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class="vector-toc-list"> <li id="toc-Metal_extractant" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Metal_extractant"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>Metal extractant</span> </div> </a> <ul id="toc-Metal_extractant-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Other_applications" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Other_applications"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2</span> <span>Other applications</span> </div> </a> <ul id="toc-Other_applications-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label 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Available in 28 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-28" 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">28 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%A3%D9%83%D8%B3%D9%8A%D9%85" title="أكسيم – Arabic" lang="ar" hreflang="ar" data-title="أكسيم" 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/Oxima" title="Oxima – Catalan" lang="ca" hreflang="ca" data-title="Oxima" 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/Oxim" title="Oxim – Czech" lang="cs" hreflang="cs" data-title="Oxim" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Oxime" title="Oxime – German" lang="de" hreflang="de" data-title="Oxime" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%9F%CE%BE%CE%AF%CE%BC%CE%B7" title="Οξίμη – Greek" lang="el" hreflang="el" data-title="Οξίμη" 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/Oxima" title="Oxima – Spanish" lang="es" hreflang="es" data-title="Oxima" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A7%DA%A9%D8%B3%DB%8C%D9%85" title="اکسیم – Persian" lang="fa" hreflang="fa" data-title="اکسیم" 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/Oxime" title="Oxime – French" lang="fr" hreflang="fr" data-title="Oxime" 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/Oxima" title="Oxima – Galician" lang="gl" hreflang="gl" data-title="Oxima" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%86%E0%A4%95%E0%A5%8D%E0%A4%B8%E0%A4%BF%E0%A4%AE" title="आक्सिम – Hindi" lang="hi" hreflang="hi" data-title="आक्सिम" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Oksima" title="Oksima – Indonesian" lang="id" hreflang="id" data-title="Oksima" 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/Ossima" title="Ossima – Italian" lang="it" hreflang="it" data-title="Ossima" 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%95%D7%A7%D7%A1%D7%99%D7%9D" title="אוקסים – Hebrew" lang="he" hreflang="he" data-title="אוקסים" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-ky mw-list-item"><a href="https://ky.wikipedia.org/wiki/%D0%9E%D0%BA%D1%81%D0%B8%D0%BC%D0%B4%D0%B5%D1%80" title="Оксимдер – Kyrgyz" lang="ky" hreflang="ky" data-title="Оксимдер" data-language-autonym="Кыргызча" data-language-local-name="Kyrgyz" class="interlanguage-link-target"><span>Кыргызча</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%9E%D0%BA%D1%81%D0%B8%D0%BC" title="Оксим – Macedonian" lang="mk" hreflang="mk" data-title="Оксим" 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/Oxime" title="Oxime – Dutch" lang="nl" hreflang="nl" data-title="Oxime" 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%AA%E3%82%AD%E3%82%B7%E3%83%A0" title="オキシム – Japanese" lang="ja" hreflang="ja" data-title="オキシム" 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/Oksymy" title="Oksymy – Polish" lang="pl" hreflang="pl" data-title="Oksymy" 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/Oxima" title="Oxima – Portuguese" lang="pt" hreflang="pt" data-title="Oxima" 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/Oxim%C4%83" title="Oximă – Romanian" lang="ro" hreflang="ro" data-title="Oximă" 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%9E%D0%BA%D1%81%D0%B8%D0%BC%D1%8B" title="Оксимы – Russian" lang="ru" hreflang="ru" data-title="Оксимы" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Oksim" title="Oksim – Serbian" lang="sr" hreflang="sr" data-title="Oksim" 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/Oksim" title="Oksim – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Oksim" 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/Oksiimit" title="Oksiimit – Finnish" lang="fi" hreflang="fi" data-title="Oksiimit" 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/Oxim" title="Oxim – Swedish" lang="sv" hreflang="sv" data-title="Oxim" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%9E%D0%BA%D1%81%D0%B8%D0%BC%D0%B8" title="Оксими – Ukrainian" lang="uk" hreflang="uk" data-title="Оксими" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li 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decoding="async" width="250" height="151" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/38/General_structure_of_oximes.svg/375px-General_structure_of_oximes.