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data-event-name="pinnable-header.vector-toc.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-toc.unpin">hide</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">(Top)</div> </a> </li> <li id="toc-Structure" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Structure"> <div class="vector-toc-text"> <span class="vector-toc-numb">1</span> <span>Structure</span> </div> </a> <ul id="toc-Structure-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Nomenclature_and_classification" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Nomenclature_and_classification"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Nomenclature and classification</span> </div> </a> <ul id="toc-Nomenclature_and_classification-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Synthesis_of_imines" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Synthesis_of_imines"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Synthesis of imines</span> </div> </a> <button aria-controls="toc-Synthesis_of_imines-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Synthesis of imines subsection</span> </button> <ul id="toc-Synthesis_of_imines-sublist" class="vector-toc-list"> <li id="toc-Carbonyl-amine_condensation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Carbonyl-amine_condensation"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Carbonyl-amine condensation</span> </div> </a> <ul id="toc-Carbonyl-amine_condensation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-From_nitriles" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#From_nitriles"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>From nitriles</span> </div> </a> <ul id="toc-From_nitriles-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Specialized_methods" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Specialized_methods"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.3</span> <span>Specialized methods</span> </div> </a> <ul id="toc-Specialized_methods-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Reactions" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Reactions</span> </div> </a> <button aria-controls="toc-Reactions-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Reactions subsection</span> </button> <ul id="toc-Reactions-sublist" class="vector-toc-list"> <li id="toc-Hydrolysis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Hydrolysis"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>Hydrolysis</span> </div> </a> <ul id="toc-Hydrolysis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Precursors_to_heterocycles" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Precursors_to_heterocycles"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2</span> <span>Precursors to heterocycles</span> </div> </a> <ul id="toc-Precursors_to_heterocycles-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Acid-base_reactions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Acid-base_reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.3</span> <span>Acid-base reactions</span> </div> </a> <ul id="toc-Acid-base_reactions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Lewis_acid-base_reactions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Lewis_acid-base_reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.4</span> <span>Lewis acid-base reactions</span> </div> </a> <ul id="toc-Lewis_acid-base_reactions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Nucleophilic_additions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Nucleophilic_additions"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.5</span> <span>Nucleophilic additions</span> </div> </a> <ul id="toc-Nucleophilic_additions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Imine_reductions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Imine_reductions"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.6</span> <span>Imine reductions</span> </div> </a> <ul id="toc-Imine_reductions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Polymerisation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Polymerisation"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.7</span> <span>Polymerisation</span> </div> </a> <ul id="toc-Polymerisation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Miscellaneous_reactions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Miscellaneous_reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.8</span> <span>Miscellaneous reactions</span> </div> </a> <ul id="toc-Miscellaneous_reactions-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Biological_role" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Biological_role"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Biological role</span> </div> </a> <ul id="toc-Biological_role-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" title="Table of Contents" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon 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Available in 34 languages" > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-34" 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">34 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%A5%D9%8A%D9%85%D9%8A%D9%86" title="إيمين – Arabic" lang="ar" hreflang="ar" data-title="إيمين" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Imina" title="Imina – Catalan" lang="ca" hreflang="ca" data-title="Imina" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Iminy" title="Iminy – Czech" lang="cs" hreflang="cs" data-title="Iminy" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Imin" title="Imin – Danish" lang="da" hreflang="da" data-title="Imin" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Imine" title="Imine – German" lang="de" hreflang="de" data-title="Imine" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Imiinid" title="Imiinid – Estonian" lang="et" hreflang="et" data-title="Imiinid" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%99%CE%BC%CE%AF%CE%BD%CE%B5%CF%82" title="Ιμίνες – Greek" lang="el" hreflang="el" data-title="Ιμίνες" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Imina" title="Imina – Spanish" lang="es" hreflang="es" data-title="Imina" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Imina" title="Imina – Basque" lang="eu" hreflang="eu" data-title="Imina" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A7%DB%8C%D9%85%DB%8C%D9%86" title="ایمین – Persian" lang="fa" hreflang="fa" data-title="ایمین" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Imine" title="Imine – French" lang="fr" hreflang="fr" data-title="Imine" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Imina" title="Imina – Galician" lang="gl" hreflang="gl" data-title="Imina" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%9D%B4%EB%AF%BC_(%ED%99%94%ED%95%99)" title="이민 (화학) – Korean" lang="ko" hreflang="ko" data-title="이민 (화학)" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Imini" title="Imini – Croatian" lang="hr" hreflang="hr" data-title="Imini" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Imina" title="Imina – Indonesian" lang="id" hreflang="id" data-title="Imina" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Immine" title="Immine – Italian" lang="it" hreflang="it" data-title="Immine" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%90%D7%99%D7%9E%D7%99%D7%9F" title="אימין – Hebrew" lang="he" hreflang="he" data-title="אימין" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%98%D0%BC%D0%B8%D0%BD%D0%B4%D0%B5%D1%80" title="Иминдер – Kazakh" lang="kk" hreflang="kk" data-title="Иминдер" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Imin" title="Imin – Hungarian" lang="hu" hreflang="hu" data-title="Imin" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%98%D0%BC%D0%B8%D0%BD" title="Имин – Macedonian" lang="mk" hreflang="mk" data-title="Имин" data-language-autonym="Македонски" data-language-local-name="Macedonian" 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/Imine" title="Imine – Dutch" lang="nl" hreflang="nl" data-title="Imine" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%A4%E3%83%9F%E3%83%B3" title="イミン – Japanese" lang="ja" hreflang="ja" data-title="イミン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Iminy" title="Iminy – Polish" lang="pl" hreflang="pl" data-title="Iminy" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Imina" title="Imina – Portuguese" lang="pt" hreflang="pt" data-title="Imina" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Imin%C4%83" title="Imină – Romanian" lang="ro" hreflang="ro" data-title="Imină" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%98%D0%BC%D0%B8%D0%BD%D1%8B" title="Имины – Russian" lang="ru" hreflang="ru" data-title="Имины" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Imin" title="Imin – Slovenian" lang="sl" hreflang="sl" data-title="Imin" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Imin" title="Imin – Serbian" lang="sr" hreflang="sr" data-title="Imin" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Imin" title="Imin – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Imin" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Imiinit" title="Imiinit – Finnish" lang="fi" hreflang="fi" data-title="Imiinit" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Imin" title="Imin – Swedish" lang="sv" hreflang="sv" data-title="Imin" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/%C4%B0min" title="İmin – Turkish" lang="tr" hreflang="tr" data-title="İmin" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%86%D0%BC%D1%96%D0%BD%D0%B8" title="Іміни – Ukrainian" lang="uk" hreflang="uk" data-title="Іміни" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E4%BA%9A%E8%83%BA" title="亚胺 – Chinese" lang="zh" hreflang="zh" data-title="亚胺" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</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/Q408057#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</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="Namespaces"> <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 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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">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Organic compound or functional group containing a C=N bond</div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Imine_general_structure_B.