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id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Thioketone</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. 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href="https://cs.wikipedia.org/wiki/Thioketony" title="Thioketony – Czech" lang="cs" hreflang="cs" data-title="Thioketony" 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/Thioketone" title="Thioketone – German" lang="de" hreflang="de" data-title="Thioketone" 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/Tiocetona" title="Tiocetona – Spanish" lang="es" hreflang="es" data-title="Tiocetona" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Tiozetona" title="Tiozetona – Basque" lang="eu" hreflang="eu" data-title="Tiozetona" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%AA%DB%8C%D9%88%DA%A9%D8%AA%D9%88%D9%86" title="تیوکتون – Persian" lang="fa" hreflang="fa" data-title="تیوکتون" 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/Thioc%C3%A9tone" title="Thiocétone – French" lang="fr" hreflang="fr" data-title="Thiocétone" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Tiochetoni" title="Tiochetoni – Italian" lang="it" hreflang="it" data-title="Tiochetoni" 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/Tioketon" title="Tioketon – Hungarian" lang="hu" hreflang="hu" data-title="Tioketon" 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/Thioketon" title="Thioketon – Dutch" lang="nl" hreflang="nl" data-title="Thioketon" 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%B1%E3%83%88%E3%83%B3" title="チオケトン – Japanese" lang="ja" hreflang="ja" data-title="チオケトン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Tiocetona" title="Tiocetona – Portuguese" lang="pt" hreflang="pt" data-title="Tiocetona" 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/Tioceton%C4%83" title="Tiocetonă – Romanian" lang="ro" hreflang="ro" data-title="Tiocetonă" 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%A2%D0%B8%D0%BE%D0%BA%D0%B5%D1%82%D0%BE%D0%BD%D1%8B" title="Тиокетоны – Russian" lang="ru" hreflang="ru" data-title="Тиокетоны" 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/Thioketone" title="Thioketone – Simple English" lang="en-simple" hreflang="en-simple" data-title="Thioketone" 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-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Tioketonit" title="Tioketonit – Finnish" lang="fi" hreflang="fi" data-title="Tioketonit" 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/Tioketon" title="Tioketon – Swedish" lang="sv" hreflang="sv" data-title="Tioketon" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%A4%E0%AF%88%E0%AE%AF%E0%AF%8B%E0%AE%95%E0%AF%80%E0%AE%9F%E0%AF%8D%E0%AE%9F%E0%AF%8B%E0%AE%A9%E0%AF%8D" title="தையோகீட்டோன் – Tamil" lang="ta" hreflang="ta" data-title="தையோகீட்டோன்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%A2%D1%96%D0%BE%D0%BA%D0%B5%D1%82%D0%BE%D0%BD%D0%B8" title="Тіокетони – Ukrainian" lang="uk" hreflang="uk" data-title="Тіокетони" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a 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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">Organic compounds with the structure >C=S</div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Thioketone_Structural_Formulae_V.1.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Thioketone_Structural_Formulae_V.1.png/250px-Thioketone_Structural_Formulae_V.1.png" decoding="async" width="140" height="138" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Thioketone_Structural_Formulae_V.1.png/330px-Thioketone_Structural_Formulae_V.1.png 2x" data-file-width="1548" data-file-height="1522" /></a><figcaption>General formula of a thioketone</figcaption></figure> <p>In <a href="/wiki/Organic_chemistry" title="Organic chemistry">organic chemistry</a>, <b>thioketones</b> (from <a href="/wiki/Ancient_Greek_language" class="mw-redirect" title="Ancient Greek language">Ancient Greek</a> <i> </i>θεῖον<i> (theion)</i> <span class="gloss-quot">'</span><span class="gloss-text"><a href="/wiki/Sulfur" title="Sulfur">sulfur</a></span><span class="gloss-quot">'</span>;<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> also known as <b>thiones</b> or <b>thiocarbonyls</b>) are <a href="/wiki/Organosulfur_compound" class="mw-redirect" title="Organosulfur compound">organosulfur compounds</a> related to conventional <a href="/wiki/Ketone" title="Ketone">ketones</a> in which the oxygen has been replaced by a sulfur.