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/38/General_structure_of_oximes.svg/500px-General_structure_of_oximes.svg.png 2x" data-file-width="1063" data-file-height="644" /></a><figcaption></figcaption></figure> <p>In <a href="/wiki/Organic_chemistry" title="Organic chemistry">organic chemistry</a>, an <b>oxime</b> is an <a href="/wiki/Organic_compound" title="Organic compound">organic compound</a> belonging to the <a href="/wiki/Imine" title="Imine">imines</a>, with the general <a href="/wiki/Chemical_formula" title="Chemical formula">formula</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">RR’C=N−OH</span>, where R is an organic <a href="/wiki/Side_chain" title="Side chain">side-chain</a> and R' may be <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a>, forming an <b>aldoxime</b>, or another organic <a href="/wiki/Functional_group" title="Functional group">group</a>, forming a <b>ketoxime</b>. O-substituted oximes form a closely related family of compounds. <b>Amidoximes</b> are oximes of <a href="/wiki/Amide" title="Amide">amides</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R<sup class="template-chem2-sup">1</sup>C(=O)NR<sup class="template-chem2-sup">2</sup>R<sup class="template-chem2-sup">3</sup></span>) with general structure <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R<sup class="template-chem2-sup">1</sup>C(=NOH)NR<sup class="template-chem2-sup">2</sup>R<sup class="template-chem2-sup">3</sup></span>. </p><p>Oximes are usually generated by the reaction of <a href="/wiki/Hydroxylamine" title="Hydroxylamine">hydroxylamine</a> with <a href="/wiki/Aldehyde" title="Aldehyde">aldehydes</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R−CH=O</span>) or <a href="/wiki/Ketone" title="Ketone">ketones</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">RR’C=O</span>). The term <i>oxime</i> dates back to the 19th century, a combination of the words <i>oxygen</i> and <i>imine</i>.<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Structure_and_properties">Structure and properties</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Oxime&action=edit&section=1" title="Edit section: Structure and properties"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>If the two side-chains on the central carbon are different from each other—either an aldoxime, or a ketoxime with two different "R" groups—the oxime can often have two different geometric <a href="/wiki/Stereoisomer" class="mw-redirect" title="Stereoisomer">stereoisomeric</a> forms according to the <a href="/wiki/E/Z_configuration" class="mw-redirect" title="E/Z configuration"><i>E</i>/<i>Z</i> configuration</a>. An older terminology of <a href="/wiki/Descriptor_(chemistry)#syn,_anti" title="Descriptor (chemistry)"><i>syn</i> and <i>anti</i></a> was used to identify especially aldoximes according to whether the R group was closer or further from the hydroxyl. Both forms are often stable enough to be separated from each other by standard techniques. </p><p>Oximes have three characteristic bands in the <a href="/wiki/Infrared_spectroscopy" title="Infrared spectroscopy">infrared spectrum</a>, whose wavelengths corresponding to the stretching vibrations of its three types of bonds: 3600 cm<sup>−1</sup> (O−H), 1665 cm<sup>−1</sup> (C=N) and 945 cm<sup>−1</sup> (N−O).<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p><p>In aqueous solution, aliphatic oximes are 10<sup>2</sup>- to 10<sup>3</sup>-fold more resistant to hydrolysis than analogous hydrazones.