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b4/Imine_general_structure_B.svg/150px-Imine_general_structure_B.svg.png" decoding="async" width="150" height="163" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b4/Imine_general_structure_B.svg/225px-Imine_general_structure_B.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b4/Imine_general_structure_B.svg/300px-Imine_general_structure_B.svg.png 2x" data-file-width="512" data-file-height="556" /></a><figcaption>The general structure of an imine</figcaption></figure> <p>In <a href="/wiki/Organic_chemistry" title="Organic chemistry">organic chemistry</a>, an <b>imine</b> (<span class="rt-commentedText nowrap"><span class="IPA nopopups noexcerpt" lang="en-fonipa"><a href="/wiki/Help:IPA/English" title="Help:IPA/English">/<span style="border-bottom:1px dotted"><span title="/ɪ/: 'i' in 'kit'">ɪ</span><span title="/ˈ/: primary stress follows">ˈ</span><span title="'m' in 'my'">m</span><span title="/iː/: 'ee' in 'fleece'">iː</span><span title="'n' in 'nigh'">n</span></span>/</a></span></span> or <span class="rt-commentedText nowrap"><span class="IPA nopopups noexcerpt" lang="en-fonipa"><a href="/wiki/Help:IPA/English" title="Help:IPA/English">/<span style="border-bottom:1px dotted"><span title="/ˈ/: primary stress follows">ˈ</span><span title="/ɪ/: 'i' in 'kit'">ɪ</span><span title="'m' in 'my'">m</span><span title="/ɪ/: 'i' in 'kit'">ɪ</span><span title="'n' in 'nigh'">n</span></span>/</a></span></span>) is a <a href="/wiki/Functional_group" title="Functional group">functional group</a> or <a href="/wiki/Organic_compound" title="Organic compound">organic compound</a> containing a <a href="/wiki/Carbon" title="Carbon">carbon</a>–<a href="/wiki/Nitrogen" title="Nitrogen">nitrogen</a> <a href="/wiki/Double_bond" title="Double bond">double bond</a> (<style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">C=N</span>). The nitrogen atom can be attached to a <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a> or an organic group (R). The carbon atom has two additional <a href="/wiki/Single_bond" title="Single bond">single bonds</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><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> Imines are common in synthetic and naturally occurring compounds and they participate in many reactions.<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> </p><p>Distinction is sometimes made between aldimines and ketimines, derived from aldehydes and ketones, respectively. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Structure">Structure</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Imine&action=edit&section=1" title="Edit section: Structure"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In imines the five core atoms (C<sub>2</sub>C=NX, ketimine; and C(H)C=NX, aldimine; X = H or C) are coplanar. Planarity results from the sp<sup>2</sup>-hybridization of the mutually <a href="/wiki/Double-bond" class="mw-redirect" title="Double-bond">double-bonded</a> carbon and the nitrogen atoms. The C=N distance is 1.29–1.31 Å for nonconjugated imines and 1.35 Å for conjugated imines. By contrast, C−N distances in <a href="/wiki/Amine" title="Amine">amines</a> and <a href="/wiki/Nitrile" title="Nitrile">nitriles</a> are 1.47 and 1.16 Å respectively.<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> Rotation about the C=N bond is slow. Using <a href="/wiki/NMR_spectroscopy" class="mw-redirect" title="NMR spectroscopy">NMR spectroscopy</a>, both <a href="/wiki/E%E2%80%93Z_notation" title="E–Z notation"><i>E</i> and <i>Z</i> isomers</a> of aldimines have been detected. Owing to steric effects, the <i>E</i> isomer is favored.<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="Nomenclature_and_classification">Nomenclature and classification</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Imine&action=edit&section=2" title="Edit section: Nomenclature and classification"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The term "imine" was coined in 1883 by the German chemist <a href="/wiki/Albert_Ladenburg" title="Albert Ladenburg">Albert Ladenburg</a>.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p><p>Usually imines refer to compounds with the general formula R<sub>2</sub>C=NR, as discussed below.<sup id="cite_ref-Fletcher_7-0" class="reference"><a href="#cite_note-Fletcher-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> In the older literature, imine refers to the <i>aza</i>-analogue of an <a href="/wiki/Epoxide" title="Epoxide">epoxide</a>. Thus, <i>ethylenimine</i> is the three-membered ring species <a href="/wiki/Aziridine" title="Aziridine">aziridine</a> C<sub>2</sub>H<sub>4</sub>NH.<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> The relationship of <b>im</b>ines to <b>am</b>ines having double and single bonds can be correlated with <a href="/wiki/Imide" title="Imide"><b>im</b>ides</a> and <a href="/wiki/Amide" title="Amide"><b>am</b>ides</a>, as in <a href="/wiki/Succinimide" title="Succinimide">succinimide</a> vs <a href="/wiki/Acetamide" title="Acetamide">acetamide</a>. </p><p>Imines are related to <a href="/wiki/Ketone" title="Ketone">ketones</a> and <a href="/wiki/Aldehyde" title="Aldehyde">aldehydes</a> by replacement of the oxygen with an NR group. When R = H, the compound is a primary imine, when R is <a href="/wiki/Hydrocarbyl" class="mw-redirect" title="Hydrocarbyl">hydrocarbyl</a>, the compound is a secondary imine. If this group is <i>not</i> a hydrogen atom, then the compound can sometimes be referred to as a <a href="/wiki/Schiff_base" title="Schiff base">Schiff base</a>.<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> When R<sup>3</sup> is OH, the imine is called an <a href="/wiki/Oxime" title="Oxime">oxime</a>, and when R<sup>3</sup> is NH<sub>2</sub> the imine is called a <a href="/wiki/Hydrazone" title="Hydrazone">hydrazone</a>. </p><p>A primary imine in which C is attached to both a hydrocarbyl and a H (derived from an aldehyde) is called a <b>primary aldimine</b>; a secondary imine with such groups is called a <b>secondary aldimine</b>.<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> A primary imine in which C is attached to two hydrocarbyls (derived from a ketone) is called a <b>primary ketimine</b>; a secondary imine with such groups is called a <b>secondary ketimine</b>.<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> </p> <ul class="gallery mw-gallery-traditional"> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Aldimine-(primary)-skeletal.svg" class="mw-file-description" title="Primary aldimine, E-isomer"><img alt="Primary aldimine, E-isomer" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7f/Aldimine-%28primary%29-skeletal.svg/103px-Aldimine-%28primary%29-skeletal.svg.png" decoding="async" width="103" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/7f/Aldimine-%28primary%29-skeletal.svg/155px-Aldimine-%28primary%29-skeletal.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/7f/Aldimine-%28primary%29-skeletal.svg/206px-Aldimine-%28primary%29-skeletal.svg.png 2x" data-file-width="512" data-file-height="596" /></a></span></div> <div class="gallerytext">Primary aldimine, <a href="/wiki/Cis-trans_isomer#E–Z_notation" class="mw-redirect" title="Cis-trans isomer">E-isomer</a></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Aldimine-(secondary)-skeletal.svg" class="mw-file-description" title="Secondary aldimine, E-isomer"><img alt="Secondary aldimine, E-isomer" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0e/Aldimine-%28secondary%29-skeletal.svg/110px-Aldimine-%28secondary%29-skeletal.svg.png" decoding="async" width="110" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0e/Aldimine-%28secondary%29-skeletal.svg/165px-Aldimine-%28secondary%29-skeletal.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0e/Aldimine-%28secondary%29-skeletal.svg/219px-Aldimine-%28secondary%29-skeletal.svg.png 2x" data-file-width="512" data-file-height="560" /></a></span></div> <div class="gallerytext">Secondary aldimine, E-isomer</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Imine-(primary)-skeletal.svg" class="mw-file-description" title="Primary ketimine"><img alt="Primary ketimine" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Imine-%28primary%29-skeletal.svg/110px-Imine-%28primary%29-skeletal.svg.png" decoding="async" width="110" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Imine-%28primary%29-skeletal.svg/165px-Imine-%28primary%29-skeletal.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Imine-%28primary%29-skeletal.svg/219px-Imine-%28primary%29-skeletal.svg.png 2x" data-file-width="512" data-file-height="560" /></a></span></div> <div class="gallerytext">Primary ketimine</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Imine-(secondary)-skeletal.svg" class="mw-file-description" title="Secondary ketimine"><img alt="Secondary ketimine" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/81/Imine-%28secondary%29-skeletal.svg/115px-Imine-%28secondary%29-skeletal.svg.png" decoding="async" width="115" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/81/Imine-%28secondary%29-skeletal.svg/173px-Imine-%28secondary%29-skeletal.