0DC; text-align:center;" colspan="2">性质 </th></tr> <tr> <td><a href="/wiki/%E5%8C%96%E5%AD%A6%E5%BC%8F" title="化学式">化学式</a> </td> <td>C<sub>12</sub>H<sub>18</sub> </td></tr> <tr> <td><a href="/wiki/%E6%91%A9%E5%B0%94%E8%B4%A8%E9%87%8F" title="摩尔质量">摩尔质量</a> </td> <td>162.27 g·mol<sup>−1</sup> </td></tr> <tr> <td>外观 </td> <td>白色晶体 </td></tr> <tr> <td><a href="/wiki/%E5%AF%86%E5%BA%A6" title="密度">密度</a> </td> <td>1.0630&#160;g&#160;cm<sup>−3</sup> </td></tr> <tr> <td><a href="/wiki/%E7%86%94%E7%82%B9" title="熔点">熔点</a> </td> <td>164.9-166.3&#160;°C(438-439&#160;K) </td></tr> <tr> <td><a href="/wiki/%E6%B2%B8%E7%82%B9" title="沸点">沸点</a> </td> <td>265.2&#160;°C(538&#160;K) </td></tr> <tr> <td><a href="/wiki/%E6%BA%B6%E8%A7%A3%E6%80%A7" class="mw-redirect" title="溶解性">溶解性</a>(<a href="/wiki/%E6%B0%B4" title="水">水</a>) </td> <td>不溶 </td></tr> <tr> <td><a href="/wiki/%E6%BA%B6%E8%A7%A3%E6%80%A7" class="mw-redirect" title="溶解性">溶解性</a> </td> <td><a href="/wiki/%E4%B9%99%E9%85%B8" title="乙酸">乙酸</a>、<a href="/wiki/%E4%B8%99%E9%85%AE" title="丙酮">丙酮</a>、<a href="/wiki/%E8%8B%AF" title="苯">苯</a>、<a href="/wiki/%E6%B0%AF%E4%BB%BF" title="氯仿">氯仿</a>、<a href="/wiki/%E4%B9%99%E9%86%9A" title="乙醚">乙醚</a>和<a href="/wiki/%E4%B9%99%E9%86%87" title="乙醇">乙醇</a> </td></tr> <tr> <td style="background:#D6E0DC; text-align:center;" colspan="2">若非注明,所有数据均出自<a href="/wiki/%E6%A0%87%E5%87%86%E7%8A%B6%E6%80%81" title="标准状态">标准状态(25 ℃,100 kPa)</a>下。 </td></tr></tbody></table> <p><b>六甲苯</b>是一种<a href="/wiki/%E7%A2%B3%E6%B0%A2%E5%8C%96%E5%90%88%E7%89%A9" class="mw-redirect" title="碳氢化合物">碳氢化合物</a>,<a href="/wiki/%E5%8C%96%E5%AD%A6%E5%BC%8F" title="化学式">化学式</a> C<sub>12</sub>H<sub>18</sub>,<a href="/wiki/%E7%BB%93%E6%9E%84%E5%BC%8F" title="结构式">结构式</a> C<sub>6</sub>(CH<sub>3</sub>)<sub>6</sub>。它是由<a href="/wiki/%E8%8B%AF" title="苯">苯</a>的六个氢原子都被<a href="/wiki/%E7%94%B2%E5%9F%BA" title="甲基">甲基</a>取代而生的化合物。1929年,<span class="ilh-all" data-orig-title="凯瑟琳·朗斯代尔" data-lang-code="en" data-lang-name="英语" data-foreign-title="Kathleen Lonsdale"><span class="ilh-page"><a href="/w/index.php?title=%E5%87%AF%E7%91%9F%E7%90%B3%C2%B7%E6%9C%97%E6%96%AF%E4%BB%A3%E5%B0%94&amp;action=edit&amp;redlink=1" class="new" title="凯瑟琳·朗斯代尔(页面不存在)">凯瑟琳·朗斯代尔</a></span><span class="noprint ilh-comment"><span class="ilh-paren">(</span><span class="ilh-lang">英语</span><span class="ilh-colon">:</span><span class="ilh-link"><a href="https://en.wikipedia.org/wiki/Kathleen_Lonsdale" class="extiw" title="en:Kathleen Lonsdale"><span lang="en" dir="auto">Kathleen Lonsdale</span></a></span><span class="ilh-paren">)</span></span></span>报告了六甲苯的<a href="/wiki/%E6%99%B6%E4%BD%93%E7%BB%93%E6%9E%84" title="晶体结构">晶体结构</a>,证明苯环是平面六边形的<sup id="cite_ref-Lonsdale_1-0" class="reference"><a href="#cite_note-Lonsdale-1"><span class="cite-bracket">&#91;</span>1<span class="cite-bracket">&#93;</span></a></sup>,从而结束了关于苯的结构的持续争论。无论是对于<a href="/wiki/X%E5%B0%84%E7%BA%BF%E6%99%B6%E4%BD%93%E5%AD%A6" title="X射线晶体学">X射线晶体学</a>抑或研究<a href="/wiki/%E8%8A%B3%E9%A6%99%E6%80%A7" title="芳香性">芳香性</a>的領域,這皆是一個具有歷史意義的成果。<sup id="cite_ref-Lydon1_2-0" class="reference"><a href="#cite_note-Lydon1-2"><span class="cite-bracket">&#91;</span>2<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Lydon2_3-0" class="reference"><a href="#cite_note-Lydon2-3"><span class="cite-bracket">&#91;</span>3<span class="cite-bracket">&#93;</span></a></sup> </p><p>六甲苯可以通过<a href="/wiki/%E8%8B%AF%E9%85%9A" title="苯酚">苯酚</a>与<a href="/wiki/%E7%94%B2%E9%86%87" title="甲醇">甲醇</a>在高温和合适的固体催化剂(如<a href="/wiki/%E6%B0%A7%E5%8C%96%E9%93%9D" title="氧化铝">氧化铝</a>)下反应而生成。<sup id="cite_ref-HMBSynth_4-0" class="reference"><a href="#cite_note-HMBSynth-4"><span class="cite-bracket">&#91;</span>4<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-HMBOrgSynth_5-0" class="reference"><a href="#cite_note-HMBOrgSynth-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-PMB_6-0" class="reference"><a href="#cite_note-PMB-6"><span class="cite-bracket">&#91;</span>6<span class="cite-bracket">&#93;</span></a></sup>这个反应的<a href="/wiki/%E5%8F%8D%E5%BA%94%E6%9C%BA%E7%90%86" title="反应机理">反应机理</a>已被广泛研究,<sup id="cite_ref-Koptyug1_7-0" class="reference"><a href="#cite_note-Koptyug1-7"><span class="cite-bracket">&#91;</span>7<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Ipatiew_8-0" class="reference"><a href="#cite_note-Ipatiew-8"><span class="cite-bracket">&#91;</span>8<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Takeshi1_9-0" class="reference"><a href="#cite_note-Takeshi1-9"><span class="cite-bracket">&#91;</span>9<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Takeshi2_10-0" class="reference"><a href="#cite_note-Takeshi2-10"><span class="cite-bracket">&#91;</span>10<span class="cite-bracket">&#93;</span></a></sup> 過程中含有几种<a href="/wiki/%E5%8F%8D%E5%BA%94%E4%B8%AD%E9%97%B4%E4%BD%93" title="反应中间体">反应中间体</a>的存在。<sup id="cite_ref-PMB_6-1" class="reference"><a href="#cite_note-PMB-6"><span class="cite-bracket">&#91;</span>6<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-CullinaneChard_11-0" class="reference"><a href="#cite_note-CullinaneChard-11"><span class="cite-bracket">&#91;</span>11<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Koptyug2_12-0" class="reference"><a href="#cite_note-Koptyug2-12"><span class="cite-bracket">&#91;</span>12<span class="cite-bracket">&#93;</span></a></sup>在合适的催化剂存在下<sup id="cite_ref-Cr_13-0" class="reference"><a href="#cite_note-Cr-13"><span class="cite-bracket">&#91;</span>13<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Ti_14-0" class="reference"><a href="#cite_note-Ti-14"><span class="cite-bracket">&#91;</span>14<span class="cite-bracket">&#93;</span></a></sup>,<a href="/wiki/%E4%BA%8C%E7%94%B2%E5%9F%BA%E4%B9%99%E7%82%94" class="mw-redirect" title="二甲基乙炔">二甲基乙炔</a>的<span class="ilh-all" data-orig-title="炔烃三聚" data-lang-code="en" data-lang-name="英语" data-foreign-title="Alkyne trimerisation"><span class="ilh-page"><a href="/w/index.php?title=%E7%82%94%E7%83%83%E4%B8%89%E8%81%9A&amp;action=edit&amp;redlink=1" class="new" title="炔烃三聚(页面不存在)">炔烃三聚</a></span><span class="noprint ilh-comment"><span class="ilh-paren">(</span><span class="ilh-lang">英语</span><span class="ilh-colon">:</span><span class="ilh-link"><a href="https://en.wikipedia.org/wiki/Alkyne_trimerisation" class="extiw" title="en:Alkyne trimerisation"><span lang="en" dir="auto">Alkyne trimerisation</span></a></span><span class="ilh-paren">)</span></span></span>也可生成六甲基苯。<sup id="cite_ref-Trimerisation_15-0" class="reference"><a href="#cite_note-Trimerisation-15"><span class="cite-bracket">&#91;</span>15<span class="cite-bracket">&#93;</span></a></sup>六甲基苯可以被氧化成<a href="/wiki/%E8%8B%AF%E5%85%AD%E7%94%B2%E9%85%B8" title="苯六甲酸">苯六甲酸</a>,<sup id="cite_ref-HMBoxidation_16-0" class="reference"><a href="#cite_note-HMBoxidation-16"><span class="cite-bracket">&#91;</span>16<span class="cite-bracket">&#93;</span></a></sup>后者的铝<a href="/wiki/%E7%9B%90_(%E5%8C%96%E5%AD%A6)" title="盐 (化学)">盐</a>存在于稀有矿物<a href="/wiki/%E8%9C%9C%E8%A0%9F%E7%9F%B3" title="蜜蠟石">蜜蠟石</a>中。<sup id="cite_ref-mellite_17-0" class="reference"><a href="#cite_note-mellite-17"><span class="cite-bracket">&#91;</span>17<span class="cite-bracket">&#93;</span></a></sup> 六甲基苯也是<a href="/wiki/%E6%9C%89%E6%A9%9F%E9%87%91%E5%B1%AC%E5%8C%96%E5%90%88%E7%89%A9" class="mw-redirect" title="有機金屬化合物">有机金属化合物</a>中的一种<a href="/wiki/%E9%85%8D%E9%AB%94" title="配體">配體</a>。<sup id="cite_ref-AreneReview_18-0" class="reference"><a href="#cite_note-AreneReview-18"><span class="cite-bracket">&#91;</span>18<span class="cite-bracket">&#93;</span></a></sup>其中一个例子是随着钌原子<a href="/wiki/%E6%B0%A7%E5%8C%96%E6%80%81" title="氧化态">氧化态</a>变化而改变结构的<a href="/w/index.php?title=%E6%9C%89%E6%9C%BA%E9%92%8C%E5%8C%96%E5%90%88%E7%89%A9&amp;action=edit&amp;redlink=1" class="new" title="有机钌化合物(页面不存在)">有机钌化合物</a>,<sup id="cite_ref-Fe_19-0" class="reference"><a href="#cite_note-Fe-19"><span class="cite-bracket">&#91;</span>19<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-RuHMB2_20-0" class="reference"><a href="#cite_note-RuHMB2-20"><span class="cite-bracket">&#91;</span>20<span class="cite-bracket">&#93;</span></a></sup>而这个变化不存在于对应的<a href="/w/index.php?title=%E6%9C%89%E6%9C%BA%E9%93%81%E5%8C%96%E5%90%88%E7%89%A9&amp;action=edit&amp;redlink=1" class="new" title="有机铁化合物(页面不存在)">有机铁化合物</a>中。<sup id="cite_ref-Fe_19-1" class="reference"><a href="#cite_note-Fe-19"><span class="cite-bracket">&#91;</span>19<span class="cite-bracket">&#93;</span></a></sup> </p><p>2016年,《<a href="/wiki/%E5%BA%94%E7%94%A8%E5%8C%96%E5%AD%A6_(%E6%9C%9F%E5%88%8A)" title="应用化学 (期刊)">应用化学</a>》<sup id="cite_ref-PyramidalAngewChem_21-0" class="reference"><a href="#cite_note-PyramidalAngewChem-21"><span class="cite-bracket">&#91;</span>21<span class="cite-bracket">&#93;</span></a></sup>報告了六甲基苯<span class="ilh-all" data-orig-title="双阳离子" data-lang-code="en" data-lang-name="英语" data-foreign-title="dication"><span class="ilh-page"><a href="/w/index.php?title=%E5%8F%8C%E9%98%B3%E7%A6%BB%E5%AD%90&amp;action=edit&amp;redlink=1" class="new" title="双阳离子(页面不存在)">双阳离子</a></span><span class="noprint ilh-comment"><span class="ilh-paren">(</span><span class="ilh-lang">英语</span><span class="ilh-colon">:</span><span class="ilh-link"><a href="https://en.wikipedia.org/wiki/dication" class="extiw" title="en:dication"><span lang="en" dir="auto">dication</span></a></span><span class="ilh-paren">)</span></span></span>的晶體結構。顯示出的結構為<a href="/wiki/%E4%BA%94%E8%A7%92%E9%8C%90" title="五角錐">五角錐</a>形,其中一個碳原子與其他六个碳原子具有鍵合相互作用。<sup id="cite_ref-PyramidalNewSci_22-0" class="reference"><a href="#cite_note-PyramidalNewSci-22"><span class="cite-bracket">&#91;</span>22<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-PyramidalC&amp;ENews_23-0" class="reference"><a href="#cite_note-PyramidalC&amp;ENews-23"><span class="cite-bracket">&#91;</span>23<span class="cite-bracket">&#93;</span></a></sup>这个结构是“空前未見的”,<sup id="cite_ref-PyramidalAngewChem_21-1" class="reference"><a href="#cite_note-PyramidalAngewChem-21"><span class="cite-bracket">&#91;</span>21<span class="cite-bracket">&#93;</span></a></sup>因为<a href="/wiki/%E7%A2%B3" title="碳">碳</a>通常的最高<a href="/wiki/%E5%8C%96%E5%90%88%E4%BB%B7" title="化合价">化合价</a>是四,而这也吸引了《<a href="/wiki/%E6%96%B0%E7%A7%91%E5%AD%B8%E4%BA%BA" title="新科學人">新科学人</a>》、<sup id="cite_ref-PyramidalNewSci_22-1" class="reference"><a href="#cite_note-PyramidalNewSci-22"><span class="cite-bracket">&#91;</span>22<span class="cite-bracket">&#93;</span></a></sup>《<a href="/wiki/%E5%8C%96%E5%AD%A6%E5%8C%96%E5%B7%A5%E6%96%B0%E9%97%BB" title="化学化工新闻">化学化工新闻</a>》<sup id="cite_ref-PyramidalC&amp;ENews_23-1" class="reference"><a href="#cite_note-PyramidalC&amp;ENews-23"><span class="cite-bracket">&#91;</span>23<span class="cite-bracket">&#93;</span></a></sup>和《<span class="ilh-all" data-orig-title="科学新闻" data-lang-code="en" data-lang-name="英语" data-foreign-title="Science News"><span class="ilh-page"><a href="/w/index.php?title=%E7%A7%91%E5%AD%A6%E6%96%B0%E9%97%BB&amp;action=edit&amp;redlink=1" class="new" title="科学新闻(页面不存在)">科学新闻</a></span><span class="noprint ilh-comment"><span class="ilh-paren">(</span><span class="ilh-lang">英语</span><span class="ilh-colon">:</span><span class="ilh-link"><a href="https://en.wikipedia.org/wiki/Science_News" class="extiw" title="en:Science News"><span lang="en" dir="auto">Science News</span></a></span><span class="ilh-paren">)</span></span></span>》等的注意。<sup id="cite_ref-PyramidalSciNews_24-0" class="reference"><a href="#cite_note-PyramidalSciNews-24"><span class="cite-bracket">&#91;</span>24<span class="cite-bracket">&#93;</span></a></sup>这种结构並没有违反<a href="/wiki/%E5%85%AB%E9%9A%85%E9%AB%94%E8%A6%8F%E5%89%87" title="八隅體規則">八隅体规则</a>,因为这些碳-碳键不是两电子键。此結構在<a href="/wiki/%E6%95%99%E8%82%B2%E5%AD%A6" title="教育学">教學</a>上可作為例子,说明碳原子“可以与四个以上的原子直接结合”。<sup id="cite_ref-PyramidalSciNews_24-1" class="reference"><a href="#cite_note-PyramidalSciNews-24"><span class="cite-bracket">&#91;</span>24<span class="cite-bracket">&#93;</span></a></sup><span class="ilh-all" data-orig-title="斯蒂芬·巴哈拉赫" data-lang-code="en" data-lang-name="英语" data-foreign-title="Steven Bachrach"><span class="ilh-page"><a href="/w/index.php?title=%E6%96%AF%E8%92%82%E8%8A%AC%C2%B7%E5%B7%B4%E5%93%88%E6%8B%89%E8%B5%AB&amp;action=edit&amp;redlink=1" class="new" title="斯蒂芬·巴哈拉赫(页面不存在)">斯蒂芬·巴哈拉赫</a></span><span class="noprint ilh-comment"><span class="ilh-paren">(</span><span class="ilh-lang">英语</span><span class="ilh-colon">:</span><span class="ilh-link"><a href="https://en.wikipedia.org/wiki/Steven_Bachrach" class="extiw" title="en:Steven Bachrach"><span lang="en" dir="auto">Steven Bachrach</span></a></span><span class="ilh-paren">)</span></span></span>證明了六甲基苯双阳离子是超配位的,而不是<a href="/wiki/%E8%B6%85%E4%BB%B7%E5%88%86%E5%AD%90" title="超价分子">超价分子</a>,并解释了其芳香性。<sup id="cite_ref-Bachrach_25-0" class="reference"><a href="#cite_note-Bachrach-25"><span class="cite-bracket">&#91;</span>25<span class="cite-bracket">&#93;</span></a></sup>此类物种中的键合可以從<a href="/wiki/%E6%9C%89%E6%9C%BA%E9%87%91%E5%B1%9E%E5%8C%96%E5%AD%A6" title="有机金属化学">有机金属化学</a>的视角描述,此想法在1975年提出,<sup id="cite_ref-HMBviaOMetChem_26-0" class="reference"><a href="#cite_note-HMBviaOMetChem-26"><span class="cite-bracket">&#91;</span>26<span class="cite-bracket">&#93;</span></a></sup>緊隨<span class="chemf nowrap">C<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left"><br />6</span>(CH<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left"><br />3</span>)<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left">2+<br />6</span></span>的發現。<sup id="cite_ref-HMBcatObs1_27-0" class="reference"><a href="#cite_note-HMBcatObs1-27"><span class="cite-bracket">&#91;</span>27<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-HMBcatObs2_28-0" class="reference"><a href="#cite_note-HMBcatObs2-28"><span class="cite-bracket">&#91;</span>28<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-HMBcatObs3_29-0" class="reference"><a href="#cite_note-HMBcatObs3-29"><span class="cite-bracket">&#91;</span>29<span class="cite-bracket">&#93;</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="性质"><span id=".E6.80.A7.E8.B4.A8"></span>性质</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E5%85%AD%E7%94%B2%E8%8B%AF&amp;action=edit&amp;section=1" title="编辑章节:性质"><span>编辑</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>六甲苯是一种<a href="/wiki/%E8%8A%B3%E9%A6%99%E5%8C%96%E5%90%88%E7%89%A9" title="芳香化合物">芳香化合物</a>,有六个π电子(符合<a href="/wiki/%E4%BC%91%E5%85%8B%E5%B0%94%E8%A7%84%E5%88%99" class="mw-redirect" title="休克尔规则">休克尔规则</a>)<a href="/wiki/%E7%A6%BB%E5%9F%9F" class="mw-redirect" title="离域">離域</a>於整個環狀平面系统之上;六个环碳原子之中的每一个都是sp<sup>2</sup> <a href="/wiki/%E6%9D%82%E5%8C%96" class="mw-redirect" title="杂化">杂化</a>並展現出<a href="/wiki/%E5%B9%B3%E9%9D%A2%E4%B8%89%E8%A7%92%E5%BD%A2%E5%88%86%E5%AD%90%E6%9E%84%E5%9E%8B" title="平面三角形分子构型">平面三角形分子构型</a>,而每一个甲基碳皆是sp<sup>3</sup>杂化並有著<a href="/wiki/%E5%9B%9B%E9%9D%A2%E4%BD%93%E5%BD%A2%E5%88%86%E5%AD%90%E6%9E%84%E5%9E%8B" title="四面体形分子构型">四面体形分子构型</a>,与其经验结构的描述一致。