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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">Cation of the form [SR3]+</div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:(CH3)3S%2B_in_the_BPh4-_salt_(code_HEYZAM).png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/62/%28CH3%293S%2B_in_the_BPh4-_salt_%28code_HEYZAM%29.png/220px-%28CH3%293S%2B_in_the_BPh4-_salt_%28code_HEYZAM%29.png" decoding="async" width="220" height="111" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/62/%28CH3%293S%2B_in_the_BPh4-_salt_%28code_HEYZAM%29.png/330px-%28CH3%293S%2B_in_the_BPh4-_salt_%28code_HEYZAM%29.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/62/%28CH3%293S%2B_in_the_BPh4-_salt_%28code_HEYZAM%29.png/440px-%28CH3%293S%2B_in_the_BPh4-_salt_%28code_HEYZAM%29.png 2x" data-file-width="1200" data-file-height="605" /></a><figcaption>Structure of (CH<sub>3</sub>)<sub>3</sub>S<sup>+</sup>. The C-S-C angles are 102° and C-S bond distance is 177 picometers.<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></figcaption></figure> <p>In <a href="/wiki/Organic_chemistry" title="Organic chemistry">organic chemistry</a>, a <b>sulfonium ion</b>, also known as <b>sulphonium ion</b> or <b>sulfanium ion</b>, is a positively-charged <a href="/wiki/Ion" title="Ion">ion</a> (a "<a href="/wiki/Cation" class="mw-redirect" title="Cation">cation</a>") featuring three organic <a href="/wiki/Substitution_(chemistry)" class="mw-redirect" title="Substitution (chemistry)">substituents</a> attached to <a href="/wiki/Sulfur" title="Sulfur">sulfur</a>. These <a href="/wiki/Organosulfur_compound" class="mw-redirect" title="Organosulfur compound">organosulfur compounds</a> have the formula <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">[SR<sub class="template-chem2-sub">3</sub>]<sup class="template-chem2-sup">+</sup></span>. Together with a negatively-charged <a href="/wiki/Counterion" title="Counterion">counterion</a>, they give <b>sulfonium salts</b>. They are typically colorless solids that are <a href="/wiki/Soluble" class="mw-redirect" title="Soluble">soluble</a> in <a href="/wiki/Organic_solvent" class="mw-redirect" title="Organic solvent">organic solvent</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-Kozhushkov_3-0" class="reference"><a href="#cite_note-Kozhushkov-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </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=Sulfonium&action=edit&section=1" title="Edit section: Synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Sulfonium compounds are usually <a href="/wiki/Chemical_synthesis" title="Chemical synthesis">synthesized</a> by the reaction of <a href="/wiki/Thioether" class="mw-redirect" title="Thioether">thioethers</a> with <a href="/wiki/Alkyl_halide" class="mw-redirect" title="Alkyl halide">alkyl halides</a>. For example, the reaction of <a href="/wiki/Dimethyl_sulfide" title="Dimethyl sulfide">dimethyl sulfide</a> with <a href="/wiki/Iodomethane" title="Iodomethane">iodomethane</a> yields <a href="/wiki/Trimethylsulfonium_iodide" class="mw-redirect" title="Trimethylsulfonium iodide">trimethylsulfonium iodide</a>: </p> <dl><dd><span class="chemf nowrap">CH<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">3</sub></span></span>–S–CH<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">3</sub></span></span></span> + <span class="chemf nowrap">CH<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">3</sub></span></span>–I</span> → <span class="chemf nowrap">(CH<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">3</sub></span></span>)<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">3</sub></span></span>S<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:0.8em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">+</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sub></span></span></span><span class="chemf nowrap">I<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:0.8em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sub></span></span></span></dd></dl> <p>The reaction proceeds by a nucleophilic substitution mechanism (S<sub>N</sub>2) where iodide is the leaving group. The rate of methylation is faster with more electrophilic methylating agents, such as <a href="/wiki/Methyl_trifluoromethanesulfonate" title="Methyl trifluoromethanesulfonate">methyl trifluoromethanesulfonate</a>. </p> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Dimethylsulfoniopropionate_Structural_Formula_V1.