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/81/Imine-%28secondary%29-skeletal.svg/231px-Imine-%28secondary%29-skeletal.svg.png 2x" data-file-width="512" data-file-height="533" /></a></span></div> <div class="gallerytext">Secondary ketimine</div> </li> </ul> <div style="clear:both;" class=""></div> <p><a href="/wiki/N-Sulfinyl_Imine" class="mw-redirect" title="N-Sulfinyl Imine">N-Sulfinyl imines</a> are a special class of imines having a sulfinyl group attached to the nitrogen atom. </p> <div class="mw-heading mw-heading2"><h2 id="Synthesis_of_imines">Synthesis of imines</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Imine&action=edit&section=3" title="Edit section: Synthesis of imines"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <dl><dd><figure class="mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Imine-synthesis.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/24/Imine-synthesis.svg/300px-Imine-synthesis.svg.png" decoding="async" width="300" height="53" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/24/Imine-synthesis.svg/450px-Imine-synthesis.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/24/Imine-synthesis.svg/600px-Imine-synthesis.svg.png 2x" data-file-width="512" data-file-height="91" /></a><figcaption>Imine synthesis from a primary amine and a carbonyl compound.</figcaption></figure></dd></dl> <div class="mw-heading mw-heading3"><h3 id="Carbonyl-amine_condensation">Carbonyl-amine condensation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Imine&action=edit&section=4" title="Edit section: Carbonyl-amine condensation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Alkylimino-de-oxo-bisubstitution" class="mw-redirect" title="Alkylimino-de-oxo-bisubstitution">Alkylimino-de-oxo-bisubstitution</a></div> <p>Imines are typically prepared by the condensation of primary amines and aldehydes.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> Ketones undergo similar reactions, but less commonly than aldehydes. In terms of mechanism, such reactions proceed via the <a href="/wiki/Nucleophilic_addition" title="Nucleophilic addition">nucleophilic addition</a> giving a <a href="/wiki/Hemiaminal" title="Hemiaminal">hemiaminal</a> -C(OH)(NHR)- intermediate, followed by an <a href="/wiki/Elimination_reaction" title="Elimination reaction">elimination</a> of water to yield the imine (see <a href="/wiki/Alkylimino-de-oxo-bisubstitution" class="mw-redirect" title="Alkylimino-de-oxo-bisubstitution">alkylimino-de-oxo-bisubstitution</a> for a detailed mechanism). The equilibrium in this reaction usually favors the <a href="/wiki/Carbonyl" class="mw-redirect" title="Carbonyl">carbonyl</a> compound and amine, so that <a href="/wiki/Azeotropic_distillation" title="Azeotropic distillation">azeotropic distillation</a> or use of a dehydrating agent, such as <a href="/wiki/Molecular_sieve" title="Molecular sieve">molecular sieves</a> or <a href="/wiki/Magnesium_sulfate" title="Magnesium sulfate">magnesium sulfate</a>, is required to favor of imine formation. In recent years, several reagents such as <a href="/wiki/Tris(2,2,2-trifluoroethyl)_borate" title="Tris(2,2,2-trifluoroethyl) borate">Tris(2,2,2-trifluoroethyl)borate</a> [B(OCH<sub>2</sub>CF<sub>3</sub>)<sub>3</sub>],<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> pyrrolidine<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> or <a href="/wiki/Titanium_ethoxide" title="Titanium ethoxide">titanium ethoxide</a> [Ti(OEt)<sub>4</sub>]<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> have been shown to catalyse imine formation. </p><p>Rarer than primary amines is the use of ammonia to give a primary imine.<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> In the case of hexafluoroacetone, the <a href="/wiki/Hemiaminal" title="Hemiaminal">hemiaminal</a> intermediate can be isolated.<sup id="cite_ref-OS_18-0" class="reference"><a href="#cite_note-OS-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="From_nitriles">From nitriles</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Imine&action=edit&section=5" title="Edit section: From nitriles"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Primary_(chemistry)" title="Primary (chemistry)">Primary</a> ketimines can be synthesized via a <a href="/wiki/Grignard_reaction" title="Grignard reaction">Grignard reaction</a> with a <a href="/wiki/Nitrile" title="Nitrile">nitrile</a>. This method is known as Moureu-Mignonac ketimine synthesis.<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> <sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> For example, <a href="/wiki/Benzophenone_imine" title="Benzophenone imine">benzophenone imine</a> can also be <a href="/wiki/Synthesis_(chemical)" class="mw-redirect" title="Synthesis (chemical)">synthesized</a> by addition of <a href="/wiki/Phenylmagnesium_bromide" title="Phenylmagnesium bromide">phenylmagnesium bromide</a> to <a href="/wiki/Benzonitrile" title="Benzonitrile">benzonitrile</a> followed by careful hydrolysis (lest the imine be hydrolyzed):<sup id="cite_ref-:0_22-0" class="reference"><a href="#cite_note-:0-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p> <dl><dd>C<sub>6</sub>H<sub>5</sub>CN + C<sub>6</sub>H<sub>5</sub>MgBr → (C<sub>6</sub>H<sub>5</sub>)<sub>2</sub>C=NMgBr</dd> <dd>(C<sub>6</sub>H<sub>5</sub>)<sub>2</sub>C=NMgBr + H<sub>2</sub>O → (C<sub>6</sub>H<sub>5</sub>)<sub>2</sub>C=NH + MgBr(OH)</dd></dl> <div class="mw-heading mw-heading3"><h3 id="Specialized_methods">Specialized methods</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Imine&action=edit&section=6" title="Edit section: Specialized methods"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Several other methods exist for the synthesis of imines. </p> <ul><li>Reaction of organic azides with metal carbenoids (produced from diazocarbonyl compounds).<sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup></li> <li>The reaction of <a href="/wiki/Ylide" title="Ylide">iminophosphoranes</a> and <a href="/wiki/Organic_azide" title="Organic azide">organic azides</a> in an <a href="/w/index.php?title=Aza-Wittig-reaction&action=edit&redlink=1" class="new" title="Aza-Wittig-reaction (page does not exist)">Aza-Wittig-reaction</a>.</li> <li>Condensation of <a href="/wiki/Carbon_acid" class="mw-redirect" title="Carbon acid">carbon acids</a> with <a href="/wiki/Nitroso" title="Nitroso">nitroso</a> compounds.</li> <li>The rearrangement of trityl N-haloamines in the <a href="/wiki/Stieglitz_rearrangement" title="Stieglitz rearrangement">Stieglitz rearrangement</a>.</li> <li>By reaction of <a href="/wiki/Alkene" title="Alkene">alkenes</a> with <a href="/wiki/Hydrazoic_acid" title="Hydrazoic acid">hydrazoic acid</a> in the <a href="/wiki/Schmidt_reaction" title="Schmidt reaction">Schmidt reaction</a>.</li> <li>By reaction of a nitrile, <a href="/wiki/Hydrochloric_acid" title="Hydrochloric acid">hydrochloric acid</a>, and an arene in the <a href="/wiki/Hoesch_reaction" title="Hoesch reaction">Hoesch reaction</a>.</li> <li>Multicomponent synthesis of 3-thiazolines in the <a href="/wiki/Asinger_reaction" title="Asinger reaction">Asinger reaction</a>.</li> <li><a href="/wiki/Thermal_decomposition" title="Thermal decomposition">Thermal decomposition</a> of <a href="/wiki/Oxime" title="Oxime">oximes</a>.<sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup></li></ul> <div class="mw-heading mw-heading2"><h2 id="Reactions">Reactions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Imine&action=edit&section=7" title="Edit section: Reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Hexafluoroacetone_imine.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/30/Hexafluoroacetone_imine.svg/150px-Hexafluoroacetone_imine.svg.png" decoding="async" width="150" height="116" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/30/Hexafluoroacetone_imine.svg/225px-Hexafluoroacetone_imine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/30/Hexafluoroacetone_imine.svg/300px-Hexafluoroacetone_imine.svg.png 2x" data-file-width="512" data-file-height="396" /></a><figcaption>Hexafluoroacetone imine is an unusual primary ketimine that is readily isolable.<sup id="cite_ref-OS_18-1" class="reference"><a href="#cite_note-OS-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup></figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Hydrolysis">Hydrolysis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Imine&action=edit&section=8" title="Edit section: Hydrolysis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The chief reaction of imines, often undesirable, is their hydrolysis back to the amine and the carbonyl precursor. </p> <dl><dd>R<sub>2</sub>C=NR' + H<sub>2</sub>O ⇌ R<sub>2</sub>C=O + R'NH<sub>2</sub></dd></dl> <div class="mw-heading mw-heading3"><h3 id="Precursors_to_heterocycles">Precursors to heterocycles</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Imine&action=edit&section=9" title="Edit section: Precursors to heterocycles"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Imines are widely used as intermediates in the synthesis of heterocycles. </p> <ul><li>Aromatic imines react with an <a href="/wiki/Enol_ether" title="Enol ether">enol ether</a> to a <a href="/wiki/Quinoline" title="Quinoline">quinoline</a> in the <a href="/wiki/Povarov_reaction" title="Povarov reaction">Povarov reaction</a>.