<sup id="cite_ref-Lonsdale_1-1" class="reference"><a href="#cite_note-Lonsdale-1"><span class="cite-bracket">&#91;</span>1<span class="cite-bracket">&#93;</span></a></sup>六甲苯是一种无色到白色,<a href="/wiki/%E6%AD%A3%E4%BA%A4%E6%99%B6%E7%B3%BB" title="正交晶系">正交晶系</a>的晶体,<sup id="cite_ref-CRC_30-0" class="reference"><a href="#cite_note-CRC-30"><span class="cite-bracket">&#91;</span>30<span class="cite-bracket">&#93;</span></a></sup><a href="/wiki/%E7%86%94%E7%82%B9" title="熔点">熔点</a> 165–166&#160;°C,<sup id="cite_ref-HMBOrgSynth_5-1" class="reference"><a href="#cite_note-HMBOrgSynth-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup><a href="/wiki/%E6%B2%B8%E7%82%B9" title="沸点">沸点</a> 268&#160;°C,<a href="/wiki/%E5%AF%86%E5%BA%A6" title="密度">密度</a>1.0630&#160;g&#160;cm<sup>−3</sup>。<sup id="cite_ref-CRC_30-1" class="reference"><a href="#cite_note-CRC-30"><span class="cite-bracket">&#91;</span>30<span class="cite-bracket">&#93;</span></a></sup>它不溶于水,但溶于有机溶剂,例如<a href="/wiki/%E8%8B%AF" title="苯">苯</a>和<a href="/wiki/%E4%B9%99%E9%86%87" title="乙醇">乙醇</a>。<sup id="cite_ref-CRC_30-2" class="reference"><a href="#cite_note-CRC-30"><span class="cite-bracket">&#91;</span>30<span class="cite-bracket">&#93;</span></a></sup> </p> <style data-mw-deduplicate="TemplateStyles:r70089473/mw-parser-output/.tmulti">.mw-parser-output .tmulti .thumbinner{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}}</style><div class="thumb tmulti tnone center"><div class="thumbinner" 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"><span typeof="mw:File"><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></span></div></div><div class="tsingle" style="width:187px;max-width:187px"><div class="thumbimage" style="height:160px;overflow:hidden"><span typeof="mw:File"><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></span></div></div></div><div class="trow" style="display:flex"><div class="thumbcaption">矿物<a href="/wiki/%E8%9C%9C%E8%A0%9F%E7%9F%B3" title="蜜蠟石">蜜蠟石</a>(左)是<a href="/wiki/%E8%8B%AF%E5%85%AD%E7%94%B2%E9%85%B8" title="苯六甲酸">苯六甲酸</a>(右)的水合铝盐</div></div></div></div> <p>矿物蜜蠟石是苯六甲酸的铝盐的<a href="/wiki/%E6%B0%B4%E5%90%88%E7%89%A9" title="水合物">水合物</a>,化学式 <span class="chemf nowrap">Al<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left"><br />2</span>[C<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left"><br />6</span>(CO<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left"><br />2</span>)<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left"><br />6</span>]&#8226;16H<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left"><br />2</span>O</span>。<sup id="cite_ref-mellite_17-1" class="reference"><a href="#cite_note-mellite-17"><span class="cite-bracket">&#91;</span>17<span class="cite-bracket">&#93;</span></a></sup>苯六甲酸本身可以从矿物中提取,<sup id="cite_ref-31" class="reference"><a href="#cite_note-31"><span class="cite-bracket">&#91;</span>31<span class="cite-bracket">&#93;</span></a></sup>随着<a href="/wiki/%E6%9C%89%E6%9C%BA%E6%B0%A7%E5%8C%96%E8%BF%98%E5%8E%9F%E5%8F%8D%E5%BA%94" title="有机氧化还原反应">還原反應</a>而产生六甲苯。相反,六甲苯也可以被<a href="/wiki/%E6%9C%89%E6%9C%BA%E6%B0%A7%E5%8C%96%E8%BF%98%E5%8E%9F%E5%8F%8D%E5%BA%94" title="有机氧化还原反应">氧化</a>成苯六甲酸:<sup id="cite_ref-HMBoxidation_16-1" class="reference"><a href="#cite_note-HMBoxidation-16"><span class="cite-bracket">&#91;</span>16<span class="cite-bracket">&#93;</span></a></sup> </p> <figure class="mw-halign-center" typeof="mw:File/Frameless"><a href="/wiki/File:%E8%8B%AF%E5%85%AD%E7%94%B2%E9%85%B8%E6%B0%A7%E5%8C%96%E9%82%84%E5%8E%9F.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/48/%E8%8B%AF%E5%85%AD%E7%94%B2%E9%85%B8%E6%B0%A7%E5%8C%96%E9%82%84%E5%8E%9F.png/400px-%E8%8B%AF%E5%85%AD%E7%94%B2%E9%85%B8%E6%B0%A7%E5%8C%96%E9%82%84%E5%8E%9F.png" decoding="async" width="400" height="118" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/48/%E8%8B%AF%E5%85%AD%E7%94%B2%E9%85%B8%E6%B0%A7%E5%8C%96%E9%82%84%E5%8E%9F.png/600px-%E8%8B%AF%E5%85%AD%E7%94%B2%E9%85%B8%E6%B0%A7%E5%8C%96%E9%82%84%E5%8E%9F.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/48/%E8%8B%AF%E5%85%AD%E7%94%B2%E9%85%B8%E6%B0%A7%E5%8C%96%E9%82%84%E5%8E%9F.png/800px-%E8%8B%AF%E5%85%AD%E7%94%B2%E9%85%B8%E6%B0%A7%E5%8C%96%E9%82%84%E5%8E%9F.png 2x" data-file-width="2456" data-file-height="726" /></a><figcaption></figcaption></figure> <p>六甲苯和氯甲烷、三氯化铝的超级亲电混合物(Me<sup>δ⊕</sup>Cl---<sup>δ⊖</sup>AlCl<sub>3</sub>的来源)会产生七甲苯阳离子,是最早被直接观察到的碳正离子之一。 </p> <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="结构"><span id=".E7.BB.93.E6.9E.84"></span>结构</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E5%85%AD%E7%94%B2%E8%8B%AF&amp;action=edit&amp;section=2" title="编辑章节:结构"><span>编辑</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>在1927年,<span class="ilh-all" data-orig-title="凯瑟琳·朗斯代尔" data-lang-code="en" data-lang-name="英语" data-foreign-title="Kathleen Lonsdale"><span class="ilh-page"><a href="/w/index.php?title=%E5%87%AF%E7%91%9F%E7%90%B3%C2%B7%E6%9C%97%E6%96%AF%E4%BB%A3%E5%B0%94&amp;action=edit&amp;redlink=1" class="new" title="凯瑟琳·朗斯代尔(页面不存在)">凯瑟琳·朗斯代尔</a></span><span class="noprint ilh-comment"><span class="ilh-paren">(</span><span class="ilh-lang">英语</span><span class="ilh-colon">:</span><span class="ilh-link"><a href="https://en.wikipedia.org/wiki/Kathleen_Lonsdale" class="extiw" title="en:Kathleen Lonsdale"><span lang="en" dir="auto">Kathleen Lonsdale</span></a></span><span class="ilh-paren">)</span></span></span>利用<a href="/wiki/%E5%85%8B%E9%87%8C%E6%96%AF%E6%89%98%E5%A4%AB%C2%B7%E8%8B%B1%E6%9E%9C%E5%B0%94%E5%BE%B7" title="克里斯托夫·英果尔德">克里斯托夫·英果尔德</a>提供的六甲苯晶體測定其<a href="/wiki/%E6%99%B6%E4%BD%93%E7%BB%93%E6%9E%84" title="晶体结构">晶体结构</a>。<sup id="cite_ref-Lydon2_3-1" class="reference"><a href="#cite_note-Lydon2-3"><span class="cite-bracket">&#91;</span>3<span class="cite-bracket">&#93;</span></a></sup> 她將<a href="/wiki/X%E5%B0%84%E7%BA%BF%E8%A1%8D%E5%B0%84" class="mw-redirect" title="X射线衍射">X射線繞射</a>分析結果發表在《<a href="/wiki/%E8%87%AA%E7%84%B6_(%E6%9C%9F%E5%88%8A)" title="自然 (期刊)">自然</a>》期刊上<sup id="cite_ref-32" class="reference"><a href="#cite_note-32"><span class="cite-bracket">&#91;</span>32<span class="cite-bracket">&#93;</span></a></sup>。朗斯代尔在《晶體與X射線》(<i>Crystals and X-Rays</i>)一書中描述了該項研究,<sup id="cite_ref-33" class="reference"><a href="#cite_note-33"><span class="cite-bracket">&#91;</span>33<span class="cite-bracket">&#93;</span></a></sup>解釋指她意識到儘管六甲苯的<span class="ilh-all" data-orig-title="单元格" data-lang-code="en" data-lang-name="英语" data-foreign-title="unit cell"><span class="ilh-page"><a href="/w/index.php?title=%E5%8D%95%E5%85%83%E6%A0%BC&amp;action=edit&amp;redlink=1" class="new" title="单元格(页面不存在)">单元格</a></span><span class="noprint ilh-comment"><span class="ilh-paren">(</span><span class="ilh-lang">英语</span><span class="ilh-colon">:</span><span class="ilh-link"><a href="https://en.wikipedia.org/wiki/unit_cell" class="extiw" title="en:unit cell"><span lang="en" dir="auto">unit cell</span></a></span><span class="ilh-paren">)</span></span></span>是<a href="/wiki/%E4%B8%89%E6%96%9C%E6%99%B6%E7%B3%BB" title="三斜晶系">三斜晶系</a>,但其<a href="/wiki/%E7%B9%9E%E5%B0%84" class="mw-redirect" title="繞射">繞射</a>圖案具有偽六邊形對稱性,這使得結構的可能性受到限制,足以讓她通過試錯法來產生結構模型。<sup id="cite_ref-Lydon2_3-2" class="reference"><a href="#cite_note-Lydon2-3"><span class="cite-bracket">&#91;</span>3<span class="cite-bracket">&#93;</span></a></sup>这项工作明确表明六甲苯是平面分子构型的,並且環内不同的碳-碳键距离皆為相同,<sup id="cite_ref-Lydon1_2-1" class="reference"><a href="#cite_note-Lydon1-2"><span class="cite-bracket">&#91;</span>2<span class="cite-bracket">&#93;</span></a></sup>为理解<a href="/wiki/%E8%8A%B3%E9%A6%99%E6%80%A7" title="芳香性">芳香性</a>的性质提供重要证据。 </p> <div class="mw-heading mw-heading2"><h2 id="制备"><span id=".E5.88.B6.E5.A4.87"></span>制备</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E5%85%AD%E7%94%B2%E8%8B%AF&amp;action=edit&amp;section=3" title="编辑章节:制备"><span>编辑</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>1880年,<span class="ilh-all" data-orig-title="约瑟夫·阿希尔·勒贝尔" data-lang-code="en" data-lang-name="英语" data-foreign-title="Joseph Achille Le Bel"><span class="ilh-page"><a href="/w/index.php?title=%E7%BA%A6%E7%91%9F%E5%A4%AB%C2%B7%E9%98%BF%E5%B8%8C%E5%B0%94%C2%B7%E5%8B%92%E8%B4%9D%E5%B0%94&amp;action=edit&amp;redlink=1" class="new" title="约瑟夫·阿希尔·勒贝尔(页面不存在)">约瑟夫·阿希尔·勒贝尔</a></span><span class="noprint ilh-comment"><span class="ilh-paren">(</span><span class="ilh-lang">英语</span><span class="ilh-colon">:</span><span class="ilh-link"><a href="https://en.wikipedia.org/wiki/Joseph_Achille_Le_Bel" class="extiw" title="en:Joseph Achille Le Bel"><span lang="en" dir="auto">Joseph Achille Le Bel</span></a></span><span class="ilh-paren">)</span></span></span>和威廉·H·葛林报告了<sup id="cite_ref-34" class="reference"><a href="#cite_note-34"><span class="cite-bracket">&#91;</span>34<span class="cite-bracket">&#93;</span></a></sup>被形容“不平凡”的,由<a href="/wiki/%E6%B0%AF%E5%8C%96%E9%94%8C" title="氯化锌">氯化锌</a><a href="/wiki/%E5%82%AC%E5%8C%96" title="催化">催化</a>的<a href="/wiki/%E4%B8%80%E9%94%85%E5%90%88%E6%88%90%E6%B3%95" title="一锅合成法">一鍋合成法</a>,過程中從<a href="/wiki/%E7%94%B2%E9%86%87" title="甲醇">甲醇</a>合成了六甲苯。<sup id="cite_ref-HMB_35-0" class="reference"><a href="#cite_note-HMB-35"><span class="cite-bracket">&#91;</span>35<span class="cite-bracket">&#93;</span></a></sup>在催化剂的熔点下(283&#160;°C),反应的<a href="/wiki/%E5%90%89%E5%B8%83%E6%96%AF%E8%83%BD" title="吉布斯能">吉布斯能</a>(ΔG)为−1090&#160;kJ&#160;mol<sup>−1</sup>,反应如下:<sup id="cite_ref-HMB_35-1" class="reference"><a href="#cite_note-HMB-35"><span class="cite-bracket">&#91;</span>35<span class="cite-bracket">&#93;</span></a></sup> </p> <dl><dd>15&#160;<span class="chemf nowrap">CH<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left"><br />3</span>OH</span> &#160; → &#160; <span class="chemf nowrap">C<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left"><br />6</span>(CH<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left"><br />3</span>)<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left"><br />6</span></span> &#160; + &#160; 3&#160;<span class="chemf nowrap">CH<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left"><br />4</span></span> &#160; + &#160; 15&#160;<span class="chemf nowrap">H<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left"><br />2</span>O</span></dd></dl> <p>勒贝勒和葛林提出了理論以解釋這個過程,內容涉及由甲醇脱水而成的<a href="/wiki/%E6%A1%A5%E8%81%94%E4%BA%9A%E7%94%B2%E5%9F%BA" title="桥联亚甲基">亚甲基</a>单元的<span class="ilh-all" data-orig-title="芳香化" data-lang-code="en" data-lang-name="英语" data-foreign-title="aromatisation"><span class="ilh-page"><a href="/w/index.php?title=%E8%8A%B3%E9%A6%99%E5%8C%96&amp;action=edit&amp;redlink=1" class="new" title="芳香化(页面不存在)">芳香化</a></span><span class="noprint ilh-comment"><span class="ilh-paren">(</span><span class="ilh-lang">英语</span><span class="ilh-colon">:</span><span class="ilh-link"><a href="https://en.wikipedia.org/wiki/aromatisation" class="extiw" title="en:aromatisation"><span lang="en" dir="auto">aromatisation</span></a></span><span class="ilh-paren">)</span></span></span>,從而生成苯環,接著在原位用<a href="/wiki/%E6%B0%AF%E7%94%B2%E7%83%B7" title="氯甲烷">氯甲烷</a>進行完全的<a href="/wiki/%E5%82%85-%E5%85%8B%E5%8F%8D%E5%BA%94" class="mw-redirect" title="傅-克反应">傅-克</a>甲基化。<sup id="cite_ref-HMB_35-2" class="reference"><a href="#cite_note-HMB-35"><span class="cite-bracket">&#91;</span>35<span class="cite-bracket">&#93;</span></a></sup>反应主要产生<a href="/wiki/%E9%A5%B1%E5%92%8C%E7%83%83" class="mw-redirect" title="饱和烃">饱和烃</a>的混合物,六甲苯为次要产物。<sup id="cite_ref-36" class="reference"><a href="#cite_note-36"><span class="cite-bracket">&#91;</span>36<span class="cite-bracket">&#93;</span></a></sup>六甲苯也是<a href="/wiki/%E5%AF%B9%E4%BA%8C%E7%94%B2%E8%8B%AF" title="对二甲苯">对二甲苯</a>傅-克烷基化成<a href="/wiki/%E5%9D%87%E5%9B%9B%E7%94%B2%E8%8B%AF" title="均四甲苯">均四甲苯</a>的副产物,而通过<a href="/wiki/%E7%83%B7%E5%9F%BA%E5%8C%96" title="烷基化">烷基化</a>均四甲苯或<a href="/wiki/%E4%BA%94%E7%94%B2%E8%8B%AF" title="五甲苯">五甲苯</a>产生的六甲苯皆有著可觀產率。<sup id="cite_ref-37" class="reference"><a href="#cite_note-37"><span class="cite-bracket">&#91;</span>37<span class="cite-bracket">&#93;</span></a></sup> </p><p>六甲苯通常在高温<a href="/wiki/%E6%B0%A3%E7%9B%B8" class="mw-redirect" title="氣相">气相</a>中通过固体催化剂下制备。早期制备六甲苯的方法包括使<a href="/wiki/%E4%B8%99%E9%85%AE" title="丙酮">丙酮</a>和甲醇蒸气的混合物在400&#160;°C的<a href="/wiki/%E6%B0%A7%E5%8C%96%E9%93%9D" title="氧化铝">氧化铝</a>催化剂下反应。<sup id="cite_ref-38" class="reference"><a href="#cite_note-38"><span class="cite-bracket">&#91;</span>38<span class="cite-bracket">&#93;</span></a></sup><a href="/wiki/%E8%8B%AF%E9%85%9A" title="苯酚">苯酚</a>和甲醇在 410–440&#160;°C 的乾燥<a href="/wiki/%E4%BA%8C%E6%B0%A7%E5%8C%96%E7%A2%B3" title="二氧化碳">二氧化碳</a>氣體中也会产生六甲苯,<sup id="cite_ref-HMBSynth_4-1" class="reference"><a href="#cite_note-HMBSynth-4"><span class="cite-bracket">&#91;</span>4<span class="cite-bracket">&#93;</span></a></sup>尽管它是作为<a href="/wiki/%E8%8B%AF%E7%94%B2%E9%86%9A" title="苯甲醚">苯甲醚</a>(甲氧基苯)、<a href="/wiki/%E7%94%B2%E9%85%9A" title="甲酚">甲酚</a>(甲基苯酚)和其他甲基化苯酚的複雜混合物的一部分而被生成。<sup id="cite_ref-CullinaneChard_11-1" class="reference"><a href="#cite_note-CullinaneChard-11"><span class="cite-bracket">&#91;</span>11<span class="cite-bracket">&#93;</span></a></sup>在《有機合成》收錄的制備方法中,甲醇和苯酚則在 530&#160;°C的氧化铝催化剂下反应,產率約為66%,<sup id="cite_ref-HMBOrgSynth_5-2" class="reference"><a href="#cite_note-HMBOrgSynth-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup>而在其他不同條件下進行的合成方法也有被報道。<sup id="cite_ref-PMB_6-2" class="reference"><a href="#cite_note-PMB-6"><span class="cite-bracket">&#91;</span>6<span class="cite-bracket">&#93;</span></a></sup> </p> <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> <p>這種表面介導反應的機制已被妥善地研究,研究的過程中着眼於如何更好地控制反應结果,<sup id="cite_ref-Ipatiew_8-1" class="reference"><a href="#cite_note-Ipatiew-8"><span class="cite-bracket">&#91;</span>8<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-39" class="reference"><a href="#cite_note-39"><span class="cite-bracket">&#91;</span>39<span class="cite-bracket">&#93;</span></a></sup>特别是在尋找具有選擇性和受控的鄰位甲基化反應。