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Available in 26 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-26" 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">26 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%AB%D9%8A%D9%88%D8%A5%D8%B3%D8%AA%D8%B1" title="ثيوإستر – Arabic" lang="ar" hreflang="ar" data-title="ثيوإستر" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Tioester" title="Tioester – Bosnian" lang="bs" hreflang="bs" data-title="Tioester" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Tio%C3%A8ster" title="Tioèster – Catalan" lang="ca" hreflang="ca" data-title="Tioèster" 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/Thioestery" title="Thioestery – Czech" lang="cs" hreflang="cs" data-title="Thioestery" 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/Thioester" title="Thioester – German" lang="de" hreflang="de" data-title="Thioester" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Tio%C3%A9ster" title="Tioéster – Spanish" lang="es" hreflang="es" data-title="Tioéster" 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%AA%DB%8C%D9%88%D8%A7%D8%B3%D8%AA%D8%B1" title="تیواستر – Persian" lang="fa" hreflang="fa" data-title="تیواستر" 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/Thioester" title="Thioester – French" lang="fr" hreflang="fr" data-title="Thioester" 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/Tio%C3%A9ster" title="Tioéster – Galician" lang="gl" hreflang="gl" data-title="Tioéster" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D4%B9%D5%AB%D5%B8%D5%A7%D5%BD%D5%A9%D5%A5%D6%80%D5%B6%D5%A5%D6%80" title="Թիոէսթերներ – Armenian" lang="hy" hreflang="hy" data-title="Թիոէսթերներ" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Tioesteri" title="Tioesteri – Italian" lang="it" hreflang="it" data-title="Tioesteri" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Tio%C3%A9szter" title="Tioészter – Hungarian" lang="hu" hreflang="hu" data-title="Tioészter" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Thio-ester" title="Thio-ester – Dutch" lang="nl" hreflang="nl" data-title="Thio-ester" 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%83%81%E3%82%AA%E3%82%A8%E3%82%B9%E3%83%86%E3%83%AB" title="チオエステル – Japanese" lang="ja" hreflang="ja" data-title="チオエステル" 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/Tioestry" title="Tioestry – Polish" lang="pl" hreflang="pl" data-title="Tioestry" 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/Tio%C3%A9ster" title="Tioéster – Portuguese" lang="pt" hreflang="pt" data-title="Tioéster" 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/Tioester" title="Tioester – Romanian" lang="ro" hreflang="ro" data-title="Tioester" 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%A1%D0%BB%D0%BE%D0%B6%D0%BD%D1%8B%D0%B5_%D1%82%D0%B8%D0%BE%D1%8D%D1%84%D0%B8%D1%80%D1%8B" title="Сложные тиоэфиры – Russian" lang="ru" hreflang="ru" data-title="Сложные тиоэфиры" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Thioester" title="Thioester – Simple English" lang="en-simple" hreflang="en-simple" data-title="Thioester" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target"><span>Simple English</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Tioester" title="Tioester – Slovak" lang="sk" hreflang="sk" data-title="Tioester" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Tioestar" title="Tioestar – Serbian" lang="sr" hreflang="sr" data-title="Tioestar" 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/Tioestar" title="Tioestar – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Tioestar" 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/Tioesterit" title="Tioesterit – Finnish" lang="fi" hreflang="fi" data-title="Tioesterit" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-tl mw-list-item"><a href="https://tl.wikipedia.org/wiki/Thioester" title="Thioester – Tagalog" lang="tl" hreflang="tl" data-title="Thioester" data-language-autonym="Tagalog" data-language-local-name="Tagalog" class="interlanguage-link-target"><span>Tagalog</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Tiyoester" title="Tiyoester – Turkish" lang="tr" hreflang="tr" data-title="Tiyoester" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E7%A1%AB%E9%85%AF" title="硫酯 – Chinese" lang="zh" hreflang="zh" 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<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">Organosulfur compounds of the form R–SC(=O)–R’</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">"Thioate" redirects here. For the ion class, see <a href="/wiki/Thiocarboxylic_acid" title="Thiocarboxylic acid">thiocarboxylic acid</a>.