</li> <li>Imines react, thermally, with <a href="/wiki/Ketenes" class="mw-redirect" title="Ketenes">ketenes</a> in [2+2] cycloadditions to form <a href="/wiki/%CE%92-lactams" class="mw-redirect" title="Β-lactams">β-lactams</a> in the <a href="/wiki/Staudinger_synthesis" title="Staudinger synthesis">Staudinger synthesis</a>.<sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> Several variants have been described.<sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-27" class="reference"><a href="#cite_note-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup></li> <li>Imine react with <a href="/wiki/Diene" title="Diene">dienes</a> in the <a href="/wiki/Imine_Diels%E2%80%93Alder_reaction" class="mw-redirect" title="Imine Diels–Alder reaction">Imine Diels-Alder reaction</a> to a tetrahydropyridine.</li> <li><a href="/wiki/Tosyl" class="mw-redirect" title="Tosyl">tosylimines</a> react with <a href="/wiki/%CE%91,%CE%B2-unsaturated_carbonyl_compound" class="mw-redirect" title="Α,β-unsaturated carbonyl compound">α,β-unsaturated carbonyl compound</a> to give <a href="/wiki/Allyl" class="mw-redirect" title="Allyl">allylic</a> <a href="/wiki/Amine" title="Amine">amines</a> in the <a href="/wiki/Aza-Baylis%E2%80%93Hillman_reaction" title="Aza-Baylis–Hillman reaction">Aza-Baylis–Hillman reaction</a>.</li></ul> <div class="mw-heading mw-heading3"><h3 id="Acid-base_reactions">Acid-base reactions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Imine&action=edit&section=10" title="Edit section: Acid-base reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Somewhat like the parent amines, imines are mildly basic and reversibly protonate to give <a href="/wiki/Iminium" title="Iminium">iminium</a> salts: </p> <dl><dd>R<sub>2</sub>C=NR' + H<sup>+</sup> <span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {<=>>}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-REL"> <mover> <mrow class="MJX-TeXAtom-OP MJX-fixedlimits"> <mstyle mathsize="0.85em"> <mrow class="MJX-TeXAtom-ORD"> <mpadded height="0" depth="0"> <mo stretchy="false">↽</mo> </mpadded> </mrow> </mstyle> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="false" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mspace width="negativethinmathspace" /> <mspace width="negativethinmathspace" /> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">⇀</mo> </mrow> </mstyle> </mrow> </mover> </mrow> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {<=>>}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/286de75351feddd1cbac5e7ebd53c4e682104d56" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: 0; margin-bottom: -0.338ex; width:3.358ex; height:2.676ex;" alt="{\displaystyle {\ce {<=>>}}}"></span> [R<sub>2</sub>C=NHR']<sup>+</sup></dd></dl> <p>Alternatively, primary imines are sufficiently acidic to allow N-alkylation, as illustrated with <a href="/wiki/Benzophenone_imine" title="Benzophenone imine">benzophenone imine</a>:<sup id="cite_ref-28" class="reference"><a href="#cite_note-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> </p> <dl><dd>(C<sub>6</sub>H<sub>5</sub>)<sub>2</sub>C=NH + CH<sub>3</sub>Li → (C<sub>6</sub>H<sub>5</sub>)<sub>2</sub>C=NLi + CH<sub>4</sub></dd> <dd>(C<sub>6</sub>H<sub>5</sub>)<sub>2</sub>C=NLi + CH<sub>3</sub>I → (C<sub>6</sub>H<sub>5</sub>)<sub>2</sub>C=NCH<sub>3</sub> + LiI</dd></dl> <div class="mw-heading mw-heading3"><h3 id="Lewis_acid-base_reactions">Lewis acid-base reactions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Imine&action=edit&section=11" title="Edit section: Lewis acid-base reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Imines are common <a href="/wiki/Ligand" title="Ligand">ligands</a> in <a href="/wiki/Coordination_chemistry" class="mw-redirect" title="Coordination chemistry">coordination chemistry</a>. Particularly popular examples are found with Schiff base ligands derived from <a href="/wiki/Salicylaldehyde" title="Salicylaldehyde">salicylaldehyde</a>, the <a href="/wiki/Salen_ligand" title="Salen ligand">salen ligands</a>. Metal-catalyzed reactions of imines proceed through such complexes. In classical <a href="/wiki/Coordination_complex" title="Coordination complex">coordination complexes</a>, imines bind metals through nitrogen. For low-valent metals, η<sup>2</sup>-imine ligands are observed. </p> <div class="mw-heading mw-heading3"><h3 id="Nucleophilic_additions">Nucleophilic additions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Imine&action=edit&section=12" title="Edit section: Nucleophilic additions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Very analogous to ketones and aldehydes, primary imines are susceptible to attack by carbanion equivalents. The method allow for the synthesis of secondary amines:<sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> </p> <dl><dd>R<sub>2</sub>C=NR' + R"Li → R<sub>2</sub>R"CN(Li)R'</dd> <dd>R<sub>2</sub>R"CN(Li)R' + H<sub>2</sub>O → R<sub>2</sub>R"CNHR' + LiOH</dd></dl> <p>This can be expanded to include <a href="/wiki/Enol" title="Enol">enolisable</a> carbons in the <a href="/wiki/Mannich_reaction" title="Mannich reaction">Mannich reaction</a>, which is a straightforward and commonly used approach for producing β-amino-carbonyl compounds.<sup id="cite_ref-31" class="reference"><a href="#cite_note-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> </p><p><span class="mw-default-size" typeof="mw:File"><a href="/wiki/File:Mannich.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/4/46/Mannich.png" decoding="async" width="562" height="79" class="mw-file-element" data-file-width="562" data-file-height="79" /></a></span> </p> <div class="mw-heading mw-heading3"><h3 id="Imine_reductions">Imine reductions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Imine&action=edit&section=13" title="Edit section: Imine reductions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Hydrogenation_of_carbon-nitrogen_double_bonds" class="mw-redirect" title="Hydrogenation of carbon-nitrogen double bonds">Hydrogenation of carbon-nitrogen double bonds</a></div> <p>Imines are reduced via <a href="/wiki/Reductive_amination" title="Reductive amination">reductive amination</a>. An imine can be reduced to an <a href="/wiki/Amine" title="Amine">amine</a> via <a href="/wiki/Hydrogenation" title="Hydrogenation">hydrogenation</a> for example in a synthesis of <i>m</i>-tolylbenzylamine:<sup id="cite_ref-32" class="reference"><a href="#cite_note-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:ImineReduction.svg" class="mw-file-description" title="Imine hydrogenation"><img alt="Imine hydrogenation" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/ImineReduction.svg/500px-ImineReduction.svg.png" decoding="async" width="500" height="134" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/ImineReduction.svg/750px-ImineReduction.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6f/ImineReduction.svg/1000px-ImineReduction.svg.png 2x" data-file-width="514" data-file-height="138" /></a></span></dd></dl> <p>Other reducing agents are <a href="/wiki/Lithium_aluminium_hydride" title="Lithium aluminium hydride">lithium aluminium hydride</a> and <a href="/wiki/Sodium_borohydride" title="Sodium borohydride">sodium borohydride</a>.<sup id="cite_ref-33" class="reference"><a href="#cite_note-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> </p><p>The <a href="/wiki/Asymmetric_synthesis" class="mw-redirect" title="Asymmetric synthesis">asymmetric</a> reduction of imines has been achieved by <a href="/wiki/Hydrosilylation" title="Hydrosilylation">hydrosilylation</a> using a rhodium-<a href="/wiki/DIOP" title="DIOP">DIOP</a> catalyst.<sup id="cite_ref-34" class="reference"><a href="#cite_note-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> Many systems have since been investigated.<sup id="cite_ref-35" class="reference"><a href="#cite_note-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Martens_36-0" class="reference"><a href="#cite_note-Martens-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> </p><p>Owing to their enhanced electrophilicity, iminium derivatives are particularly susceptible to reduction to the amines. Such reductions can be achieved by <a href="/wiki/Transfer_hydrogenation" title="Transfer hydrogenation">transfer hydrogenation</a> or by the stoichiometric action of <a href="/wiki/Sodium_cyanoborohydride" title="Sodium cyanoborohydride">sodium cyanoborohydride</a>. Since imines derived from unsymmetrical ketones are <a href="/wiki/Prochiral" class="mw-redirect" title="Prochiral">prochiral</a>, their reduction defines a route to chiral amines. </p> <div class="mw-heading mw-heading3"><h3 id="Polymerisation">Polymerisation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Imine&action=edit&section=14" title="Edit section: Polymerisation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Unhindered aldimines tend to cyclize, as illustrated by the condensation of <a href="/wiki/Methylamine" title="Methylamine">methylamine</a> and <a href="/wiki/Formaldehyde" title="Formaldehyde">formaldehyde</a>, which gives the <a href="/wiki/Hexahydro-1,3,5-triazine" title="Hexahydro-1,3,5-triazine">hexahydro-1,3,5-triazine</a>. </p><p>Imine polymers (<a href="/wiki/Polyimine" title="Polyimine">polyimines</a>) can be synthesised from multivalent <a href="/wiki/Aldehydes" class="mw-redirect" title="Aldehydes">aldehydes</a> and <a href="/wiki/Amines" class="mw-redirect" title="Amines">amines</a>.<sup id="cite_ref-37" class="reference"><a href="#cite_note-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> The polymerisation reaction proceeds directly when the aldehyde and amine monomers are mixed together at room temperature. In most cases, (small) amounts of solvent may still be required. Polyimines are particularly interesting materials because of their application as <a href="/wiki/Vitrimers" title="Vitrimers">vitrimers</a>. Owing to the dynamic covalent nature of the imine bonds, polyimines can be recycled relatively easily. Furthermore, polyimines are known for their self-healing behaviour.