<sup id="cite_ref-Takeshi1_9-1" class="reference"><a href="#cite_note-Takeshi1-9"><span class="cite-bracket">&#91;</span>9<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Takeshi2_10-1" class="reference"><a href="#cite_note-Takeshi2-10"><span class="cite-bracket">&#91;</span>10<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-40" class="reference"><a href="#cite_note-40"><span class="cite-bracket">&#91;</span>40<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-41" class="reference"><a href="#cite_note-41"><span class="cite-bracket">&#91;</span>41<span class="cite-bracket">&#93;</span></a></sup>苯甲醚<sup id="cite_ref-CullinaneChard_11-2" class="reference"><a href="#cite_note-CullinaneChard-11"><span class="cite-bracket">&#91;</span>11<span class="cite-bracket">&#93;</span></a></sup>和五甲苯<sup id="cite_ref-PMB_6-3" class="reference"><a href="#cite_note-PMB-6"><span class="cite-bracket">&#91;</span>6<span class="cite-bracket">&#93;</span></a></sup>皆被報告為此過程的反應中間體。<span class="ilh-all" data-orig-title="华伦汀·科普秋格" data-lang-code="en" data-lang-name="英语" data-foreign-title="Valentin Koptyug"><span class="ilh-page"><a href="/w/index.php?title=%E5%8D%8E%E4%BC%A6%E6%B1%80%C2%B7%E7%A7%91%E6%99%AE%E7%A7%8B%E6%A0%BC&amp;action=edit&amp;redlink=1" class="new" title="华伦汀·科普秋格(页面不存在)">华伦汀·科普秋格</a></span><span class="noprint ilh-comment"><span class="ilh-paren">(</span><span class="ilh-lang">英语</span><span class="ilh-colon">:</span><span class="ilh-link"><a href="https://en.wikipedia.org/wiki/Valentin_Koptyug" class="extiw" title="en:Valentin Koptyug"><span lang="en" dir="auto">Valentin Koptyug</span></a></span><span class="ilh-paren">)</span></span></span>和同事发现,六甲基环己二烯酮的<a href="/wiki/%E5%BC%82%E6%9E%84%E4%BD%93" class="mw-redirect" title="异构体">异构体</a>(2,3,4,4,5,6-和2,3,4,5,6,6-)亦是反應中的中間體,经過<a href="/wiki/%E9%87%8D%E6%8E%92%E5%8F%8D%E6%87%89" class="mw-redirect" title="重排反應">重排反應</a>而形成六甲苯。<sup id="cite_ref-Koptyug1_7-1" class="reference"><a href="#cite_note-Koptyug1-7"><span class="cite-bracket">&#91;</span>7<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Koptyug2_12-1" class="reference"><a href="#cite_note-Koptyug2-12"><span class="cite-bracket">&#91;</span>12<span class="cite-bracket">&#93;</span></a></sup> </p><p><a href="/wiki/2-%E4%B8%81%E7%82%94" title="2-丁炔">2-丁炔</a><span class="ilh-all" data-orig-title="炔烃三聚" data-lang-code="en" data-lang-name="英语" data-foreign-title="Alkyne trimerisation"><span class="ilh-page"><a href="/w/index.php?title=%E7%82%94%E7%83%83%E4%B8%89%E8%81%9A&amp;action=edit&amp;redlink=1" class="new" title="炔烃三聚(页面不存在)">三聚</a></span><span class="noprint ilh-comment"><span class="ilh-paren">(</span><span class="ilh-lang">英语</span><span class="ilh-colon">:</span><span class="ilh-link"><a href="https://en.wikipedia.org/wiki/Alkyne_trimerisation" class="extiw" title="en:Alkyne trimerisation"><span lang="en" dir="auto">Alkyne trimerisation</span></a></span><span class="ilh-paren">)</span></span></span>也可以生成六甲苯。<sup id="cite_ref-Trimerisation_15-1" class="reference"><a href="#cite_note-Trimerisation-15"><span class="cite-bracket">&#91;</span>15<span class="cite-bracket">&#93;</span></a></sup>此反应可被三苯基三(四氢呋喃)铬<sup id="cite_ref-Cr_13-1" class="reference"><a href="#cite_note-Cr-13"><span class="cite-bracket">&#91;</span>13<span class="cite-bracket">&#93;</span></a></sup>或<a href="/wiki/%E5%9B%9B%E6%B0%AF%E5%8C%96%E9%92%9B" title="四氯化钛">四氯化钛</a>與<a href="/wiki/%E4%B8%89%E5%BC%82%E4%B8%81%E5%9F%BA%E9%93%9D" title="三异丁基铝">三异丁基铝</a>的<a href="/wiki/%E9%85%8D%E5%90%88%E7%89%A9" title="配合物">配合物</a>催化。<sup id="cite_ref-Ti_14-1" class="reference"><a href="#cite_note-Ti-14"><span class="cite-bracket">&#91;</span>14<span class="cite-bracket">&#93;</span></a></sup> </p> <figure class="mw-halign-center" typeof="mw:File/Frameless"><a href="/wiki/File:2-%E4%B8%81%E7%82%94%E7%92%B0%E4%B8%89%E8%81%9A.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/06/2-%E4%B8%81%E7%82%94%E7%92%B0%E4%B8%89%E8%81%9A.png/350px-2-%E4%B8%81%E7%82%94%E7%92%B0%E4%B8%89%E8%81%9A.png" decoding="async" width="350" height="129" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/06/2-%E4%B8%81%E7%82%94%E7%92%B0%E4%B8%89%E8%81%9A.png/525px-2-%E4%B8%81%E7%82%94%E7%92%B0%E4%B8%89%E8%81%9A.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/06/2-%E4%B8%81%E7%82%94%E7%92%B0%E4%B8%89%E8%81%9A.png/700px-2-%E4%B8%81%E7%82%94%E7%92%B0%E4%B8%89%E8%81%9A.png 2x" data-file-width="1680" data-file-height="617" /></a><figcaption></figcaption></figure> <div class="mw-heading mw-heading2"><h2 id="用处"><span id=".E7.94.A8.E5.A4.84"></span>用处</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E5%85%AD%E7%94%B2%E8%8B%AF&amp;action=edit&amp;section=4" title="编辑章节:用处"><span>编辑</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>六甲苯可用作<span class="ilh-all" data-orig-title="氦-3核磁共振" data-lang-code="en" data-lang-name="英语" data-foreign-title="Helium-3 nuclear magnetic resonance"><span class="ilh-page"><a href="/w/index.php?title=%E6%B0%A6-3%E6%A0%B8%E7%A3%81%E5%85%B1%E6%8C%AF&amp;action=edit&amp;redlink=1" class="new" title="氦-3核磁共振(页面不存在)"><sup>3</sup>He-NMR 光谱测试</a></span><span class="noprint ilh-comment"><span class="ilh-paren">(</span><span class="ilh-lang">英语</span><span class="ilh-colon">:</span><span class="ilh-link"><a href="https://en.wikipedia.org/wiki/Helium-3_nuclear_magnetic_resonance" class="extiw" title="en:Helium-3 nuclear magnetic resonance"><span lang="en" dir="auto">Helium-3 nuclear magnetic resonance</span></a></span><span class="ilh-paren">)</span></span></span>的溶剂。<sup id="cite_ref-42" class="reference"><a href="#cite_note-42"><span class="cite-bracket">&#91;</span>42<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="反应"><span id=".E5.8F.8D.E5.BA.94"></span>反应</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E5%85%AD%E7%94%B2%E8%8B%AF&amp;action=edit&amp;section=5" title="编辑章节:反应"><span>编辑</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>它會和<a href="/wiki/%E8%8B%A6%E5%9F%BA%E6%B0%AF" title="苦基氯">苦基氯</a>反應形成 1:1 加合物。<sup id="cite_ref-43" class="reference"><a href="#cite_note-43"><span class="cite-bracket">&#91;</span>43<span class="cite-bracket">&#93;</span></a></sup> </p><p>它亦會被<a href="/wiki/%E4%B8%89%E6%B0%9F%E8%BF%87%E6%B0%A7%E4%B9%99%E9%85%B8" title="三氟过氧乙酸">三氟过氧乙酸</a>或<a href="/wiki/%E8%BF%87%E6%B0%A7%E5%8C%96%E6%B0%A2" title="过氧化氢">过氧化氢</a>氧化,产生 2,3,4,5,6,6-六甲基-2,4-环己二烯酮:<sup id="cite_ref-44" class="reference"><a href="#cite_note-44"><span class="cite-bracket">&#91;</span>44<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Koptyug1_7-2" class="reference"><a href="#cite_note-Koptyug1-7"><span class="cite-bracket">&#91;</span>7<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Koptyug2_12-2" class="reference"><a href="#cite_note-Koptyug2-12"><span class="cite-bracket">&#91;</span>12<span class="cite-bracket">&#93;</span></a></sup> </p> <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> <p>就像苯本身一样,六甲苯中富含电子的芳香系统使其能在<a href="/wiki/%E6%9C%89%E6%9C%BA%E9%87%91%E5%B1%9E%E5%8C%96%E5%AD%A6" title="有机金属化学">有机金属化学</a>中充当<a href="/wiki/%E9%85%8D%E9%AB%94" title="配體">配體</a>。<sup id="cite_ref-AreneReview_18-1" class="reference"><a href="#cite_note-AreneReview-18"><span class="cite-bracket">&#91;</span>18<span class="cite-bracket">&#93;</span></a></sup> 甲基是<span class="ilh-all" data-orig-title="推电子基" data-lang-code="en" data-lang-name="英语" data-foreign-title="Electron donating group"><span class="ilh-page"><a href="/w/index.php?title=%E6%8E%A8%E7%94%B5%E5%AD%90%E5%9F%BA&amp;action=edit&amp;redlink=1" class="new" title="推电子基(页面不存在)">推电子基</a></span><span class="noprint ilh-comment"><span class="ilh-paren">(</span><span class="ilh-lang">英语</span><span class="ilh-colon">:</span><span class="ilh-link"><a href="https://en.wikipedia.org/wiki/Electron_donating_group" class="extiw" title="en:Electron donating group"><span lang="en" dir="auto">Electron donating group</span></a></span><span class="ilh-paren">)</span></span></span>,使得相对于苯,它将中心环的碱性提高六到七个<a href="/wiki/%E6%95%B0%E9%87%8F%E7%BA%A7" title="数量级">数量级</a>。<sup id="cite_ref-45" class="reference"><a href="#cite_note-45"><span class="cite-bracket">&#91;</span>45<span class="cite-bracket">&#93;</span></a></sup>有各种金属中心的<a href="/wiki/%E6%9C%89%E6%A9%9F%E9%87%91%E5%B1%AC%E5%8C%96%E5%90%88%E7%89%A9" class="mw-redirect" title="有機金屬化合物">这些配合物</a>已被报告,包括钴、<sup id="cite_ref-CoRh_46-0" class="reference"><a href="#cite_note-CoRh-46"><span class="cite-bracket">&#91;</span>46<span class="cite-bracket">&#93;</span></a></sup>铬、<sup id="cite_ref-Cr_13-2" class="reference"><a href="#cite_note-Cr-13"><span class="cite-bracket">&#91;</span>13<span class="cite-bracket">&#93;</span></a></sup>铁、<sup id="cite_ref-Fe_19-2" class="reference"><a href="#cite_note-Fe-19"><span class="cite-bracket">&#91;</span>19<span class="cite-bracket">&#93;</span></a></sup>铼、<sup id="cite_ref-47" class="reference"><a href="#cite_note-47"><span class="cite-bracket">&#91;</span>47<span class="cite-bracket">&#93;</span></a></sup>铑、<sup id="cite_ref-CoRh_46-1" class="reference"><a href="#cite_note-CoRh-46"><span class="cite-bracket">&#91;</span>46<span class="cite-bracket">&#93;</span></a></sup>钌<sup id="cite_ref-RuHMB2_20-1" class="reference"><a href="#cite_note-RuHMB2-20"><span class="cite-bracket">&#91;</span>20<span class="cite-bracket">&#93;</span></a></sup>和钛。<sup id="cite_ref-Ti_14-2" class="reference"><a href="#cite_note-Ti-14"><span class="cite-bracket">&#91;</span>14<span class="cite-bracket">&#93;</span></a></sup>钴和铑和六甲苯化学式 <span class="chemf nowrap">[M(C<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left"><br />6</span>(CH<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left"><br />3</span>)<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left"><br />6</span>)<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left"><br />2</span>]</span><sup><i>n</i>+</sup> (M&#160;=&#160;Co, Fe, Rh, Ru; <i>n</i>&#160;=&#160;1,&#160;2) 的<a href="/wiki/%E5%A4%B9%E5%BF%83%E9%85%8D%E5%90%88%E7%89%A9" class="mw-redirect" title="夹心配合物">夹心配合物</a><a href="/wiki/%E9%98%B3%E7%A6%BB%E5%AD%90" class="mw-redirect" title="阳离子">阳离子</a>,其中金属中心和两个芳烃的π电子结合,并且可以通过配体交换从适当的金属盐轻松合成,例如:<sup id="cite_ref-CoRh_46-2" class="reference"><a href="#cite_note-CoRh-46"><span class="cite-bracket">&#91;</span>46<span class="cite-bracket">&#93;</span></a></sup> </p> <dl><dd><span class="chemf nowrap">CoBr<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left"><br />2</span></span> &#160; + &#160; 2&#160;<span class="chemf nowrap">AlBr<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left"><br />3</span></span> &#160; → &#160; <span class="chemf nowrap">[Co(C<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left"><br />6</span>(CH<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left"><br />3</span>)<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left"><br />6</span>)<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left"><br />2</span>]<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:0.8em;font-size:70%;text-align:left">2+<br /></span></span> &#160; + &#160; 2&#160;<span class="chemf nowrap">AlBr<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left">−<br />4</span></span></dd></dl> <p>这些配合物可以参与<a href="/wiki/%E6%B0%A7%E5%8C%96%E8%BF%98%E5%8E%9F%E5%8F%8D%E5%BA%94" title="氧化还原反应">氧化还原反应</a>。铑和钴配合物的<span class="ilh-all" data-orig-title="双阳离子" data-lang-code="en" data-lang-name="英语" data-foreign-title="dication"><span class="ilh-page"><a href="/w/index.php?title=%E5%8F%8C%E9%98%B3%E7%A6%BB%E5%AD%90&amp;action=edit&amp;redlink=1" class="new" title="双阳离子(页面不存在)">双阳离子</a></span><span class="noprint ilh-comment"><span class="ilh-paren">(</span><span class="ilh-lang">英语</span><span class="ilh-colon">:</span><span class="ilh-link"><a href="https://en.wikipedia.org/wiki/dication" class="extiw" title="en:dication"><span lang="en" dir="auto">dication</span></a></span><span class="ilh-paren">)</span></span></span>可以用合适的活性金属(钴配合物用铝还原,铑配合物用锌还原)进行单电子还原,描述钴配合物的反应方程式如下:<sup id="cite_ref-CoRh_46-3" class="reference"><a href="#cite_note-CoRh-46"><span class="cite-bracket">&#91;</span>46<span class="cite-bracket">&#93;</span></a></sup> </p> <dl><dd>3&#160;<span class="chemf nowrap">[Co(C<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left"><br />6</span>(CH<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left"><br />3</span>)<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left"><br />6</span>)<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left"><br />2</span>]<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:0.8em;font-size:70%;text-align:left">2+<br /></span></span> &#160; + &#160; Al &#160; → &#160; 3&#160;<span class="chemf nowrap">[Co(C<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left"><br />6</span>(CH<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left"><br />3</span>)<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left"><br />6</span>)<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left"><br />2</span>]<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:0.8em;font-size:70%;text-align:left">+<br /></span></span> &#160; + &#160; <span class="chemf nowrap">Al<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:0.8em;font-size:70%;text-align:left">3+<br /></span></span></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>[Ru(C<sub>6</sub>(CH<sub>3</sub>)<sub>6</sub>)<sub>2</sub>]<sup><i>n</i>+</sup> 的结构变化<sup id="cite_ref-RuHMB2_20-2" class="reference"><a href="#cite_note-RuHMB2-20"><span class="cite-bracket">&#91;</span>20<span class="cite-bracket">&#93;</span></a></sup><br />左:<i>n</i>&#160;=&#160;2, [Ru<sup>II</sup>(η<sup>6</sup>-C<sub>6</sub>(CH<sub>3</sub>)<sub>6</sub>)<sub>2</sub>]<sup>2+</sup><br />右:<i>n</i>&#160;=&#160;0, [Ru<sup>0</sup>(η<sup>4</sup>-C<sub>6</sub>(CH<sub>3</sub>)<sub>6</sub>)(η<sup>6</sup>-C<sub>6</sub>(CH<sub>3</sub>)<sub>6</sub>)]<br />为清楚起见省略了甲基。与碳-钌键合相关的电子对是红色的</figcaption></figure> <p>在<a href="/w/index.php?title=%E6%9C%89%E6%9C%BA%E9%92%8C%E5%8C%96%E5%AD%A6&amp;action=edit&amp;redlink=1" class="new" title="有机钌化学(页面不存在)">有机钌化学</a>中,双阳离子和电中性物种在<a href="/wiki/%E4%B9%99%E8%85%88" title="乙腈">乙腈</a>中的还原电位为 −1.02&#160;V,<sup id="cite_ref-Fe_19-3" class="reference"><a href="#cite_note-Fe-19"><span class="cite-bracket">&#91;</span>19<span class="cite-bracket">&#93;</span></a></sup>并且伴随着结构的变化。