<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> Instead of a structure of <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<sub class="template-chem2-sub">2</sub>C=O</span>, thioketones have the structure <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">R<sub class="template-chem2-sub">2</sub>C=S</span>, which is reflected by the prefix "<a href="/wiki/Thio-" title="Thio-">thio-</a>" in the name of the functional group. Thus the simplest thioketone is <a href="/wiki/Thioacetone" title="Thioacetone">thioacetone</a>, the sulfur analog of <a href="/wiki/Acetone" title="Acetone">acetone</a>. Unhindered alkylthioketones typically tend to form <a href="/wiki/Polymers" class="mw-redirect" title="Polymers">polymers</a> or <a href="/wiki/Cyclic_compound" title="Cyclic compound">rings</a>.<sup id="cite_ref-handbook_3-0" class="reference"><a href="#cite_note-handbook-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><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> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Structure_and_bonding">Structure and bonding</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Thioketone&action=edit&section=1" title="Edit section: Structure and bonding"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The C=S bond length of thiobenzophenone is 1.63 Å, which is comparable to 1.64 Å, the C=S bond length of thioformaldehyde, measured in the gas phase. Due to steric interactions, the phenyl groups are not coplanar and the dihedral angle SC-CC is 36°.<sup id="cite_ref-Sustmann_5-0" class="reference"><a href="#cite_note-Sustmann-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Unhindered dialkylthiones polymerize or oligomerize but thio<a href="/wiki/Camphor" title="Camphor">camphor</a> is well characterized red solid.<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> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Ph2CS.JPG" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8c/Ph2CS.JPG/250px-Ph2CS.JPG" decoding="async" width="150" height="108" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8c/Ph2CS.JPG/330px-Ph2CS.JPG 2x" data-file-width="965" data-file-height="695" /></a><figcaption>Solution and solid samples of thiobenzophenone. The blue color is consistent with a small HOMO–LUMO gap associated with the thiocarbonyl functional group.</figcaption></figure> <p>Consistent with the <a href="/wiki/Double_bond_rule" title="Double bond rule">double bond rule</a>, most alkyl thioketones are unstable with respect to dimerization.<sup id="cite_ref-Organosulfur_7-0" class="reference"><a href="#cite_note-Organosulfur-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> The energy difference between the p orbitals of sulfur and carbon is greater than that between oxygen and carbon in ketones.<sup id="cite_ref-Fisera_8-0" class="reference"><a href="#cite_note-Fisera-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> The relative difference in energy and diffusity of the atomic orbitals of sulfur compared with carbon results in poor overlap of the atomic orbitals and the energy gap between the <a href="/wiki/HOMO_and_LUMO" title="HOMO and LUMO">HOMO and LUMO</a> is thus reduced for C=S <a href="/wiki/Molecular_orbital" title="Molecular orbital">molecular orbitals</a> relative to C=O.<sup id="cite_ref-Sustmann_5-1" class="reference"><a href="#cite_note-Sustmann-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> The striking blue appearance of thiobenzophenone is attributed to <a href="/wiki/Molecular_electronic_transition" title="Molecular electronic transition">π→ π* transitions</a> upon the absorption of red light.