<sup id="cite_ref-38" class="reference"><a href="#cite_note-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-39" class="reference"><a href="#cite_note-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Miscellaneous_reactions">Miscellaneous reactions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Imine&action=edit&section=15" title="Edit section: Miscellaneous reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Akin to <a href="/wiki/Pinacol_coupling" class="mw-redirect" title="Pinacol coupling">pinacol couplings</a>, imines are susceptible to reductive coupling leading to 1,2-<a href="/wiki/Diamine" title="Diamine">diamines</a>. <sup id="cite_ref-40" class="reference"><a href="#cite_note-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> </p><p>Imine are oxidized with <a href="/wiki/Meta-chloroperoxybenzoic_acid" class="mw-redirect" title="Meta-chloroperoxybenzoic acid">meta-chloroperoxybenzoic acid</a> (mCPBA) to give an <a href="/wiki/Oxaziridine" title="Oxaziridine">oxaziridines</a>. </p><p>Imines are intermediates in the alkylation of amines with formic acid in the <a href="/wiki/Eschweiler-Clarke_reaction" class="mw-redirect" title="Eschweiler-Clarke reaction">Eschweiler-Clarke reaction</a>. </p><p>A rearrangement in carbohydrate chemistry involving an imine is the <a href="/wiki/Amadori_rearrangement" title="Amadori rearrangement">Amadori rearrangement</a>. </p><p>A methylene transfer reaction of an imine by an unstabilised sulphonium <a href="/wiki/Ylide" title="Ylide">ylide</a> can give an <a href="/wiki/Aziridines" title="Aziridines">aziridine</a> system. Imine react with <a href="/wiki/Phosphite_ester" title="Phosphite ester">dialkylphosphite</a> in the <a href="/wiki/Pudovik_reaction" title="Pudovik reaction">Pudovik reaction</a> and <a href="/wiki/Kabachnik%E2%80%93Fields_reaction" title="Kabachnik–Fields reaction">Kabachnik–Fields reaction</a> </p> <div class="mw-heading mw-heading2"><h2 id="Biological_role">Biological role</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Imine&action=edit&section=16" title="Edit section: Biological role"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Imines are common in nature.<sup id="cite_ref-41" class="reference"><a href="#cite_note-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-42" class="reference"><a href="#cite_note-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/Pyridoxal_phosphate" title="Pyridoxal phosphate">pyridoxal phosphate</a>-dependent enzymes (PLP enzymes) catalyze myriad reactions involving aldimines (or Schiff bases).<sup id="cite_ref-43" class="reference"><a href="#cite_note-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> Cyclic imines are also substrates for many <a href="/wiki/Imine_reductase" title="Imine reductase">imine reductase</a> enzymes.<sup id="cite_ref-44" class="reference"><a href="#cite_note-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:PLP_mechanism.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3f/PLP_mechanism.svg/800px-PLP_mechanism.svg.png" decoding="async" width="800" height="400" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3f/PLP_mechanism.svg/1200px-PLP_mechanism.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3f/PLP_mechanism.svg/1600px-PLP_mechanism.svg.png 2x" data-file-width="1055" data-file-height="528" /></a><figcaption> Steps in pyridoxal phosphate-mediated reactions of <a href="/wiki/Alanine" title="Alanine">alanine</a> and <a href="/wiki/Cysteine" title="Cysteine">cysteine</a>, illustrating one biological role for aldimines.</figcaption></figure> <p><br /> </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Imine&action=edit&section=17" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Enamine" title="Enamine">Enamine</a></li> <li><a href="/wiki/Schiff_base" title="Schiff base">Schiff base</a></li> <li><a href="/wiki/Carboximidate" title="Carboximidate">Carboximidate</a></li> <li><a href="/wiki/Oxazolidine" title="Oxazolidine">Oxazolidine</a></li> <li>Other functional groups with a C=N double bond: <a href="/wiki/Oximes" class="mw-redirect" title="Oximes">oximes</a>, <a href="/wiki/Hydrazone" title="Hydrazone">hydrazones</a></li> <li>Other functional groups with a C N triple bond: <a href="/wiki/Nitrile" title="Nitrile">nitriles</a>, <a href="/wiki/Isonitrile" class="mw-redirect" title="Isonitrile">isonitriles</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Imine&action=edit&section=18" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist reflist-columns references-column-width reflist-columns-2"> <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="/wiki/International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">IUPAC</a>, <i><a href="/wiki/IUPAC_books#Gold_Book" class="mw-redirect" title="IUPAC books">Compendium of Chemical Terminology</a></i>, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "<a rel="nofollow" class="external text" href="https://goldbook.iupac.org/terms/view/I02957.html">imines</a>". <style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1351%2Fgoldbook.I02957">10.1351/goldbook.I02957</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"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMarch1985" class="citation book cs1">March, Jerry (1985). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=ZKqWAQAACAAJ"><i>Advanced Organic Chemistry Reactions, Mechanisms and Structure</i></a> (3rd ed.). New York: Wiley, inc. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0-471-85472-7" title="Special:BookSources/0-471-85472-7"><bdi>0-471-85472-7</bdi></a>. <a href="/wiki/OCLC_(identifier)" class="mw-redirect" title="OCLC (identifier)">OCLC</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/oclc/642506595">642506595</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Advanced+Organic+Chemistry+Reactions%2C+Mechanisms+and+Structure&rft.edition=3rd&rft.pub=New+York%3A+Wiley%2C+inc.&rft.date=1985&rft_id=info%3Aoclcnum%2F642506595&rft.isbn=0-471-85472-7&rft.aulast=March&rft.aufirst=Jerry&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DZKqWAQAACAAJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3AImine" class="Z3988"></span></span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSaul_Patai1970" class="citation book cs1">Saul Patai, ed. (1970). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=yfsoAAAAYAAJ"><i>Carbon–Nitrogen Double Bonds</i></a>. PATai's Chemistry of Functional Groups. John Wiley & Sons. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F9780470771204">10.1002/9780470771204</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780471669425" title="Special:BookSources/9780471669425"><bdi>9780471669425</bdi></a>. <a href="/wiki/OCLC_(identifier)" class="mw-redirect" title="OCLC (identifier)">OCLC</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/oclc/639112179">639112179</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Carbon%E2%80%93Nitrogen+Double+Bonds&rft.series=PATai%27s+Chemistry+of+Functional+Groups&rft.pub=John+Wiley+%26+Sons&rft.date=1970&rft_id=info%3Aoclcnum%2F639112179&rft_id=info%3Adoi%2F10.1002%2F9780470771204&rft.isbn=9780471669425&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DyfsoAAAAYAAJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3AImine" class="Z3988"></span></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFC._Sandorfy1970" class="citation book cs1">C. Sandorfy (1970). "General and theoretical aspects". In Saul Patai (ed.). <i>Carbon–Nitrogen Double Bonds</i>. PATai's Chemistry of Functional Groups. John Wiley & Sons. pp. <span class="nowrap">1–</span>60. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F9780470771204.ch1">10.1002/9780470771204.ch1</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780470771204" title="Special:BookSources/9780470771204"><bdi>9780470771204</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=General+and+theoretical+aspects&rft.btitle=Carbon%E2%80%93Nitrogen+Double+Bonds&rft.series=PATai%27s+Chemistry+of+Functional+Groups&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1-%3C%2Fspan%3E60&rft.pub=John+Wiley+%26+Sons&rft.date=1970&rft_id=info%3Adoi%2F10.1002%2F9780470771204.ch1&rft.isbn=9780470771204&rft.au=C.+Sandorfy&rfr_id=info%3Asid%2Fen.wikipedia.org%3AImine" class="Z3988"></span></span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBjørgoBoydWatsonJennings1974" class="citation journal cs1">Bjørgo, Johannes; Boyd, Derek R.; Watson, Christopher G.; Jennings, W. Brian; Jerina, Donald M. (1974). "<i>E–Z</i>-isomerism in Aldimines". <i>J. Chem. Soc., Perkin Trans. 2</i> (9): <span class="nowrap">1081–</span>1084. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2FP29740001081">10.1039/P29740001081</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Chem.+Soc.%2C+Perkin+Trans.+2&rft.atitle=E%E2%80%93Z-isomerism+in+Aldimines&rft.issue=9&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1081-%3C%2Fspan%3E1084&rft.date=1974&rft_id=info%3Adoi%2F10.1039%2FP29740001081&rft.aulast=Bj%C3%B8rgo&rft.aufirst=Johannes&rft.au=Boyd%2C+Derek+R.&rft.au=Watson%2C+Christopher+G.&rft.au=Jennings%2C+W.+Brian&rft.au=Jerina%2C+Donald+M.