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cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-ellipsis mw-ui-icon-wikimedia-ellipsis"></span> <span class="vector-dropdown-label-text">个人工具</span> </label> <div class="vector-dropdown-content"> <div id="p-personal" class="vector-menu mw-portlet mw-portlet-personal user-links-collapsible-item" title="用户菜单" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="pt-sitesupport" class="user-links-collapsible-item mw-list-item"><a href="https://donate.wikimedia.org/?utm_source=donate&utm_medium=sidebar&utm_campaign=spontaneous&uselang=zh-hans"><span>资助维基百科</span></a></li><li id="pt-createaccount" class="user-links-collapsible-item mw-list-item"><a href="/w/index.php?title=Special:%E5%88%9B%E5%BB%BA%E8%B4%A6%E6%88%B7&returnto=%E8%85%88" 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> 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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"></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-历史" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#历史"> <div class="vector-toc-text"> <span class="vector-toc-numb">1</span> <span>历史</span> </div> </a> <ul id="toc-历史-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-合成" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#合成"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>合成</span> </div> </a> <ul id="toc-合成-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">3</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-水解反应" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#水解反应"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>水解反应</span> </div> </a> <ul id="toc-水解反应-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-还原反应" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#还原反应"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>还原反应</span> </div> </a> <ul id="toc-还原反应-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-亲核反应" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#亲核反应"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.3</span> <span>亲核反应</span> </div> </a> <ul id="toc-亲核反应-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-烷基化反应" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#烷基化反应"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.4</span> <span>烷基化反应</span> </div> </a> <ul id="toc-烷基化反应-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-杂记" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#杂记"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.5</span> <span>杂记</span> </div> </a> <ul id="toc-杂记-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-有机氨基腈" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#有机氨基腈"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>有机氨基腈</span> </div> </a> <ul id="toc-有机氨基腈-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-腈氧化物" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#腈氧化物"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>腈氧化物</span> </div> </a> <ul id="toc-腈氧化物-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-参见" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#参见"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>参见</span> </div> </a> <ul id="toc-参见-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-参考文献" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#参考文献"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>参考文献</span> </div> </a> <ul id="toc-参考文献-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-外部链接" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#外部链接"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>外部链接</span> </div> </a> <ul id="toc-外部链接-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" > <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">腈</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。45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-45" 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">45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-af mw-list-item"><a href="https://af.wikipedia.org/wiki/Nitriel" title="Nitriel – 南非荷兰语" lang="af" hreflang="af" data-title="Nitriel" data-language-autonym="Afrikaans" data-language-local-name="南非荷兰语" class="interlanguage-link-target"><span>Afrikaans</span></a></li><li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D9%86%D8%AA%D8%B1%D9%8A%D9%84" title="نتريل – 阿拉伯语" lang="ar" hreflang="ar" data-title="نتريل" 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-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Nitril" title="Nitril – 阿塞拜疆语" lang="az" hreflang="az" data-title="Nitril" data-language-autonym="Azərbaycanca" data-language-local-name="阿塞拜疆语" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%9D%D1%96%D1%82%D1%80%D1%8B%D0%BB%D1%8B" title="Нітрылы – 白俄罗斯语" lang="be" hreflang="be" data-title="Нітрылы" data-language-autonym="Беларуская" data-language-local-name="白俄罗斯语" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Nitril" title="Nitril – 加泰罗尼亚语" lang="ca" hreflang="ca" data-title="Nitril" data-language-autonym="Català" data-language-local-name="加泰罗尼亚语" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Nitril" title="Nitril – 捷克语" lang="cs" hreflang="cs" data-title="Nitril" data-language-autonym="Čeština" data-language-local-name="捷克语" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Nitril" title="Nitril – 丹麦语" lang="da" hreflang="da" data-title="Nitril" data-language-autonym="Dansk" data-language-local-name="丹麦语" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de badge-Q17437796 badge-featuredarticle mw-list-item" title="典范条目"><a href="https://de.wikipedia.org/wiki/Nitrile" title="Nitrile – 德语" lang="de" hreflang="de" data-title="Nitrile" data-language-autonym="Deutsch" data-language-local-name="德语" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%9D%CE%B9%CF%84%CF%81%CE%AF%CE%BB%CE%B9%CE%BF" title="Νιτρίλιο – 希腊语" lang="el" hreflang="el" data-title="Νιτρίλιο" data-language-autonym="Ελληνικά" data-language-local-name="希腊语" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-en mw-list-item"><a href="https://en.wikipedia.org/wiki/Nitrile" title="Nitrile – 英语" lang="en" hreflang="en" data-title="Nitrile" 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/Nitrilo" title="Nitrilo – 世界语" lang="eo" hreflang="eo" data-title="Nitrilo" 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-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Nitrilo" title="Nitrilo – 西班牙语" lang="es" hreflang="es" data-title="Nitrilo" data-language-autonym="Español" data-language-local-name="西班牙语" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Nitriilid" title="Nitriilid – 爱沙尼亚语" lang="et" hreflang="et" data-title="Nitriilid" data-language-autonym="Eesti" data-language-local-name="爱沙尼亚语" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Nitrilo" title="Nitrilo – 巴斯克语" lang="eu" hreflang="eu" data-title="Nitrilo" data-language-autonym="Euskara" data-language-local-name="巴斯克语" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D9%86%DB%8C%D8%AA%D8%B1%DB%8C%D9%84" title="نیتریل – 波斯语" lang="fa" hreflang="fa" data-title="نیتریل" 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/Nitriilit" title="Nitriilit – 芬兰语" lang="fi" hreflang="fi" data-title="Nitriilit" 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/Nitrile" title="Nitrile – 法语" lang="fr" hreflang="fr" data-title="Nitrile" data-language-autonym="Français" data-language-local-name="法语" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Nitrilo" title="Nitrilo – 加利西亚语" lang="gl" hreflang="gl" data-title="Nitrilo" data-language-autonym="Galego" data-language-local-name="加利西亚语" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%A0%D7%99%D7%98%D7%A8%D7%99%D7%9C" title="ניטריל – 希伯来语" lang="he" hreflang="he" data-title="ניטריל" data-language-autonym="עברית" data-language-local-name="希伯来语" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Nitrili" title="Nitrili – 克罗地亚语" lang="hr" hreflang="hr" data-title="Nitrili" data-language-autonym="Hrvatski" data-language-local-name="克罗地亚语" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Nitrilek" title="Nitrilek – 匈牙利语" lang="hu" hreflang="hu" data-title="Nitrilek" data-language-autonym="Magyar" data-language-local-name="匈牙利语" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D5%86%D5%AB%D5%BF%D6%80%D5%AB%D5%AC%D5%B6%D5%A5%D6%80" title="Նիտրիլներ – 亚美尼亚语" lang="hy" hreflang="hy" data-title="Նիտրիլներ" data-language-autonym="Հայերեն" data-language-local-name="亚美尼亚语" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Nitril" title="Nitril – 印度尼西亚语" lang="id" hreflang="id" data-title="Nitril" 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/Nitrili" title="Nitrili – 意大利语" lang="it" hreflang="it" data-title="Nitrili" 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%8B%E3%83%88%E3%83%AA%E3%83%AB" title="ニトリル – 日语" lang="ja" hreflang="ja" data-title="ニトリル" 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-ka mw-list-item"><a href="https://ka.wikipedia.org/wiki/%E1%83%9C%E1%83%98%E1%83%A2%E1%83%A0%E1%83%98%E1%83%9A%E1%83%94%E1%83%91%E1%83%98" title="ნიტრილები – 格鲁吉亚语" lang="ka" hreflang="ka" data-title="ნიტრილები" data-language-autonym="ქართული" data-language-local-name="格鲁吉亚语" class="interlanguage-link-target"><span>ქართული</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EB%82%98%EC%9D%B4%ED%8A%B8%EB%A6%B4" title="나이트릴 – 韩语" lang="ko" hreflang="ko" data-title="나이트릴" data-language-autonym="한국어" data-language-local-name="韩语" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-la mw-list-item"><a href="https://la.wikipedia.org/wiki/Nitrile" title="Nitrile – 拉丁语" lang="la" hreflang="la" data-title="Nitrile" data-language-autonym="Latina" data-language-local-name="拉丁语" class="interlanguage-link-target"><span>Latina</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Nitrili" title="Nitrili – 拉脱维亚语" lang="lv" hreflang="lv" data-title="Nitrili" data-language-autonym="Latviešu" data-language-local-name="拉脱维亚语" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%9D%D0%B8%D1%82%D1%80%D0%B8%D0%BB" title="Нитрил – 马其顿语" lang="mk" hreflang="mk" data-title="Нитрил" data-language-autonym="Македонски" data-language-local-name="马其顿语" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Nitril" title="Nitril – 荷兰语" lang="nl" hreflang="nl" data-title="Nitril" 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-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Nitril" title="Nitril – 书面挪威语" lang="nb" hreflang="nb" data-title="Nitril" data-language-autonym="Norsk bokmål" data-language-local-name="书面挪威语" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Nitryle" title="Nitryle – 波兰语" lang="pl" hreflang="pl" data-title="Nitryle" data-language-autonym="Polski" data-language-local-name="波兰语" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Nitrila" title="Nitrila – 葡萄牙语" lang="pt" hreflang="pt" data-title="Nitrila" data-language-autonym="Português" data-language-local-name="葡萄牙语" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Nitril" title="Nitril – 罗马尼亚语" lang="ro" hreflang="ro" data-title="Nitril" 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%9D%D0%B8%D1%82%D1%80%D0%B8%D0%BB%D1%8B" title="Нитрилы – 俄语" lang="ru" hreflang="ru" data-title="Нитрилы" 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/Nitril" title="Nitril – 塞尔维亚-克罗地亚语" lang="sh" hreflang="sh" data-title="Nitril" 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-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Nitrile" title="Nitrile – Simple English" lang="en-simple" hreflang="en-simple" data-title="Nitrile" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target"><span>Simple English</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Nitril" title="Nitril – 斯洛伐克语" lang="sk" hreflang="sk" data-title="Nitril" data-language-autonym="Slovenčina" data-language-local-name="斯洛伐克语" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Nitril" title="Nitril – 塞尔维亚语" lang="sr" hreflang="sr" data-title="Nitril" 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-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Nitril" title="Nitril – 瑞典语" lang="sv" hreflang="sv" data-title="Nitril" data-language-autonym="Svenska" data-language-local-name="瑞典语" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Nitril" title="Nitril – 土耳其语" lang="tr" hreflang="tr" data-title="Nitril" data-language-autonym="Türkçe" data-language-local-name="土耳其语" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%9D%D1%96%D1%82%D1%80%D0%B8%D0%BB%D0%B8" title="Нітрили – 乌克兰语" lang="uk" hreflang="uk" data-title="Нітрили" 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-wuu mw-list-item"><a href="https://wuu.wikipedia.org/wiki/%E8%85%88" title="腈 – 吴语" lang="wuu" hreflang="wuu" data-title="腈" data-language-autonym="吴语" data-language-local-name="吴语" class="interlanguage-link-target"><span>吴语</span></a></li><li class="interlanguage-link interwiki-zh-yue mw-list-item"><a href="https://zh-yue.wikipedia.org/wiki/%E8%85%88" title="腈 – 粤语" lang="yue" hreflang="yue" data-title="腈" data-language-autonym="粵語" data-language-local-name="粤语" class="interlanguage-link-target"><span>粵語</span></a></li> </ul> <div 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mw-list-item"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q333936" title="链接到连接的数据仓库项目[g]" accesskey="g"><span>维基数据项目</span></a></li> </ul> </div> </div> </div> </div> </div> </div> </nav> </div> </div> </div> <div class="vector-column-end"> <div class="vector-sticky-pinned-container"> <nav