<sup id="cite_ref-Fisera_8-1" class="reference"><a href="#cite_note-Fisera-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> Thiocamphor is red. </p> <div class="mw-heading mw-heading2"><h2 id="Preparative_methods">Preparative methods</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Thioketone&action=edit&section=2" title="Edit section: Preparative methods"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Thiones are usually prepared from ketones using reagents that exchange S and O atoms. A common reagent is <a href="/wiki/Phosphorus_pentasulfide" title="Phosphorus pentasulfide">phosphorus pentasulfide</a>,<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> although that reagent also tends to induce side-reactions.<sup id="cite_ref-PKet_10-0" class="reference"><a href="#cite_note-PKet-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 928">: 928 </span></sup> <a href="/wiki/Lawesson%27s_reagent" title="Lawesson's reagent">Lawesson's reagent</a> is related. Other methods uses a mixture of <a href="/wiki/Hydrogen_chloride" title="Hydrogen chloride">hydrogen chloride</a> combined with <a href="/wiki/Hydrogen_sulfide" title="Hydrogen sulfide">hydrogen sulfide</a>. <a href="/wiki/Bis(trimethylsilyl)sulfide" title="Bis(trimethylsilyl)sulfide">Bis(trimethylsilyl)sulfide</a> has also been employed.<sup id="cite_ref-handbook_3-1" class="reference"><a href="#cite_note-handbook-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><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> Thiones can also be prepared from geminal dichlorides,<sup id="cite_ref-PKet_10-1" class="reference"><a href="#cite_note-PKet-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 927">: 927 </span></sup> but geminal dichlorides are typically prepared from ketones as well. </p><p>There are no general methods to oxidize <a href="/wiki/Methylene_group" title="Methylene group">methylene groups</a> to thioketones,<sup id="cite_ref-PKet_10-2" class="reference"><a href="#cite_note-PKet-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Pages: 929–930">: 929–930 </span></sup> reflecting <a href="/wiki/Sulfur" title="Sulfur">sulfur</a>'s comparable <a href="/wiki/Electronegativity" title="Electronegativity">electronegativity</a> to <a href="/wiki/Carbon" title="Carbon">carbon</a>. </p><p><a href="/wiki/Thiobenzophenone" title="Thiobenzophenone">Thiobenzophenone</a> [(C<sub>6</sub>H<sub>5</sub>)<sub>2</sub>CS] is a stable deep <a href="/wiki/Blue" title="Blue">blue</a> compound that dissolves readily in organic solvents. It photooxidizes in air to <a href="/wiki/Benzophenone" title="Benzophenone">benzophenone</a> and sulfur. Since its discovery, a variety of related thiones have been prepared.<sup id="cite_ref-Oka_12-0" class="reference"><a href="#cite_note-Oka-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Thiosulfines">Thiosulfines</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Thioketone&action=edit&section=3" title="Edit section: Thiosulfines"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Thiosulfines, also called thiocarbonyl <i>S</i>-sulfides, are compounds with the formula R<sub>2</sub>CSS. Although superficially appearing to be <a href="/wiki/Cumulene" title="Cumulene">cumulenes</a>, with the linkage R<sub>2</sub>C=S=S, they are more usefully classified as <a href="/wiki/1,3-dipole" title="1,3-dipole">1,3-dipoles</a> and indeed participate in <a href="/wiki/1,3-dipolar_cycloaddition" class="mw-redirect" title="1,3-dipolar cycloaddition">1,3-dipolar cycloadditions</a>. Thiosulfines are proposed to exist in equilibrium with <a href="/wiki/Dithiirane" class="mw-redirect" title="Dithiirane">dithiiranes</a>, three-membered CS<sub>2</sub> rings. Thiosulfines are often invoked as intermediates in mechanistic discussions of the chemistry of thiones. For example, thiobenzophenone decomposes upon oxidation to the 1,2,4-<a href="/w/index.php?title=Trithiolane&action=edit&redlink=1" class="new" title="Trithiolane (page does not exist)">trithiolane</a> (Ph<sub>2</sub>C)<sub>2</sub>S<sub>3</sub>, which arises via the cycloaddition of Ph<sub>2</sub>CSS to its parent Ph<sub>2</sub>CS.