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AImine" class="Z3988"></span></span> </li> <li id="cite_note-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-6">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLadenburg1883" class="citation journal cs1 cs1-prop-foreign-lang-source">Ladenburg, A. (1883). <a rel="nofollow" class="external text" href="https://babel.hathitrust.org/cgi/pt?id=osu.32435060218708;view=1up;seq=31">"Ueber die Imine"</a> [About imines]. <i>Berichte der Deutschen Chemischen Gesellschaft</i> (in German). <b>16</b>: <span class="nowrap">1149–</span>1152. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fcber.188301601259">10.1002/cber.188301601259</a>. <q>From p. 1150: Denn offenbar gehört auch das Piperidin in die Klasse der von mir gesuchten Verbindungen, für welche der Name Imine durch die bestehende Nomenklatur angezeigt ist.</q> [For obviously piperidine also belongs in the class of compounds that are sought by me, for which the name "imines" is indicated by the prevailing nomenclature.]</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Berichte+der+Deutschen+Chemischen+Gesellschaft&rft.atitle=Ueber+die+Imine&rft.volume=16&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1149-%3C%2Fspan%3E1152&rft.date=1883&rft_id=info%3Adoi%2F10.1002%2Fcber.188301601259&rft.aulast=Ladenburg&rft.aufirst=A.&rft_id=https%3A%2F%2Fbabel.hathitrust.org%2Fcgi%2Fpt%3Fid%3Dosu.32435060218708%3Bview%3D1up%3Bseq%3D31&rfr_id=info%3Asid%2Fen.wikipedia.org%3AImine" class="Z3988"></span></span> </li> <li id="cite_note-Fletcher-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-Fletcher_7-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation book cs1">"Amines and Imines". <a rel="nofollow" class="external text" href="https://books.google.com/books?id=xQrwAAAAMAAJ"><i>Nomenclature of Organic Compounds</i></a>. Advances in Chemistry. Vol. 126. American Chemical Society. 1974. pp. <span class="nowrap">180–</span>188. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fba-1974-0126.ch023">10.1021/ba-1974-0126.ch023</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780841201910" title="Special:BookSources/9780841201910"><bdi>9780841201910</bdi></a>. <a href="/wiki/OCLC_(identifier)" class="mw-redirect" title="OCLC (identifier)">OCLC</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/oclc/922539">922539</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Amines+and+Imines&rft.btitle=Nomenclature+of+Organic+Compounds&rft.series=Advances+in+Chemistry&rft.pages=%3Cspan+class%3D%22nowrap%22%3E180-%3C%2Fspan%3E188&rft.pub=American+Chemical+Society&rft.date=1974&rft_id=info%3Aoclcnum%2F922539&rft_id=info%3Adoi%2F10.1021%2Fba-1974-0126.ch023&rft.isbn=9780841201910&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DxQrwAAAAMAAJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3AImine" class="Z3988"></span></span> </li> <li id="cite_note-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-8">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation journal cs1"><a rel="nofollow" class="external text" href="http://orgsyn.org/demo.aspx?prep=CV4P0433">"Ethylenimine"</a>. <i><a href="/wiki/Organic_Syntheses" title="Organic Syntheses">Organic Syntheses</a></i>. <b>30</b>: 38. 1950. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.15227%2Forgsyn.030.0038">10.15227/orgsyn.030.0038</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Organic+Syntheses&rft.atitle=Ethylenimine&rft.volume=30&rft.pages=38&rft.date=1950&rft_id=info%3Adoi%2F10.15227%2Forgsyn.030.0038&rft_id=http%3A%2F%2Forgsyn.org%2Fdemo.aspx%3Fprep%3DCV4P0433&rfr_id=info%3Asid%2Fen.wikipedia.org%3AImine" class="Z3988"></span></span> </li> <li id="cite_note-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-9">^</a></b></span> <span class="reference-text"><a href="/wiki/International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">IUPAC</a>, <i><a href="/wiki/IUPAC_books#Gold_Book" class="mw-redirect" title="IUPAC books">Compendium of Chemical Terminology</a></i>, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "<a rel="nofollow" class="external text" href="https://goldbook.iupac.org/terms/view/S05498.html">Schiff base</a>". <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1351%2Fgoldbook.S05498">10.1351/goldbook.S05498</a></span> </li> <li id="cite_note-10"><span class="mw-cite-backlink"><b><a href="#cite_ref-10">^</a></b></span> <span class="reference-text"><a href="/wiki/International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">IUPAC</a>, <i><a href="/wiki/IUPAC_books#Gold_Book" class="mw-redirect" title="IUPAC books">Compendium of Chemical Terminology</a></i>, 2nd ed. (the "Gold Book") (1997). 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title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Current+Opinion+in+Chemical+Biology&rft.atitle=Imine+reductases+%28IREDs%29&rft.volume=37&rft.pages=%3Cspan+class%3D%22nowrap%22%3E19-%3C%2Fspan%3E25&rft.date=2017&rft_id=info%3Adoi%2F10.1016%2Fj.cbpa.2016.11.022&rft_id=info%3Apmid%2F28038349&rft.aulast=Mangas-Sanchez&rft.aufirst=Juan&rft.au=France%2C+Scott+P&rft.au=Montgomery%2C+Sarah+L&rft.au=Aleku%2C+Godwin+A&rft.au=Man%2C+Henry&rft.au=Sharma%2C+Mahima&rft.au=Ramsden%2C+Jeremy+I&rft.au=Grogan%2C+Gideon&rft.au=Turner%2C+Nicholas+J&rft_id=https%3A%2F%2Flinkinghub.elsevier.com%2Fretrieve%2Fpii%2FS1367593116301880&rfr_id=info%3Asid%2Fen.wikipedia.org%3AImine" class="Z3988"></span></span> </li> </ol></div> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist 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colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><style data-mw-deduplicate="TemplateStyles:r1239400231">.mw-parser-output .navbar{display:inline;font-size:88%;font-weight:normal}.mw-parser-output .navbar-collapse{float:left;text-align:left}.mw-parser-output .navbar-boxtext{word-spacing:0}.mw-parser-output .navbar ul{display:inline-block;white-space:nowrap;line-height:inherit}.mw-parser-output .navbar-brackets::before{margin-right:-0.125em;content:"[ "}.mw-parser-output .navbar-brackets::after{margin-left:-0.125em;content:" ]"}.mw-parser-output .navbar li{word-spacing:-0.125em}.mw-parser-output .navbar a>span,.mw-parser-output .navbar a>abbr{text-decoration:inherit}.mw-parser-output .navbar-mini abbr{font-variant:small-caps;border-bottom:none;text-decoration:none;cursor:inherit}.mw-parser-output .navbar-ct-full{font-size:114%;margin:0 7em}.mw-parser-output .navbar-ct-mini{font-size:114%;margin:0 4em}html.skin-theme-clientpref-night .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Functional_groups" title="Template:Functional groups"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Functional_groups" title="Template talk:Functional groups"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Functional_groups" title="Special:EditPage/Template:Functional groups"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Functional_groups729" style="font-size:114%;margin:0 4em"><a href="/wiki/Functional_group" title="Functional group">Functional groups</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hydrocarbon" title="Hydrocarbon">Hydrocarbons</a> <br /><span class="nobold">(only C and H)</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Alkyl" class="mw-redirect" title="Alkyl">Alkyl</a> <ul><li><a href="/wiki/Methyl_group" title="Methyl group">Methyl</a></li> <li><a href="/wiki/Ethyl_group" title="Ethyl group">Ethyl</a></li> <li><a href="/wiki/Propyl_group" title="Propyl group">Propyl</a></li> <li><a href="/wiki/Cyclopropyl" class="mw-redirect" title="Cyclopropyl">Cyclopropyl</a></li> <li><a href="/wiki/Butyl_group" title="Butyl group">Butyl</a></li> <li><a href="/wiki/Pentyl_group" title="Pentyl group">Pentyl</a></li></ul></li> <li><a href="/wiki/Methylene_group" title="Methylene group">Methylene</a> <ul><li><a href="/wiki/Methylene_bridge" title="Methylene bridge">Bridge</a></li> <li><a href="/wiki/Methine_group" title="Methine group">Methine</a></li></ul></li> <li><a href="/wiki/Alkene" title="Alkene">Alkene</a> <ul><li><a href="/wiki/Vinyl_group" title="Vinyl group">Vinyl</a></li> <li><a href="/wiki/Allyl_group" title="Allyl group">Allyl</a></li> <li><a href="/wiki/Propenyl" title="Propenyl">1-Propenyl</a></li> <li><a href="/wiki/Crotyl_group" title="Crotyl group">Crotyl</a></li> <li><a href="/wiki/Allenes" title="Allenes">Allene</a></li> <li><a href="/wiki/Cumulene" title="Cumulene">Cumulene</a></li></ul></li> <li><a href="/wiki/Aryl" class="mw-redirect" title="Aryl">Aryl</a> <ul><li><a href="/wiki/Phenyl_group" title="Phenyl group">Phenyl</a></li> <li><a href="/wiki/Benzyl_group" title="Benzyl group">Benzyl</a></li></ul></li> <li><a href="/wiki/Alkyne" title="Alkyne">Alkyne</a></li> <li><a href="/wiki/Carbene" title="Carbene">Carbene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Only <a href="/wiki/Carbon" title="Carbon">carbon</a>, <br /><a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a>, <br />and <a href="/wiki/Oxygen" title="Oxygen">oxygen</a> <br /><span class="nobold">(only C, H and O)</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">R-O-R</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetal" title="Acetal">Acetal</a></li> <li><a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">Alcohol</a></li> <li><a href="/wiki/Alkoxy_group" title="Alkoxy group">Alkoxy</a> <ul><li><a href="/wiki/Methoxy_group" title="Methoxy group">Methoxy</a></li></ul></li> <li><a href="/wiki/Ether" title="Ether">Ether</a> <ul><li><a href="/wiki/Enol_ether" title="Enol ether">Enol ether</a></li> <li><a href="/wiki/Epoxide" title="Epoxide">Epoxide</a></li></ul></li> <li><a href="/wiki/Organic_peroxides" title="Organic peroxides">Peroxy</a> <ul><li><a href="/wiki/Hydroperoxide" title="Hydroperoxide">Hydroperoxy</a></li> <li><a href="/wiki/Dioxirane" title="Dioxirane">Dioxiranes</a></li></ul></li> <li><a