<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> <div class="mw-heading mw-heading2"><h2 id="Preparation">Preparation</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Oxime&action=edit&section=2" title="Edit section: Preparation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Oximes can be synthesized by <a href="/wiki/Condensation_reaction" title="Condensation reaction">condensation</a> of an aldehyde or a ketone with <a href="/wiki/Hydroxylamine" title="Hydroxylamine">hydroxylamine</a>. The condensation of aldehydes with hydroxylamine gives aldoximes, and ketoximes are produced from ketones and hydroxylamine. In general, oximes exist as colorless <a href="/wiki/Crystal" title="Crystal">crystals</a> or as thick liquids and are poorly soluble in water. Therefore, oxime formation can be used for the identification of <a href="/wiki/Ketone" title="Ketone">ketone</a> or aldehyde functional groups. </p><p>Oximes can also be obtained from reaction of <a href="/wiki/Nitrite" title="Nitrite">nitrites</a> such as <a href="/wiki/Isoamyl_Nitrite" class="mw-redirect" title="Isoamyl Nitrite">isoamyl nitrite</a> with compounds containing an acidic hydrogen atom. Examples are the reaction of <a href="/wiki/Ethyl_acetoacetate" title="Ethyl acetoacetate">ethyl acetoacetate</a> and <a href="/wiki/Sodium_nitrite" title="Sodium nitrite">sodium nitrite</a> in <a href="/wiki/Acetic_acid" title="Acetic acid">acetic acid</a>,<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><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> the reaction of <a href="/wiki/Methyl_ethyl_ketone" class="mw-redirect" title="Methyl ethyl ketone">methyl ethyl ketone</a> with <a href="/wiki/Ethyl_nitrite" title="Ethyl nitrite">ethyl nitrite</a> in <a href="/wiki/Hydrochloric_acid" title="Hydrochloric acid">hydrochloric acid</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> and a similar reaction with <a href="/wiki/Propiophenone" title="Propiophenone">propiophenone</a>,<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> the reaction of <a href="/wiki/Phenacyl_chloride" title="Phenacyl chloride">phenacyl chloride</a>,<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 reaction of <a href="/wiki/Malononitrile" title="Malononitrile">malononitrile</a> with sodium nitrite in acetic acid<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> </p><p>A conceptually related reaction is the <a href="/wiki/Japp%E2%80%93Klingemann_reaction" title="Japp–Klingemann reaction">Japp–Klingemann reaction</a>. </p> <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=Oxime&action=edit&section=3" title="Edit section: Reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The <a href="/wiki/Hydrolysis" title="Hydrolysis">hydrolysis</a> of oximes proceeds easily by heating in the presence of various <a href="/wiki/Acid#Common_acids" title="Acid">inorganic acids</a>, and the oximes decompose into the corresponding ketones or aldehydes, and hydroxylamines. The reduction of oximes by <a href="/wiki/Sodium" title="Sodium">sodium</a> metal,<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 href="/wiki/Sodium_amalgam" title="Sodium amalgam">sodium amalgam</a>, <a href="/wiki/Hydrogenation" title="Hydrogenation">hydrogenation</a>, or reaction with <a href="/wiki/Hydride" title="Hydride">hydride</a> reagents produces <a href="/wiki/Amine" title="Amine">amines</a>.<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> Typically the <a href="/wiki/Reduction_(chemistry)" class="mw-redirect" title="Reduction (chemistry)">reduction</a> of aldoximes gives both primary amines and secondary amines; however, reaction conditions can be altered (such as the addition of <a href="/wiki/Potassium_hydroxide" title="Potassium hydroxide">potassium hydroxide</a> in a 1/30 molar ratio) to yield solely primary amines.<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> </p><p>In general, oximes can be changed to the corresponding <a href="/wiki/Amide" title="Amide">amide</a> derivatives by treatment with various acids. This reaction is called <a href="/wiki/Beckmann_rearrangement" title="Beckmann rearrangement">Beckmann rearrangement</a>.<sup id="cite_ref-Clayden-2012_13-0" class="reference"><a href="#cite_note-Clayden-2012-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> In this reaction, a <a href="/wiki/Hydroxyl_group" class="mw-redirect" title="Hydroxyl group">hydroxyl group</a> is exchanged with the group that is in the anti position of the hydroxyl group. The amide derivatives that are obtained by Beckmann rearrangement can be transformed into a <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acid</a> by means of hydrolysis (base or acid catalyzed). Beckmann rearrangement is used for the industrial synthesis of <a href="/wiki/Caprolactam" title="Caprolactam">caprolactam</a> (see applications below). </p><p>The <b>Ponzio reaction</b> (1906)<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> concerning the conversion of <i>m</i>-nitrobenzaldoxime to <i>m</i>-nitrophenyldinitromethane using <a href="/wiki/Dinitrogen_tetroxide" title="Dinitrogen tetroxide">dinitrogen tetroxide</a> was the result of research into <a href="/wiki/Trinitrotoluene" class="mw-redirect" title="Trinitrotoluene">TNT</a> analogues:<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:Ponzio_Synthesis_V2.svg" class="mw-file-description" title="Ponzio reaction"><img alt="Ponzio reaction" src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9f/Ponzio_Synthesis_V2.svg/350px-Ponzio_Synthesis_V2.svg.png" decoding="async" width="350" height="130" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9f/Ponzio_Synthesis_V2.svg/525px-Ponzio_Synthesis_V2.