<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-heading2"><h2 id="External_links_and_further_reading">External links and further reading</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Thioketone&action=edit&section=4" title="Edit section: External links and further reading"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><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="CITEREFKrotoLandsbergSuffolkVodden1974" class="citation journal cs1">Kroto, H.; Landsberg, B. M.; Suffolk, R. J.; Vodden, A. (1974). "The photoelectron and microwave spectra of the unstable species thioacetaldehyde, CH<sub>3</sub>CHS, and thioacetone, (CH<sub>3</sub>)<sub>2</sub>CS". <i>Chemical Physics Letters</i>. <b>29</b> (2): <span class="nowrap">265–</span>269. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1974CPL....29..265K">1974CPL....29..265K</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0009-2614%2874%2985029-3">10.1016/0009-2614(74)85029-3</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chemical+Physics+Letters&rft.atitle=The+photoelectron+and+microwave+spectra+of+the+unstable+species+thioacetaldehyde%2C+CH%3Csub%3E3%3C%2Fsub%3ECHS%2C+and+thioacetone%2C+%28CH%3Csub%3E3%3C%2Fsub%3E%29%3Csub%3E2%3C%2Fsub%3ECS&rft.volume=29&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E265-%3C%2Fspan%3E269&rft.date=1974&rft_id=info%3Adoi%2F10.1016%2F0009-2614%2874%2985029-3&rft_id=info%3Abibcode%2F1974CPL....29..265K&rft.aulast=Kroto&rft.aufirst=H.&rft.au=Landsberg%2C+B.+M.&rft.au=Suffolk%2C+R.+J.&rft.au=Vodden%2C+A.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AThioketone" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFCooper2005" class="citation book cs1">Cooper, N.J. (2005). "Thioaldehydes and Thioketones". <i>Comprehensive Organic Functional Group Transformations II</i>. pp. <span class="nowrap">355–</span>396. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FB0-08-044655-8%2F00053-2">10.1016/B0-08-044655-8/00053-2</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-08-044655-4" title="Special:BookSources/978-0-08-044655-4"><bdi>978-0-08-044655-4</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Thioaldehydes+and+Thioketones&rft.btitle=Comprehensive+Organic+Functional+Group+Transformations+II&rft.pages=%3Cspan+class%3D%22nowrap%22%3E355-%3C%2Fspan%3E396&rft.date=2005&rft_id=info%3Adoi%2F10.1016%2FB0-08-044655-8%2F00053-2&rft.isbn=978-0-08-044655-4&rft.aulast=Cooper&rft.aufirst=N.J.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AThioketone" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFMurai2018" class="citation journal cs1">Murai, Toshiaki (2018). "The Construction and Application of C=S Bonds". <i>Topics in Current Chemistry</i>. <b>376</b> (4): 31. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2Fs41061-018-0209-0">10.1007/s41061-018-0209-0</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/29987439">29987439</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:51605664">51605664</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Topics+in+Current+Chemistry&rft.atitle=The+Construction+and+Application+of+C%3DS+Bonds&rft.volume=376&rft.issue=4&rft.pages=31&rft.date=2018&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A51605664%23id-name%3DS2CID&rft_id=info%3Apmid%2F29987439&rft_id=info%3Adoi%2F10.1007%2Fs41061-018-0209-0&rft.aulast=Murai&rft.aufirst=Toshiaki&rfr_id=info%3Asid%2Fen.wikipedia.org%3AThioketone" class="Z3988"></span></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=Thioketone&action=edit&section=5" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Thial" title="Thial">Thial</a>, for a description of thioaldehydes.</li> <li><a href="/wiki/Thioketene" title="Thioketene">Thioketene</a></li> <li><a href="/wiki/Sulfene" title="Sulfene">Sulfene</a></li> <li><a href="/wiki/Selone" title="Selone">Selone</a> (often called selenone)</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=Thioketone&action=edit&section=6" 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"><a rel="nofollow" class="external text" href="https://www.perseus.tufts.edu/hopper/text?doc=Perseus%3Atext%3A1999.04.0057%3Aentry%3Dqei%3Don1">θεῖον</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20170510073237/http://www.perseus.tufts.edu/hopper/text?doc=Perseus%3Atext%3A1999.04.0057%3Aentry%3Dqei%3Don1">Archived</a> 2017-05-10 