class="vector-page-tools-landmark" aria-label="页面工具"> <div id="vector-page-tools-pinned-container" class="vector-pinned-container"> </div> </nav> <nav class="vector-appearance-landmark" aria-label="外观"> <div id="vector-appearance-pinned-container" class="vector-pinned-container"> <div id="vector-appearance" class="vector-appearance vector-pinnable-element"> <div class="vector-pinnable-header vector-appearance-pinnable-header vector-pinnable-header-pinned" data-feature-name="appearance-pinned" data-pinnable-element-id="vector-appearance" data-pinned-container-id="vector-appearance-pinned-container" data-unpinned-container-id="vector-appearance-unpinned-container" > <div class="vector-pinnable-header-label">外观</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-appearance.pin">移至侧栏</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-appearance.unpin">隐藏</button> </div> </div> </div> </nav> </div> </div> <div id="bodyContent" class="vector-body" aria-labelledby="firstHeading" data-mw-ve-target-container> <div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">维基百科，自由的百科全书</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="zh" dir="ltr"><div role="note" class="hatnote navigation-not-searchable"><span typeof="mw:File"><a href="/wiki/Wikipedia:%E6%B6%88%E6%AD%A7%E4%B9%89" title="Wikipedia:消歧义"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5f/Disambig_gray.svg/25px-Disambig_gray.svg.png" decoding="async" width="25" height="19" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5f/Disambig_gray.svg/38px-Disambig_gray.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5f/Disambig_gray.svg/50px-Disambig_gray.svg.png 2x" data-file-width="220" data-file-height="168" /></a></span><style data-mw-deduplicate="TemplateStyles:r74069148">body:not(.skin-minerva) .mw-parser-output .ifmobile>.mobile{display:none}body.skin-minerva .mw-parser-output .ifmobile>.nomobile{display:inherit;display:initial}</style><span class="ifmobile"><span class="nomobile">  </span><span class="mobile"></span></span>此條目介紹的是有机化合物基团。关于合成橡胶材料，请见「<b><a href="/wiki/%E4%B8%81%E8%85%88%E6%A9%A1%E8%83%B6" title="丁腈橡胶">丁腈橡胶</a></b>」。</div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Nitrile_Structural_Formulae_V.1.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c7/Nitrile_Structural_Formulae_V.1.png/220px-Nitrile_Structural_Formulae_V.1.png" decoding="async" width="220" height="48" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c7/Nitrile_Structural_Formulae_V.1.png/330px-Nitrile_Structural_Formulae_V.1.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c7/Nitrile_Structural_Formulae_V.1.png/440px-Nitrile_Structural_Formulae_V.1.png 2x" data-file-width="1017" data-file-height="220" /></a><figcaption>氰基的结构: 官能团被突出为<span style="color:blue;">蓝色</span>.</figcaption></figure> <p><b><style data-mw-deduplicate="TemplateStyles:r80905552">.mw-parser-output ruby.zy{text-align:justify;text-justify:none}.mw-parser-output ruby.zy>rp{user-select:none}.mw-parser-output ruby.zy>rt{font-feature-settings:"ruby"1;font-size:90%;user-select:none}.mw-parser-output ruby.zy>rt+rt{padding-left:0.15em}</style><ruby class="zy center"><rb>腈</rb><rp>（</rp><rt lang="zh-Latn-pinyin">jīng</rt><rp>）</rp></ruby></b>（英語：<span lang="en">nitrile</span>）是指任何带有 –<a href="/wiki/%E7%A2%B3" title="碳">C</a>≡<a href="/wiki/%E6%B0%AE" title="氮">N</a> <a href="/wiki/%E5%AE%98%E8%83%BD%E5%9B%A2" title="官能团">官能团</a>的<a href="/wiki/%E6%9C%89%E6%9C%BA%E5%8C%96%E5%90%88%E7%89%A9" title="有机化合物">有机化合物</a><sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>。 </p><p>−<a href="/wiki/%E7%A2%B3" title="碳">C</a>≡<a href="/wiki/%E6%B0%AE" title="氮">N</a> <a href="/wiki/%E5%9F%BA%E5%9B%A2" class="mw-redirect" title="基团">基团</a>称作<a href="/wiki/%E6%B0%B0%E5%9F%BA" class="mw-redirect" title="氰基">氰基</a>，在 −CN 基团中<a href="/wiki/%E7%A2%B3" title="碳">碳</a>原子和<a href="/wiki/%E6%B0%AE" title="氮">氮</a>原子通过三键键合在一起。<a href="/wiki/%E6%97%A0%E6%9C%BA%E5%8C%96%E5%AD%A6" title="无机化学">无机化学</a>中带有此官能团者為<a href="/wiki/%E6%B0%B0" title="氰">氰</a>，而不称“腈”。<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p><p>许多含氰基的化合物都具有高<a href="/wiki/%E6%AF%92%E6%80%A7" title="毒性">毒性</a>。 </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="历史"><span id=".E5.8E.86.E5.8F.B2"></span>历史</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E8%85%88&action=edit&section=1" title="编辑章节：历史"><span>编辑</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/%E6%B0%A2%E6%B0%B0%E9%85%B8" class="mw-redirect" title="氢氰酸">氢氰酸</a>首次由<a href="/wiki/%E5%8D%A1%E5%B0%94%C2%B7%E5%A8%81%E5%BB%89%C2%B7%E8%88%8D%E5%8B%92" title="卡尔·威廉·舍勒">卡尔·威廉·舍勒</a>于1782年成功合成。<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> 1811年，由<a href="/wiki/%E7%BA%A6%E7%91%9F%E5%A4%AB%C2%B7%E8%B7%AF%E6%98%93%C2%B7%E7%9B%96-%E5%90%95%E8%90%A8%E5%85%8B" title="约瑟夫·路易·盖-吕萨克">约瑟夫·路易·盖-吕萨克</a>合成出纯净的氢氰酸，这是一种剧毒且具挥发性的酸。氰基苯甲酸首先由<a href="/wiki/%E5%BC%97%E9%87%8C%E5%BE%B7%E9%87%8C%E5%B8%8C%C2%B7%E7%BB%B4%E5%8B%92" title="弗里德里希·维勒">弗里德里希·维勒</a>和<a href="/wiki/%E5%B0%A4%E6%96%AF%E5%9B%BE%E6%96%AF%C2%B7%E5%86%AF%C2%B7%E6%9D%8E%E6%AF%94%E5%B8%8C" title="尤斯图斯·冯·李比希">尤斯图斯·冯·李比希</a>合成，但是由于当时的合成收率很低结果没有得到其理化数据，也没有得到它的假定结构。<a href="/w/index.php?title=%E6%B3%B0%E5%A5%A5%E8%8F%B2%E5%8B%92-%E6%9C%B1%E5%B0%94%C2%B7%E7%9A%AE%E4%B9%90%E8%8C%A8&action=edit&redlink=1" class="new" title="泰奥菲勒-朱尔·皮乐茨（页面不存在）">泰奥菲勒-朱尔·皮乐茨</a>于1834年合成出了<a href="/wiki/%E4%B8%99%E8%85%88" title="丙腈">丙腈</a>并且假设此化合物是一个含有氢氰酸的醚类化合物。<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> <a href="/w/index.php?title=Hermann_Fehling&action=edit&redlink=1" class="new" title="Hermann Fehling（页面不存在）">Hermann Fehling</a>于1844年通过加热苯甲酸铵合成了<a href="/wiki/%E8%8B%AF%E8%85%88" class="mw-redirect" title="苯腈">苯腈</a>，这是首个获得足够量以用于化学研究合成方法。他通过加热<a href="/wiki/%E7%94%B2%E9%85%B8%E9%93%B5" title="甲酸铵">甲酸铵</a>的结果比对得到的物质以确定该结构。他为该新发现的化合物命名为腈，而这也成为了官能团的名称。<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="合成"><span id=".E5.90.88.E6.88.90"></span>合成</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E8%85%88&action=edit&section=2" title="编辑章节：合成"><span>编辑</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>工业中, 主要合成腈的方法是<a href="/wiki/%E6%B0%A8%E6%B0%A7%E5%8C%96" title="氨氧化">氨氧化</a>和<a href="/w/index.php?title=%E6%B0%A2%E6%B0%B0%E5%8C%96&action=edit&redlink=1" class="new" title="氢氰化（页面不存在）">氢氰化</a>。这两种路线都符合<a href="/wiki/%E7%BB%BF%E8%89%B2%E5%8C%96%E5%AD%A6" title="绿色化学">绿色化学</a>，因为在反应中不会产生等当量的盐。在氨氧化反应中，烃分子在氨的存在下被部分氧化，这个转化被用于大量的合成丙烯腈。