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9f/Ponzio_Synthesis_V2.svg/700px-Ponzio_Synthesis_V2.svg.png 2x" data-file-width="505" data-file-height="188" /></a></span></dd></dl> <p>In the <a href="/wiki/Neber_rearrangement" title="Neber rearrangement">Neber rearrangement</a> certain oximes are converted to the corresponding alpha-amino ketones. </p><p>Oximes can be <a href="/wiki/Dehydration_reaction" title="Dehydration reaction">dehydrated</a> using <a href="/wiki/Acid_anhydride" title="Acid anhydride">acid anhydrides</a> to yield corresponding <a href="/wiki/Nitrile" title="Nitrile">nitriles</a>. </p><p>Certain amidoximes react with <a href="/wiki/Benzenesulfonyl_chloride" title="Benzenesulfonyl chloride">benzenesulfonyl chloride</a> to make substituted <a href="/wiki/Urea" title="Urea">ureas</a> in the <b>Tiemann rearrangement</b>:<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><sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:Tiemann_rearragement.png" class="mw-file-description" title="Tiemann rearragement"><img alt="Tiemann rearragement" src="//upload.wikimedia.org/wikipedia/commons/d/d9/Tiemann_rearragement.png" decoding="async" width="650" height="156" class="mw-file-element" data-file-width="626" data-file-height="150" /></a></span></dd></dl> <div style="clear:left;" class=""></div> <div class="mw-heading mw-heading2"><h2 id="Uses">Uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Oxime&action=edit&section=4" title="Edit section: Uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In their largest application, an oxime is an intermediate in the industrial production of <a href="/wiki/Caprolactam" title="Caprolactam">caprolactam</a>, a precursor to <a href="/wiki/Nylon_6" title="Nylon 6">Nylon 6</a>. About half of the world's supply of <a href="/wiki/Cyclohexanone" title="Cyclohexanone">cyclohexanone</a>, more than a million tonnes annually, is converted to the oxime. In the presence of <a href="/wiki/Sulfuric_acid" title="Sulfuric acid">sulfuric acid</a> <a href="/wiki/Catalyst" class="mw-redirect" title="Catalyst">catalyst</a>, the oxime undergoes the <a href="/wiki/Beckmann_rearrangement" title="Beckmann rearrangement">Beckmann rearrangement</a> to give the cyclic amide caprolactam:<sup id="cite_ref-Ullmann_18-0" class="reference"><a href="#cite_note-Ullmann-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><dl><dd><span typeof="mw:File"><a href="/wiki/File:Caprolactam_Synth.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0b/Caprolactam_Synth.png/340px-Caprolactam_Synth.png" decoding="async" width="340" height="98" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0b/Caprolactam_Synth.png/510px-Caprolactam_Synth.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0b/Caprolactam_Synth.png/680px-Caprolactam_Synth.png 2x" data-file-width="905" data-file-height="261" /></a></span></dd></dl></dd></dl> <div class="mw-heading mw-heading3"><h3 id="Metal_extractant">Metal extractant</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Oxime&action=edit&section=5" title="Edit section: Metal extractant"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:NIMGLO12.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5d/NIMGLO12.png/220px-NIMGLO12.png" decoding="async" width="220" height="332" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5d/NIMGLO12.png/330px-NIMGLO12.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5d/NIMGLO12.png/440px-NIMGLO12.png 2x" data-file-width="1200" data-file-height="1809" /></a><figcaption>Structure of <a href="/wiki/Nickel_bis(dimethylglyoximate)" title="Nickel bis(dimethylglyoximate)">Nickel bis(dimethylglyoximate)</a>.</figcaption></figure> <p>Oximes are commonly used as ligands and sequestering agents for metal ions. <a href="/wiki/Dimethylglyoxime" title="Dimethylglyoxime">Dimethylglyoxime</a> (dmgH<sub>2</sub>) is a reagent for the analysis of nickel and a popular ligand in its own right. In the typical reaction, a metal reacts with two equivalents of dmgH<sub>2</sub> concomitant with ionization of one proton. <a href="/wiki/Salicylaldoxime" title="Salicylaldoxime">Salicylaldoxime</a> is a <a href="/wiki/Chelator" class="mw-redirect" title="Chelator">chelator</a> in <a href="/wiki/Hydrometallurgy" title="Hydrometallurgy">hydrometallurgy</a>.