</div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Thioester-2D-A.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/90/Thioester-2D-A.svg/150px-Thioester-2D-A.svg.png" decoding="async" width="150" height="134" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/90/Thioester-2D-A.svg/225px-Thioester-2D-A.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/90/Thioester-2D-A.svg/300px-Thioester-2D-A.svg.png 2x" data-file-width="475" data-file-height="425" /></a><figcaption>General structure of a thioester, where R and R' are <a href="/wiki/Organyl" class="mw-redirect" title="Organyl">organyl</a> groups, or <a href="/wiki/Hydrogen" title="Hydrogen">H</a> in the case of R.</figcaption></figure> <p>In <a href="/wiki/Organic_chemistry" title="Organic chemistry">organic chemistry</a>, <b>thioesters</b> are <a href="/wiki/Organosulfur_compounds" class="mw-redirect" title="Organosulfur compounds">organosulfur compounds</a> with the molecular structure <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">R−C(=O)−S−R’</span>. They are analogous to <a href="/wiki/Carboxylate_ester" class="mw-redirect" title="Carboxylate ester">carboxylate esters</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R−C(=O)−O−R’</span>) with the sulfur in the thioester replacing oxygen in the carboxylate ester, as implied by the <a href="/wiki/Thio-" title="Thio-">thio-</a> prefix. They are the product of <a href="/wiki/Esterification" class="mw-redirect" title="Esterification">esterification</a> of a <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acid</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R−C(=O)−O−H</span>) with a <a href="/wiki/Thiol" title="Thiol">thiol</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R'−S−H</span>). In <a href="/wiki/Biochemistry" title="Biochemistry">biochemistry</a>, the best-known thioesters are derivatives of <a href="/wiki/Coenzyme_A" title="Coenzyme A">coenzyme A</a>, e.g., <a href="/wiki/Acetyl-CoA" title="Acetyl-CoA">acetyl-CoA</a>.<sup id="cite_ref-PATAI_1-0" class="reference"><a href="#cite_note-PATAI-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> The R and R' represent <a href="/wiki/Organyl" class="mw-redirect" title="Organyl">organyl</a> groups, or <a href="/wiki/Hydrogen" title="Hydrogen">H</a> in the case of R. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Synthesis">Synthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Thioester&action=edit&section=1" title="Edit section: Synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>One route to thioesters involves the reaction of an <a href="/wiki/Acid_chloride" class="mw-redirect" title="Acid chloride">acid chloride</a> with an <a href="/wiki/Alkali_metal" title="Alkali metal">alkali metal</a> salt of a thiol:<sup id="cite_ref-PATAI_1-1" class="reference"><a href="#cite_note-PATAI-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">RSNa + R'COCl → R'COSR + NaCl</span></dd></dl> <p>Another common route entails the displacement of <a href="/wiki/Halide" title="Halide">halides</a> by the alkali metal salt of a <a href="/wiki/Thiocarboxylic_acid" title="Thiocarboxylic acid">thiocarboxylic acid</a>. For example, thioacetate esters are commonly prepared by <a href="/wiki/Alkylation" title="Alkylation">alkylation</a> of <a href="/wiki/Potassium_thioacetate" title="Potassium thioacetate">potassium thioacetate</a>:<sup id="cite_ref-PATAI_1-2" class="reference"><a href="#cite_note-PATAI-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>COSK + RX → CH<sub class="template-chem2-sub">3</sub>COSR + KX</span></dd></dl> <p>The analogous alkylation of an acetate salt is rarely practiced. The alkylation can be conducted using <a href="/wiki/Mannich_base" title="Mannich base">Mannich bases</a> and the thiocarboxylic acid: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>COSH + R'<sub class="template-chem2-sub">2</sub>NCH<sub