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a>, Henry George Liddell, Robert Scott, <i>A Greek–English Lexicon</i></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"><a href="/wiki/International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">IUPAC</a>, <i><a href="/wiki/IUPAC_books#Gold_Book" class="mw-redirect" title="IUPAC books">Compendium of Chemical Terminology</a></i>, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "<a rel="nofollow" class="external text" href="https://goldbook.iupac.org/terms/view/T06356.html">Thioketones</a>". <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1351%2Fgoldbook.T06356">10.1351/goldbook.T06356</a></span> </li> <li id="cite_note-handbook-3"><span class="mw-cite-backlink">^ <a href="#cite_ref-handbook_3-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-handbook_3-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFKuhnVerani2007" class="citation book cs1">Kuhn, N.; Verani, G. (2007). "Chalcogenone C=E compounds". <i>Handbook of Chalcogen Chemistry: New Perspectives in Sulfur, Selenium and Tellurium</i>. Royal Society of Chemistry. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2F9781847557575-00107">10.1039/9781847557575-00107</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Chalcogenone+C%3DE+compounds&rft.btitle=Handbook+of+Chalcogen+Chemistry%3A+New+Perspectives+in+Sulfur%2C+Selenium+and+Tellurium&rft.pub=Royal+Society+of+Chemistry&rft.date=2007&rft_id=info%3Adoi%2F10.1039%2F9781847557575-00107&rft.aulast=Kuhn&rft.aufirst=N.&rft.au=Verani%2C+G.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AThioketone" class="Z3988"></span></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFE._Champaigne1966" class="citation book cs1">E. Champaigne (1966). "Thioketones". In Saul Patai (ed.). <i>The Carbonyl Group</i>. PATAI'S Chemistry of Functional Groups. Vol. 1. John Wiley & Sons Ltd. p. 916. <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%2F9780470771051.ch17">10.1002/9780470771051.ch17</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780470771051" title="Special:BookSources/9780470771051"><bdi>9780470771051</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Thioketones&rft.btitle=The+Carbonyl+Group&rft.series=PATAI%27S+Chemistry+of+Functional+Groups&rft.pages=916&rft.pub=John+Wiley+%26+Sons+Ltd.&rft.date=1966&rft_id=info%3Adoi%2F10.1002%2F9780470771051.ch17&rft.isbn=9780470771051&rft.au=E.+Champaigne&rfr_id=info%3Asid%2Fen.wikipedia.org%3AThioketone" class="Z3988"></span></span> </li> <li id="cite_note-Sustmann-5"><span class="mw-cite-backlink">^ <a href="#cite_ref-Sustmann_5-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Sustmann_5-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text">Sustmann, R.; Sicking, W.; Huisgen, R. 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"New Thione Chemistry". Pure Appl. Chem., 1996, 68, 789-798. <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1351%2Fpac199668040789">10.1351/pac199668040789</a></span> </li> <li id="cite_note-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-9">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFPolshettiwarKaushik2004" class="citation journal cs1">Polshettiwar, Vivek; Kaushik, M. P. (2004). "A new, efficient and simple method for the thionation of ketones to thioketones using P<sub>4</sub>S<sub>10</sub>/Al<sub>2</sub>O<sub>3</sub>". <i>Tetrahedron Letters</i>. <b>45</b> (33): <span class="nowrap">6255–</span>6257. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.tetlet.2004.06.091">10.1016/j.tetlet.2004.06.091</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Tetrahedron+Letters&rft.atitle=A+new%2C+efficient+and+simple+method+for+the+thionation+of+ketones+to+thioketones+using+P%3Csub%3E4%3C%2Fsub%3ES%3Csub%3E10%3C%2Fsub%3E%2FAl%3Csub%3E2%3C%2Fsub%3EO%3Csub%3E3%3C%2Fsub%3E&rft.volume=45&rft.issue=33&rft.pages=%3Cspan+class%3D%22nowrap%22%3E6255-%3C%2Fspan%3E6257&rft.date=2004&rft_id=info%3Adoi%2F10.1016%2Fj.tetlet.2004.06.091&rft.aulast=Polshettiwar&rft.aufirst=Vivek&rft.au=Kaushik%2C+M.+P.