<sup id="cite_ref-RuHMB2_20-3" class="reference"><a href="#cite_note-RuHMB2-20"><span class="cite-bracket">&#91;</span>20<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-48" class="reference"><a href="#cite_note-48"><span class="cite-bracket">&#91;</span>48<span class="cite-bracket">&#93;</span></a></sup>随着钌中心<a href="/wiki/%E6%B0%A7%E5%8C%96%E6%80%81" title="氧化态">氧化态</a>的变化,其中一个六甲苯配体的<a href="/wiki/%E5%93%88%E6%99%AE%E6%89%98%E6%95%B8" title="哈普托數">哈普托数</a>会变化。[Ru(η<sup>6</sup>-C<sub>6</sub>(CH<sub>3</sub>)<sub>6</sub>)<sub>2</sub>]<sup>2+</sup> 会还原成 [Ru(η<sup>4</sup>-C<sub>6</sub>(CH<sub>3</sub>)<sub>6</sub>)(η<sup>6</sup>-C<sub>6</sub>(CH<sub>3</sub>)<sub>6</sub>)],<sup id="cite_ref-RuHMB2_20-4" class="reference"><a href="#cite_note-RuHMB2-20"><span class="cite-bracket">&#91;</span>20<span class="cite-bracket">&#93;</span></a></sup>它的结构变化是用来遵守<a href="/wiki/18%E7%94%B5%E5%AD%90%E8%A7%84%E5%88%99" title="18电子规则">18电子规则</a>,增强稳定性。 </p><p>类似的铁(II)配合物的单电子还原可逆(在乙醇水溶液中为−0.48&#160;V),但双电子还原(−1.46&#160;V)不可逆,<sup id="cite_ref-Fe_19-4" class="reference"><a href="#cite_note-Fe-19"><span class="cite-bracket">&#91;</span>19<span class="cite-bracket">&#93;</span></a></sup>表明它的结构变化不同于在钌配合物中发现的结构变化。 </p> <div class="mw-heading mw-heading3"><h3 id="双阳离子"><span id=".E5.8F.8C.E9.98.B3.E7.A6.BB.E5.AD.90"></span>双阳离子</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E5%85%AD%E7%94%B2%E8%8B%AF&amp;action=edit&amp;section=6" title="编辑章节:双阳离子"><span>编辑</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r85100532">.mw-parser-output .hatnote{font-size:small}.mw-parser-output div.hatnote{padding-left:2em;margin-bottom:0.8em;margin-top:0.8em}.mw-parser-output .hatnote-notice-img::after{content:"\202f \202f \202f \202f "}.mw-parser-output .hatnote-notice-img-small::after{content:"\202f \202f "}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}body.skin-minerva .mw-parser-output .hatnote-notice-img,body.skin-minerva .mw-parser-output .hatnote-notice-img-small{display:none}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">主条目:<span class="ilh-all" data-orig-title="锥型碳阳离子" data-lang-code="en" data-lang-name="英语" data-foreign-title="Pyramidal carbocation"><span class="ilh-page"><a href="/w/index.php?title=%E9%94%A5%E5%9E%8B%E7%A2%B3%E9%98%B3%E7%A6%BB%E5%AD%90&amp;action=edit&amp;redlink=1" class="new" title="锥型碳阳离子(页面不存在)">锥型碳阳离子</a></span><span class="noprint ilh-comment"><span class="ilh-paren">(</span><span class="ilh-lang">英语</span><span class="ilh-colon">:</span><span class="ilh-link"><a href="https://en.wikipedia.org/wiki/Pyramidal_carbocation" class="extiw" title="en:Pyramidal carbocation"><span lang="en" dir="auto">Pyramidal carbocation</span></a></span><span class="ilh-paren">)</span></span></span></div> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Pyramidal_dikation,_hexamethyl.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c9/Pyramidal_dikation%2C_hexamethyl.jpg/220px-Pyramidal_dikation%2C_hexamethyl.jpg" decoding="async" width="220" height="177" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c9/Pyramidal_dikation%2C_hexamethyl.jpg/330px-Pyramidal_dikation%2C_hexamethyl.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c9/Pyramidal_dikation%2C_hexamethyl.jpg/440px-Pyramidal_dikation%2C_hexamethyl.jpg 2x" data-file-width="742" data-file-height="598" /></a><figcaption>化学式 <span class="chemf nowrap">C<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left"><br />6</span>(CH<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left"><br />3</span>)<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left">2+<br />6</span></span>的<span class="ilh-all" data-orig-title="锥型碳阳离子" data-lang-code="en" data-lang-name="英语" data-foreign-title="Pyramidal carbocation"><span class="ilh-page"><a href="/w/index.php?title=%E9%94%A5%E5%9E%8B%E7%A2%B3%E9%98%B3%E7%A6%BB%E5%AD%90&amp;action=edit&amp;redlink=1" class="new" title="锥型碳阳离子(页面不存在)">锥型碳阳离子</a></span><span class="noprint ilh-comment"><span class="ilh-paren">(</span><span class="ilh-lang">英语</span><span class="ilh-colon">:</span><span class="ilh-link"><a href="https://en.wikipedia.org/wiki/Pyramidal_carbocation" class="extiw" title="en:Pyramidal carbocation"><span lang="en" dir="auto">Pyramidal carbocation</span></a></span><span class="ilh-paren">)</span></span></span></figcaption></figure> <p><span class="chemf nowrap">C<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left"><br />6</span>(CH<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left"><br />3</span>)<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left"><br />6</span>H<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:0.8em;font-size:70%;text-align:left">+<br /></span></span>在1960年代对<a href="/w/index.php?title=%E5%85%AD%E7%94%B2%E5%9F%BA%E6%9D%9C%E7%93%A6%E8%8B%AF&amp;action=edit&amp;redlink=1" class="new" title="六甲基杜瓦苯(页面不存在)">六甲基杜瓦苯</a>的调查中首次报道,<sup id="cite_ref-49" class="reference"><a href="#cite_note-49"><span class="cite-bracket">&#91;</span>49<span class="cite-bracket">&#93;</span></a></sup>基于<a href="/wiki/%E6%A0%B8%E7%A3%81%E5%85%B1%E6%8C%AF" title="核磁共振">核磁共振</a>的证据提出了五角錐结构,<sup id="cite_ref-50" class="reference"><a href="#cite_note-50"><span class="cite-bracket">&#91;</span>50<span class="cite-bracket">&#93;</span></a></sup>随后得到无序的<sup id="cite_ref-PyramidalAngewChem_21-2" class="reference"><a href="#cite_note-PyramidalAngewChem-21"><span class="cite-bracket">&#91;</span>21<span class="cite-bracket">&#93;</span></a></sup>晶体结构数据的支持。<sup id="cite_ref-51" class="reference"><a href="#cite_note-51"><span class="cite-bracket">&#91;</span>51<span class="cite-bracket">&#93;</span></a></sup>1970年代初期,由赫普克·霍赫芬领导的理论工作预测了五角錐形的双阳离子 <span class="chemf nowrap">C<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left"><br />6</span>(CH<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left"><br />3</span>)<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left">2+<br />6</span></span>的存在,并且该意见很快得到了实验证据的支持。<sup id="cite_ref-HMBcatObs1_27-1" class="reference"><a href="#cite_note-HMBcatObs1-27"><span class="cite-bracket">&#91;</span>27<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-HMBcatObs2_28-1" class="reference"><a href="#cite_note-HMBcatObs2-28"><span class="cite-bracket">&#91;</span>28<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-HMBcatObs3_29-1" class="reference"><a href="#cite_note-HMBcatObs3-29"><span class="cite-bracket">&#91;</span>29<span class="cite-bracket">&#93;</span></a></sup>对苯在极低温度(低于 4K)下的双电子氧化的<a href="/wiki/%E5%85%89%E8%B0%B1%E5%AD%A6" title="光谱学">光谱学</a>研究表明,形成六边形的双阳离子,然后迅速重新排列成五角錐结构:<sup id="cite_ref-52" class="reference"><a href="#cite_note-52"><span class="cite-bracket">&#91;</span>52<span class="cite-bracket">&#93;</span></a></sup> </p> <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><span class="chemf nowrap">C<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left"><br />6</span>(CH<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left"><br />3</span>)<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left">2+<br />6</span></span>有<a href="/wiki/%E4%BA%94%E8%A7%92%E9%8C%90" title="五角錐">五角锥</a>结构</figcaption></figure> <p>一般預料六甲苯的雙電子氧化會令其重排為<span class="ilh-all" data-orig-title="錐型碳陽離子" data-lang-code="en" data-lang-name="英语" data-foreign-title="Pyramidal carbocation"><span class="ilh-page"><a href="/w/index.php?title=%E9%8C%90%E5%9E%8B%E7%A2%B3%E9%99%BD%E9%9B%A2%E5%AD%90&amp;action=edit&amp;redlink=1" class="new" title="錐型碳陽離子(页面不存在)">錐型碳陽離子</a></span><span class="noprint ilh-comment"><span class="ilh-paren">(</span><span class="ilh-lang">英语</span><span class="ilh-colon">:</span><span class="ilh-link"><a href="https://en.wikipedia.org/wiki/Pyramidal_carbocation" class="extiw" title="en:Pyramidal carbocation"><span lang="en" dir="auto">Pyramidal carbocation</span></a></span><span class="ilh-paren">)</span></span></span>,但以此方法試圖批量合成的嘗試皆沒有成功。<sup id="cite_ref-PyramidalAngewChem_21-3" class="reference"><a href="#cite_note-PyramidalAngewChem-21"><span class="cite-bracket">&#91;</span>21<span class="cite-bracket">&#93;</span></a></sup>然而,在2016年霍赫芬的方法受到了改進,連帶得出了<span class="chemf nowrap">[C<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left"><br />6</span>(CH<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left"><br />3</span>)<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left"><br />6</span>][SbF<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left"><br />6</span>]<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left"><br />2</span>&#8226;HSO<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left"><br />3</span>F</span>的高質素晶體結構。它的锥高为 1.18&#160;<a href="/wiki/%E5%9F%83%E6%A0%BC%E6%96%AF%E7%89%B9%E6%9C%97" class="mw-redirect" title="埃格斯特朗">埃格斯特朗</a>,五个甲基都略高于底面,<sup id="cite_ref-PyramidalAngewChem_21-4" class="reference"><a href="#cite_note-PyramidalAngewChem-21"><span class="cite-bracket">&#91;</span>21<span class="cite-bracket">&#93;</span></a></sup>形成<a href="/wiki/%E5%9B%9B%E9%9D%A2%E4%BD%93%E5%BD%A2%E5%88%86%E5%AD%90%E6%9E%84%E5%9E%8B#反轉的四面体构型" title="四面体形分子构型">反转的四面体构型</a>。它的制备方法是六甲基杜瓦苯的<a href="/wiki/%E7%8E%AF%E6%B0%A7%E5%8C%96%E7%89%A9" class="mw-redirect" title="环氧化物">环氧化物</a>和<a href="/wiki/%E9%AD%94%E9%85%B8" title="魔酸">魔酸</a>反应,离去氧离子 (<span class="chemf nowrap">O<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:0.8em;font-size:70%;text-align:left">2−<br /></span></span>),形成双阳离子:<sup id="cite_ref-PyramidalAngewChem_21-5" class="reference"><a href="#cite_note-PyramidalAngewChem-21"><span class="cite-bracket">&#91;</span>21<span class="cite-bracket">&#93;</span></a></sup> </p> <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> <p>儘管先前的間接光谱證據和理論計算均已表明它們的存在,但對於‘帶有一個僅與其他碳原子結合的六配位碳’的特殊化學物種所做的分離和結構測定仍是前所未有的,<sup id="cite_ref-PyramidalAngewChem_21-6" class="reference"><a href="#cite_note-PyramidalAngewChem-21"><span class="cite-bracket">&#91;</span>21<span class="cite-bracket">&#93;</span></a></sup>并吸引了《<a href="/wiki/%E5%8C%96%E5%AD%A6%E5%8C%96%E5%B7%A5%E6%96%B0%E9%97%BB" title="化学化工新闻">化学化工新闻</a>》、<sup id="cite_ref-PyramidalC&amp;ENews_23-2" class="reference"><a href="#cite_note-PyramidalC&amp;ENews-23"><span class="cite-bracket">&#91;</span>23<span class="cite-bracket">&#93;</span></a></sup>《<a href="/wiki/%E6%96%B0%E7%A7%91%E5%AD%B8%E4%BA%BA" title="新科學人">新科学人</a>》、<sup id="cite_ref-PyramidalNewSci_22-2" class="reference"><a href="#cite_note-PyramidalNewSci-22"><span class="cite-bracket">&#91;</span>22<span class="cite-bracket">&#93;</span></a></sup>《<span class="ilh-all" data-orig-title="科学新闻" data-lang-code="en" data-lang-name="英语" data-foreign-title="Science News"><span class="ilh-page"><a href="/w/index.php?title=%E7%A7%91%E5%AD%A6%E6%96%B0%E9%97%BB&amp;action=edit&amp;redlink=1" class="new" title="科学新闻(页面不存在)">科学新闻</a></span><span class="noprint ilh-comment"><span class="ilh-paren">(</span><span class="ilh-lang">英语</span><span class="ilh-colon">:</span><span class="ilh-link"><a href="https://en.wikipedia.org/wiki/Science_News" class="extiw" title="en:Science News"><span lang="en" dir="auto">Science News</span></a></span><span class="ilh-paren">)</span></span></span>》<sup id="cite_ref-PyramidalSciNews_24-2" class="reference"><a href="#cite_note-PyramidalSciNews-24"><span class="cite-bracket">&#91;</span>24<span class="cite-bracket">&#93;</span></a></sup>和ZME Science评论。<sup id="cite_ref-53" class="reference"><a href="#cite_note-53"><span class="cite-bracket">&#91;</span>53<span class="cite-bracket">&#93;</span></a></sup>碳的<a href="/wiki/%E5%8C%96%E5%90%88%E4%BB%B7" title="化合价">化合价</a>为四,而该例角锥顶点上的那个碳原子和六个原子键合,并不寻常。<sup id="cite_ref-PyramidalC&amp;ENews_23-3" class="reference"><a href="#cite_note-PyramidalC&amp;ENews-23"><span class="cite-bracket">&#91;</span>23<span class="cite-bracket">&#93;</span></a></sup>该分子是芳香性的,在五角錐的底部与其顶点之间的五个键中总共只有六个电子,可以避免违反<a href="/wiki/%E5%85%AB%E9%9A%85%E9%AB%94%E8%A6%8F%E5%89%87" title="八隅體規則">八隅体规则</a>。也就是说,五角錐的每个斜边只有部分键,而不是一个正常的<a href="/wiki/%E5%85%B1%E4%BB%B7%E9%94%AE" title="共价键">共价键</a>。尽管顶部的碳确实与六个原子键合,但它总共使用不超过八个电子。<sup id="cite_ref-HMBviaOMetChem_26-1" class="reference"><a href="#cite_note-HMBviaOMetChem-26"><span class="cite-bracket">&#91;</span>26<span class="cite-bracket">&#93;</span></a></sup> </p><p>注意形成双阳离子五角錐斜边的弱键(在结构中显示为虚线),它的<a href="/wiki/%E9%94%AE%E7%BA%A7" title="键级">键级</a>约为 0.54,因此总键级为 5&#160;×&#160;0.54&#160;+&#160;1&#160;=&#160;3.7&#160;&lt;&#160;4,所以此物种不是<a href="/wiki/%E8%B6%85%E4%BB%B7%E5%88%86%E5%AD%90" title="超价分子">超价分子</a>,但它是超配位分子。<sup id="cite_ref-Bachrach_25-1" class="reference"><a href="#cite_note-Bachrach-25"><span class="cite-bracket">&#91;</span>25<span class="cite-bracket">&#93;</span></a></sup>双阳离子中,有三種不同的碳-碳键,一則環上的鍵,具有芳香性;二則環到甲基的單鍵;三則斜边,是弱的部分键。其差異也反映在碳-碳<a href="/wiki/%E9%94%AE%E9%95%BF" title="键长">键长</a>中:环的碳-碳键长为 <span class="nowrap">1.439–1.445&#160;Å</span>(最短),环到甲基的碳-碳键长为 <span class="nowrap">1.479–1.489&#160;Å</span>(居中),而环到六配位碳的碳-碳键长为<span class="nowrap">1.694–1.715&#160;Å</span>(最長)<sup id="cite_ref-PyramidalAngewChem_21-7" class="reference"><a href="#cite_note-PyramidalAngewChem-21"><span class="cite-bracket">&#91;</span>21<span class="cite-bracket">&#93;</span></a></sup>。从有机金属化学的角度来看,该物种可以被视为 <span class="nowrap">[(η<span class="chemf nowrap"><span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:0.8em;font-size:85%;text-align:left">5<br /></span>–C<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left"><br />5</span>(CH<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left"><br />3</span>)<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left"><br />5</span>)C(CH<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left"><br />3</span></span>)]<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:0.8em;font-size:85%;text-align:left"><br /></span></span>。<sup id="cite_ref-HMBviaOMetChem_26-2" class="reference"><a href="#cite_note-HMBviaOMetChem-26"><span class="cite-bracket">&#91;</span>26<span class="cite-bracket">&#93;</span></a></sup>此理解下,碳(IV)的中心 (<span class="chemf nowrap">C<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:0.8em;font-size:70%;text-align:left">4+<br /></span></span>),與一个芳香性的 η<sup>5</sup>–<a href="/wiki/%E7%8E%AF%E6%88%8A%E4%BA%8C%E7%83%AF" title="环戊二烯">环戊二烯</a>阴离子(六个电子)和甲基阴离子(两个电子)鍵結,從而满足八隅体规则,类似于相关的气相<a href="/wiki/%E6%9C%89%E6%9C%BA%E9%94%8C%E5%8C%96%E5%90%88%E7%89%A9" title="有机锌化合物">有机锌化合物</a> <span class="nowrap">[(η<span class="chemf nowrap"><span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:0.8em;font-size:85%;text-align:left">5<br /></span>–C<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left"><br />5</span>(CH<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left"><br />3</span>)<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left"><br />5</span>)Zn(CH<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left"><br />3</span></span>)]</span> ,其有同樣的配體键结到锌(II)中心(<span class="chemf nowrap">Zn<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:0.8em;font-size:70%;text-align:left">2+<br /></span></span>),符合<a href="/wiki/18%E7%94%B5%E5%AD%90%E8%A7%84%E5%88%99" title="18电子规则">18电子规则</a>。