class="template-chem2-sub">2</sub>OH → CH<sub class="template-chem2-sub">3</sub>COSCH<sub class="template-chem2-sub">2</sub>NR'<sub class="template-chem2-sub">2</sub> + H<sub class="template-chem2-sub">2</sub>O</span></dd></dl> <p>Thioesters can be prepared by condensation of thiols and carboxylic acids in the presence of <a href="/wiki/Desiccant" title="Desiccant">dehydrating agents</a>:<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><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> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">RSH + R'CO<sub class="template-chem2-sub">2</sub>H → RSC(O)R' + H<sub class="template-chem2-sub">2</sub>O</span></dd></dl> <p>A typical dehydration agent is <a href="/wiki/N,N%27-Dicyclohexylcarbodiimide" title="N,N'-Dicyclohexylcarbodiimide">DCC</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> Efforts to improve the sustainability of thioester synthesis have also been reported utilising safer coupling reagent <a href="/wiki/Propanephosphonic_acid_anhydride" title="Propanephosphonic acid anhydride">T3P</a> and greener solvent <a href="/wiki/Cyclopentanone" title="Cyclopentanone">cyclopentanone</a>.<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> <a href="/wiki/Acid_anhydride" title="Acid anhydride">Acid anhydrides</a> and some <a href="/wiki/Lactone" title="Lactone">lactones</a> also give thioesters upon treatment with thiols in the presence of a base. </p><p>Thioesters can be conveniently prepared from alcohols by the <a href="/wiki/Mitsunobu_reaction" title="Mitsunobu reaction">Mitsunobu reaction</a>, using <a href="/wiki/Thioacetic_acid" title="Thioacetic acid">thioacetic 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> </p><p>They also arise via <a href="/wiki/Carbonylation" title="Carbonylation">carbonylation</a> of <a href="/wiki/Alkyne" title="Alkyne">alkynes</a> and <a href="/wiki/Alkene" title="Alkene">alkenes</a> in the presence of thiols.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p> <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=Thioester&action=edit&section=2" title="Edit section: Reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Thioesters hydrolyze to thiols and the carboxylic acid: </p> <dl><dd>RC(O)SR' + H<sub>2</sub>O → RCO<sub>2</sub>H + RSH</dd></dl> <p>The carbonyl center in thioesters is more reactive toward amine than oxygen nucleophiles, giving <a href="/wiki/Amide" title="Amide">amides</a>: </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:FormationofAmides.png" class="mw-file-description" title="Formation of amides from thioesters"><img alt="Formation of amides from thioesters" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2c/FormationofAmides.png/500px-FormationofAmides.png" decoding="async" width="500" height="80" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/2c/FormationofAmides.png/750px-FormationofAmides.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/2c/FormationofAmides.png/1000px-FormationofAmides.png 2x" data-file-width="1808" data-file-height="288" /></a></span></dd></dl> <p>This reaction is exploited in <a href="/wiki/Native_chemical_ligation" title="Native chemical ligation">native chemical ligation</a>, a protocol for <a href="/wiki/Peptide_synthesis" title="Peptide synthesis">peptide synthesis</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> </p><p>In a related reaction, thioesters can be converted into esters.<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> Thioacetate esters can also be cleaved with methanethiol in the presence of stoichiometric base, as illustrated in the preparation of pent-4-yne-1-thiol:<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> </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">H<sub class="template-chem2-sub">3</sub>C(CH<sub class="template-chem2-sub">2</sub>)<sub class="template-chem2-sub">3</sub>OMs + KSAc → H<sub class="template-chem2-sub">3</sub>C(CH<sub class="template-chem2-sub">2</sub>)<sub class="template-chem2-sub">3</sub>SAc + KOMs</span></dd> <dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">H<sub class="template-chem2-sub">3</sub>C(CH<sub class="template-chem2-sub">2</sub>)<sub class="template-chem2-sub">3</sub>SAc + HSMe → H<sub class="template-chem2-sub">3</sub>C(CH<sub