<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p><p>Amidoximes such as polyacrylamidoxime can be used to capture trace amounts of <a href="/wiki/Uranium" title="Uranium">uranium</a> from sea water.<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> In 2017 researchers announced a configuration that absorbed up to nine times as much <a href="/wiki/Uranyl" title="Uranyl">uranyl</a> as previous fibers without saturating.<sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Other_applications">Other applications</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Oxime&action=edit&section=6" title="Edit section: Other applications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li>Oxime compounds are used as antidotes for <a href="/wiki/Nerve_agent" title="Nerve agent">nerve agents</a>. A nerve agent inactivates <a href="/wiki/Acetylcholinesterase" title="Acetylcholinesterase">acetylcholinesterase</a> by phosphorylation. Oxime compounds can reactivate acetylcholinesterase by attaching to phosphorus, forming an oxime-phosphonate, which then splits away from the acetylcholinesterase molecule. Oxime nerve-agent antidotes are <a href="/wiki/Pralidoxime" title="Pralidoxime">pralidoxime</a> (also known as <a href="/wiki/2-PAM" class="mw-redirect" title="2-PAM">2-PAM</a>), <a href="/wiki/Obidoxime" title="Obidoxime">obidoxime</a>, methoxime, <a href="/wiki/HI-6" class="mw-redirect" title="HI-6">HI-6</a>, Hlo-7, and <a href="/wiki/Trimedoxime_bromide" title="Trimedoxime bromide">TMB-4</a>.<sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> The effectiveness of the oxime treatment depends on the particular nerve agent used.<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> <li><a href="/wiki/Perillartine" title="Perillartine">Perillartine</a>, the oxime of <a href="/wiki/Perillaldehyde" title="Perillaldehyde">perillaldehyde</a>, is used as an artificial sweetener in Japan. It is 2000 times sweeter than <a href="/wiki/Sucrose" title="Sucrose">sucrose</a>.</li> <li>Diaminoglyoxime is a key precursor to various compounds containing the highly reactive <a href="/wiki/Furazan" title="Furazan">furazan</a> ring.</li> <li><a href="/wiki/Methyl_ethyl_ketoxime" class="mw-redirect" title="Methyl ethyl ketoxime">Methyl ethyl ketoxime</a> is a skin-preventing additive in many oil-based paints.</li> <li>Buccoxime and 5-methyl-3-heptanone oxime ("Stemone") are perfume ingredients.<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></li> <li><a href="/wiki/Fluvoxamine" title="Fluvoxamine">Fluvoxamine</a> is used as an antidepressant.</li></ul> <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=Oxime&action=edit&section=7" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Category:Oximes" title="Category:Oximes">Category:Oximes</a> – specific chemicals containing this functional group</li> <li><a href="/wiki/Nitrone" title="Nitrone">Nitrone</a> – the <i>N</i>-oxide of an imine</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=Oxime&action=edit&section=8" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text">The name "oxime" is derived from "oximide" (i.e., <i>oxy-</i> + amide). According to the German organic chemist <a href="/wiki/Victor_Meyer" class="mw-redirect" title="Victor Meyer">Victor Meyer</a> (1848–1897) – who, with Alois Janny, synthesized the first oximes – an "oximide" was an organic compound containing the group (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">=N−OH</span>) attached to a carbon atom. The existence of oximides was questioned at the time (ca. 1882). (See page 1164 of: Victor Meyer und Alois Janny (1882a) <a rel="nofollow" class="external text" href="http://gallica.bnf.fr/ark:/12148/bpt6k90694n/f1165.langEN">"Ueber stickstoffhaltige Acetonderivate"</a> (On nitrogenous derivatives of acetone), <span title="German-language text"><i lang="de">Berichte der Deutschen chemischen Gesellschaft</i></span>, <b>15</b>: 1164–1167.) However, in 1882, Meyer and Janny succeeded in synthesizing methylglyoxime (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>C(=NOH)CH(=NOH)</span>), which they named "<span title="German-language text"><i lang="de">Acetoximsäure</i></span>" (acetoximic acid) (Meyer & Janny, 1882a, p. 1166). Subsequently, they synthesized 2-propanone, oxime (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub>C=NOH</span>), which they named "<span title="German-language text"><i lang="de">Acetoxim</i></span>" (acetoxime), in analogy with <span title="German-language text"><i lang="de">Acetoximsäure</i></span>. From Victor Meyer and Alois Janny (1882b) <a rel="nofollow" class="external text" href="http://gallica.bnf.fr/ark:/12148/bpt6k90694n/f1323.image.langEN">"Ueber die Einwirkung von Hydroxylamin auf Aceton"</a> (On the effect of hydroxylamine on acetone), <span title="German-language text"><i lang="de">Berichte der Deutschen chemischen Gesellschaft</i></span>, <b>15</b>: 1324–1326, page 1324: <span title="German-language text"><i lang="de">"Die Substanz, welche wir, wegen ihrer nahen Beziehungen zur Acetoximsäure, und da sie keine sauren Eigenschaften besitzt, vorläufig Acetoxim nennen wollen, …"</i></span> (The substance, which we – on account of its close relations to acetoximic acid, and since it possesses no acid properties – will, for the present, name "acetoxime," … )</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"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFReusch,_W." class="citation web cs1">Reusch, W. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20100621013212/http://www.cem.msu.edu/~reusch/VirtTxtJml/Spectrpy/InfraRed/infrared.htm">"Infrared Spectroscopy"</a>. <i>Virtual Textbook of Organic Chemistry</i>. <a href="/wiki/Michigan_State_University" title="Michigan State University">Michigan State University</a>. Archived from <a rel="nofollow" class="external text" href="http://www.cem.msu.edu/~reusch/VirtTxtJml/Spectrpy/InfraRed/infrared.htm">the original</a> on 21 June 2010<span class="reference-accessdate">. Retrieved <span class="nowrap">6 July</span> 2009</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Virtual+Textbook+of+Organic+Chemistry&rft.atitle=Infrared+Spectroscopy&rft.au=Reusch%2C+W.&rft_id=http%3A%2F%2Fwww.cem.msu.edu%2F~reusch%2FVirtTxtJml%2FSpectrpy%2FInfraRed%2Finfrared.htm&rfr_id=info%3Asid%2Fen.wikipedia.org%3AOxime" 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="CITEREFKaliaRaines2008" class="citation journal cs1">Kalia, J.; Raines, R. T. 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"Review of oximes in the antidotal treatment of poisoning by organophosphorus nerve agents". <i>Journal of Toxicology: Clinical Toxicology</i>. <b>40</b> (6): 803–16. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1081%2FCLT-120015840">10.1081/CLT-120015840</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/12475193">12475193</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:20536869">20536869</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Toxicology%3A+Clinical+Toxicology&rft.atitle=Review+of+oximes+in+the+antidotal+treatment+of+poisoning+by+organophosphorus+nerve+agents&rft.volume=40&rft.issue=6&rft.pages=803-16&rft.date=2002&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A20536869%23id-name%3DS2CID&rft_id=info%3Apmid%2F12475193&rft_id=info%3Adoi%2F10.1081%2FCLT-120015840&rft.au=Kassa%2C+J.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AOxime" class="Z3988"></span></span> </li> <li id="cite_note-25"><span class="mw-cite-backlink"><b><a href="#cite_ref-25">^</a></b></span> <span class="reference-text">Johannes Panten and Horst Surburg "Flavors and Fragrances, 2. Aliphatic Compounds" in Ullmann's Encyclopedia of Industrial Chemistry, 2015, Wiley-VCH, Weinheim.<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/10.1002%2F14356007.t11_t01">10.1002/14356007.t11_t01</a></span> </li> </ol></div></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 dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl dl,.mw-parser-output .hlist dl ol,.mw-parser-output .hlist dl ul,.mw-parser-output .hlist ol dl,.mw-parser-output .hlist ol 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style="padding:0 0.25em"> <ul><li><a href="/wiki/Metadoxine" title="Metadoxine">Metadoxine</a></li> <li><a href="/wiki/Thiamine" title="Thiamine">Thiamine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Barbiturate_overdose" title="Barbiturate overdose">Barbiturate<br /> overdose</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/Bemegride" title="Bemegride">Bemegride</a></li> <li><a href="/wiki/Etamivan" title="Etamivan">Ethamivan</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Benzodiazepine_overdose" title="Benzodiazepine overdose">Benzodiazepine<br /> overdose</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/Cyprodenate" title="Cyprodenate">Cyprodenate</a></li> <li><a