href="/wiki/Ethylenedioxy" title="Ethylenedioxy">Ethylenedioxy</a></li> <li><a href="/wiki/Methylenedioxy" title="Methylenedioxy">Methylenedioxy</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Carbonyl_group" title="Carbonyl group">carbonyl</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acyl_group" title="Acyl group">Acyl</a> <ul><li><a href="/wiki/Acetyl_group" title="Acetyl group">Acetyl</a></li> <li><a href="/wiki/Acryloyl_group" class="mw-redirect" title="Acryloyl group">Acryloyl</a></li> <li><a href="/wiki/Benzoyl_group" title="Benzoyl group">Benzoyl</a></li></ul></li> <li><a href="/wiki/Aldehyde" title="Aldehyde">Aldehyde</a> <ul><li><a href="/wiki/Ketene" title="Ketene">Ketene</a></li></ul></li> <li><a href="/wiki/Ketone" title="Ketone">Ketone</a></li> <li><a href="/wiki/Ynone" title="Ynone">Ynone</a></li> <li><a href="/wiki/Reductone" title="Reductone">Reductone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">carboxy</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Carboxylic_acid" title="Carboxylic acid">Carboxyl</a> <ul><li><a href="/wiki/Acetoxy_group" title="Acetoxy group">Acetoxy</a></li> <li><a href="/wiki/Carboxylic_anhydride" class="mw-redirect" title="Carboxylic anhydride">Anhydride</a></li></ul></li> <li><a href="/wiki/Ester" title="Ester">Ester</a> <ul><li><a href="/wiki/Orthoester" class="mw-redirect" title="Orthoester">Orthoester</a></li></ul></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Only one <br />element, <br />not being <br />carbon, <br />hydrogen, <br />or oxygen <br /><span class="nobold">(one element, <br />not C, H or O)</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nitrogen" title="Nitrogen">Nitrogen</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Amine" title="Amine">Amine</a> <ul><li><a href="/wiki/Enamine" title="Enamine">Enamine</a></li> <li><a href="/wiki/Quaternary_ammonium_cation" title="Quaternary ammonium cation">Ammonium</a></li></ul></li> <li><a href="/wiki/Hydrazines" title="Hydrazines">Hydrazo</a></li> <li><a href="/wiki/Nitrene" title="Nitrene">Nitrene</a></li> <li><a class="mw-selflink selflink">Imine</a></li> <li><a href="/wiki/Oxime" title="Oxime">Oxime</a></li> <li><a href="/wiki/Hydrazone" title="Hydrazone">Hydrazone</a></li> <li><a href="/wiki/Azo_compound" title="Azo compound">Azo</a></li> <li><a href="/wiki/Amide_(functional_group)" title="Amide (functional group)">Amide</a></li> <li><a href="/wiki/Imidate" class="mw-redirect" title="Imidate">Imidate</a></li> <li><a href="/wiki/Amidine" title="Amidine">Amidine</a></li> <li><a href="/wiki/Carbamate" title="Carbamate">Carbamate</a></li> <li><a href="/wiki/Imide" title="Imide">Imide</a></li> <li><a href="/wiki/Nitrile" title="Nitrile">Nitrile</a></li> <li><a href="/wiki/Isocyanide" title="Isocyanide">Isonitrile</a></li> <li><a href="/wiki/Cyanate_ester" title="Cyanate ester">Cyanate</a></li> <li><a href="/wiki/Isocyanate" title="Isocyanate">Isocyanate</a></li> <li><a href="/wiki/Nitrate_ester" title="Nitrate ester">Nitrate</a></li> <li><a href="/wiki/Nitrite_ester" class="mw-redirect" title="Nitrite ester">Nitrite</a></li> <li><a href="/wiki/Nitro_compound" title="Nitro compound">Nitro</a></li> <li><a href="/wiki/Nitroso" title="Nitroso">Nitroso</a></li> <li><a href="/wiki/NONOate" title="NONOate">NONOate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Silicon" title="Silicon">Silicon</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Silane" title="Silane">Silane</a> <ul><li><a href="/wiki/Hydrosilane" class="mw-redirect" title="Hydrosilane">Hydrosilane</a></li> <li><a href="/wiki/Chlorosilane" title="Chlorosilane">Chlorosilane</a></li></ul></li> <li><a href="/wiki/Organosilicon_chemistry#Silenes" title="Organosilicon chemistry">Silene</a></li> <li><a href="/wiki/Silanol" title="Silanol">Silanol</a></li> <li><a href="/wiki/Siloxide" title="Siloxide">Siloxide</a></li> <li><a href="/wiki/Siloxane" title="Siloxane">Siloxane</a></li> <li><a href="/wiki/Silanone" title="Silanone">Silanone</a></li> <li><a href="/wiki/Silyl_ether" title="Silyl ether">Silether</a></li> <li><a href="/wiki/Metalloles" class="mw-redirect" title="Metalloles">Silole</a></li> <li><a href="/wiki/Silatrane" class="mw-redirect" title="Silatrane">Silatrane</a></li> <li><a href="/wiki/Silicate" title="Silicate">Silicate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phosphorus" title="Phosphorus">Phosphorus</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Organophosphate" title="Organophosphate">Phosphate</a> <ul><li><a href="/wiki/Phosphodiester" class="mw-redirect" title="Phosphodiester">Phosphodiester</a></li></ul></li> <li><a href="/wiki/Phosphonate" title="Phosphonate">Phosphonate</a> <ul><li><a href="/wiki/Phosphite_ester" title="Phosphite ester">Phosphite</a></li></ul></li> <li><a href="/wiki/Phosphonite" title="Phosphonite">Phosphonous</a></li> <li><a href="/wiki/Phosphinate" title="Phosphinate">Phosphinate</a></li> <li><a href="/wiki/Phosphine_oxide" title="Phosphine oxide">Phosphine oxide</a></li> <li><a href="/wiki/Organophosphine" title="Organophosphine">Phosphine</a> <ul><li><a href="/wiki/Phosphonium" title="Phosphonium">Phosphonium</a></li></ul></li> <li><a href="/wiki/Phosphaalkene" title="Phosphaalkene">Phosphaalkene</a></li> <li><a href="/wiki/Phosphaalkyne" title="Phosphaalkyne">Phosphaalkyne</a></li> <li><a href="/wiki/1-Phosphaallenes" title="1-Phosphaallenes">Phosphaallene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sulfur" title="Sulfur">Sulfur</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Thiol" title="Thiol">Thiol</a></li> <li><a href="/wiki/Thioether" class="mw-redirect" title="Thioether">Thioether</a> <ul><li><a href="/wiki/Sulfonium" title="Sulfonium">Sulfonium</a></li></ul></li> <li><a href="/wiki/Persulfide" title="Persulfide">Persulfide</a></li> <li><a href="/wiki/Disulfide" title="Disulfide">Disulfide</a></li> <li><a href="/wiki/Sulfenic_acid" title="Sulfenic acid">Sulfenic acid</a></li> <li><a href="/wiki/Thiosulfinate" title="Thiosulfinate">Thiosulfinate</a></li> <li><a href="/wiki/Sulfoxide" title="Sulfoxide">Sulfoxide</a></li> <li><a href="/wiki/Thiosulfonate" title="Thiosulfonate">Thiosulfonate</a></li> <li><a href="/wiki/Sulfinic_acid" title="Sulfinic acid">Sulfinic acid</a></li> <li><a href="/wiki/Sulfone" title="Sulfone">Sulfone</a></li> <li><a href="/wiki/Sulfonic_acid" title="Sulfonic acid">Sulfonic acid</a></li> <li><a href="/wiki/Thioketone" title="Thioketone">Thioketone</a></li> <li><a href="/wiki/Thial" title="Thial">Thial</a></li> <li><a href="/wiki/Thioester" title="Thioester">Thioester</a></li> <li><a href="/wiki/Thionoester" class="mw-redirect" title="Thionoester">Thionoester</a></li> <li><a href="/wiki/Thioxanthate" title="Thioxanthate">Thioxanthate</a></li> <li><a href="/wiki/Xanthate" title="Xanthate">Xanthate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Boron" title="Boron">Boron</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Boronic_acid" title="Boronic acid">Boronic acid</a></li> <li><a href="/wiki/Borinic_acid" title="Borinic acid">Borinic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Selenium" title="Selenium">Selenium</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Selenol" title="Selenol">Selenol</a></li> <li><a href="/wiki/Selenonic_acid" title="Selenonic acid">Selenonic acid</a></li> <li><a href="/wiki/Seleninic_acid" title="Seleninic acid">Seleninic acid</a></li> <li><a href="/wiki/Selenenic_acid" title="Selenenic acid">Selenenic acid</a></li> <li><a href="/wiki/Selone" title="Selone">Selone</a></li> <li><a href="/wiki/Selenide#Inorganic_selenides" title="Selenide">Selenoether</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Tellurium" title="Tellurium">Tellurium</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Tellurol" title="Tellurol">Tellurol</a></li> <li><a href="/wiki/Telluroketone" title="Telluroketone">Telluroketone</a></li> <li><a href="/wiki/Telluride_(chemistry)#Organic_tellurides" title="Telluride (chemistry)">telluroether</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Polonium" title="Polonium">Polonium</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Polonium_hydride#Properties" title="Polonium hydride">Polonol</a></li> <li><a href="/wiki/Organopolonium_chemistry" title="Organopolonium chemistry">Polonoether</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i><a href="/wiki/Halocarbon" title="Halocarbon">Halo</a></i></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Haloalkane" title="Haloalkane">Haloalkane</a> <ul><li><a href="/wiki/Fluoroethyl" title="Fluoroethyl">Fluoroethyl</a></li> <li><a href="/wiki/Trifluoromethyl" class="mw-redirect" title="Trifluoromethyl">Trifluoromethyl</a></li> <li><a href="/wiki/Trichloromethyl_group" title="Trichloromethyl group">Trichloromethyl</a></li> <li><a href="/wiki/Trifluoromethoxy_group" title="Trifluoromethoxy group">Trifluoromethoxy</a></li> <li><a href="/wiki/Iodane" class="mw-redirect" title="Iodane">Hypervalent iodine</a></li></ul></li> <li><a href="/wiki/Vinyl_halide" title="Vinyl halide">Vinyl halide</a> <ul><li><a href="/wiki/Vinyl_iodide_functional_group" title="Vinyl iodide functional group">Iodide</a></li></ul></li> <li><a href="/wiki/Acyl_halide" title="Acyl halide">Acyl halide</a> <ul><li><a href="/wiki/Acyl_chloride" title="Acyl chloride">Chloride</a></li></ul></li> <li><a href="/wiki/Perchlorate_ester" class="mw-redirect" title="Perchlorate ester">Perchlorate</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Isothiocyanate" title="Isothiocyanate">Isothiocyanate</a></li> <li><a href="/wiki/Phosphoramides" title="Phosphoramides">Phosphoramides</a></li> <li><a href="/wiki/Sulfenyl_chloride" title="Sulfenyl