<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p> <dl><dd>CH<sub>3</sub>CH=CH<sub>2</sub> + 3/2 O<sub>2</sub> + NH<sub>3</sub> → NCCH=CH<sub>2</sub> + 3 H<sub>2</sub>O</dd></dl> <p>利用氢氰酸从<a href="/wiki/1,3-%E4%B8%81%E4%BA%8C%E7%83%AF" class="mw-redirect" title="1,3-丁二烯">1,3-丁二烯</a>合成<a href="/wiki/%E5%B7%B1%E4%BA%8C%E8%85%88" title="己二腈">己二腈</a>的例子： </p> <dl><dd>CH<sub>2</sub>=CH-CH=CH<sub>2</sub> + 2 HCN → NC(CH<sub>2</sub>)<sub>4</sub>CN</dd></dl> <p>在许多特殊的应用中，腈还可以通过下列方法进行合成： </p> <ul><li><a href="/wiki/%E4%BA%B2%E6%A0%B8%E5%8F%96%E4%BB%A3%E5%8F%8D%E5%BA%94" title="亲核取代反应">脂肪族亲核取代反应</a>：在<a href="/wiki/Kolbe%E8%85%88%E5%90%88%E6%88%90" class="mw-redirect" title="Kolbe腈合成">Kolbe腈合成</a>中，<a href="/wiki/%E5%8D%A4%E4%BB%A3%E7%83%83" class="mw-redirect" title="卤代烃">卤代烃</a>和金属<a href="/wiki/%E6%B0%B0%E5%8C%96%E7%89%A9" title="氰化物">氰化物</a>（氰盐）反应。芳香腈通过<a href="/wiki/Rosenmund-von_Braun%E5%90%88%E6%88%90%E6%B3%95" class="mw-redirect" title="Rosenmund-von Braun合成法">Rosenmund-von Braun合成法</a>制备。</li> <li>通过一级酰胺的<a href="/wiki/%E8%84%B1%E6%B0%B4%E5%8F%8D%E5%BA%94" class="mw-redirect" title="脱水反应">脱水</a>制备腈。许多试剂都可以用来作为脱水试剂：<a href="/w/index.php?title=%E4%BA%8C%E6%B0%AF%E7%A3%B7%E9%85%B8%E7%94%B2%E9%85%AF&action=edit&redlink=1" class="new" title="二氯磷酸甲酯（页面不存在）">二氯磷酸甲酯</a>和<a href="/wiki/DBU_(%E5%8C%96%E5%AD%A6)" class="mw-redirect" title="DBU (化学)">DBU</a>的组合试剂就是其中的一种。</li></ul> <p>图例为<a href="/wiki/%E8%8B%AF%E7%94%B2%E9%85%B0%E8%83%BA" title="苯甲酰胺">苯甲酰胺</a>转化为<a href="/wiki/%E8%8B%AF%E7%94%B2%E8%85%88" title="苯甲腈">苯甲腈</a>：<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Amidedehydration.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/70/Amidedehydration.png/400px-Amidedehydration.png" decoding="async" width="400" height="304" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/70/Amidedehydration.png/600px-Amidedehydration.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/70/Amidedehydration.png/800px-Amidedehydration.png 2x" data-file-width="987" data-file-height="751" /></a><figcaption>酰胺的脱水反应</figcaption></figure></dd></dl> <dl><dd>反应中的两个中间体是酰胺的<a href="/wiki/%E4%BA%92%E5%8F%98%E5%BC%82%E6%9E%84%E4%BD%93" title="互变异构体">互变异构体</a><b>A</b>,以及它的<a href="/wiki/%E6%9C%89%E6%9C%BA%E7%A3%B7%E9%85%B8%E9%85%AF" class="mw-redirect" title="有机磷酸酯">磷酸酯</a><b>B</b>。</dd></dl> <ul><li>通过二级酰胺的<a href="/wiki/%E8%84%B1%E6%B0%B4%E5%8F%8D%E5%BA%94" class="mw-redirect" title="脱水反应">脱水</a>(<a href="/wiki/Von_Braun%E9%85%B0%E8%83%BA%E9%99%8D%E8%A7%A3%E5%8F%8D%E5%BA%94" class="mw-redirect" title="Von Braun酰胺降解反应">von Braun酰胺降解反应</a>)合成腈。</li> <li><a href="/wiki/%E9%86%9B%E8%82%9F" class="mw-redirect" title="醛肟">醛肟</a>、<a href="/wiki/%E4%B8%89%E4%B9%99%E8%83%BA" title="三乙胺">三乙胺</a>/<a href="/wiki/%E4%BA%8C%E6%B0%A7%E5%8C%96%E7%A1%AB" title="二氧化硫">二氧化硫</a>、<a href="/wiki/%E6%B2%B8%E7%9F%B3" title="沸石">沸石</a>或者<a href="/wiki/%E7%A1%AB%E9%85%B0%E6%B0%AF" title="硫酰氯">硫酰氯</a>的<a href="/wiki/%E8%84%B1%E6%B0%B4%E5%8F%8D%E5%BA%94" class="mw-redirect" title="脱水反应">脱水</a>合成腈。</li> <li><a href="/wiki/%E9%86%9B" title="醛">醛</a>、<a href="/wiki/%E7%BE%9F%E8%83%BA" title="羟胺">羟胺</a>和<a href="/wiki/%E7%A1%AB%E9%85%B8%E9%92%A0" title="硫酸钠">硫酸钠</a>通过<a href="/wiki/%E4%B8%80%E9%94%85%E6%B3%95" class="mw-redirect" title="一锅法">一锅法</a>合成腈。</li></ul> <dl><dd>图例为一项研究中，一个芳香或脂肪醛和羟氨、无水硫酸钠在无溶剂反应中，通过<a href="/w/index.php?title=%E5%BE%AE%E6%B3%A2%E5%8C%96%E5%AD%A6&action=edit&redlink=1" class="new" title="微波化学（页面不存在）">微波反应</a>历经肟中间体合成腈化合物。<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup></dd></dl> <dl><dd><figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Aldehyde_to_nitril_conversion.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c7/Aldehyde_to_nitril_conversion.png/500px-Aldehyde_to_nitril_conversion.png" decoding="async" width="500" height="111" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/c/c7/Aldehyde_to_nitril_conversion.png 1.5x" data-file-width="653" data-file-height="145" /></a><figcaption>醛由一锅法制备腈</figcaption></figure></dd></dl> <ul><li>从<a href="/wiki/%E8%8A%B3%E9%A6%99%E7%BE%A7%E9%85%B8" class="mw-redirect" title="芳香羧酸">芳香羧酸</a>合成腈(<a href="/wiki/Letts%E8%85%88%E5%90%88%E6%88%90" title="Letts腈合成">Letts腈合成</a>)。</li> <li>在<a href="/wiki/Sandmeyer%E5%8F%8D%E5%BA%94" class="mw-redirect" title="Sandmeyer反应">Sandmeyer反应</a>中，芳香腈从<a href="/wiki/%E5%81%B6%E6%B0%AE%E5%8C%96%E5%90%88%E7%89%A9" class="mw-redirect" title="偶氮化合物">偶氮化合物</a>合成。</li> <li>一个引入氰基的商业化试剂：<a href="/w/index.php?title=%E6%B0%B0%E5%9F%BA%E4%BA%8C%E4%B9%99%E5%9F%BA%E9%93%9D&action=edit&redlink=1" class="new" title="氰基二乙基铝（页面不存在）">氰基二乙基铝</a>（Et<sub>2</sub>AlCN）可以通过<a href="/wiki/%E4%B8%89%E4%B9%99%E5%9F%BA%E9%93%9D" title="三乙基铝">三乙基铝</a>和HCN合成。<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup>.这个试剂被用于对<a href="/wiki/%E9%85%AE" title="酮">酮</a>类的<a href="/wiki/%E4%BA%B2%E6%A0%B8%E5%8A%A0%E6%88%90%E5%8F%8D%E5%BA%94" title="亲核加成反应">亲核加成反应</a>。<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> 例如其应用：<a href="/w/index.php?title=Kuwajima%E7%B4%AB%E6%9D%89%E9%86%87%E5%85%A8%E5%90%88%E6%88%90&action=edit&redlink=1" class="new" title="Kuwajima紫杉醇全合成（页面不存在）">Kuwajima紫杉醇全合成</a>。</li> <li>氰离子很容易让二溴化合物发生偶联反应。α,α'-二溴<a href="/wiki/%E5%B7%B1%E4%BA%8C%E9%85%B8" title="己二酸">己二酸</a>与<a href="/wiki/%E6%B0%B0%E5%8C%96%E9%92%A0" title="氰化钠">氰化钠</a>在<a href="/wiki/%E4%B9%99%E9%86%87" title="乙醇">乙醇</a>当中反应得到氰基<a href="/wiki/%E7%8E%AF%E4%B8%81%E7%83%B7" title="环丁烷">环丁烷</a>:<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup></li></ul> <dl><dd><figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Cyclobutane_by_cyanide_mediated_dibromide_coupling.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/26/Cyclobutane_by_cyanide_mediated_dibromide_coupling.svg/400px-Cyclobutane_by_cyanide_mediated_dibromide_coupling.svg.png" decoding="async" width="400" height="242" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/26/Cyclobutane_by_cyanide_mediated_dibromide_coupling.svg/600px-Cyclobutane_by_cyanide_mediated_dibromide_coupling.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/26/Cyclobutane_by_cyanide_mediated_dibromide_coupling.svg/800px-Cyclobutane_by_cyanide_mediated_dibromide_coupling.svg.png 2x" data-file-width="900" data-file-height="545" /></a><figcaption>氰基诱导的偶联反应</figcaption></figure></dd></dl> <dl><dd>在<a href="/w/index.php?title=Franchimont%E5%8F%8D%E5%BA%94&action=edit&redlink=1" class="new" title="Franchimont反应（页面不存在）">Franchimont反应</a>（A. P. N. Franchimont，1872年）中，一个α－溴代羧酸在氰基水解和脱羧反应后发生了二聚反应。<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup></dd></dl> <ul><li>芳香腈可以通过三氯甲基芳基亚胺(RC(CCl<sub>3</sub>)=NH)的碱性水解来合成，即<a href="/w/index.php?title=Houben-Fischer%E5%90%88%E6%88%90&action=edit&redlink=1" class="new" title="Houben-Fischer合成（页面不存在）">Houben-Fischer合成</a>。<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup></li></ul> <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=%E8%85%88&action=edit&section=3" title="编辑章节：反应"><span>编辑</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>氰基基团可以在不同的的条件和试剂中进行不同的反应，包括：水解反应、氢化反应、还原反应或者成为离去基团（氰基）而进行取代反应。 </p> <div class="mw-heading mw-heading3"><h3 id="水解反应"><span id=".E6.B0.B4.E8.A7.A3.E5.8F.8D.E5.BA.94"></span>水解反应</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E8%85%88&action=edit&section=4" title="编辑章节：水解反应"><span>编辑</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>水解腈RCN在酸性或者碱性条件下会经过不同的水解历程，得到<a href="/wiki/%E9%85%B0%E8%83%BA" title="酰胺">酰胺</a> RC(=O)NH<sub>2</sub>然后继续水解再得到羧酸RCOOH。腈的水解被普遍认为是制备羧酸的最佳方法之一。然而这些酸、碱催化的反应对于制备酰胺都有一定的局限性。主要的局限性在于：无论是酸或碱催化的反应，最终中和过程会导致大量的氰盐生成，从而引起<a href="/wiki/%E6%B1%A1%E6%9F%93" title="污染">污染</a>问题。 </p><p>腈完全水解的方程式为：<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p> <dl><dd>RCN + 2 H<sub>2</sub>O + HCl —<sup><u>Δ</u></sup>→ RCOOH + NH<sub>4</sub>Cl</dd> <dd>RCN + H<sub>2</sub>O + NaOH —<sup><u>Δ</u></sup>→ RCOONa + NH<sub>3</sub></dd></dl> <div class="mw-heading mw-heading3"><h3 id="还原反应"><span id=".E8.BF.98.E5.8E.9F.E5.8F.8D.E5.BA.94"></span>还原反应</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E8%85%88&action=edit&section=5" title="编辑章节：还原反应"><span>编辑</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>在<a href="/wiki/%E6%9C%89%E6%9C%BA%E8%BF%98%E5%8E%9F%E5%8F%8D%E5%BA%94" class="mw-redirect" title="有机还原反应">有机还原反应</a>中，腈通过氢气和<a href="/wiki/%E9%95%8D" title="镍">镍</a><a href="/wiki/%E5%82%AC%E5%8C%96%E5%89%82" title="催化剂">催化剂</a>进行还原，产物是一个氨。（参见<a href="/w/index.php?title=%E8%85%88%E7%9A%84%E8%BF%98%E5%8E%9F&action=edit&redlink=1" class="new" title="腈的还原（页面不存在）">腈的还原</a>）。腈还原成亚胺然后进行水解反应得到<a href="/wiki/%E9%86%9B" title="醛">醛</a>，即<a href="/wiki/Stephen%E9%86%9B%E5%90%88%E6%88%90" class="mw-redirect" title="Stephen醛合成">Stephen醛合成</a>。 </p> <div class="mw-heading mw-heading3"><h3 id="亲核反应"><span id=".E4.BA.B2.E6.A0.B8.E5.8F.8D.E5.BA.94"></span>亲核反应</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E8%85%88&action=edit&section=6" title="编辑章节：亲核反应"><span>编辑</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>氰基碳原子是一个亲核中心，因此可以发生亲核加成反应： </p> <ul><li>和<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>发生<a href="/wiki/Blaise%E5%8F%8D%E5%BA%94" class="mw-redirect" title="Blaise反应">Blaise反应</a>。</li> <li>和<a href="/wiki/%E9%86%87" title="醇">醇</a>发生<a href="/wiki/Pinner%E5%8F%8D%E5%BA%94" class="mw-redirect" title="Pinner反应">Pinner反应</a>。</li> <li>类似的反应：<a href="/wiki/%E8%83%BA" title="胺">胺</a>、<a href="/wiki/%E8%82%8C%E6%B0%A8%E9%85%B8" title="肌氨酸">肌氨酸</a>和<a href="/wiki/%E6%B0%A8%E8%85%88" class="mw-redirect" title="氨腈">氨腈</a>反应得到<a href="/wiki/%E8%82%8C%E9%85%B8" title="肌酸">肌酸</a>。<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup></li> <li>腈通过<a href="/wiki/Houben-Hoesch%E5%8F%8D%E5%BA%94" class="mw-redirect" title="Houben-Hoesch反应">Houben-Hoesch反应</a>得到<a href="/wiki/%E9%85%AE" title="酮">酮</a>，该反应机理就是<a href="/wiki/%E5%82%85%EF%BC%8D%E5%85%8B%E5%8F%8D%E5%BA%94" class="mw-redirect" title="傅－克反应">Friedel-Crafts酰化反应</a>。</li></ul> <div class="mw-heading mw-heading3"><h3 id="烷基化反应"><span id=".E7.83.B7.E5.9F.BA.E5.8C.96.E5.8F.8D.E5.BA.94"></span>烷基化反应</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E8%85%88&action=edit&section=7" title="编辑章节：烷基化反应"><span>编辑</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>去质子的氰基能作为强有力的亲核试剂而用于烷基化亲电试剂，这里关键在于氰基离子 CN 的较小位阻和它独特的稳定性。这些特性都使得高位阻碳－碳键的合成可以理想的通过腈中间体来达成，因此腈中间体广泛的应用于合成药物靶分子和医药原料。<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="杂记"><span id=".E6.9D.82.E8.AE.B0"></span>杂记</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E8%85%88&action=edit&section=8" title="编辑章节：杂记"><span>编辑</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li>在<a href="/w/index.php?title=%E8%BF%98%E5%8E%9F%E5%8E%BB%E6%B0%B0%E5%9F%BA%E5%8F%8D%E5%BA%94&action=edit&redlink=1" class="new" title="还原去氰基反应（页面不存在）">还原去氰基反应</a>（reductive decyanation）中，氰基被氢原子取代。<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> 如：用<a href="/wiki/HMPA" class="mw-redirect" title="HMPA">HMPA</a>和金属<a href="/wiki/%E9%92%BE" title="钾">钾</a>在<a href="/wiki/%E5%8F%94%E4%B8%81%E9%86%87" title="叔丁醇">叔丁醇</a>中发生<a href="/w/index.php?title=%E6%BA%B6%E8%A7%A3%E9%87%91%E5%B1%9E%E8%BF%98%E5%8E%9F%E5%8F%8D%E5%BA%94&action=edit&redlink=1" class="new" title="溶解金属还原反应（页面不存在）">溶解金属还原反应</a>。α-氨基腈可以通过<a href="/wiki/%E5%9B%9B%E6%B0%A2%E9%94%82%E9%93%9D" class="mw-redirect" title="四氢锂铝">四氢锂铝</a>去氰基。</li> <li>腈在碱性条件下可以发生自身的亲核加成反应，即<a href="/wiki/Thorpe%E5%8F%8D%E5%BA%94" class="mw-redirect" title="Thorpe反应">Thorpe反应</a>。</li> <li>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，腈对<a href="/wiki/%E7%82%94%E7%83%83" title="炔烃">炔烃</a>进行加成反应，称为<a href="/w/index.php?title=%E7%A2%B3%E6%B0%B0%E5%8C%96%E5%8F%8D%E5%BA%94&action=edit&redlink=1" class="new" title="碳氰化反应（页面不存在）">碳氰化反应</a>（carbocyanation）:<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup></li></ul> <dl><dd><figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Carbocyanation.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f7/Carbocyanation.png/600px-Carbocyanation.png" decoding="async" width="600" height="263" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f7/Carbocyanation.png/900px-Carbocyanation.png 1.5x, //upload.wikimedia.org/wikipedia/commons/f/f7/Carbocyanation.png 2x" data-file-width="994" data-file-height="435" /></a><figcaption>碳氰化反应 Nakao 2007</figcaption></figure></dd></dl> <div class="mw-heading mw-heading2"><h2 id="有机氨基腈"><span id=".E6.9C.89.E6.9C.BA.E6.B0.A8.E5.9F.BA.E8.85.88"></span>有机氨基腈</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E8%85%88&action=edit&section=9" title="编辑章节：有机氨基腈"><span>编辑</span></a><span class="mw-editsection-bracket">]</span></span></div> <div role="note" class="hatnote navigation-not-searchable">参见：<a href="/wiki/Von_Braun%E5%8F%8D%E5%BA%94" class="mw-redirect" title="Von Braun反应">von Braun反应</a></div> <p><a href="/w/index.php?title=%E6%B0%A8%E5%9F%BA%E8%85%88&action=edit&redlink=1" class="new" title="氨基腈（页面不存在）">氨基腈</a>（Cyanamides）是一种N－氰基的化合物，具有通式：R<sub>1</sub>R<sub>2</sub>N-CN，它相似于无机化合物<a href="/wiki/%E6%B0%B0%E8%83%BA" class="mw-redirect" title="氰胺">氰胺</a>(cyanamide)。 </p> <div class="mw-heading mw-heading2"><h2 id="腈氧化物"><span id=".E8.85.88.E6.B0.A7.E5.8C.96.E7.89.A9"></span>腈氧化物</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E8%85%88&action=edit&section=10" title="编辑章节：腈氧化物"><span>编辑</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/w/index.php?title=%E8%85%88%E6%B0%A7%E5%8C%96%E7%89%A9&action=edit&redlink=1" class="new" title="腈氧化物（页面不存在）">腈氧化物</a>具有通式R-CNO。 </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:Nitrile-oxide-2D-B.png" class="mw-file-description" title="General structure nitrile oxide"><img alt="General structure nitrile oxide" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d9/Nitrile-oxide-2D-B.png/200px-Nitrile-oxide-2D-B.png" decoding="async" width="200" height="63" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d9/Nitrile-oxide-2D-B.png/300px-Nitrile-oxide-2D-B.