class="template-chem2-sub">2</sub>)<sub class="template-chem2-sub">3</sub>SH + MeSAc</span></dd></dl> <p>A reaction unique to thioesters is the <a href="/wiki/Fukuyama_coupling" title="Fukuyama coupling">Fukuyama coupling</a>, in which the thioester is coupled with an <a href="/wiki/Organozinc_halide" class="mw-redirect" title="Organozinc halide">organozinc halide</a> by a palladium catalyst to give a ketone. </p> <dl><dd><span class="mw-default-size" typeof="mw:File"><a href="/wiki/File:FukuyamaCoupling.svg" class="mw-file-description" title="Fukuyama coupling"><img alt="Fukuyama coupling" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2b/FukuyamaCoupling.svg/411px-FukuyamaCoupling.svg.png" decoding="async" width="411" height="101" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/2b/FukuyamaCoupling.svg/617px-FukuyamaCoupling.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/2b/FukuyamaCoupling.svg/822px-FukuyamaCoupling.svg.png 2x" data-file-width="411" data-file-height="101" /></a></span></dd></dl> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:NCL_mechanism.pdf" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/91/NCL_mechanism.pdf/page1-300px-NCL_mechanism.pdf.jpg" decoding="async" width="300" height="232" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/91/NCL_mechanism.pdf/page1-450px-NCL_mechanism.pdf.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/91/NCL_mechanism.pdf/page1-600px-NCL_mechanism.pdf.jpg 2x" data-file-width="987" data-file-height="762" /></a><figcaption>Thioesters are components of the <a href="/wiki/Native_chemical_ligation" title="Native chemical ligation">native chemical ligation</a> method for peptide synthesis.</figcaption></figure> <div class="mw-heading mw-heading2"><h2 id="Biochemistry">Biochemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Thioester&action=edit&section=3" title="Edit section: Biochemistry"><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 selfref">See also: <a href="/wiki/Category:Thioesters_of_coenzyme_A" title="Category:Thioesters of coenzyme A">Category:Thioesters of coenzyme A</a></div> <figure class="mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Acetyl-CoA-2D.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/ea/Acetyl-CoA-2D.svg/320px-Acetyl-CoA-2D.svg.png" decoding="async" width="320" height="117" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/ea/Acetyl-CoA-2D.svg/480px-Acetyl-CoA-2D.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/ea/Acetyl-CoA-2D.svg/640px-Acetyl-CoA-2D.svg.png 2x" data-file-width="512" data-file-height="187" /></a><figcaption>Structure of <a href="/wiki/Acetyl-CoA" title="Acetyl-CoA">acetyl coenzyme A</a>, a thioester that is a key intermediate in the biosynthesis of many biomolecules.</figcaption></figure> <p>Thioesters are common <a href="/wiki/Reaction_intermediate" title="Reaction intermediate">intermediates</a> in many biosynthetic reactions, including the formation and degradation of <a href="/wiki/Fatty_acid" title="Fatty acid">fatty acids</a> and <a href="/wiki/Mevalonate" class="mw-redirect" title="Mevalonate">mevalonate</a>, precursor to steroids. Examples include <a href="/wiki/Malonyl-CoA" title="Malonyl-CoA">malonyl-CoA</a>, <a href="/wiki/Acetoacetyl-CoA" title="Acetoacetyl-CoA">acetoacetyl-CoA</a>, <a href="/wiki/Propionyl-CoA" title="Propionyl-CoA">propionyl-CoA</a>, <a href="/wiki/Cinnamoyl-CoA" title="Cinnamoyl-CoA">cinnamoyl-CoA</a>, and <a href="/wiki/Acyl_carrier_protein" title="Acyl carrier protein">acyl carrier protein</a> (ACP) thioesters. <a href="/wiki/Acetogenesis" title="Acetogenesis">Acetogenesis</a> proceeds via the formation of <a href="/wiki/Acetyl-CoA" title="Acetyl-CoA">acetyl-CoA</a>. The biosynthesis of <a href="/wiki/Lignin" title="Lignin">lignin</a>, which comprises a large fraction of the Earth's land biomass, proceeds via a thioester derivative of <a href="/wiki/Caffeic_acid" title="Caffeic acid">caffeic acid</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> These thioesters arise analogously to those prepared synthetically, the difference being that the dehydration agent is ATP. In addition, thioesters play an important role in the tagging of proteins with <a href="/wiki/Ubiquitin" title="Ubiquitin">ubiquitin</a>, which tags the protein for degradation. </p><p>Oxidation of the sulfur atom in thioesters (<a href="/wiki/Thiolactone" title="Thiolactone">thiolactones</a>) is postulated in the bioactivation of the antithrombotic prodrugs <a href="/wiki/Ticlopidine" title="Ticlopidine">ticlopidine</a>, <a href="/wiki/Clopidogrel" title="Clopidogrel">clopidogrel</a>, and <a href="/wiki/Prasugrel" title="Prasugrel">prasugrel</a>.