<sup id="cite_ref-Cp*ZnMe_54-0" class="reference"><a href="#cite_note-Cp*ZnMe-54"><span class="cite-bracket">&#91;</span>54<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-55" class="reference"><a href="#cite_note-55"><span class="cite-bracket">&#91;</span>55<span class="cite-bracket">&#93;</span></a></sup> </p> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r70089473/mw-parser-output/.tmulti"><div class="thumb tmulti tnone center"><div class="thumbinner" 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"><span typeof="mw:File"><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></span></div></div><div class="tsingle" style="width:204px;max-width:204px"><div class="thumbimage" style="height:161px;overflow:hidden"><span typeof="mw:File"><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></span></div></div></div><div class="trow" style="display:flex"><div class="thumbcaption">左图:<span class="chemf nowrap">C<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left"><br />6</span>(CH<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left"><br />3</span>)<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left">2+<br />6</span></span>的结构,由<span class="ilh-all" data-orig-title="斯蒂芬·巴哈拉赫" data-lang-code="en" data-lang-name="英语" data-foreign-title="Steven Bachrach"><span class="ilh-page"><a href="/w/index.php?title=%E6%96%AF%E8%92%82%E8%8A%AC%C2%B7%E5%B7%B4%E5%93%88%E6%8B%89%E8%B5%AB&amp;action=edit&amp;redlink=1" class="new" title="斯蒂芬·巴哈拉赫(页面不存在)">斯蒂芬·巴哈拉赫</a></span><span class="noprint ilh-comment"><span class="ilh-paren">(</span><span class="ilh-lang">英语</span><span class="ilh-colon">:</span><span class="ilh-link"><a href="https://en.wikipedia.org/wiki/Steven_Bachrach" class="extiw" title="en:Steven Bachrach"><span lang="en" dir="auto">Steven Bachrach</span></a></span><span class="ilh-paren">)</span></span></span>绘制<sup id="cite_ref-Bachrach_25-2" class="reference"><a href="#cite_note-Bachrach-25"><span class="cite-bracket">&#91;</span>25<span class="cite-bracket">&#93;</span></a></sup><br />右图:相关的有机金属化合物 [(η<span class="chemf nowrap"><span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:0.8em;font-size:85%;text-align:left">5<br /></span>–C<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left"><br />5</span>(CH<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left"><br />3</span>)<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left"><br />5</span>)Zn(CH<span style="line-height:1.2em;text-indent:0em;display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;font-size:70%;text-align:left"><br />3</span></span>)]<sup id="cite_ref-Cp*ZnMe_54-1" class="reference"><a href="#cite_note-Cp*ZnMe-54"><span class="cite-bracket">&#91;</span>54<span class="cite-bracket">&#93;</span></a></sup></div></div></div></div> <p>對其評論指出“虽然我们被教导碳只能有四个朋友,但碳其實可以與四个以上的原子相關聯,这一点非常重要”,評論並補充指“從我們一般認為碳-碳键是雙電子鍵的想法出發,碳原子並不會形成六個鍵。”<sup id="cite_ref-PyramidalSciNews_24-3" class="reference"><a href="#cite_note-PyramidalSciNews-24"><span class="cite-bracket">&#91;</span>24<span class="cite-bracket">&#93;</span></a></sup>“這一切都是關於讓化學家為無奇不有而感到驚訝的挑戰和可能性。”<sup id="cite_ref-PyramidalNewSci_22-3" class="reference"><a href="#cite_note-PyramidalNewSci-22"><span class="cite-bracket">&#91;</span>22<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="参考资料"><span id=".E5.8F.82.E8.80.83.E8.B5.84.E6.96.99"></span>参考资料</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E5%85%AD%E7%94%B2%E8%8B%AF&amp;action=edit&amp;section=7" title="编辑章节:参考资料"><span>编辑</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="reflist columns references-column-width" style="-moz-column-width: 30em; -webkit-column-width: 30em; column-width: 30em; list-style-type: decimal;"> <ol class="references"> <li id="cite_note-Lonsdale-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-Lonsdale_1-0"><sup><b>1.0</b></sup></a> <a href="#cite_ref-Lonsdale_1-1"><sup><b>1.1</b></sup></a></span> <span class="reference-text"><cite class="citation journal"><a href="/w/index.php?title=Kathleen_Lonsdale&amp;action=edit&amp;redlink=1" class="new" title="Kathleen Lonsdale(页面不存在)">Lonsdale, Kathleen</a>. The Structure of the Benzene Ring in Hexamethylbenzene. <a href="/wiki/Proc._R._Soc._A" class="mw-redirect" title="Proc. R. Soc. A">Proc. R. Soc. A</a>. 1929, <b>123</b> (792): 494–515. <span class="plainlinks"><a rel="nofollow" class="external text" href="https://doi.org/10.1098%2Frspa.1929.0081"><span title="數位物件識別號">doi:10.1098/rspa.1929.0081</span></a>&#8239;<span typeof="mw:File"><span title="可免费查阅"><img alt="可免费查阅" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Lock-green.svg/9px-Lock-green.svg.png" decoding="async" width="9" height="14" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Lock-green.svg/14px-Lock-green.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/65/Lock-green.svg/18px-Lock-green.svg.png 2x" data-file-width="512" data-file-height="813" /></span></span></span>.</cite><span title="ctx_ver=Z39.88-2004&amp;rfr_id=info%3Asid%2Fzh.wikipedia.org%3A%E5%85%AD%E7%94%B2%E8%8B%AF&amp;rft.atitle=The+Structure+of+the+Benzene+Ring+in+Hexamethylbenzene&amp;rft.aufirst=Kathleen&amp;rft.aulast=Lonsdale&amp;rft.date=1929&amp;rft.genre=article&amp;rft.issue=792&amp;rft.jtitle=Proc.+R.+Soc.+A&amp;rft.pages=494-515&amp;rft.volume=123&amp;rft_id=info%3Adoi%2F10.1098%2Frspa.1929.0081&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal" class="Z3988"><span style="display:none;">&#160;</span></span></span> </li> <li id="cite_note-Lydon1-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-Lydon1_2-0"><sup><b>2.0</b></sup></a> <a href="#cite_ref-Lydon1_2-1"><sup><b>2.1</b></sup></a></span> <span class="reference-text"><cite class="citation journal">Lydon, John. <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> <span style="font-size:85%;">(PDF)</span>. Newsletter of the History of Physcis Group. January 2006, (19): 8–11 <span class="reference-accessdate"> &#91;<span class="nowrap">2021-08-29</span>&#93;</span>. (原始内容<a rel="nofollow" class="external text" href="https://web.archive.org/web/20170109184854/https://www.iop.org/activity/groups/subject/hp/newsletter/archive/file_66399.pdf">存档</a> <span style="font-size:85%;">(PDF)</span>于2017-01-09).</cite><span title="ctx_ver=Z39.88-2004&amp;rfr_id=info%3Asid%2Fzh.wikipedia.org%3A%E5%85%AD%E7%94%B2%E8%8B%AF&amp;rft.atitle=A+Welcome+to+Leeds&amp;rft.aufirst=John&amp;rft.aulast=Lydon&amp;rft.date=2006-01&amp;rft.genre=article&amp;rft.issue=19&amp;rft.jtitle=Newsletter+of+the+History+of+Physcis+Group&amp;rft.pages=8-11&amp;rft_id=https%3A%2F%2Fwww.iop.org%2Factivity%2Fgroups%2Fsubject%2Fhp%2Fnewsletter%2Farchive%2Ffile_66399.pdf&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal" class="Z3988"><span style="display:none;">&#160;</span></span></span> </li> <li id="cite_note-Lydon2-3"><span class="mw-cite-backlink">^ <a href="#cite_ref-Lydon2_3-0"><sup><b>3.0</b></sup></a> <a href="#cite_ref-Lydon2_3-1"><sup><b>3.1</b></sup></a> <a href="#cite_ref-Lydon2_3-2"><sup><b>3.2</b></sup></a></span> <span class="reference-text"><cite class="citation journal">Lydon, John. <a rel="nofollow" class="external text" href="https://www.iop.org/activity/groups/subject/hp/newsletter/archive/file_66191.pdf">Letters</a> <span style="font-size:85%;">(PDF)</span>. Newsletter of the History of Physcis Group. July 2006, (20): 34–35 <span class="reference-accessdate"> &#91;<span class="nowrap">2021-08-29</span>&#93;</span>. (原始内容<a rel="nofollow" class="external text" href="https://web.archive.org/web/20150906094434/http://www.iop.org/activity/groups/subject/hp/newsletter/archive/file_66191.pdf">存档</a> <span style="font-size:85%;">(PDF)</span>于2015-09-06).</cite><span title="ctx_ver=Z39.88-2004&amp;rfr_id=info%3Asid%2Fzh.wikipedia.org%3A%E5%85%AD%E7%94%B2%E8%8B%AF&amp;rft.atitle=Letters&amp;rft.aufirst=John&amp;rft.aulast=Lydon&amp;rft.date=2006-07&amp;rft.genre=article&amp;rft.issue=20&amp;rft.jtitle=Newsletter+of+the+History+of+Physcis+Group&amp;rft.pages=34-35&amp;rft_id=https%3A%2F%2Fwww.iop.org%2Factivity%2Fgroups%2Fsubject%2Fhp%2Fnewsletter%2Farchive%2Ffile_66191.pdf&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal" class="Z3988"><span style="display:none;">&#160;</span></span></span> </li> <li id="cite_note-HMBSynth-4"><span class="mw-cite-backlink">^ <a href="#cite_ref-HMBSynth_4-0"><sup><b>4.0</b></sup></a> <a href="#cite_ref-HMBSynth_4-1"><sup><b>4.1</b></sup></a></span> <span class="reference-text"><cite class="citation journal">Briner, E.; Plüss, W.; Paillard, H. Recherches sur la déshydration catalytique des systèmes phénols-alcools &#91;Research on the catalytic dehydration of phenol-alcohol systems&#93;. <a href="/wiki/Helv._Chim._Acta" class="mw-redirect" title="Helv. Chim. Acta">Helv. Chim. Acta</a>. 1924, <b>7</b> (1): 1046–1056. <a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fhlca.192400701132"><span title="數位物件識別號">doi:10.1002/hlca.192400701132</span></a> <span style="font-family: sans-serif; cursor: default; color:var(--color-subtle, #54595d); font-size: 0.8em; bottom: 0.1em; font-weight: bold;" title="连接到法语网页">(法语)</span>.</cite><span title="ctx_ver=Z39.88-2004&amp;rfr_id=info%3Asid%2Fzh.wikipedia.org%3A%E5%85%AD%E7%94%B2%E8%8B%AF&amp;rft.atitle=Recherches+sur+la+d%C3%A9shydration+catalytique+des+syst%C3%A8mes+ph%C3%A9nols-alcools&amp;rft.au=Paillard%2C+H.&amp;rft.au=Pl%C3%BCss%2C+W.&amp;rft.aufirst=E.&amp;rft.aulast=Briner&amp;rft.date=1924&amp;rft.genre=article&amp;rft.issue=1&amp;rft.jtitle=Helv.+Chim.+Acta&amp;rft.pages=1046-1056&amp;rft.volume=7&amp;rft_id=info%3Adoi%2F10.1002%2Fhlca.192400701132&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal" class="Z3988"><span style="display:none;">&#160;</span></span></span> </li> <li id="cite_note-HMBOrgSynth-5"><span class="mw-cite-backlink">^ <a href="#cite_ref-HMBOrgSynth_5-0"><sup><b>5.0</b></sup></a> <a href="#cite_ref-HMBOrgSynth_5-1"><sup><b>5.1</b></sup></a> <a href="#cite_ref-HMBOrgSynth_5-2"><sup><b>5.2</b></sup></a></span> <span class="reference-text"><cite style="font-style:normal">&#32;(1955)&#32;"<a rel="nofollow" class="external text" href="http://www.orgsyn.org/demo.aspx?prep=cv4p0520">Hexamethylbenzene</a>". <i><a href="/wiki/%E6%9C%89%E6%9C%BA%E5%90%88%E6%88%90_(%E6%9C%9F%E5%88%8A)" title="有机合成 (期刊)">Org. Synth.</a></i>&#32;<b>35</b>: 73;&#32;<i>Coll. Vol.</i> <b>4</b>:&#32;520.</cite><span class="Z3988" title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.atitle=Hexamethylbenzene &amp;rft.date=1955&amp;rft.volume=35&amp;rft.pages=73&amp;rft_id=info:doi/10.15227%2Forgsyn.035.0073">&#160;</span></span> </li> <li id="cite_note-PMB-6"><span class="mw-cite-backlink">^ <a href="#cite_ref-PMB_6-0"><sup><b>6.0</b></sup></a> <a href="#cite_ref-PMB_6-1"><sup><b>6.1</b></sup></a> <a href="#cite_ref-PMB_6-2"><sup><b>6.2</b></sup></a> <a href="#cite_ref-PMB_6-3"><sup><b>6.3</b></sup></a></span> <span class="reference-text"><cite class="citation journal">Landis, Phillip S.; Haag, Werner O. Formation of Hexamethylbenzene from Phenol and Methanol. <a href="/wiki/J._Org._Chem." class="mw-redirect" title="J. Org. Chem.">J. Org. Chem.</a> 1963, <b>28</b> (2): 585. <a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fjo01037a517"><span title="數位物件識別號">doi:10.1021/jo01037a517</span></a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rfr_id=info%3Asid%2Fzh.wikipedia.org%3A%E5%85%AD%E7%94%B2%E8%8B%AF&amp;rft.atitle=Formation+of+Hexamethylbenzene+from+Phenol+and+Methanol&amp;rft.au=Haag%2C+Werner+O.&amp;rft.aufirst=Phillip+S.&amp;rft.aulast=Landis&amp;rft.date=1963&amp;rft.genre=article&amp;rft.issue=2&amp;rft.jtitle=J.+Org.+Chem.&amp;rft.pages=585&amp;rft.volume=28&amp;rft_id=info%3Adoi%2F10.1021%2Fjo01037a517&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal" class="Z3988"><span style="display:none;">&#160;</span></span></span> </li> <li id="cite_note-Koptyug1-7"><span class="mw-cite-backlink">^ <a href="#cite_ref-Koptyug1_7-0"><sup><b>7.0</b></sup></a> <a href="#cite_ref-Koptyug1_7-1"><sup><b>7.1</b></sup></a> <a href="#cite_ref-Koptyug1_7-2"><sup><b>7.2</b></sup></a></span> <span class="reference-text"><cite class="citation journal">Krysin, A. P.; <a href="/w/index.php?title=Valentin_Koptyug&amp;action=edit&amp;redlink=1" class="new" title="Valentin Koptyug(页面不存在)">Koptyug, V. A.</a> 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.&amp;action=edit&amp;redlink=1" class="new" title="Russ. Chem. Bull.(页面不存在)">Russ. Chem. Bull.</a> 1969, <b>18</b> (7): 1479–1482. <a rel="nofollow" class="external text" href="https://doi.org/10.1007%2FBF00908756"><span title="數位物件識別號">doi:10.1007/BF00908756</span></a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rfr_id=info%3Asid%2Fzh.wikipedia.org%3A%E5%85%AD%E7%94%B2%E8%8B%AF&amp;rft.atitle=Reaction+of+phenols+with+alcohols+on+aluminum+oxide+II.+The+mechanism+of+hexamethylbenzene+formation+from+phenol+and+methyl+alcohol&amp;rft.au=Koptyug%2C+V.+A.&amp;rft.aufirst=A.+P.&amp;rft.aulast=Krysin&amp;rft.date=1969&amp;rft.genre=article&amp;rft.issue=7&amp;rft.jtitle=Russ.+Chem.+Bull.&amp;rft.pages=1479-1482&amp;rft.volume=18&amp;rft_id=info%3Adoi%2F10.1007%2FBF00908756&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal" class="Z3988"><span style="display:none;">&#160;</span></span></span> </li> <li id="cite_note-Ipatiew-8"><span class="mw-cite-backlink">^ <a href="#cite_ref-Ipatiew_8-0"><sup><b>8.0</b></sup></a> <a href="#cite_ref-Ipatiew_8-1"><sup><b>8.1</b></sup></a></span> <span class="reference-text"><cite class="citation journal">Ipatiew, W.; Petrow, A. D. Über die katalytische Kondensation von Aceton bei hohen Temperaturen und Drucken. (I. Mitteilung) &#91;On the catalytic condensation of acetone at high temperatures and pressures. (I. Communication)&#93;. <a href="/w/index.php?title=Ber._Dtsch._Chem._Ges._A/B&amp;action=edit&amp;redlink=1" class="new" title="Ber. Dtsch. Chem. Ges. A/B(页面不存在)">Ber. Dtsch. Chem. Ges. A/B</a>. 