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AThioketone" class="Z3988"></span></span> </li> <li id="cite_note-PKet-10"><span class="mw-cite-backlink">^ <a href="#cite_ref-PKet_10-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-PKet_10-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-PKet_10-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFCampaigne1979" class="citation book cs1">Campaigne, E. 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title="Special:EditPage/Template:Functional groups"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Functional_groups729" style="font-size:114%;margin:0 4em"><a href="/wiki/Functional_group" title="Functional group">Functional groups</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hydrocarbon" title="Hydrocarbon">Hydrocarbons</a> <br /><span class="nobold">(only C and H)</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Alkyl" class="mw-redirect" title="Alkyl">Alkyl</a> <ul><li><a href="/wiki/Methyl_group" title="Methyl group">Methyl</a></li> <li><a href="/wiki/Ethyl_group" title="Ethyl group">Ethyl</a></li> <li><a href="/wiki/Propyl_group" title="Propyl group">Propyl</a></li> <li><a href="/wiki/Cyclopropyl" class="mw-redirect" title="Cyclopropyl">Cyclopropyl</a></li> <li><a href="/wiki/Butyl_group" title="Butyl group">Butyl</a></li> <li><a href="/wiki/Pentyl_group" title="Pentyl group">Pentyl</a></li></ul></li> <li><a href="/wiki/Methylene_group" title="Methylene group">Methylene</a> <ul><li><a href="/wiki/Methylene_bridge" title="Methylene bridge">Bridge</a></li> <li><a href="/wiki/Methine_group" title="Methine group">Methine</a></li></ul></li> <li><a href="/wiki/Alkene" title="Alkene">Alkene</a> <ul><li><a href="/wiki/Vinyl_group" title="Vinyl group">Vinyl</a></li> <li><a href="/wiki/Allyl_group" title="Allyl group">Allyl</a></li> <li><a href="/wiki/Propenyl" title="Propenyl">1-Propenyl</a></li> <li><a href="/wiki/Crotyl_group" title="Crotyl group">Crotyl</a></li> <li><a href="/wiki/Allenes" title="Allenes">Allene</a></li> <li><a href="/wiki/Cumulene" title="Cumulene">Cumulene</a></li></ul></li> <li><a href="/wiki/Aryl" class="mw-redirect" title="Aryl">Aryl</a> <ul><li><a href="/wiki/Phenyl_group" title="Phenyl group">Phenyl</a></li> <li><a href="/wiki/Benzyl_group" title="Benzyl group">Benzyl</a></li></ul></li> <li><a href="/wiki/Alkyne" title="Alkyne">Alkyne</a></li> <li><a href="/wiki/Carbene" title="Carbene">Carbene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Only <a href="/wiki/Carbon" title="Carbon">carbon</a>, <br /><a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a>, <br />and <a href="/wiki/Oxygen" title="Oxygen">oxygen</a> <br /><span class="nobold">(only C, H and O)</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">R-O-R</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetal" title="Acetal">Acetal</a></li> <li><a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">Alcohol</a></li> <li><a href="/wiki/Alkoxy_group" title="Alkoxy group">Alkoxy</a> <ul><li><a href="/wiki/Methoxy_group" title="Methoxy group">Methoxy</a></li></ul></li> <li><a href="/wiki/Ether" title="Ether">Ether</a> <ul><li><a href="/wiki/Enol_ether" title="Enol ether">Enol ether</a></li> <li><a href="/wiki/Epoxide" title="Epoxide">Epoxide</a></li></ul></li> <li><a href="/wiki/Organic_peroxides" title="Organic peroxides">Peroxy</a> <ul><li><a href="/wiki/Hydroperoxide" title="Hydroperoxide">Hydroperoxy</a></li> <li><a href="/wiki/Dioxirane" title="Dioxirane">Dioxiranes</a></li></ul></li> <li><a href="/wiki/Ethylenedioxy" title="Ethylenedioxy">Ethylenedioxy</a></li> <li><a href="/wiki/Methylenedioxy" title="Methylenedioxy">Methylenedioxy</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Carbonyl_group" title="Carbonyl group">carbonyl</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acyl_group" title="Acyl group">Acyl</a> <ul><li><a href="/wiki/Acetyl_group" title="Acetyl group">Acetyl</a></li> <li><a href="/wiki/Acryloyl_group" class="mw-redirect" title="Acryloyl group">Acryloyl</a></li> <li><a href="/wiki/Benzoyl_group" title="Benzoyl group">Benzoyl</a></li></ul></li> <li><a href="/wiki/Aldehyde" title="Aldehyde">Aldehyde</a> <ul><li><a href="/wiki/Ketene" title="Ketene">Ketene</a></li></ul></li> <li><a