<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> </p> <div class="mw-heading mw-heading3"><h3 id="Thioesters_and_the_origin_of_life">Thioesters and the origin of life</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Thioester&action=edit&section=4" title="Edit section: Thioesters and the origin of life"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>As posited in a "Thioester World", thioesters are possible precursors to life.<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> As <a href="/wiki/Christian_de_Duve" title="Christian de Duve">Christian de Duve</a> explains: </p> <blockquote><p>It is revealing that thioesters are obligatory intermediates in several key processes in which <a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a> is either used or regenerated. Thioesters are involved in the synthesis of all <a href="/wiki/Esters" class="mw-redirect" title="Esters">esters</a>, including those found in complex <a href="/wiki/Lipid" title="Lipid">lipids</a>. They also participate in the synthesis of a number of other cellular components, including <a href="/wiki/Peptide" title="Peptide">peptides</a>, <a href="/wiki/Fatty_acid" title="Fatty acid">fatty acids</a>, <a href="/wiki/Sterol" title="Sterol">sterols</a>, <a href="/wiki/Terpene" title="Terpene">terpenes</a>, <a href="/wiki/Porphyrin" title="Porphyrin">porphyrins</a>, and others. In addition, thioesters are formed as key intermediates in several particularly ancient processes that result in the assembly of ATP. In both these instances, the thioester is closer than ATP to the process that uses or yields energy. In other words, thioesters could have actually played the role of ATP in a "thioester world" initially devoid of ATP. Eventually, [these] thioesters could have served to usher in ATP through its ability to support the formation of bonds between <a href="/wiki/Phosphate_group" class="mw-redirect" title="Phosphate group">phosphate groups</a>.</p></blockquote> <p>However, due to the high free energy change of thioester's hydrolysis and correspondingly their low equilibrium constants, it is unlikely that these compounds could have accumulated abiotically to any significant extent especially in hydrothermal vent conditions.<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> <div class="mw-heading mw-heading2"><h2 id="Thionoesters">Thionoesters</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Thioester&action=edit&section=5" title="Edit section: Thionoesters"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Thionoester_general_structure.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/32/Thionoester_general_structure.png/150px-Thionoester_general_structure.png" decoding="async" width="150" height="113" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/32/Thionoester_general_structure.png/225px-Thionoester_general_structure.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/32/Thionoester_general_structure.png/300px-Thionoester_general_structure.png 2x" data-file-width="1080" data-file-height="810" /></a><figcaption>General structure of a thionoester, where R and R' are <a href="/wiki/Organyl" class="mw-redirect" title="Organyl">organyl</a> groups, or <a href="/wiki/Hydrogen" title="Hydrogen">H</a> in the case of R</figcaption></figure> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Methyl-thionobenzoate-2D-skeletal.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Methyl-thionobenzoate-2D-skeletal.png/150px-Methyl-thionobenzoate-2D-skeletal.png" decoding="async" width="150" height="115" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Methyl-thionobenzoate-2D-skeletal.png/225px-Methyl-thionobenzoate-2D-skeletal.