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d9/Nitrile-oxide-2D-B.png/400px-Nitrile-oxide-2D-B.png 2x" data-file-width="1100" data-file-height="345" /></a></span></dd></dl> <div class="mw-heading mw-heading2"><h2 id="参见"><span id=".E5.8F.82.E8.A7.81"></span>参见</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E8%85%88&action=edit&section=11" title="编辑章节：参见"><span>编辑</span></a><span class="mw-editsection-bracket">]</span></span></div> <div role="navigation" aria-label="Portals" class="noprint portal plainlist tright" style="margin:0.5em 0 0.5em 1em;border:solid #aaa 1px"> <ul 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href="/wiki/%E8%85%88%E9%92%A0" title="腈钠">腈钠</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="参考文献"><span id=".E5.8F.82.E8.80.83.E6.96.87.E7.8C.AE"></span>参考文献</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E8%85%88&action=edit&section=12" title="编辑章节：参考文献"><span>编辑</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="reflist references-column-width" style="-moz-column-width: 35em; -webkit-column-width: 35em; column-width: 35em; list-style-type: decimal;"> <ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><a href="/w/index.php?title=IUPAC_Gold_Book&action=edit&redlink=1" class="new" title="IUPAC Gold Book（页面不存在）">IUPAC Gold Book</a> <a rel="nofollow" class="external text" href="http://goldbook.iupac.org/N04151.html"><i>nitriles</i></a> （<a rel="nofollow" class="external text" href="//web.archive.org/web/20170325181035/http://goldbook.iupac.org/N04151.html">页面存档备份</a>，存于<a href="/wiki/%E4%BA%92%E8%81%94%E7%BD%91%E6%A1%A3%E6%A1%88%E9%A6%86" title="互联网档案馆">互联网档案馆</a>）</span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text">NCBI-MeSH <a rel="nofollow" class="external text" href="http://www.ncbi.nlm.nih.gov/mesh/68009570"><i>Nitriles</i></a> （<a rel="nofollow" class="external text" href="//web.archive.org/web/20210427121632/http://www.ncbi.nlm.nih.gov/mesh/68009570">页面存档备份</a>，存于<a href="/wiki/%E4%BA%92%E8%81%94%E7%BD%91%E6%A1%A3%E6%A1%88%E9%A6%86" title="互联网档案馆">互联网档案馆</a>）</span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text"><cite class="citation journal">David T. 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Soc.</a> <span style="font-size:85%;">(Communication)</span><span style="display:none;font-size:100%" class="error citation-comment">使用<code style="color:inherit; border:inherit; padding:inherit;">|format=</code>需要含有<code style="color:inherit; border:inherit; padding:inherit;">|url=</code> (<a href="/wiki/Help:%E5%BC%95%E6%96%87%E6%A0%BC%E5%BC%8F1%E9%94%99%E8%AF%AF#format_missing_url" title="Help:引文格式1错误">帮助</a>)</span>. 2007, <b>129</b> (9): 2428–2429. <a rel="nofollow" class="external text" href="//www.ncbi.nlm.nih.gov/pubmed/17295484"><span title="公共医学识别码">PMID 17295484</span></a>. <a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fja067364x"><span title="數位物件識別號">doi:10.1021/ja067364x</span></a>.</cite><span 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href="/wiki/%E5%9C%8B%E9%9A%9B%E7%B4%94%E5%8C%96%E5%AD%B8%E5%92%8C%E6%87%89%E7%94%A8%E5%8C%96%E5%AD%B8%E8%81%AF%E5%90%88%E6%9C%83" title="國際純化學和應用化學聯合會">國際純化學和應用化學聯合會</a>，<i><a href="/wiki/IUPAC%E5%91%BD%E5%90%8D%E6%B3%95#IUPAC顏色書" title="IUPAC命名法">化學術語概略</a></i>，第二版。（金皮書）(1997)。在線校正版: (2006–) "<a rel="nofollow" class="external text" href="https://goldbook.iupac.org/N04151.html">nitrile</a>"。<a href="/wiki/DOI" title="DOI">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1351%2Fgoldbook.N04151">10.1351/goldbook.N04151</a></li> <li><a href="/wiki/%E5%9C%8B%E9%9A%9B%E7%B4%94%E5%8C%96%E5%AD%B8%E5%92%8C%E6%87%89%E7%94%A8%E5%8C%96%E5%AD%B8%E8%81%AF%E5%90%88%E6%9C%83" title="國際純化學和應用化學聯合會">國際純化學和應用化學聯合會</a>，<i><a href="/wiki/IUPAC%E5%91%BD%E5%90%8D%E6%B3%95#IUPAC顏色書" title="IUPAC命名法">化學術語概略</a></i>，第二版。（金皮書）(1997)。在線校正版: (2006–) "<a rel="nofollow" class="external text" href="https://goldbook.iupac.org/C01486.html">cyanide</a>"。<a href="/wiki/DOI" 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style="width:100%;padding:0px"><div style="padding:0em 0.25em"> <ul><li><a href="/wiki/%E4%B9%99%E8%85%88" title="乙腈">乙腈</a>（CH<sub>3</sub>CN）</li> <li><a href="/wiki/%E4%B8%99%E8%85%88" title="丙腈">丙腈</a>（C<sub>2</sub>H<sub>5</sub>CN）</li> <li><a href="/wiki/%E4%B8%81%E8%85%88" title="丁腈">丁腈</a>（C<sub>3</sub>H<sub>7</sub>CN）(<a href="/wiki/%E6%AD%A3%E4%B8%81%E8%85%88" title="正丁腈">正丁腈</a>(CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CN)、<a href="/wiki/%E7%95%B0%E4%B8%81%E8%85%88" title="異丁腈">異丁腈</a> ((CH<sub>3</sub>)<sub>2</sub>CHCN) )</li> <li><a href="/w/index.php?title=%E6%88%8A%E8%85%88&action=edit&redlink=1" class="new" title="戊腈（页面不存在）">戊腈</a>（C<sub>4</sub>H<sub>9</sub>CN）(<a href="/wiki/%E6%96%B0%E6%88%8A%E8%85%88" title="新戊腈">新戊腈</a>((CH<sub>3</sub>)<sub>3</sub>CCN))</li> <li><a href="/w/index.php?title=%E5%B7%B1%E8%85%88&action=edit&redlink=1" class="new" title="己腈（页面不存在）">己腈</a>（C<sub>5</sub>H<sub>11</sub>CN）</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">双氰基饱和腈</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/%E4%B8%99%E4%BA%8C%E8%85%88" title="丙二腈">丙二腈</a>（CH<sub>2</sub>(CN)<sub>2</sub>）</li> <li><a href="/wiki/%E4%B8%81%E4%BA%8C%E8%85%88" title="丁二腈">丁二腈</a>（C<sub>2</sub>H<sub>4</sub>(CN)<sub>2</sub>）</li> <li><a href="/wiki/%E6%88%8A%E4%BA%8C%E8%85%88" title="戊二腈">戊二腈</a>（C<sub>3</sub>H<sub>6</sub>(CN)<sub>2</sub>）</li> <li><a href="/wiki/%E5%B7%B1%E4%BA%8C%E8%85%88" title="己二腈">己二腈</a>（C<sub>4</sub>H<sub>8</sub>(CN)<sub>2</sub>）</li> <li><a href="/wiki/%E5%BA%9A%E4%BA%8C%E8%85%88" title="庚二腈">庚二腈</a>（C<sub>5</sub>H<sub>10</sub>(CN)<sub>2</sub>）</li> <li><a href="/w/index.php?title=%E8%BE%9B%E4%BA%8C%E8%85%88&action=edit&redlink=1" class="new" title="辛二腈（页面不存在）">辛二腈</a>（C<sub>6</sub>H<sub>12</sub>(CN)<sub>2</sub>）</li> <li><a href="/w/index.php?title=%E5%A3%AC%E4%BA%8C%E8%85%88&action=edit&redlink=1" class="new" title="壬二腈（页面不存在）">壬二腈</a>（C<sub>7</sub>H<sub>14</sub>(CN)<sub>2</sub>）</li> <li><a href="/wiki/%E7%99%B8%E4%BA%8C%E8%85%88" title="癸二腈">癸二腈</a>（C<sub>8</sub>H<sub>16</sub>(CN)<sub>2</sub>）</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">不饱和腈</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0px"><div style="padding:0em 0.25em"> <ul><li><a href="/wiki/%E6%B0%B0%E5%9F%BA%E4%B9%99%E7%82%94" title="氰基乙炔">氰基乙炔</a>（HCCCN）</li> <li><a href="/wiki/%E4%B8%99%E7%83%AF%E8%85%88" title="丙烯腈">丙烯腈</a>（C<sub>2</sub>H<sub>3</sub>CN）</li> <li><a href="/wiki/%E7%8E%AF%E4%B8%99%E5%9F%BA%E8%85%88" title="环丙基腈">环丙基腈</a>（(CH<sub>2</sub>)<sub>2</sub>CHCN）</li> <li><a