href="/wiki/Ketone" title="Ketone">Ketone</a></li> <li><a href="/wiki/Ynone" title="Ynone">Ynone</a></li> <li><a href="/wiki/Reductone" title="Reductone">Reductone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">carboxy</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Carboxylic_acid" title="Carboxylic acid">Carboxyl</a> <ul><li><a href="/wiki/Acetoxy_group" title="Acetoxy group">Acetoxy</a></li> <li><a href="/wiki/Carboxylic_anhydride" class="mw-redirect" title="Carboxylic anhydride">Anhydride</a></li></ul></li> <li><a href="/wiki/Ester" title="Ester">Ester</a> <ul><li><a href="/wiki/Orthoester" class="mw-redirect" title="Orthoester">Orthoester</a></li></ul></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Only one <br />element, <br />not being <br />carbon, <br />hydrogen, <br />or oxygen <br /><span class="nobold">(one element, <br />not C, H or O)</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nitrogen" title="Nitrogen">Nitrogen</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Amine" title="Amine">Amine</a> <ul><li><a href="/wiki/Enamine" title="Enamine">Enamine</a></li> <li><a href="/wiki/Quaternary_ammonium_cation" title="Quaternary ammonium cation">Ammonium</a></li></ul></li> <li><a href="/wiki/Hydrazines" title="Hydrazines">Hydrazo</a></li> <li><a href="/wiki/Nitrene" title="Nitrene">Nitrene</a></li> <li><a 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/Silicon" title="Silicon">Silicon</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Silane" title="Silane">Silane</a> <ul><li><a href="/wiki/Hydrosilane" class="mw-redirect" title="Hydrosilane">Hydrosilane</a></li> <li><a href="/wiki/Chlorosilane" title="Chlorosilane">Chlorosilane</a></li></ul></li> <li><a href="/wiki/Organosilicon_chemistry#Silenes" title="Organosilicon chemistry">Silene</a></li> <li><a href="/wiki/Silanol" title="Silanol">Silanol</a></li> <li><a href="/wiki/Siloxide" title="Siloxide">Siloxide</a></li> <li><a href="/wiki/Siloxane" title="Siloxane">Siloxane</a></li> <li><a href="/wiki/Silanone" title="Silanone">Silanone</a></li> <li><a href="/wiki/Silyl_ether" title="Silyl ether">Silether</a></li> <li><a href="/wiki/Metalloles" class="mw-redirect" title="Metalloles">Silole</a></li> <li><a href="/wiki/Silatrane" class="mw-redirect" title="Silatrane">Silatrane</a></li> <li><a href="/wiki/Silicate" title="Silicate">Silicate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phosphorus" title="Phosphorus">Phosphorus</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Organophosphate" title="Organophosphate">Phosphate</a> <ul><li><a href="/wiki/Phosphodiester" class="mw-redirect" title="Phosphodiester">Phosphodiester</a></li></ul></li> <li><a href="/wiki/Phosphonate" title="Phosphonate">Phosphonate</a> <ul><li><a href="/wiki/Phosphite_ester" title="Phosphite ester">Phosphite</a></li></ul></li> <li><a href="/wiki/Phosphonite" title="Phosphonite">Phosphonous</a></li> <li><a href="/wiki/Phosphinate" title="Phosphinate">Phosphinate</a></li> <li><a href="/wiki/Phosphine_oxide" title="Phosphine oxide">Phosphine oxide</a></li> <li><a href="/wiki/Organophosphine" title="Organophosphine">Phosphine</a> <ul><li><a href="/wiki/Phosphonium" title="Phosphonium">Phosphonium</a></li></ul></li> <li><a href="/wiki/Phosphaalkene" title="Phosphaalkene">Phosphaalkene</a></li> <li><a href="/wiki/Phosphaalkyne" title="Phosphaalkyne">Phosphaalkyne</a></li> <li><a href="/wiki/1-Phosphaallenes" title="1-Phosphaallenes">Phosphaallene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sulfur" title="Sulfur">Sulfur</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Thiol" title="Thiol">Thiol</a></li> <li><a href="/wiki/Thioether" class="mw-redirect" title="Thioether">Thioether</a> <ul><li><a href="/wiki/Sulfonium" title="Sulfonium">Sulfonium</a></li> <li><a href="/wiki/Thia-crown_ether" title="Thia-crown ether">Thia-crown ether</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 class="mw-selflink selflink">Thioketone</a></li> <li><a href="/wiki/Thial" title="Thial">Thial</a></li> <li><a href="/wiki/Thioester" title="Thioester">Thioester</a></li> <li><a href="/wiki/Thionoester" class="mw-redirect" title="Thionoester">Thionoester</a></li> <li><a