chloride">Sulfenyl chloride</a></li> <li><a href="/wiki/Sulfonamide" title="Sulfonamide">Sulfonamide</a></li> <li><a href="/wiki/Organic_thiocyanates" title="Organic thiocyanates">Thiocyanate</a></li> <li><a href="/wiki/Sulfinylamine" title="Sulfinylamine">Sulfinylamines</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt><span class="nobold">See also</span></dt> <dd><i><a href="/wiki/Chemical_classification" class="mw-redirect" title="Chemical classification">chemical classification</a></i></dd> <dd><i><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">chemical nomenclature</a></i> <dl><dd><a href="/wiki/IUPAC_nomenclature_of_inorganic_chemistry" title="IUPAC nomenclature of inorganic chemistry">inorganic</a></dd> <dd><a href="/wiki/IUPAC_nomenclature_of_organic_chemistry" title="IUPAC nomenclature of organic chemistry">organic</a></dd></dl></dd></dl> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Nitrogen_species87" 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="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Nitrogen_compounds" title="Template:Nitrogen compounds"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Nitrogen_compounds" title="Template talk:Nitrogen compounds"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Nitrogen_compounds" title="Special:EditPage/Template:Nitrogen compounds"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Nitrogen_species87" style="font-size:114%;margin:0 4em"><a href="/wiki/Nitrogen" title="Nitrogen">Nitrogen</a> species</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Hydrides</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ammonia" title="Ammonia">NH<sub>3</sub></a></li> <li><a href="/wiki/Ammonium" title="Ammonium">NH<sub>4</sub><sup>+</sup></a></li> <li><a href="/wiki/Metal_amides#Alkali_metal_amides" title="Metal amides">NH<sub>2</sub><sup>−</sup></a></li> <li><a href="/wiki/Nitride" title="Nitride">N<sup>3−</sup></a></li> <li><a href="/wiki/Hydroxylamine" title="Hydroxylamine">NH<sub>2</sub>OH</a></li> <li><a href="/wiki/Hydrazine" title="Hydrazine">N<sub>2</sub>H<sub>4</sub></a></li> <li><a href="/wiki/Hydrazoic_acid" title="Hydrazoic acid">HN<sub>3</sub></a></li> <li><a href="/wiki/Azide" title="Azide">N<sub>3</sub><sup>−</sup></a></li> <li><a href="/wiki/Nitrogen_pentahydride" title="Nitrogen pentahydride"><i>NH<sub>5</sub></i></a> (?)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Organic</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Amine" title="Amine">NR<sub>3</sub></a></li> <li><a class="mw-selflink selflink">>C=NR</a></li> <li><a href="/wiki/Amide" title="Amide">−CONR<sub>2</sub></a></li> <li><a href="/wiki/Nitrile" title="Nitrile">−CN</a></li> <li><a href="/wiki/Hydrogen_cyanide" title="Hydrogen cyanide">HCN</a></li> <li><a href="/wiki/Cyanide" title="Cyanide">CN<sup>−</sup></a></li> <li><a href="/wiki/Cyanogen" title="Cyanogen">(CN)<sub>2</sub></a></li> <li><a href="/wiki/Cyanamide" title="Cyanamide">H<sub>2</sub>NCN</a></li> <li><a href="/wiki/Cyanate" title="Cyanate">HOCN</a></li> <li><a href="/wiki/Isocyanate" title="Isocyanate">HNCO</a></li> <li><a href="/wiki/Isothiocyanate" title="Isothiocyanate">HNCS</a></li> <li><a href="/wiki/Diazomethane" title="Diazomethane">CH<sub>2</sub>N<sub>2</sub></a></li> <li><a href="/wiki/Nitroso" title="Nitroso">–NO</a></li> <li><a href="/wiki/Nitro_compound" title="Nitro compound">–NO<sub>2</sub></a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nitrogen_oxide" title="Nitrogen oxide">Oxides</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Nitric_oxide" title="Nitric oxide">NO</a> / <a href="/wiki/Dinitrogen_dioxide" title="Dinitrogen dioxide">(NO)<sub>2</sub></a></li> <li><a href="/wiki/Dinitrogen_trioxide" title="Dinitrogen trioxide">N<sub>2</sub>O<sub>3</sub></a></li> <li><a href="/wiki/Nitrous_acid" title="Nitrous acid">HNO<sub>2</sub></a> / <a href="/wiki/Nitrite" title="Nitrite">NO<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1.2em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span></a> / <a href="/wiki/Nitrosonium" title="Nitrosonium">NO<sup>+</sup></a></li> <li><a href="/wiki/Nitrogen_dioxide" title="Nitrogen dioxide">NO<sub>2</sub></a> / <a href="/wiki/Dinitrogen_tetroxide" title="Dinitrogen tetroxide">(NO<sub>2</sub>)<sub>2</sub></a></li> <li><a href="/wiki/Dinitrogen_pentoxide" title="Dinitrogen pentoxide">N<sub>2</sub>O<sub>5</sub></a></li> <li><a href="/wiki/Nitric_acid" title="Nitric acid">HNO<sub>3</sub></a> / <a href="/wiki/Nitrate" title="Nitrate">NO<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1.2em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">3</sub></span></span></a> / <a href="/wiki/Nitronium" class="mw-redirect" title="Nitronium">NO<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1.2em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">+</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span></a></li> <li><a href="/wiki/Nitrate_radical" title="Nitrate radical">NO<sub>3</sub></a></li> <li><a href="/wiki/Nitroxyl" title="Nitroxyl">HNO</a> / <a href="/wiki/Hyponitrous_acid" title="Hyponitrous acid">(HON)<sub>2</sub></a> / <a href="/wiki/Hyponitrite" title="Hyponitrite">N<sub>2</sub>O<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1.2em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">2−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span></a> / <a href="/wiki/Nitrous_oxide" title="Nitrous oxide">N<sub>2</sub>O</a></li> <li><a href="/wiki/Nitramide" title="Nitramide">H<sub>2</sub>NNO<sub>2</sub></a></li> <li><a href="/wiki/Peroxynitrous_acid" title="Peroxynitrous acid">HO<sub>2</sub>NO</a> / <a href="/wiki/Peroxynitrite" title="Peroxynitrite">ONOO<sup>−</sup></a></li> <li><a href="/wiki/Peroxynitric_acid" title="Peroxynitric acid">HO<sub>2</sub>NO<sub>2</sub></a> / <a href="/wiki/Peroxynitrate" title="Peroxynitrate">O<sub>2</sub>NOO<sup>−</sup></a></li> <li><a href="/wiki/Orthonitrate" title="Orthonitrate">NO<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1.2em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">3−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">4</sub></span></span></a></li> <li><a href="/wiki/Nitroxylic_acid" title="Nitroxylic acid">H<sub>4</sub>N<sub>2</sub>O<sub>4</sub></a> / <a href="/wiki/Angeli%27s_salt" title="Angeli's salt">N<sub>2</sub>O<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1.2em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">2−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">3</sub></span></span></a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Halides</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Nitrogen_monofluoride" title="Nitrogen monofluoride">NF</a></li> <li><a href="/wiki/Nitrogen_difluoride" title="Nitrogen difluoride">NF<sub>2</sub></a></li> <li><a href="/wiki/Nitrogen_trifluoride" title="Nitrogen trifluoride">NF<sub>3</sub></a></li> <li><a href="/wiki/Nitrogen_pentafluoride" title="Nitrogen pentafluoride"><i>NF<sub>5</sub></i></a> (?)</li> <li><a href="/wiki/Nitrogen_trichloride" title="Nitrogen trichloride">NCl<sub>3</sub></a></li> <li><a href="/wiki/Nitrogen_tribromide" title="Nitrogen tribromide">NBr<sub>3</sub></a></li> <li><a href="/wiki/Nitrogen_triiodide" title="Nitrogen triiodide">NI<sub>3</sub></a></li> <li><a href="/wiki/Fluorine_azide" title="Fluorine azide">FN<sub>3</sub></a></li> <li><a href="/wiki/Chlorine_azide" title="Chlorine azide">ClN<sub>3</sub></a></li> <li><a href="/wiki/Bromine_azide" title="Bromine azide">BrN<sub>3</sub></a></li> <li><a href="/wiki/Iodine_azide" title="Iodine azide">IN<sub>3</sub></a></li> <li><a href="/wiki/Fluoroamine" title="Fluoroamine">NH<sub>2</sub>F</a></li> <li><a href="/wiki/Dinitrogen_difluoride" title="Dinitrogen difluoride">N<sub>2</sub>F<sub>2</sub></a></li> <li><a href="/wiki/Monochloramine" title="Monochloramine">NH<sub>2</sub>Cl</a></li> <li><a href="/w/index.php?title=Difluoramine&action=edit&redlink=1" class="new" title="Difluoramine (page does not exist)">NHF<sub>2</sub></a></li> <li><a href="/wiki/Dichloramine" title="Dichloramine">NHCl<sub>2</sub></a></li> <li><a href="/w/index.php?title=Dibromamine&action=edit&redlink=1" class="new" title="Dibromamine (page does not exist)">NHBr<sub>2</sub></a></li> <li><a href="/w/index.php?title=Diiodoamine&action=edit&redlink=1" class="new" title="Diiodoamine (page does not exist)">NHI<sub>2</sub></a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Oxidation_state" title="Oxidation state">Oxidation states</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"><span style="font-size:112%;"><b><a href="/wiki/Nitride" title="Nitride">−3</a></b></span>, <a href="/wiki/Hydrazine" title="Hydrazine">−2</a>, <a href="/wiki/Hydroxylamine" title="Hydroxylamine">−1</a>, 0, <a href="/wiki/Nitroxyl" title="Nitroxyl">+1</a>, <a href="/wiki/Nitric_oxide" title="Nitric oxide">+2</a>, <span style="font-size:112%;"><b><a href="/wiki/Nitrite" title="Nitrite">+3</a></b></span>, <a href="/wiki/Nitrogen_dioxide" title="Nitrogen dioxide">+4</a>, <span style="font-size:112%;"><b><a href="/wiki/Nitrate" title="Nitrate">+5</a></b></span> (a strongly <a href="/wiki/Acid" title="Acid">acidic</a> oxide)</div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox authority-control" aria-label="Navbox489" style="padding:3px"><table class="nowraplinks hlist navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Help:Authority_control" title="Help:Authority control">Authority control databases</a>: National <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q408057#identifiers" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" 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