1926, <b>59</b> (8): 2035–2038. <a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fcber.19260590859"><span title="數位物件識別號">doi:10.1002/cber.19260590859</span></a> <span style="font-family: sans-serif; cursor: default; color:var(--color-subtle, #54595d); font-size: 0.8em; bottom: 0.1em; font-weight: bold;" title="连接到德语网页">(德语)</span>.</cite><span title="ctx_ver=Z39.88-2004&amp;rfr_id=info%3Asid%2Fzh.wikipedia.org%3A%E5%85%AD%E7%94%B2%E8%8B%AF&amp;rft.atitle=%C3%9Cber+die+katalytische+Kondensation+von+Aceton+bei+hohen+Temperaturen+und+Drucken.+%28I.+Mitteilung%29&amp;rft.au=Petrow%2C+A.+D.&amp;rft.aufirst=W.&amp;rft.aulast=Ipatiew&amp;rft.date=1926&amp;rft.genre=article&amp;rft.issue=8&amp;rft.jtitle=Ber.+Dtsch.+Chem.+Ges.+A%2FB&amp;rft.pages=2035-2038&amp;rft.volume=59&amp;rft_id=info%3Adoi%2F10.1002%2Fcber.19260590859&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal" class="Z3988"><span style="display:none;">&#160;</span></span></span> </li> <li id="cite_note-Takeshi1-9"><span class="mw-cite-backlink">^ <a href="#cite_ref-Takeshi1_9-0"><sup><b>9.0</b></sup></a> <a href="#cite_ref-Takeshi1_9-1"><sup><b>9.1</b></sup></a></span> <span class="reference-text"><cite class="citation journal">Kotanigawa, Takeshi; Yamamoto, Mitsuyoshi; Shimokawa, Katsuyoshi; Yoshida, Yuji. <a rel="nofollow" class="external text" href="https://archive.org/details/sim_bulletin-of-the-chemical-society-of-japan_1971-07_44_7/page/1961">Methylation of Phenol over Metallic Oxides</a>. Bulletin of the Chemical Society of Japan. 1971, <b>44</b> (7): 1961–1964. <span class="plainlinks"><a rel="nofollow" class="external text" href="https://doi.org/10.1246%2Fbcsj.44.1961"><span title="數位物件識別號">doi:10.1246/bcsj.44.1961</span></a>&#8239;<span typeof="mw:File"><span title="可免费查阅"><img alt="可免费查阅" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Lock-green.svg/9px-Lock-green.svg.png" decoding="async" width="9" height="14" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Lock-green.svg/14px-Lock-green.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/65/Lock-green.svg/18px-Lock-green.svg.png 2x" data-file-width="512" data-file-height="813" /></span></span></span>.</cite><span title="ctx_ver=Z39.88-2004&amp;rfr_id=info%3Asid%2Fzh.wikipedia.org%3A%E5%85%AD%E7%94%B2%E8%8B%AF&amp;rft.atitle=Methylation+of+Phenol+over+Metallic+Oxides&amp;rft.au=Shimokawa%2C+Katsuyoshi&amp;rft.au=Yamamoto%2C+Mitsuyoshi&amp;rft.au=Yoshida%2C+Yuji&amp;rft.aufirst=Takeshi&amp;rft.aulast=Kotanigawa&amp;rft.date=1971&amp;rft.genre=article&amp;rft.issue=7&amp;rft.jtitle=Bulletin+of+the+Chemical+Society+of+Japan&amp;rft.pages=1961-1964&amp;rft.volume=44&amp;rft_id=https%3A%2F%2Farchive.org%2Fdetails%2Fsim_bulletin-of-the-chemical-society-of-japan_1971-07_44_7%2Fpage%2F1961&amp;rft_id=info%3Adoi%2F10.1246%2Fbcsj.44.1961&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal" class="Z3988"><span style="display:none;">&#160;</span></span></span> </li> <li id="cite_note-Takeshi2-10"><span class="mw-cite-backlink">^ <a href="#cite_ref-Takeshi2_10-0"><sup><b>10.0</b></sup></a> <a href="#cite_ref-Takeshi2_10-1"><sup><b>10.1</b></sup></a></span> <span class="reference-text"><cite class="citation journal">Kotanigawa, Takeshi. Mechanisms for the Reaction of Phenol with Methanol over the ZnO–Fe<sub>2</sub>O<sub>3</sub> Catalyst. <a href="/w/index.php?title=Bull._Chem._Soc._Jpn.&amp;action=edit&amp;redlink=1" class="new" title="Bull. Chem. Soc. Jpn.(页面不存在)">Bull. Chem. Soc. 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R.; Brintzinger, H. H. <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="/w/index.php?title=J._Organomet._Chem.&amp;action=edit&amp;redlink=1" class="new" title="J. Organomet. Chem.(页面不存在)">J. Organomet. Chem.</a> 1977, <b>127</b> (1): 45–54. <a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0022-328X%2800%2984196-0"><span title="數位物件識別號">doi:10.1016/S0022-328X(00)84196-0</span></a>. <span class="plainlinks"><a rel="nofollow" class="external text" href="//hdl.handle.net/2027.42%2F22975"><span title="Handle System">hdl:2027.42/22975</span></a>&#8239;<span typeof="mw:File"><span title="可免费查阅"><img alt="可免费查阅" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Lock-green.svg/9px-Lock-green.svg.png" decoding="async" width="9" height="14" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Lock-green.svg/14px-Lock-green.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/65/Lock-green.svg/18px-Lock-green.svg.png 2x" data-file-width="512" data-file-height="813" /></span></span></span>.</cite><span title="ctx_ver=Z39.88-2004&amp;rfr_id=info%3Asid%2Fzh.wikipedia.org%3A%E5%85%AD%E7%94%B2%E8%8B%AF&amp;rft.atitle=Reactions+of+Bis%28hexamethylbenzene%29iron%280%29+with+Carbon+Monoxide+and+with+Unsaturated+Hydrocarbons&amp;rft.au=Brintzinger%2C+H.+H.&amp;rft.aufirst=S.+R.&amp;rft.aulast=Weber&amp;rft.date=1977&amp;rft.genre=article&amp;rft.issue=1&amp;rft.jtitle=J.+Organomet.+Chem.&amp;rft.pages=45-54&amp;rft.volume=127&amp;rft_id=http%3A%2F%2Fnbn-resolving.de%2Furn%3Anbn%3Ade%3Absz%3A352-238659&amp;rft_id=info%3Adoi%2F10.1016%2FS0022-328X%2800%2984196-0&amp;rft_id=info%3Ahdl%2F2027.42%2F22975&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal" class="Z3988"><span style="display:none;">&#160;</span></span></span> </li> <li id="cite_note-HMBoxidation-16"><span class="mw-cite-backlink">^ <a href="#cite_ref-HMBoxidation_16-0"><sup><b>16.0</b></sup></a> <a href="#cite_ref-HMBoxidation_16-1"><sup><b>16.1</b></sup></a></span> <span class="reference-text"><cite class="citation journal">Wibaut, J. P.; Overhoff, J.; Jonker, E. W.; Gratama, K. On the preparation of mellitic acid from hexa-methylbenzene and on the hexachloride of mellitic acid. <a href="/w/index.php?title=Recl._Trav._Chim._Pays-Bas&amp;action=edit&amp;redlink=1" class="new" title="Recl. Trav. Chim. Pays-Bas(页面不存在)">Recl. Trav. Chim. 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Minerals – Their Constitution and Origin 2nd. <a href="/wiki/Cambridge_University_Press" class="mw-redirect" title="Cambridge University Press">Cambridge University Press</a>. 2016 <span class="reference-accessdate"> &#91;<span class="nowrap">2021-08-29</span>&#93;</span>. <a href="/wiki/Special:%E7%BD%91%E7%BB%9C%E4%B9%A6%E6%BA%90/9781316423684" title="Special:网络书源/9781316423684"><span title="国际标准书号">ISBN</span>&#160;9781316423684</a>. (<a rel="nofollow" class="external text" href="https://books.google.com/books?id=TMaSDQAAQBAJ&amp;pg=PT1361&amp;dq=mellite">原始内容</a>存档于2022-03-14).</cite><span title="ctx_ver=Z39.88-2004&amp;rfr_id=info%3Asid%2Fzh.wikipedia.org%3A%E5%85%AD%E7%94%B2%E8%8B%AF&amp;rft.atitle=Organic+Minerals&amp;rft.au=Bulakh%2C+Andrey&amp;rft.aufirst=Hans-Rudolf&amp;rft.aulast=Wenk&amp;rft.btitle=Minerals+%E2%80%93+Their+Constitution+and+Origin&amp;rft.date=2016&amp;rft.edition=2nd&amp;rft.genre=bookitem&amp;rft.isbn=9781316423684&amp;rft.pub=Cambridge+University+Press&amp;rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DTMaSDQAAQBAJ%26pg%3DPT1361%26dq%3Dmellite&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook" class="Z3988"><span style="display:none;">&#160;</span></span></span> </li> <li id="cite_note-AreneReview-18"><span class="mw-cite-backlink">^ <a href="#cite_ref-AreneReview_18-0"><sup><b>18.0</b></sup></a> <a href="#cite_ref-AreneReview_18-1"><sup><b>18.1</b></sup></a></span> <span class="reference-text"><cite class="citation journal">Pampaloni, Guido. Aromatic hydrocarbons as ligands. Recent advances in the synthesis, the reactivity and the applications of bis(<i>η</i><sup>6</sup>-arene) complexes. <a href="/w/index.php?title=Coord._Chem._Rev.&amp;action=edit&amp;redlink=1" class="new" title="Coord. Chem. Rev.(页面不存在)">Coord. Chem. Rev.</a> 2010, <b>254</b> (5–6): 402–419. <a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.ccr.2009.05.014"><span title="數位物件識別號">doi:10.1016/j.ccr.2009.05.014</span></a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rfr_id=info%3Asid%2Fzh.wikipedia.org%3A%E5%85%AD%E7%94%B2%E8%8B%AF&amp;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&amp;rft.aufirst=Guido&amp;rft.aulast=Pampaloni&amp;rft.date=2010&amp;rft.genre=article&amp;rft.issue=5%E2%80%936&amp;rft.jtitle=Coord.+Chem.+Rev.&amp;rft.pages=402-419&amp;rft.volume=254&amp;rft_id=info%3Adoi%2F10.1016%2Fj.ccr.2009.05.014&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal" class="Z3988"><span style="display:none;">&#160;</span></span></span> </li> <li id="cite_note-Fe-19"><span class="mw-cite-backlink">^ <a href="#cite_ref-Fe_19-0"><sup><b>19.0</b></sup></a> <a href="#cite_ref-Fe_19-1"><sup><b>19.1</b></sup></a> <a href="#cite_ref-Fe_19-2"><sup><b>19.2</b></sup></a> <a href="#cite_ref-Fe_19-3"><sup><b>19.3</b></sup></a> <a href="#cite_ref-Fe_19-4"><sup><b>19.4</b></sup></a></span> <span class="reference-text"><cite class="citation book">Kotz, John C. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20210829045745/https://books.google.com/books?id=zgUHCAAAQBAJ&amp;pg=PA110&amp;dq=hexamethylbenzene">The Electrochemistry of Transition Metal Organometallic Compounds</a>. Fry, Albert J.; Britton, Wayne E. (编). Topics in Organic Electrochemistry. <a href="/wiki/Springer_Science_%26_Business_Media" class="mw-redirect" title="Springer Science &amp; Business Media">Springer Science &amp; Business Media</a>. 1986: 83–176 <span class="reference-accessdate"> &#91;<span class="nowrap">2021-08-29</span>&#93;</span>. <a href="/wiki/Special:%E7%BD%91%E7%BB%9C%E4%B9%A6%E6%BA%90/9781489920348" title="Special:网络书源/9781489920348"><span title="国际标准书号">ISBN</span>&#160;9781489920348</a>. (<a rel="nofollow" class="external text" href="https://books.google.com/books?id=zgUHCAAAQBAJ&amp;pg=PA110&amp;dq=hexamethylbenzene">原始内容</a>存档于2021-08-29).</cite><span title="ctx_ver=Z39.88-2004&amp;rfr_id=info%3Asid%2Fzh.wikipedia.org%3A%E5%85%AD%E7%94%B2%E8%8B%AF&amp;rft.atitle=The+Electrochemistry+of+Transition+Metal+Organometallic+Compounds&amp;rft.aufirst=John+C.&amp;rft.aulast=Kotz&amp;rft.btitle=Topics+in+Organic+Electrochemistry&amp;rft.date=1986&amp;rft.genre=bookitem&amp;rft.isbn=9781489920348&amp;rft.pages=83-176&amp;rft.pub=Springer+Science+%26+Business+Media&amp;rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DzgUHCAAAQBAJ%26pg%3DPA110%26dq%3Dhexamethylbenzene&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook" class="Z3988"><span style="display:none;">&#160;</span></span></span> </li> <li id="cite_note-RuHMB2-20"><span class="mw-cite-backlink">^ <a href="#cite_ref-RuHMB2_20-0"><sup><b>20.0</b></sup></a> <a href="#cite_ref-RuHMB2_20-1"><sup><b>20.1</b></sup></a> <a href="#cite_ref-RuHMB2_20-2"><sup><b>20.2</b></sup></a> <a href="#cite_ref-RuHMB2_20-3"><sup><b>20.3</b></sup></a> <a href="#cite_ref-RuHMB2_20-4"><sup><b>20.4</b></sup></a></span> <span class="reference-text"><cite class="citation journal">Huttner, Gottfried; Lange, Siegfried; <a href="/wiki/Ernst_Otto_Fischer" class="mw-redirect" title="Ernst Otto Fischer">Fischer, Ernst O.</a> 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> 1971, <b>10</b> (8): 556–557. <a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fanie.197105561"><span title="數位物件識別號">doi:10.1002/anie.197105561</span></a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rfr_id=info%3Asid%2Fzh.wikipedia.org%3A%E5%85%AD%E7%94%B2%E8%8B%AF&amp;rft.atitle=Molecular+Structure+of+Bis%28Hexamethylbenzene%29Ruthenium%280%29&amp;rft.au=Fischer%2C+Ernst+O.&amp;rft.au=Lange%2C+Siegfried&amp;rft.aufirst=Gottfried&amp;rft.aulast=Huttner&amp;rft.date=1971&amp;rft.genre=article&amp;rft.issue=8&amp;rft.jtitle=Angew.+Chem.+Int.+Ed.+Engl.&amp;rft.pages=556-557&amp;rft.volume=10&amp;rft_id=info%3Adoi%2F10.1002%2Fanie.197105561&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal" class="Z3988"><span style="display:none;">&#160;</span></span></span> </li> <li id="cite_note-PyramidalAngewChem-21"><span class="mw-cite-backlink">^ <a href="#cite_ref-PyramidalAngewChem_21-0"><sup><b>21.0</b></sup></a> <a href="#cite_ref-PyramidalAngewChem_21-1"><sup><b>21.1</b></sup></a> <a href="#cite_ref-PyramidalAngewChem_21-2"><sup><b>21.2</b></sup></a> <a href="#cite_ref-PyramidalAngewChem_21-3"><sup><b>21.3</b></sup></a> <a href="#cite_ref-PyramidalAngewChem_21-4"><sup><b>21.4</b></sup></a> <a href="#cite_ref-PyramidalAngewChem_21-5"><sup><b>21.5</b></sup></a> <a href="#cite_ref-PyramidalAngewChem_21-6"><sup><b>21.6</b></sup></a> <a href="#cite_ref-PyramidalAngewChem_21-7"><sup><b>21.7</b></sup></a></span> <span class="reference-text"><cite class="citation journal">Malischewski, Moritz; <a href="/w/index.php?title=Konrad_Seppelt&amp;action=edit&amp;redlink=1" class="new" title="Konrad Seppelt(页面不存在)">Seppelt, Konrad</a>. Crystal Structure Determination of the Pentagonal-Pyramidal Hexamethylbenzene Dication C<sub>6</sub>(CH<sub>3</sub>)<sub>6</sub><sup>2+</sup>. <a href="/wiki/Angew._Chem._Int._Ed." class="mw-redirect" title="Angew. Chem. Int. Ed.">Angew. Chem. Int. Ed.</a> 2017, <b>56</b> (1): 368–370. <a rel="nofollow" class="external text" href="//www.ncbi.nlm.nih.gov/pubmed/27885766"><span title="公共医学识别码">PMID&#160;27885766</span></a>. <a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fanie.201608795"><span title="數位物件識別號">doi:10.1002/anie.201608795</span></a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rfr_id=info%3Asid%2Fzh.wikipedia.org%3A%E5%85%AD%E7%94%B2%E8%8B%AF&amp;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&amp;rft.au=Seppelt%2C+Konrad&amp;rft.aufirst=Moritz&amp;rft.aulast=Malischewski&amp;rft.date=2017&amp;rft.genre=article&amp;rft.issue=1&amp;rft.jtitle=Angew.+Chem.+Int.+Ed.&amp;rft.pages=368-370&amp;rft.volume=56&amp;rft_id=info%3Adoi%2F10.1002%2Fanie.201608795&amp;rft_id=info%3Apmid%2F27885766&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal" class="Z3988"><span style="display:none;">&#160;</span></span></span> </li> <li id="cite_note-PyramidalNewSci-22"><span class="mw-cite-backlink">^ <a href="#cite_ref-PyramidalNewSci_22-0"><sup><b>22.0</b></sup></a> <a href="#cite_ref-PyramidalNewSci_22-1"><sup><b>22.1</b></sup></a> <a href="#cite_ref-PyramidalNewSci_22-2"><sup><b>22.2</b></sup></a> <a href="#cite_ref-PyramidalNewSci_22-3"><sup><b>22.3</b></sup></a></span> <span class="reference-text"><cite class="citation journal">Boyle, Rebecca. <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" class="mw-redirect" title="New Scientist">New Scientist</a>. 