href="/wiki/Flumazenil" title="Flumazenil">Flumazenil</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/GHB_overdose" class="mw-redirect" title="GHB overdose">GHB overdose</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/Physostigmine" title="Physostigmine">Physostigmine</a></li> <li><a href="/wiki/SCH-50911" title="SCH-50911">SCH-50911</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nerve_agent" title="Nerve agent">Nerve agent</a> /<br /> <a href="/wiki/Organophosphate_poisoning" title="Organophosphate poisoning">Organophosphate<br /> poisoning</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/Atropine" title="Atropine">Atropine</a><sup>#</sup></li> <li><a href="/wiki/Biperiden" title="Biperiden">Biperiden</a></li> <li><a href="/wiki/Diazepam" title="Diazepam">Diazepam</a><sup>#</sup></li> <li><a class="mw-selflink selflink">Oximes</a> <ul><li><a href="/wiki/Obidoxime" title="Obidoxime">Obidoxime</a></li> <li><a href="/wiki/Pralidoxime" title="Pralidoxime">Pralidoxime</a></li></ul></li> <li><i>see also:</i> <a href="/wiki/Cholinesterase" title="Cholinesterase">Cholinesterase</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Opioid_overdose" title="Opioid overdose">Opioid overdose</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/Diprenorphine" title="Diprenorphine">Diprenorphine</a></li> <li><a href="/wiki/Doxapram" title="Doxapram">Doxapram</a></li> <li><a href="/wiki/Nalmefene" title="Nalmefene">Nalmefene</a></li> <li><a href="/wiki/Nalorphine" title="Nalorphine">Nalorphine</a></li> <li><a href="/wiki/Naloxone" title="Naloxone">Naloxone</a><sup>#</sup></li> <li><a href="/wiki/Naltrexone" title="Naltrexone">Naltrexone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Reversal of<br /> <a href="/wiki/Neuromuscular-blocking_drug" title="Neuromuscular-blocking drug">neuromuscular blockade</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/Sugammadex" title="Sugammadex">Sugammadex</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Circulatory_system" title="Circulatory system">Circulatory<br /> system</a></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/Beta_blocker#Adverse_effects" title="Beta blocker">Beta blocker</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/Glucagon" title="Glucagon">Glucagon</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Digoxin_toxicity" title="Digoxin toxicity">Digoxin toxicity</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/Digoxin_immune_fab" title="Digoxin immune fab">Digoxin immune fab</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Anticoagulant" title="Anticoagulant">Anticoagulants</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>against <a href="/wiki/Direct_Xa_inhibitor" class="mw-redirect" title="Direct Xa inhibitor">direct Xa inhibitors</a> (<a href="/wiki/Andexanet_alfa" title="Andexanet alfa">Andexanet alfa</a>)</li> <li>against <a href="/wiki/Heparin" title="Heparin">heparin</a> (<a href="/wiki/Protamine_sulfate" title="Protamine sulfate">Protamine</a><sup>#</sup>)</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-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/Arsenic_poisoning" title="Arsenic poisoning">Arsenic poisoning</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/Dimercaprol" title="Dimercaprol">Dimercaprol</a><sup>#</sup></li> <li><a href="/wiki/Dimercaptosuccinic_acid" class="mw-redirect" title="Dimercaptosuccinic acid">Succimer</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Cyanide_poisoning" title="Cyanide poisoning">Cyanide poisoning</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/4-Dimethylaminophenol" title="4-Dimethylaminophenol">4-Dimethylaminophenol</a></li> <li><a href="/wiki/Hydroxocobalamin" title="Hydroxocobalamin">Hydroxocobalamin</a></li> <li><i><a href="/wiki/Nitrite" title="Nitrite">nitrite</a></i> <ul><li><a href="/wiki/Amyl_nitrite" title="Amyl nitrite">Amyl nitrite</a></li> <li><a href="/wiki/Sodium_nitrite" title="Sodium nitrite">Sodium nitrite</a><sup>#</sup></li></ul></li> <li><a href="/wiki/Sodium_thiosulfate_(medical_use)" title="Sodium thiosulfate (medical use)">Sodium thiosulfate</a><sup>#</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hydrofluoric_acid" title="Hydrofluoric acid">Hydrofluoric acid</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/Calcium_gluconate" title="Calcium gluconate">Calcium gluconate</a><sup>#</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Methanol" title="Methanol">Methanol</a> /<br /> <a href="/wiki/Ethylene_glycol_poisoning" title="Ethylene glycol poisoning">Ethylene glycol<br /> poisoning</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>Primary alcohols: <a href="/wiki/Alcohol_(medicine)" class="mw-redirect" title="Alcohol (medicine)">Ethanol</a></li> <li><a href="/wiki/Fomepizole" title="Fomepizole">Fomepizole</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Paracetamol_poisoning" title="Paracetamol poisoning">Paracetamol toxicity</a><br /> (Acetaminophen)</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/Acetylcysteine" title="Acetylcysteine">Acetylcysteine</a><sup>#</sup></li> <li><a href="/wiki/Glutathione" title="Glutathione">Glutathione</a></li> <li><a href="/wiki/Methionine" title="Methionine">Methionine</a><sup>#</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Toxic_metal" class="mw-redirect" title="Toxic metal">Toxic metals</a> (<a href="/wiki/Cadmium_poisoning" title="Cadmium poisoning">cadmium</a> <ul><li><a href="/wiki/Lead_poisoning" title="Lead poisoning">lead</a></li> <li><a href="/wiki/Mercury_poisoning" title="Mercury poisoning">mercury</a></li> <li><a href="/wiki/Thallium_poisoning" title="Thallium poisoning">thallium</a>)</li></ul></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <li><a href="/wiki/Dimercaprol" title="Dimercaprol">Dimercaprol</a><sup>#</sup></li> <li><a href="/wiki/Ethylenediaminetetraacetic_acid" title="Ethylenediaminetetraacetic acid">Edetates</a></li> <li><a href="/wiki/Prussian_blue" title="Prussian blue">Prussian blue</a><sup>#</sup></li> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Iodine-131" title="Iodine-131">iodine-131</a></i> <ul><li><a href="/wiki/Potassium_iodide" title="Potassium iodide">Potassium iodide</a></li></ul></li> <li><a href="/wiki/Methylene_blue" title="Methylene blue">Methylthioninium chloride</a><sup>#</sup></li> <li><i><a href="/wiki/Oxidizing_agent" title="Oxidizing agent">oxidizing agent</a></i> <ul><li><a href="/wiki/Potassium_permanganate" title="Potassium permanganate">Potassium permanganate</a></li></ul></li> <li><a href="/wiki/Prednisolone/promethazine" title="Prednisolone/promethazine">Prednisolone/promethazine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Emetic" class="mw-redirect" title="Emetic">Emetic</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/Copper(II)_sulfate" title="Copper(II) sulfate">Copper sulfate</a></li> <li><a href="/wiki/Psychotria_ipecacuanha" class="mw-redirect" title="Psychotria ipecacuanha">Ipecacuanha</a> <ul><li><a href="/wiki/Syrup_of_ipecac" title="Syrup of ipecac">Syrup of ipecac</a></li></ul></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="background: transparent; padding: 0px;"><div><div class="hlist"> <ul><li><sup>#</sup><a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li><sup>‡</sup><a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li><sup>†</sup><a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li><sup>§</sup>Never to phase III</li></ul></li></ul> </div></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"><style data-mw-deduplicate="TemplateStyles:r886047488">.mw-parser-output .nobold{font-weight:normal}</style><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r886047488"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r886047488"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r886047488"></div><div role="navigation" class="navbox" aria-labelledby="Functional_groups" style="padding:3px"><table class="nowraplinks hlist 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: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_groups" 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 href="/wiki/Imine" title="Imine">Imine</a></li> <li><a class="mw-selflink selflink">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/Phosphorus" title="Phosphorus">Phosphorus</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/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-odd" 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/Sulfide_(organic)" class="mw-redirect" title="Sulfide (organic)">Sulfide</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-even" 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-odd" 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></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-even" 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></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 authority-control" aria-label="Navbox" 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