href="/wiki/Thioxanthate" title="Thioxanthate">Thioxanthate</a></li> <li><a href="/wiki/Xanthate" title="Xanthate">Xanthate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Boron" title="Boron">Boron</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Boronic_acid" title="Boronic acid">Boronic acid</a></li> <li><a href="/wiki/Borinic_acid" title="Borinic acid">Borinic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Selenium" title="Selenium">Selenium</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Selenol" title="Selenol">Selenol</a></li> <li><a href="/wiki/Selenonic_acid" title="Selenonic acid">Selenonic acid</a></li> <li><a href="/wiki/Seleninic_acid" title="Seleninic acid">Seleninic acid</a></li> <li><a href="/wiki/Selenenic_acid" title="Selenenic acid">Selenenic acid</a></li> <li><a href="/wiki/Selone" title="Selone">Selone</a></li> <li><a href="/wiki/Selenide#Inorganic_selenides" title="Selenide">Selenoether</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Tellurium" title="Tellurium">Tellurium</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Tellurol" title="Tellurol">Tellurol</a></li> <li><a href="/wiki/Telluroketone" title="Telluroketone">Telluroketone</a></li> <li><a href="/wiki/Telluride_(chemistry)#Organic_tellurides" title="Telluride (chemistry)">telluroether</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Polonium" title="Polonium">Polonium</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Polonium_hydride#Properties" title="Polonium hydride">Polonol</a></li> <li><a href="/wiki/Organopolonium_chemistry" title="Organopolonium chemistry">Polonoether</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i><a href="/wiki/Halocarbon" title="Halocarbon">Halo</a></i></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Haloalkane" title="Haloalkane">Haloalkane</a> <ul><li><a href="/wiki/Fluoroethyl" title="Fluoroethyl">Fluoroethyl</a></li> <li><a href="/wiki/Trifluoromethyl" class="mw-redirect" title="Trifluoromethyl">Trifluoromethyl</a></li> <li><a href="/wiki/Trichloromethyl_group" title="Trichloromethyl group">Trichloromethyl</a></li> <li><a href="/wiki/Trifluoromethoxy_group" title="Trifluoromethoxy group">Trifluoromethoxy</a></li> <li><a href="/wiki/Iodane" class="mw-redirect" title="Iodane">Hypervalent iodine</a></li></ul></li> <li><a href="/wiki/Vinyl_halide" title="Vinyl halide">Vinyl halide</a> <ul><li><a href="/wiki/Vinyl_iodide_functional_group" title="Vinyl iodide functional group">Iodide</a></li></ul></li> <li><a href="/wiki/Acyl_halide" title="Acyl halide">Acyl halide</a> <ul><li><a href="/wiki/Acyl_chloride" title="Acyl chloride">Chloride</a></li></ul></li> <li><a href="/wiki/Perchlorate_ester" class="mw-redirect" title="Perchlorate ester">Perchlorate</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Isothiocyanate" title="Isothiocyanate">Isothiocyanate</a></li> <li><a href="/wiki/Phosphoramides" title="Phosphoramides">Phosphoramides</a></li> <li><a href="/wiki/Sulfenyl_chloride" title="Sulfenyl chloride">Sulfenyl chloride</a></li> <li><a href="/wiki/Sulfonamide" title="Sulfonamide">Sulfonamide</a></li> <li><a href="/wiki/Organic_thiocyanates" title="Organic thiocyanates">Thiocyanate</a></li> <li><a href="/wiki/Sulfinylamine" title="Sulfinylamine">Sulfinylamines</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt><span class="nobold">See also</span></dt> <dd><i><a href="/wiki/Chemical_classification" class="mw-redirect" title="Chemical classification">chemical classification</a></i></dd> <dd><i><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">chemical nomenclature</a></i> <dl><dd><a href="/wiki/IUPAC_nomenclature_of_inorganic_chemistry" title="IUPAC nomenclature of inorganic chemistry">inorganic</a></dd> <dd><a href="/wiki/IUPAC_nomenclature_of_organic_chemistry" title="IUPAC nomenclature of organic chemistry">organic</a></dd></dl></dd></dl> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox authority-control" aria-label="Navbox390" style="padding:3px"><table class="nowraplinks hlist navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th 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