14 January 2017, (3108) <span class="reference-accessdate"> &#91;<span class="nowrap">14 January</span> 2017&#93;</span>. (原始内容<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/">存档</a>于2017-01-16).</cite><span title="ctx_ver=Z39.88-2004&amp;rfr_id=info%3Asid%2Fzh.wikipedia.org%3A%E5%85%AD%E7%94%B2%E8%8B%AF&amp;rft.atitle=Carbon+seen+bonding+with+six+other+atoms+for+the+first+time&amp;rft.aufirst=Rebecca&amp;rft.aulast=Boyle&amp;rft.date=2017-01-14&amp;rft.genre=article&amp;rft.issue=3108&amp;rft.jtitle=New+Scientist&amp;rft_id=https%3A%2F%2Fwww.newscientist.com%2Farticle%2Fmg23331084-900-carbon-seen-bonding-with-six-other-atoms-for-the-first-time%2F&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal" class="Z3988"><span style="display:none;">&#160;</span></span></span> </li> <li id="cite_note-PyramidalC&amp;ENews-23"><span class="mw-cite-backlink">^ <a href="#cite_ref-PyramidalC&amp;ENews_23-0"><sup><b>23.0</b></sup></a> <a href="#cite_ref-PyramidalC&amp;ENews_23-1"><sup><b>23.1</b></sup></a> <a href="#cite_ref-PyramidalC&amp;ENews_23-2"><sup><b>23.2</b></sup></a> <a href="#cite_ref-PyramidalC&amp;ENews_23-3"><sup><b>23.3</b></sup></a></span> <span class="reference-text"><cite class="citation journal">Ritter, Stephen K. <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>. 19 December 2016, <b>94</b> (49): 13 <span class="reference-accessdate"> &#91;<span class="nowrap">2021-08-29</span>&#93;</span>. <a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fcen-09449-scicon007"><span title="數位物件識別號">doi:10.1021/cen-09449-scicon007</span></a>. (原始内容<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">存档</a>于2017-01-09).</cite><span title="ctx_ver=Z39.88-2004&amp;rfr_id=info%3Asid%2Fzh.wikipedia.org%3A%E5%85%AD%E7%94%B2%E8%8B%AF&amp;rft.atitle=Six+bonds+to+carbon%3A+Confirmed&amp;rft.aufirst=Stephen+K.&amp;rft.aulast=Ritter&amp;rft.date=2016-12-19&amp;rft.genre=article&amp;rft.issue=49&amp;rft.jtitle=Chem.+Eng.+News&amp;rft.pages=13&amp;rft.volume=94&amp;rft_id=http%3A%2F%2Fcen.acs.org%2Farticles%2F94%2Fi49%2FSix-bonds-carbon-Confirmed.html&amp;rft_id=info%3Adoi%2F10.1021%2Fcen-09449-scicon007&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal" class="Z3988"><span style="display:none;">&#160;</span></span></span> </li> <li id="cite_note-PyramidalSciNews-24"><span class="mw-cite-backlink">^ <a href="#cite_ref-PyramidalSciNews_24-0"><sup><b>24.0</b></sup></a> <a href="#cite_ref-PyramidalSciNews_24-1"><sup><b>24.1</b></sup></a> <a href="#cite_ref-PyramidalSciNews_24-2"><sup><b>24.2</b></sup></a> <a href="#cite_ref-PyramidalSciNews_24-3"><sup><b>24.3</b></sup></a></span> <span class="reference-text"><cite class="citation journal">Hamers, Laurel. <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="/w/index.php?title=Science_News&amp;action=edit&amp;redlink=1" class="new" title="Science News(页面不存在)">Science News</a>. 24 December 2016, <b>190</b> (13): 17 <span class="reference-accessdate"> &#91;<span class="nowrap">2021-08-29</span>&#93;</span>. (原始内容<a rel="nofollow" class="external text" href="https://web.archive.org/web/20170203045239/https://www.sciencenews.org/article/carbon-can-exceed-four-bond-limit">存档</a>于2017-02-03).</cite><span title="ctx_ver=Z39.88-2004&amp;rfr_id=info%3Asid%2Fzh.wikipedia.org%3A%E5%85%AD%E7%94%B2%E8%8B%AF&amp;rft.atitle=Carbon+can+exceed+four-bond+limit&amp;rft.aufirst=Laurel&amp;rft.aulast=Hamers&amp;rft.date=2016-12-24&amp;rft.genre=article&amp;rft.issue=13&amp;rft.jtitle=Science+News&amp;rft.pages=17&amp;rft.volume=190&amp;rft_id=https%3A%2F%2Fwww.sciencenews.org%2Farticle%2Fcarbon-can-exceed-four-bond-limit&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal" class="Z3988"><span style="display:none;">&#160;</span></span></span> </li> <li id="cite_note-Bachrach-25"><span class="mw-cite-backlink">^ <a href="#cite_ref-Bachrach_25-0"><sup><b>25.0</b></sup></a> <a href="#cite_ref-Bachrach_25-1"><sup><b>25.1</b></sup></a> <a href="#cite_ref-Bachrach_25-2"><sup><b>25.2</b></sup></a></span> <span class="reference-text"><cite class="citation web"><a href="/w/index.php?title=Steven_Bachrach&amp;action=edit&amp;redlink=1" class="new" title="Steven Bachrach(页面不存在)">Bachrach, Steven M.</a> <a rel="nofollow" class="external text" href="http://comporgchem.com/blog/?page_id=3929">A six-coordinate carbon atom</a>. comporgchem.com. 17 January 2017 <span class="reference-accessdate"> &#91;<span class="nowrap">18 January</span> 2017&#93;</span>. (原始内容<a rel="nofollow" class="external text" href="https://web.archive.org/web/20170119050221/http://comporgchem.com/blog/?p=3929">存档</a>于2017-01-19).</cite><span title="ctx_ver=Z39.88-2004&amp;rfr_id=info%3Asid%2Fzh.wikipedia.org%3A%E5%85%AD%E7%94%B2%E8%8B%AF&amp;rft.atitle=A+six-coordinate+carbon+atom&amp;rft.aufirst=Steven+M.&amp;rft.aulast=Bachrach&amp;rft.date=2017-01-17&amp;rft.genre=unknown&amp;rft.jtitle=comporgchem.com&amp;rft_id=http%3A%2F%2Fcomporgchem.com%2Fblog%2F%3Fpage_id%3D3929&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal" class="Z3988"><span style="display:none;">&#160;</span></span></span> </li> <li id="cite_note-HMBviaOMetChem-26"><span class="mw-cite-backlink">^ <a href="#cite_ref-HMBviaOMetChem_26-0"><sup><b>26.0</b></sup></a> <a href="#cite_ref-HMBviaOMetChem_26-1"><sup><b>26.1</b></sup></a> <a href="#cite_ref-HMBviaOMetChem_26-2"><sup><b>26.2</b></sup></a></span> <span class="reference-text"><cite class="citation journal">Hogeveen, Hepke; Kwant, Peter W. Pyramidal mono- and dications. Bridge between organic and organometallic chemistry. <a href="/w/index.php?title=Acc._Chem._Res.&amp;action=edit&amp;redlink=1" class="new" title="Acc. Chem. Res.(页面不存在)">Acc. Chem. Res.</a> 1975, <b>8</b> (12): 413–420. <a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Far50096a004"><span title="數位物件識別號">doi:10.1021/ar50096a004</span></a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rfr_id=info%3Asid%2Fzh.wikipedia.org%3A%E5%85%AD%E7%94%B2%E8%8B%AF&amp;rft.atitle=Pyramidal+mono-+and+dications.+Bridge+between+organic+and+organometallic+chemistry&amp;rft.au=Kwant%2C+Peter+W.&amp;rft.aufirst=Hepke&amp;rft.aulast=Hogeveen&amp;rft.date=1975&amp;rft.genre=article&amp;rft.issue=12&amp;rft.jtitle=Acc.+Chem.+Res.&amp;rft.pages=413-420&amp;rft.volume=8&amp;rft_id=info%3Adoi%2F10.1021%2Far50096a004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal" class="Z3988"><span style="display:none;">&#160;</span></span></span> </li> <li id="cite_note-HMBcatObs1-27"><span class="mw-cite-backlink">^ <a href="#cite_ref-HMBcatObs1_27-0"><sup><b>27.0</b></sup></a> <a href="#cite_ref-HMBcatObs1_27-1"><sup><b>27.1</b></sup></a></span> <span class="reference-text"><cite class="citation journal">Hogeveen, Hepke; Kwant, Peter W. Direct observation of a remarkably stable dication of unusual structure: (CCH<sub>3</sub>)<sub>6</sub><sup>2⊕</sup>. <a href="/wiki/Tetrahedron_Lett." class="mw-redirect" title="Tetrahedron Lett.">Tetrahedron Lett.</a> 1973, <b>14</b> (19): 1665–1670. <a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0040-4039%2801%2996023-X"><span title="數位物件識別號">doi:10.1016/S0040-4039(01)96023-X</span></a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rfr_id=info%3Asid%2Fzh.wikipedia.org%3A%E5%85%AD%E7%94%B2%E8%8B%AF&amp;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&amp;rft.au=Kwant%2C+Peter+W.&amp;rft.aufirst=Hepke&amp;rft.aulast=Hogeveen&amp;rft.date=1973&amp;rft.genre=article&amp;rft.issue=19&amp;rft.jtitle=Tetrahedron+Lett.&amp;rft.pages=1665-1670&amp;rft.volume=14&amp;rft_id=info%3Adoi%2F10.1016%2FS0040-4039%2801%2996023-X&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal" class="Z3988"><span style="display:none;">&#160;</span></span></span> </li> <li id="cite_note-HMBcatObs2-28"><span class="mw-cite-backlink">^ <a href="#cite_ref-HMBcatObs2_28-0"><sup><b>28.0</b></sup></a> <a href="#cite_ref-HMBcatObs2_28-1"><sup><b>28.1</b></sup></a></span> <span class="reference-text"><cite class="citation journal">Hogeveen, Hepke; Kwant, Peter W.; Postma, J.; van Duynen, P. Th. Electronic spectra of pyramidal dications, (CCH<sub>3</sub>)<sub>6</sub><sup>2+</sup> and (CCH)<sub>6</sub><sup>2+</sup>. <a href="/wiki/Tetrahedron_Lett." class="mw-redirect" title="Tetrahedron Lett.">Tetrahedron Lett.</a> 1974, <b>15</b> (49–50): 4351–4354. <a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0040-4039%2801%2992161-6"><span title="數位物件識別號">doi:10.1016/S0040-4039(01)92161-6</span></a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rfr_id=info%3Asid%2Fzh.wikipedia.org%3A%E5%85%AD%E7%94%B2%E8%8B%AF&amp;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&amp;rft.au=Kwant%2C+Peter+W.&amp;rft.au=Postma%2C+J.&amp;rft.au=van+Duynen%2C+P.+Th.&amp;rft.aufirst=Hepke&amp;rft.aulast=Hogeveen&amp;rft.date=1974&amp;rft.genre=article&amp;rft.issue=49%E2%80%9350&amp;rft.jtitle=Tetrahedron+Lett.&amp;rft.pages=4351-4354&amp;rft.volume=15&amp;rft_id=info%3Adoi%2F10.1016%2FS0040-4039%2801%2992161-6&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal" class="Z3988"><span style="display:none;">&#160;</span></span></span> </li> <li id="cite_note-HMBcatObs3-29"><span class="mw-cite-backlink">^ <a href="#cite_ref-HMBcatObs3_29-0"><sup><b>29.0</b></sup></a> <a href="#cite_ref-HMBcatObs3_29-1"><sup><b>29.1</b></sup></a></span> <span class="reference-text"><cite class="citation journal">Hogeveen, Hepke; Kwant, Peter W. 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Organometallics 3rd. <a href="/wiki/John_Wiley_%26_Sons" class="mw-redirect" title="John Wiley &amp; Sons">John Wiley &amp; Sons</a>. 2006: 59–85 <span class="reference-accessdate"> &#91;<span class="nowrap">2021-08-29</span>&#93;</span>. <a href="/wiki/Special:%E7%BD%91%E7%BB%9C%E4%B9%A6%E6%BA%90/9783527805143" title="Special:网络书源/9783527805143"><span title="国际标准书号">ISBN</span>&#160;9783527805143</a>. 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href="/wiki/%E5%A3%AC%E7%83%B7" title="壬烷">壬烷</a></li> <li><a href="/wiki/%E7%99%B8%E7%83%B7" title="癸烷">癸烷</a></li> <li><a href="/wiki/Template:%E7%83%B7%E7%83%83" title="Template:烷烃">其它</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;width:8">支链烷烃</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0px"><div style="padding:0em 0.25em"> <ul><li><a href="/wiki/%E5%BC%82%E4%B8%81%E7%83%B7" title="异丁烷">异丁烷</a></li> <li><a href="/wiki/%E5%BC%82%E6%88%8A%E7%83%B7" title="异戊烷">异戊烷</a></li> <li><a href="/wiki/3-%E7%94%B2%E5%9F%BA%E6%88%8A%E7%83%B7" title="3-甲基戊烷">3-甲基戊烷</a></li> <li><a href="/wiki/%E6%96%B0%E6%88%8A%E7%83%B7" title="新戊烷">新戊烷</a></li> <li><a href="/wiki/2-%E7%94%B2%E5%9F%BA%E6%88%8A%E7%83%B7" title="2-甲基戊烷">异己烷</a></li> <li><a href="/wiki/2-%E7%94%B2%E5%9F%BA%E5%B7%B1%E7%83%B7" title="2-甲基己烷">异庚烷</a></li> <li><a href="/wiki/2,2,4-%E4%B8%89%E7%94%B2%E5%9F%BA%E6%88%8A%E7%83%B7" title="2,2,4-三甲基戊烷">异辛烷</a></li> <li><a href="/wiki/2-%E7%94%B2%E5%9F%BA%E8%BE%9B%E7%83%B7" title="2-甲基辛烷">异壬烷</a></li> <li><a href="/w/index.php?title=%E5%BC%82%E7%99%B8%E7%83%B7&amp;action=edit&amp;redlink=1" class="new" title="异癸烷(页面不存在)">异癸烷</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;width:8"><a href="/wiki/%E7%8E%AF%E7%83%B7%E7%83%83" title="环烷烃">环烷烃</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0px"><div style="padding:0em 0.25em"> <ul><li><a href="/wiki/%E7%92%B0%E4%B8%99%E7%83%B7" title="環丙烷">环丙烷</a></li> <li><a href="/wiki/%E7%8E%AF%E4%B8%81%E7%83%B7" title="环丁烷">环丁烷</a></li> <li><a href="/wiki/%E7%8E%AF%E6%88%8A%E7%83%B7" title="环戊烷">环戊烷</a></li> <li><a href="/wiki/%E7%8E%AF%E5%B7%B1%E7%83%B7" title="环己烷">环己烷</a></li> <li><a href="/wiki/%E7%8E%AF%E5%BA%9A%E7%83%B7" title="环庚烷">环庚烷</a></li> <li><a href="/wiki/%E7%8E%AF%E8%BE%9B%E7%83%B7" title="环辛烷">环辛烷</a></li> <li><a href="/wiki/%E7%8E%AF%E5%A3%AC%E7%83%B7" title="环壬烷">环壬烷</a></li> <li><a href="/wiki/%E7%8E%AF%E7%99%B8%E7%83%B7" title="环癸烷">环癸烷</a></li> <li><a href="/wiki/Template:%E7%8E%AF%E7%83%B7%E7%83%83" title="Template:环烷烃">其它</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;width:8"><a href="/wiki/%E7%83%B7%E5%9F%BA%E7%8E%AF%E7%83%B7%E7%83%83" title="烷基环烷烃">烷基环烷烃</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0px"><div style="padding:0em 0.25em"> <ul><li><a href="/wiki/%E7%94%B2%E5%9F%BA%E7%8E%AF%E4%B8%99%E7%83%B7" title="甲基环丙烷">甲基环丙烷</a></li> <li><a href="/wiki/%E7%94%B2%E5%9F%BA%E7%8E%AF%E4%B8%81%E7%83%B7" title="甲基环丁烷">甲基环丁烷</a></li> <li><a href="/wiki/%E7%94%B2%E5%9F%BA%E7%8E%AF%E6%88%8A%E7%83%B7" title="甲基环戊烷">甲基环戊烷</a></li> <li><a href="/wiki/%E7%94%B2%E5%9F%BA%E7%92%B0%E5%B7%B1%E7%83%B7" title="甲基環己烷">甲基环己烷</a></li> <li><a href="/w/index.php?title=%E5%BC%82%E4%B8%99%E5%9F%BA%E7%8E%AF%E5%B7%B1%E7%83%B7&amp;action=edit&amp;redlink=1" class="new" title="异丙基环己烷(页面不存在)">异丙基环己烷</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;width:8"><a href="/w/index.php?title=%E4%BA%8C%E7%8E%AF%E7%83%B7%E7%83%83&amp;action=edit&amp;redlink=1" class="new" title="二环烷烃(页面不存在)">二环烷烃</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0px"><div style="padding:0em 0.25em"> <ul><li><a href="/wiki/%E6%88%BF%E7%83%B7" title="房烷">房烷</a></li> <li><a href="/wiki/%E9%99%8D%E5%86%B0%E7%89%87%E7%83%B7" title="降冰片烷">降冰片烷</a></li> <li><a href="/wiki/%E8%90%98%E7%83%B7" class="mw-redirect" title="萘烷">萘烷</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;width:8"><a href="/w/index.php?title=%E5%A4%9A%E7%8E%AF%E7%83%B7%E7%83%83&amp;action=edit&amp;redlink=1" class="new" title="多环烷烃(页面不存在)">多环烷烃</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0px"><div style="padding:0em 0.25em"> <ul><li><a href="/wiki/%E9%87%91%E5%88%9A%E7%83%B7" title="金刚烷">金刚烷</a></li> <li><a href="/w/index.php?title=%E9%92%BB%E7%9F%B3%E7%83%B7&amp;action=edit&amp;redlink=1" class="new" title="钻石烷(页面不存在)">钻石烷</a></li> <li><a href="/w/index.php?title=%E8%8F%B2%E7%83%B7&amp;action=edit&amp;redlink=1" class="new" title="菲烷(页面不存在)">菲烷</a></li> <li><a href="/w/index.php?title=%E7%B1%BB%E5%9B%BA%E7%83%B7&amp;action=edit&amp;redlink=1" class="new" title="类固烷(页面不存在)">类固烷</a></li> <li><a href="/wiki/%E7%AB%8B%E6%96%B9%E7%83%B7" title="立方烷">立方烷</a></li> <li><a href="/wiki/%E6%A3%B1%E6%9F%B1%E7%83%B7" class="mw-redirect" title="棱柱烷">棱柱烷</a></li> <li><a href="/wiki/%E6%AD%A3%E5%8D%81%E4%BA%8C%E9%9D%A2%E4%BD%93%E7%83%B7" title="正十二面体烷">正十二面体烷</a></li> <li><a href="/wiki/%E7%AF%AE%E7%83%B7" title="篮烷">篮烷</a></li> <li><a href="/w/index.php?title=%E6%95%99%E5%A0%82%E7%83%B7&amp;action=edit&amp;redlink=1" class="new" title="教堂烷(页面不存在)">教堂烷</a></li> <li><a