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Methyl-thionobenzoate-2D-skeletal.png/300px-Methyl-thionobenzoate-2D-skeletal.png 2x" data-file-width="1100" data-file-height="845" /></a><figcaption><a href="/wiki/Skeletal_formula" title="Skeletal formula">Skeletal formula</a> of methyl thionobenzoate</figcaption></figure> <p><b>Thionoesters</b> are isomeric with thioesters. In a thionoester, sulfur replaces the carbonyl oxygen in an ester. Methyl thionobenzoate is C<sub>6</sub>H<sub>5</sub>C(S)OCH<sub>3</sub>. Such compounds are typically prepared by the reaction of the <a href="/wiki/Thioacyl_chloride" title="Thioacyl chloride">thioacyl chloride</a> with an alcohol.<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> </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Thionoester-from-thioacyl-chloride-2D-skeletal.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/79/Thionoester-from-thioacyl-chloride-2D-skeletal.png/380px-Thionoester-from-thioacyl-chloride-2D-skeletal.png" decoding="async" width="380" height="79" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/79/Thionoester-from-thioacyl-chloride-2D-skeletal.png/570px-Thionoester-from-thioacyl-chloride-2D-skeletal.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/79/Thionoester-from-thioacyl-chloride-2D-skeletal.png/760px-Thionoester-from-thioacyl-chloride-2D-skeletal.png 2x" data-file-width="1100" data-file-height="230" /></a><figcaption></figcaption></figure> <p>They can also be made by the reaction of <a href="/wiki/Lawesson%27s_reagent" title="Lawesson's reagent">Lawesson's reagent</a> with esters or by treating <a href="/wiki/Pinner_salt" class="mw-redirect" title="Pinner salt">pinner salts</a> with <a href="/wiki/Hydrogen_sulfide" title="Hydrogen sulfide">hydrogen sulfide</a>. </p><p>Various thionoesters may be prepared through the <a href="/wiki/Transesterification" title="Transesterification">transesterification</a> of an existing methyl thionoester with an alcohol under base-catalyzed conditions.<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> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Transesterification_of_Thionoesters.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/dd/Transesterification_of_Thionoesters.png/380px-Transesterification_of_Thionoesters.png" decoding="async" width="380" height="48" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/dd/Transesterification_of_Thionoesters.png/570px-Transesterification_of_Thionoesters.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/dd/Transesterification_of_Thionoesters.png/760px-Transesterification_of_Thionoesters.png 2x" data-file-width="1178" data-file-height="150" /></a><figcaption></figcaption></figure><p><a href="/wiki/Xanthate" title="Xanthate">Xanthates</a><sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> and <a href="/wiki/Thioamide" title="Thioamide">thioamides</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> can be transformed to thionoesters under metal-catalyzed cross-coupling conditions. </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=Thioester&action=edit&section=6" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Thiocarboxylic_acid" title="Thiocarboxylic acid">Thiocarboxylic acid</a></li> <li><a href="/wiki/Thiocarbonate" title="Thiocarbonate">Thiocarbonate</a></li> <li><a href="/wiki/Liebeskind%E2%80%93Srogl_coupling" title="Liebeskind–Srogl coupling">Liebeskind–Srogl coupling</a></li> <li><a href="/wiki/2,2%27-Dipyridyldisulfide" title="2,2'-Dipyridyldisulfide">Aldrithiol-2</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=Thioester&action=edit&section=7" 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-PATAI-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-PATAI_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-PATAI_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-PATAI_1-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text">Matthys J. 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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"><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_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 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/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 class="mw-selflink selflink">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><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" 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