href="/w/index.php?title=%E4%B8%81%E7%83%AF%E8%85%88&action=edit&redlink=1" class="new" title="丁烯腈（页面不存在）">丁烯腈</a>（CH<sub>3</sub>CH=CHCN）</li> <li><a href="/w/index.php?title=%E7%83%AF%E4%B8%99%E5%9F%BA%E6%B0%B0&action=edit&redlink=1" class="new" title="烯丙基氰（页面不存在）">烯丙基氰</a>（CH<sub>2</sub>=CHCH<sub>2</sub>CN）</li> <li><a href="/wiki/%E8%8B%AF%E7%94%B2%E8%85%88" title="苯甲腈">苯甲腈</a>（PhCN）</li> <li><a href="/wiki/%E8%8B%AF%E4%B9%99%E8%85%88" title="苯乙腈">苯乙腈</a>（PhCH<sub>2</sub>CN）</li> <li><a href="/wiki/%E9%82%BB%E8%8B%AF%E4%BA%8C%E7%94%B2%E8%85%88" title="邻苯二甲腈">邻苯二甲腈</a></li> <li><a href="/wiki/%E9%96%93%E8%8B%AF%E4%BA%8C%E7%94%B2%E8%85%88" title="間苯二甲腈">間苯二甲腈</a></li> <li><a href="/wiki/%E5%AF%B9%E8%8B%AF%E4%BA%8C%E7%94%B2%E8%85%88" title="对苯二甲腈">对苯二甲腈</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">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/%E4%B8%89%E6%B0%B0%E5%9F%BA%E7%94%B2%E7%83%B7" title="三氰基甲烷">三氰基甲烷</a>（HC(CN)<sub>3</sub>）</li> <li><a href="/wiki/%E5%9B%9B%E6%B0%B0%E7%94%B2%E7%83%B7" class="mw-redirect" title="四氰甲烷">四氰甲烷</a>（C(CN)<sub>4</sub>）</li> <li><a href="/wiki/%E6%B0%B0%E4%B9%99%E9%85%B8" title="氰乙酸">氰乙酸</a>（C<sub>3</sub>H<sub>3</sub>NO<sub>2</sub>）</li> <li><a href="/wiki/%E5%AF%B9%E6%B0%B0%E5%9F%BA%E8%8B%AF%E7%94%B2%E9%85%B8" title="对氰基苯甲酸">对氰基苯甲酸</a>（NCC<sub>6</sub>H<sub>4</sub>COOH）</li> <li><a href="/wiki/%E4%B8%99%E9%85%AE%E6%B0%B0%E9%86%87" title="丙酮氰醇">丙酮氰醇</a>（C<sub>4</sub>H<sub>7</sub>NO）</li> <li><a href="/wiki/%E5%81%B6%E6%B0%AE%E4%BA%8C%E5%BC%82%E4%B8%81%E8%85%88" title="偶氮二异丁腈">偶氮二异丁腈</a>（C<sub>8</sub>H<sub>12</sub>N<sub>4</sub>）</li> <li><a href="/wiki/%E8%85%88%E9%92%A0" title="腈钠">腈钠</a>（RNaCHCN）</li> <li><a href="/wiki/%E4%B8%89%E6%B0%9F%E4%B9%99%E8%85%88" title="三氟乙腈">三氟乙腈</a>（CF<sub>3</sub>CN）</li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r84265675"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r84261037"></div><div role="navigation" class="navbox" aria-labelledby="有机官能团" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="collapsible-title navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r84265675"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r84244141"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:%E5%AE%98%E8%83%BD%E5%9B%A2" title="Template:官能团"><abbr title="查看该模板">查</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:%E5%AE%98%E8%83%BD%E5%9B%A2" title="Template talk:官能团"><abbr title="讨论该模板">论</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:%E7%BC%96%E8%BE%91%E9%A1%B5%E9%9D%A2/Template:%E5%AE%98%E8%83%BD%E5%9B%A2" title="Special:编辑页面/Template:官能团"><abbr title="编辑该模板">编</abbr></a></li></ul></div><div id="有机官能团" style="font-size:110%;margin:0 5em">有机<a href="/wiki/%E5%AE%98%E8%83%BD%E5%9B%A2" title="官能团">官能团</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">碳氢</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0px"><div style="padding:0em 0.25em"> <ul><li><a href="/wiki/%E7%83%B7%E7%83%83" title="烷烃">烷烃</a></li> <li><a href="/wiki/%E7%83%B7%E5%9F%BA" title="烷基">烷基</a> <ul><li><a href="/wiki/%E7%94%B2%E5%9F%BA" title="甲基">甲基</a></li> <li><a href="/wiki/%E4%B9%99%E5%9F%BA" title="乙基">乙基</a></li> <li><a href="/wiki/%E4%B8%99%E5%9F%BA" title="丙基">丙基</a></li> <li><a href="/wiki/%E4%B8%81%E5%9F%BA" title="丁基">丁基</a></li> <li><a href="/wiki/%E6%88%8A%E5%9F%BA" title="戊基">戊基</a></li></ul></li> <li><a href="/wiki/%E7%B4%AF%E7%A7%AF%E4%BA%8C%E7%83%AF%E7%83%83" title="累积二烯烃">累积二烯烃</a></li> <li><a href="/wiki/%E7%83%AF%E7%83%83" title="烯烃">烯烃</a> <ul><li><a href="/wiki/%E4%B9%99%E7%83%AF%E5%9F%BA" title="乙烯基">乙烯基</a></li> <li><a href="/w/index.php?title=%E4%B8%99%E7%83%AF%E5%9F%BA&action=edit&redlink=1" class="new" title="丙烯基（页面不存在）">丙烯基</a></li> <li><a href="/wiki/%E7%83%AF%E4%B8%99%E5%9F%BA" title="烯丙基">烯丙基</a></li></ul></li> <li><a href="/wiki/%E7%82%94%E7%83%83" title="炔烃">炔烃</a> <ul><li><a href="/wiki/%E4%B9%99%E7%82%94%E5%9F%BA" title="乙炔基">乙炔基</a></li></ul></li> <li><a href="/wiki/%E8%8B%84%E5%9F%BA" title="苄基">苄基</a></li> <li><a href="/wiki/%E5%8D%A1%E5%AE%BE" title="卡宾">卡宾</a></li> <li><a href="/wiki/%E4%BA%9A%E7%94%B2%E5%9F%BA" title="亚甲基">亚甲基</a></li> <li><a href="/wiki/%E6%AC%A1%E7%94%B2%E5%9F%BA" title="次甲基">次甲基</a></li> <li><a href="/wiki/%E8%8B%AF%E5%9F%BA" title="苯基">苯基</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">碳氢氧</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%">一个氧</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%BE%9F%E5%9F%BA" title="羟基">羟基</a> <ul><li><a href="/wiki/%E9%86%87" title="醇">醇</a> <ul><li><a href="/wiki/%E7%BE%9F%E7%94%B2%E5%9F%BA" title="羟甲基">羟甲基</a></li></ul></li> <li><a href="/wiki/%E9%85%9A" title="酚">酚</a></li> <li><a href="/wiki/%E7%83%AF%E9%86%87" title="烯醇">烯醇</a></li> <li><a href="/wiki/%E7%82%94%E9%86%87" title="炔醇">炔醇</a></li></ul></li> <li><a href="/wiki/%E9%86%9A" title="醚">醚</a>与烃氧基 <ul><li><a href="/wiki/%E7%83%B7%E6%B0%A7%E5%9F%BA" title="烷氧基">烷氧基</a> <ul><li><a href="/wiki/%E7%94%B2%E6%B0%A7%E5%9F%BA" title="甲氧基">甲氧基</a></li></ul></li> <li><a href="/wiki/%E9%86%9A#命名" title="醚">烯氧基与芳烃氧基等</a></li> <li>一<a href="/wiki/%F0%AB%AB%87" title="𫫇">氧杂</a>环基与<a href="/wiki/%E7%8E%AF%E6%B0%A7%E5%8C%96%E5%90%88%E7%89%A9" title="环氧化合物">环氧基</a></li></ul></li> <li><a href="/wiki/%E9%85%B0%E5%9F%BA" title="酰基">酰基</a> <ul><li><a href="/wiki/%E4%B9%99%E9%85%B0%E5%9F%BA" title="乙酰基">乙酰基</a></li> <li><a href="/wiki/%E4%B8%99%E7%83%AF%E9%85%B0%E5%9F%BA" title="丙烯酰基">丙烯酰基</a></li> <li><a href="/wiki/%E8%8B%AF%E7%94%B2%E9%85%B0%E5%9F%BA" title="苯甲酰基">苯甲酰基</a></li></ul></li> <li><a href="/wiki/%E7%BE%B0%E5%9F%BA" title="羰基">羰基</a> <ul><li><a href="/wiki/%E9%86%9B" title="醛">醛</a></li> <li><a href="/wiki/%E9%85%AE" title="酮">酮</a></li> <li><a href="/wiki/%E7%83%AF%E9%85%AE" title="烯酮">烯酮</a></li> <li><a href="/wiki/%E7%82%94%E9%85%AE" title="炔酮">炔酮</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">两个氧</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%BE%A7%E5%9F%BA" title="羧基">羧基</a></li> <li><a href="/wiki/%E4%B9%99%E9%85%B0%E6%B0%A7%E5%9F%BA" title="乙酰氧基">乙酰氧基</a></li> <li><a href="/wiki/%E9%85%AF" title="酯">酯</a></li> <li>二<a href="/wiki/%F0%AB%AB%87" title="𫫇">氧杂</a>环基与<a href="/wiki/%E4%BA%9E%E7%94%B2%E4%BA%8C%E6%B0%A7%E5%9F%BA" title="亞甲二氧基">亞甲二氧基</a></li> <li><a href="/wiki/%E6%9C%89%E6%9C%BA%E8%BF%87%E6%B0%A7%E5%8C%96%E7%89%A9" title="有机过氧化物">有机过氧化物</a> <ul><li><a href="/wiki/%E8%BF%87%E6%B0%A7%E5%8C%96%E9%85%AE" title="过氧化酮">过氧化酮</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">三个氧</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%85%B8%E9%85%90" title="酸酐">酸酐</a></li> <li><a href="/wiki/%E8%BF%87%E6%B0%A7%E9%85%B8" title="过氧酸">过氧酸</a></li> <li>三<a href="/wiki/%F0%AB%AB%87" title="𫫇">氧杂</a>环基</li> <li><a href="/wiki/%E5%8E%9F%E9%85%B8%E9%85%AF" title="原酸酯">原酸酯</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">除碳氢氧外<br /><u>仅一种</u>元素</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%">氮</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%">无氧</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%83%BA" title="胺">胺</a></li> <li><a href="/wiki/%E7%83%AF%E8%83%BA" title="烯胺">烯胺</a></li> <li><a href="/wiki/%E5%81%B6%E6%B0%AE%E5%8C%96%E7%89%A9" title="偶氮化物">偶氮化物</a></li> <li><a href="/wiki/%E4%BA%9A%E8%83%BA" title="亚胺">亚胺</a></li> <li><a href="/wiki/%E8%85%99" title="腙">腙</a></li> <li><a class="mw-selflink selflink">腈</a></li> <li><a href="/wiki/%E8%83%8D" title="胍">胍</a></li> <li><a href="/wiki/%E5%BC%82%E8%85%88" title="异腈">异腈</a></li> <li><a href="/wiki/%E5%93%8C%E5%95%B6" title="哌啶">哌啶</a></li> <li><a href="/wiki/%E5%90%A1%E5%95%B6" title="吡啶">吡啶</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">有氧</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/%E6%B0%B0%E9%85%B8%E7%9B%90" title="氰酸盐">氰酸酯</a></li> <li><a href="/wiki/%E5%B0%BF%E7%B4%A0" title="尿素">尿素</a></li> <li><a href="/wiki/%E8%82%9F" title="肟">肟</a></li> <li><a href="/wiki/%E7%BE%9F%E8%83%BA" title="羟胺">羟胺</a></li> <li><a href="/wiki/%E9%85%B0%E8%83%BA" title="酰胺">酰胺</a> <ul><li><a href="/wiki/%E9%85%B0%E4%BA%9A%E8%83%BA" title="酰亚胺">酰亚胺</a></li></ul></li> <li><a href="/wiki/%E5%BC%82%E6%B0%B0%E9%85%B8%E9%85%AF" title="异氰酸酯">异氰酸酯</a></li> <li><a href="/wiki/%E7%A1%9D%E5%9F%BA%E5%8C%96%E5%90%88%E7%89%A9" title="硝基化合物">硝基化合物</a></li> <li><a href="/wiki/%E4%BA%9A%E7%A1%9D%E5%9F%BA%E5%8C%96%E5%90%88%E7%89%A9" title="亚硝基化合物">亚硝基化合物</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">磷</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%86%A6%E9%85%B8%E9%85%AF" title="膦酸酯">膦酸酯</a></li> <li><a href="/wiki/%E4%BA%9E%E8%86%A6%E9%85%B8%E4%BA%8C%E9%85%AF" title="亞膦酸二酯">亞膦酸二酯</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">硫</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%">二价</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%A1%AB%E9%86%9A" title="硫醚">硫醚</a></li> <li><a href="/wiki/%E9%9B%99%E7%A1%AB%E9%8D%B5" title="雙硫鍵">二硫醚</a></li> <li><a href="/wiki/%E7%A1%AB%E9%86%87" title="硫醇">硫醇</a></li> <li><a href="/wiki/%E7%A1%AB%E9%85%AF" title="硫酯">硫酯</a></li> <li><a href="/wiki/%E7%A1%AB%E8%84%B2" title="硫脲">硫脲</a></li> <li><a href="/wiki/%E7%A1%AB%E4%BB%A3%E7%BE%A7%E9%85%B8" title="硫代羧酸">硫代羧酸</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">四价</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/%E4%BA%9A%E7%A0%9C" title="亚砜">亚砜</a></li> <li><a href="/wiki/%E4%BA%9E%E7%A1%AB%E9%85%B8%E9%85%AF" title="亞硫酸酯">亞硫酸酯</a></li> <li><a href="/wiki/%E4%BA%9A%E7%A3%BA%E9%85%B8" title="亚磺酸">亚磺酸</a></li> <li><a href="/wiki/%E6%AC%A1%E7%A3%BA%E9%85%B8" title="次磺酸">次磺酸</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">六价</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%A0%9C" title="砜">砜</a></li> <li><a href="/wiki/%E7%A3%BA%E9%85%B8" title="磺酸">磺酸</a></li> <li><a href="/wiki/%E7%A1%AB%E9%85%B8%E9%85%AF" title="硫酸酯">硫酸酯</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">硒</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%A1%92%E9%86%87" title="硒醇">硒醇</a></li> <li><a href="/w/index.php?title=%E7%A1%92%E9%85%B8%E9%85%AF&action=edit&redlink=1" class="new" title="硒酸酯（页面不存在）">硒酸酯</a></li> <li><a href="/wiki/%E7%A1%92%E9%85%AE" title="硒酮">硒酮</a></li> <li><a href="/wiki/%E6%9C%89%E6%9C%BA%E6%AC%A1%E7%A1%92%E9%85%B8" title="有机次硒酸">次硒酸</a></li> <li><a href="/wiki/%E6%9C%89%E6%9C%BA%E4%BA%9A%E7%A1%92%E9%85%B8" title="有机亚硒酸">亚硒酸</a></li> <li><a href="/wiki/%E6%9C%89%E6%9C%BA%E7%A1%92%E9%85%B8" title="有机硒酸">硒酸</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">碲</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%A2%B2%E9%86%87" title="碲醇">碲醇</a></li> <li><a href="/wiki/%E7%A2%B2%E9%85%AE" title="碲酮">碲酮</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">卤素</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%8D%A4%E4%BB%A3%E7%83%B7%E7%83%83" title="卤代烷烃">卤代烷烃</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">其他情况</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/%E5%BC%82%E7%A1%AB%E6%B0%B0%E9%85%B8%E9%85%AF" title="异硫氰酸酯">异硫氰酸酯</a></li> <li><a href="/wiki/%E7%A1%AB%E6%B0%B0%E9%85%B8%E9%85%AF" title="硫氰酸酯">硫氰酸酯</a></li> <li><a href="/wiki/%E7%A1%92%E6%B0%B0%E9%85%B8%E9%85%AF" title="硒氰酸酯">硒氰酸酯</a></li> <li><a href="/wiki/%E6%9C%89%E6%9C%BA%E7%A1%BC%E9%85%B8" title="有机硼酸">硼酸</a></li> <li><a href="/w/index.php?title=%E7%A1%BC%E9%85%B8%E9%85%AF&action=edit&redlink=1" class="new" title="硼酸酯（页面不存在）">硼酸酯</a></li> <li><span class="ilh-all" data-orig-title="磷酰胺" data-lang-code="en" data-lang-name="英语" data-foreign-title="phosphoramides"><span class="ilh-page"><a href="/w/index.php?title=%E7%A3%B7%E9%85%B0%E8%83%BA&action=edit&redlink=1" class="new" title="磷酰胺（页面不存在）">磷酰胺</a></span><span class="noprint ilh-comment">（<span class="ilh-lang">英语</span><span class="ilh-colon">：</span><span class="ilh-link"><a href="https://en.wikipedia.org/wiki/phosphoramides" class="extiw" title="en:phosphoramides"><span lang="en" dir="auto">phosphoramides</span></a></span>）</span></span></li> <li><a href="/wiki/%E7%A3%BA%E9%85%B0%E8%83%BA" title="磺酰胺">磺酰胺</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div>另见：<span class="ilh-all" data-orig-title="化学分类" data-lang-code="en" data-lang-name="英语" data-foreign-title="Chemical classification"><span class="ilh-page"><a href="/w/index.php?title=%E5%8C%96%E5%AD%A6%E5%88%86%E7%B1%BB&action=edit&redlink=1" class="new" title="化学分类（页面不存在）">化学分类</a></span><span class="noprint ilh-comment">（<span class="ilh-lang">英语</span><span class="ilh-colon">：</span><span class="ilh-link"><a href="https://en.wikipedia.org/wiki/Chemical_classification" class="extiw" title="en:Chemical classification"><span lang="en" dir="auto">Chemical classification</span></a></span>）</span></span><span style="white-space:nowrap; font-weight:bold;"> ·</span> <a href="/wiki/%E5%8C%96%E5%AD%A6%E5%91%BD%E5%90%8D%E6%B3%95" class="mw-redirect" title="化学命名法">化学命名法</a>(<a href="/wiki/%E6%97%A0%E6%9C%BA%E5%8C%96%E5%AD%A6%E5%91%BD%E5%90%8D%E6%B3%95" title="无机化学命名法">无机物</a>、<a href="/wiki/IUPAC%E6%9C%89%E6%9C%BA%E7%89%A9%E5%91%BD%E5%90%8D%E6%B3%95" title="IUPAC有机物命名法">有机物</a>)<span style="white-space:nowrap; font-weight:bold;"> ·</span> <a href="/wiki/%E9%87%91%E5%B1%9E%E6%9C%89%E6%9C%BA%E5%8C%96%E5%90%88%E7%89%A9" class="mw-redirect" title="金属有机化合物">金属有机化合物</a></div></td></tr></tbody></table></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">检索自“<a dir="ltr" href="https://zh.wikipedia.org/w/index.php?title=腈&oldid=80250205">https://zh.wikipedia.org/w/index.php?title=腈&oldid=80250205</a>”</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div 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