href="/wiki/%E5%AE%9D%E5%A1%94%E7%83%B7" title="宝塔烷">宝塔烷</a></li> <li><a href="/wiki/%E6%89%AD%E6%9B%B2%E7%83%B7" title="扭曲烷">扭曲烷</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;width:8">其它</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0px"><div style="padding:0em 0.25em"> <ul><li><a href="/w/index.php?title=%E8%9E%BA%E7%83%B7&amp;action=edit&amp;redlink=1" class="new" title="螺烷(页面不存在)">螺烷</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/%E4%B8%8D%E9%A5%B1%E5%92%8C%E7%83%83" title="不饱和烃">不饱和烃</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0px"><div style="padding:0em 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;width:8.5em;"><a href="/wiki/%E7%83%AF%E7%83%83" title="烯烃">烯烃</a><br />C<sub><i>n</i></sub>H<sub>2<i>n</i></sub></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0px"><div style="padding:0em 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;width:8">直链烯烃</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0px"><div style="padding:0em 0.25em"> <ul><li><a href="/wiki/%E4%B9%99%E7%83%AF" title="乙烯">乙烯</a></li> <li><a href="/wiki/%E4%B8%99%E7%83%AF" title="丙烯">丙烯</a></li> <li><a href="/wiki/%E4%B8%81%E7%83%AF" title="丁烯">丁烯</a></li> <li><a href="/wiki/%E6%88%8A%E7%83%AF" title="戊烯">戊烯</a></li> <li><a href="/wiki/%E5%B7%B1%E7%83%AF" title="己烯">己烯</a></li> <li><a href="/wiki/%E5%BA%9A%E7%83%AF" title="庚烯">庚烯</a></li> <li><a href="/wiki/%E8%BE%9B%E7%83%AF" title="辛烯">辛烯</a></li> <li><a href="/wiki/%E5%A3%AC%E7%83%AF" title="壬烯">壬烯</a></li> <li><a href="/wiki/%E7%99%B8%E7%83%AF" title="癸烯">癸烯</a></li> <li><a href="/wiki/Template:%E7%83%AF%E7%83%83" title="Template:烯烃">其它</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;width:8">支链烯烃</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0px"><div style="padding:0em 0.25em"> <ul><li><a href="/wiki/%E5%BC%82%E4%B8%81%E7%83%AF" title="异丁烯">异丁烯</a></li> <li><a href="/w/index.php?title=%E5%BC%82%E6%88%8A%E7%83%AF&amp;action=edit&amp;redlink=1" class="new" title="异戊烯(页面不存在)">异戊烯</a></li> <li><a href="/w/index.php?title=%E5%BC%82%E5%B7%B1%E7%83%AF&amp;action=edit&amp;redlink=1" class="new" title="异己烯(页面不存在)">异己烯</a></li> <li><a href="/w/index.php?title=%E5%BC%82%E5%BA%9A%E7%83%AF&amp;action=edit&amp;redlink=1" class="new" title="异庚烯(页面不存在)">异庚烯</a></li> <li><a href="/w/index.php?title=%E5%BC%82%E8%BE%9B%E7%83%AF&amp;action=edit&amp;redlink=1" class="new" title="异辛烯(页面不存在)">异辛烯</a></li> <li><a href="/w/index.php?title=%E5%BC%82%E5%A3%AC%E7%83%AF&amp;action=edit&amp;redlink=1" class="new" title="异壬烯(页面不存在)">异壬烯</a></li> <li><a href="/w/index.php?title=%E5%BC%82%E7%99%B8%E7%83%AF&amp;action=edit&amp;redlink=1" class="new" title="异癸烯(页面不存在)">异癸烯</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;width:8.5em;"><a href="/wiki/%E7%82%94%E7%83%83" title="炔烃">炔烃</a><br />C<sub><i>n</i></sub>H<sub>2<i>n</i> − 2</sub></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0px"><div style="padding:0em 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;width:8">直链炔烃</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0px"><div style="padding:0em 0.25em"> <ul><li><a href="/wiki/%E4%B9%99%E7%82%94" title="乙炔">乙炔</a></li> <li><a href="/wiki/%E4%B8%99%E7%82%94" title="丙炔">丙炔</a></li> <li><a href="/wiki/%E4%B8%81%E7%82%94" title="丁炔">丁炔</a></li> <li><a href="/wiki/%E6%88%8A%E7%82%94" title="戊炔">戊炔</a></li> <li><a href="/wiki/3-%E5%B7%B1%E7%82%94" title="3-己炔">己炔</a></li> <li><a href="/wiki/%E5%BA%9A%E7%82%94" title="庚炔">庚炔</a></li> <li><a href="/wiki/%E8%BE%9B%E7%82%94" title="辛炔">辛炔</a></li> <li><a href="/wiki/%E5%A3%AC%E7%82%94" title="壬炔">壬炔</a></li> <li><a href="/wiki/1-%E7%99%B8%E7%82%94" title="1-癸炔">癸炔</a></li> <li><a href="/wiki/Template:%E7%82%94%E7%83%B4" title="Template:炔烴">其它</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;width:8">支链炔烃</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0px"><div style="padding:0em 0.25em"> <ul><li><a href="/w/index.php?title=%E5%BC%82%E6%88%8A%E7%82%94&amp;action=edit&amp;redlink=1" class="new" title="异戊炔(页面不存在)">异戊炔</a></li> <li><a href="/w/index.php?title=%E5%BC%82%E5%B7%B1%E7%82%94&amp;action=edit&amp;redlink=1" class="new" title="异己炔(页面不存在)">异己炔</a></li> <li><a href="/w/index.php?title=%E5%BC%82%E5%BA%9A%E7%82%94&amp;action=edit&amp;redlink=1" class="new" title="异庚炔(页面不存在)">异庚炔</a></li> <li><a href="/w/index.php?title=%E5%BC%82%E8%BE%9B%E7%82%94&amp;action=edit&amp;redlink=1" class="new" title="异辛炔(页面不存在)">异辛炔</a></li> <li><a href="/w/index.php?title=%E5%BC%82%E5%A3%AC%E7%82%94&amp;action=edit&amp;redlink=1" class="new" title="异壬炔(页面不存在)">异壬炔</a></li> <li><a href="/w/index.php?title=%E5%BC%82%E7%99%B8%E7%82%94&amp;action=edit&amp;redlink=1" class="new" title="异癸炔(页面不存在)">异癸炔</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;width:8.5em;"><a href="/wiki/%E7%8E%AF%E7%83%AF%E7%83%83" title="环烯烃">环烯烃</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0px"><div style="padding:0em 0.25em"> <ul><li><a href="/wiki/%E7%8E%AF%E4%B8%99%E7%83%AF" title="环丙烯">环丙烯</a></li> <li><a href="/wiki/%E7%8E%AF%E4%B8%81%E7%83%AF" title="环丁烯">环丁烯</a></li> <li><a href="/wiki/%E7%8E%AF%E6%88%8A%E7%83%AF" title="环戊烯">环戊烯</a></li> <li><a href="/wiki/%E7%8E%AF%E5%B7%B1%E7%83%AF" title="环己烯">环己烯</a></li> <li><a href="/wiki/%E7%8E%AF%E5%BA%9A%E7%83%AF" title="环庚烯">环庚烯</a></li> <li><a href="/wiki/%E7%8E%AF%E8%BE%9B%E7%83%AF" title="环辛烯">环辛烯</a></li> <li><a href="/wiki/%E7%8E%AF%E5%A3%AC%E7%83%AF" title="环壬烯">环壬烯</a></li> <li><a href="/wiki/%E7%8E%AF%E7%99%B8%E7%83%AF" title="环癸烯">环癸烯</a></li> <li><a href="/wiki/Template:%E7%8E%AF%E7%83%AF%E7%83%83" title="Template:环烯烃">其它</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;width:8.5em;"><a href="/w/index.php?title=%E7%83%B7%E5%9F%BA%E7%8E%AF%E7%83%AF%E7%83%83&amp;action=edit&amp;redlink=1" class="new" title="烷基环烯烃(页面不存在)">烷基环烯烃</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0px"><div style="padding:0em 0.25em"> <ul><li><a href="/w/index.php?title=1-Methylcyclopropene&amp;action=edit&amp;redlink=1" class="new" title="1-Methylcyclopropene(页面不存在)">甲基环丙烯</a></li> <li><a href="/w/index.php?title=%E7%94%B2%E5%9F%BA%E7%8E%AF%E4%B8%81%E7%83%AF&amp;action=edit&amp;redlink=1" class="new" title="甲基环丁烯(页面不存在)">甲基环丁烯</a></li> <li><a href="/w/index.php?title=%E7%94%B2%E5%9F%BA%E7%8E%AF%E6%88%8A%E7%83%AF&amp;action=edit&amp;redlink=1" class="new" title="甲基环戊烯(页面不存在)">甲基环戊烯</a></li> <li><a href="/wiki/%E7%94%B2%E5%9F%BA%E7%8E%AF%E5%B7%B1%E7%83%AF" title="甲基环己烯">甲基环己烯</a></li> <li><a href="/w/index.php?title=%E5%BC%82%E4%B8%99%E5%9F%BA%E7%8E%AF%E5%B7%B1%E7%83%AF&amp;action=edit&amp;redlink=1" class="new" title="异丙基环己烯(页面不存在)">异丙基环己烯</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;width:8.5em;"><a href="/w/index.php?title=%E4%BA%8C%E7%8E%AF%E7%83%AF%E7%83%83&amp;action=edit&amp;redlink=1" class="new" title="二环烯烃(页面不存在)">二环烯烃</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0px"><div style="padding:0em 0.25em"> <ul><li><a href="/wiki/%E9%99%8D%E5%86%B0%E7%89%87%E7%83%AF" title="降冰片烯">降冰片烯</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;width:8.5em;"><a href="/wiki/%E7%8E%AF%E7%82%94%E7%83%83" title="环炔烃">环炔烃</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0px"><div style="padding:0em 0.25em"> <ul><li><a href="/wiki/%E7%8E%AF%E7%82%94%E7%83%83" title="环炔烃">环丙炔</a></li> <li><a href="/w/index.php?title=%E7%8E%AF%E4%B8%81%E7%82%94&amp;action=edit&amp;redlink=1" class="new" title="环丁炔(页面不存在)">环丁炔</a></li> <li><a href="/w/index.php?title=%E7%8E%AF%E6%88%8A%E7%82%94&amp;action=edit&amp;redlink=1" class="new" title="环戊炔(页面不存在)">环戊炔</a></li> <li><a href="/w/index.php?title=%E7%8E%AF%E5%B7%B1%E7%82%94&amp;action=edit&amp;redlink=1" class="new" title="环己炔(页面不存在)">环己炔</a></li> <li><a href="/w/index.php?title=%E7%8E%AF%E5%BA%9A%E7%82%94&amp;action=edit&amp;redlink=1" class="new" title="环庚炔(页面不存在)">环庚炔</a></li> <li><a href="/wiki/%E7%8E%AF%E8%BE%9B%E7%82%94" title="环辛炔">环辛炔</a></li> <li><a href="/wiki/%E7%8E%AF%E5%A3%AC%E7%82%94" title="环壬炔">环壬炔</a></li> <li><a href="/w/index.php?title=%E7%8E%AF%E7%99%B8%E7%82%94&amp;action=edit&amp;redlink=1" class="new" title="环癸炔(页面不存在)">环癸炔</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;width:8.5em;"><a href="/wiki/%E4%BA%8C%E7%83%AF" class="mw-redirect" title="二烯">二烯</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0px"><div style="padding:0em 0.25em"> <ul><li><a href="/wiki/%E4%B8%99%E4%BA%8C%E7%83%AF" title="丙二烯">丙二烯</a></li> <li><a href="/wiki/%E4%B8%81%E4%BA%8C%E7%83%AF" title="丁二烯">丁二烯</a></li> <li><a href="/wiki/%E6%88%8A%E4%BA%8C%E7%83%AF" title="戊二烯">戊二烯</a></li> <li><a href="/w/index.php?title=%E5%B7%B1%E4%BA%8C%E7%83%AF&amp;action=edit&amp;redlink=1" class="new" title="己二烯(页面不存在)">己二烯</a></li> <li><a href="/w/index.php?title=%E5%BA%9A%E4%BA%8C%E7%83%AF&amp;action=edit&amp;redlink=1" class="new" title="庚二烯(页面不存在)">庚二烯</a></li> <li><a href="/wiki/1,7-%E8%BE%9B%E4%BA%8C%E7%83%AF" title="1,7-辛二烯">辛二烯</a></li> <li><a href="/w/index.php?title=%E5%A3%AC%E4%BA%8C%E7%83%AF&amp;action=edit&amp;redlink=1" class="new" title="壬二烯(页面不存在)">壬二烯</a></li> <li><a href="/w/index.php?title=%E7%99%B8%E4%BA%8C%E7%83%AF&amp;action=edit&amp;redlink=1" class="new" title="癸二烯(页面不存在)">癸二烯</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;width:8.5em;">其它</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0px"><div style="padding:0em 0.25em"> <ul><li><a href="/w/index.php?title=%E4%B8%89%E7%83%AF&amp;action=edit&amp;redlink=1" class="new" title="三烯(页面不存在)">三烯</a></li> <li><a href="/w/index.php?title=%E4%BA%8C%E7%82%94&amp;action=edit&amp;redlink=1" class="new" title="二炔(页面不存在)">二炔</a></li> <li><a href="/wiki/%E7%B4%AF%E7%A7%AF%E5%A4%9A%E7%83%AF%E7%83%83" title="累积多烯烃">连多烯</a></li> <li><a href="/wiki/%E7%8E%AF%E8%BE%9B%E5%9B%9B%E7%83%AF" title="环辛四烯">环辛四烯</a></li> <li><a href="/w/index.php?title=%E7%8E%AF%E5%8D%81%E4%BA%8C%E4%B8%89%E7%83%AF&amp;action=edit&amp;redlink=1" class="new" title="环十二三烯(页面不存在)">环十二三烯</a></li> <li><a href="/w/index.php?title=%E7%83%AF%E7%82%94&amp;action=edit&amp;redlink=1" class="new" title="烯炔(页面不存在)">烯炔</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/%E8%8A%B3%E9%A6%99%E7%83%83" title="芳香烃">芳香烃</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0px"><div style="padding:0em 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;width:8.5em;"><a href="/wiki/%E5%A4%9A%E7%92%B0%E8%8A%B3%E9%A6%99%E7%83%B4" title="多環芳香烴">多环芳香烃</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0px"><div style="padding:0em 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;width:8.5em;"><a href="/wiki/%E5%B9%B6%E8%8B%AF" title="并苯">并苯</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0px"><div style="padding:0em 0.25em"> <ul><li><a href="/wiki/%E8%90%98" title="萘">萘</a></li> <li><a href="/wiki/%E8%92%BD" title="蒽">蒽</a></li> <li><a href="/wiki/%E5%B9%B6%E5%9B%9B%E8%8B%AF" title="并四苯">并四苯</a></li> <li><a href="/wiki/%E5%B9%B6%E4%BA%94%E8%8B%AF" title="并五苯">并五苯</a></li> <li><a href="/wiki/%E5%B9%B6%E5%85%AD%E8%8B%AF" title="并六苯">并六苯</a></li> <li><a href="/wiki/%E5%B9%B6%E4%B8%83%E8%8B%AF" title="并七苯">并七苯</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;width:8.5em;">其它</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0px"><div style="padding:0em 0.25em"> <ul><li><a href="/wiki/%E8%96%81" title="薁">薁</a></li> <li><a href="/wiki/%E8%8A%B4" title="芴">芴</a></li> <li><a href="/wiki/%E8%9E%BA%E7%83%AF" title="螺烯">螺烯</a></li> <li><a href="/wiki/%E5%9C%88%E7%83%AF" title="圈烯">圈烯</a></li> <li><a href="/wiki/%E4%B8%81%E6%90%AD%E7%83%AF" title="丁搭烯">丁搭烯</a></li> <li><a href="/wiki/%E8%8F%B2" title="菲">菲</a></li> <li><a href="/wiki/%E4%93%9B" title="䓛">䓛</a></li> <li><a href="/wiki/%E8%8A%98" title="芘">芘</a></li> <li><a href="/wiki/%E7%A2%97%E7%83%AF" title="碗烯">碗烯</a></li> <li><a href="/wiki/%E5%87%AF%E5%BA%93%E5%8B%92%E7%83%AF" title="凯库勒烯">凯库勒烯</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;width:8.5em;"><a href="/w/index.php?title=%E7%83%B7%E5%9F%BA%E8%8B%AF&amp;action=edit&amp;redlink=1" class="new" title="烷基苯(页面不存在)">烷基苯</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0px"><div style="padding:0em 0.25em"> <ul><li><a href="/wiki/%E7%94%B2%E8%8B%AF" title="甲苯">甲苯</a></li> <li><a href="/wiki/%E4%BA%8C%E7%94%B2%E8%8B%AF" title="二甲苯">二甲苯</a></li> <li><a href="/wiki/%E4%B9%99%E8%8B%AF" title="乙苯">乙苯</a></li> <li><a href="/wiki/%E5%BC%82%E4%B8%99%E8%8B%AF" title="异丙苯">异丙苯</a></li> <li><a href="/wiki/%E8%8B%AF%E4%B9%99%E7%83%AF" title="苯乙烯">苯乙烯</a></li> <li><a href="/wiki/%E5%9D%87%E4%B8%89%E7%94%B2%E8%8B%AF" title="均三甲苯">均三甲苯</a></li> <li><a href="/wiki/%E5%81%8F%E4%B8%89%E7%94%B2%E8%8B%AF" title="偏三甲苯">偏三甲苯</a></li> <li><a href="/wiki/%E9%82%BB%E4%B8%89%E7%94%B2%E8%8B%AF" class="mw-redirect" title="邻三甲苯">邻三甲苯</a></li> <li><a href="/wiki/%E5%BC%82%E4%B8%99%E5%9F%BA%E7%94%B2%E8%8B%AF" title="异丙基甲苯">异丙基甲苯</a></li> <li><a class="mw-selflink selflink">六甲苯</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;width:8.5em;">其它</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0px"><div style="padding:0em 0.25em"> <ul><li><a href="/wiki/%E8%8B%AF" title="苯">苯</a></li> <li><a href="/w/index.php?title=%E7%8E%AF%E4%B8%99%E7%83%AF%E5%9F%BA%E8%87%AA%E7%94%B1%E5%9F%BA&amp;action=edit&amp;redlink=1" class="new" title="环丙烯基自由基(页面不存在)">环丙烯基自由基</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:azzurro;">其它</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0px"><div style="padding:0em 0.25em"> <ul><li><a href="/wiki/%E8%BD%AE%E7%83%AF" title="轮烯">轮烯</a></li> <li><a href="/w/index.php?title=%E8%BD%AE%E7%82%94&amp;action=edit&amp;redlink=1" class="new" title="轮炔(页面不存在)">轮炔</a></li> <li><a href="/wiki/%E8%84%82%E7%8E%AF%E6%97%8F%E5%8C%96%E5%90%88%E7%89%A9" title="脂环族化合物">脂环族化合物</a></li> <li><a href="/w/index.php?title=%E7%9F%B3%E6%B2%B9%E8%83%B6&amp;action=edit&amp;redlink=1" class="new" title="石油胶(页面不存在)">石油胶</a></li></ul> </div></td></tr></tbody></table></div> <p class="mw-empty-elt"> </p> <!-- NewPP limit report Parsed by mw‐web.codfw.main‐56d8db5f6f‐drm54 Cached time: 20250213081850 Cache expiry: 2592000 Reduced expiry: false Complications: [show‐toc] CPU time usage: 1.495 seconds Real time usage: 1.690 seconds Preprocessor visited node count: 16914/1000000 Post‐expand include size: 391236/2097152 bytes Template argument size: 24862/2097152 bytes Highest expansion depth: 23/100 Expensive parser function count: 6/500 Unstrip recursion depth: 0/20 Unstrip post‐expand size: 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