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e2/Dimethylsulfoniopropionate_Structural_Formula_V1.svg/220px-Dimethylsulfoniopropionate_Structural_Formula_V1.svg.png" decoding="async" width="220" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e2/Dimethylsulfoniopropionate_Structural_Formula_V1.svg/330px-Dimethylsulfoniopropionate_Structural_Formula_V1.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e2/Dimethylsulfoniopropionate_Structural_Formula_V1.svg/440px-Dimethylsulfoniopropionate_Structural_Formula_V1.svg.png 2x" data-file-width="298" data-file-height="163" /></a><figcaption><a href="/wiki/Dimethylsulfoniopropionate" title="Dimethylsulfoniopropionate">Dimethylsulfoniopropionate</a> (DMSP), is found in marine <a href="/wiki/Phytoplankton" title="Phytoplankton">phytoplankton</a> and <a href="/wiki/Seaweeds" class="mw-redirect" title="Seaweeds">seaweeds</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></figcaption></figure> <div class="mw-heading mw-heading2"><h2 id="Inversion">Inversion</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sulfonium&action=edit&section=2" title="Edit section: Inversion"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Sulfonium ions with three different substituents are chiral owing to their pyramidal structure. Unlike the isoelectronic oxonium ions (R<sub>3</sub>O<sup>+</sup>), chiral sulfonium ions are resolvable into optically stable enantiomers.<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> [Me(Et)SCH<sub>2</sub>CO<sub>2</sub>H]<sup>+</sup> is the first chiral sulfonium cation to be resolved into enantiomers.<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> The barrier to inversion ranges from 100 to 130 kJ/mol.<sup id="cite_ref-Kozhushkov_3-1" class="reference"><a href="#cite_note-Kozhushkov-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Applications_and_occurrence">Applications and occurrence</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sulfonium&action=edit&section=3" title="Edit section: Applications and occurrence"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Biochemistry">Biochemistry</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sulfonium&action=edit&section=4" title="Edit section: Biochemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The sulfonium (more specifically <a href="/wiki/Methionine" title="Methionine">methioninium</a>) species <a href="/wiki/S-Adenosylmethionine" class="mw-redirect" title="S-Adenosylmethionine"><i>S</i>-adenosylmethionine</a> occurs widely in nature, where it is used as a source of the adenosoyl or methyl radicals. These radicals participate in the <a href="/wiki/Biosynthesis" title="Biosynthesis">biosynthesis</a> of many compounds.<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><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> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:S-Adenosyl-L-methionin.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a7/S-Adenosyl-L-methionin.svg/200px-S-Adenosyl-L-methionin.svg.png" decoding="async" width="200" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a7/S-Adenosyl-L-methionin.svg/300px-S-Adenosyl-L-methionin.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a7/S-Adenosyl-L-methionin.svg/400px-S-Adenosyl-L-methionin.svg.png 2x" data-file-width="440" data-file-height="264" /></a><figcaption>Structure of <a href="/wiki/S-Adenosylmethionine" class="mw-redirect" title="S-Adenosylmethionine"><i>S</i>-adenosylmethionine</a>.</figcaption></figure> <p>Other naturally-occurring sulfonium species are <a href="/wiki/S-Methylmethionine" title="S-Methylmethionine"><i>S</i>-methylmethionine</a> (<a href="/wiki/Methionine" title="Methionine">methioninium</a>) and the related <a href="/wiki/Dimethylsulfoniopropionate" title="Dimethylsulfoniopropionate">dimethylsulfoniopropionate</a> (DMSP). </p> <div class="mw-heading mw-heading3"><h3 id="Organic_synthesis">Organic synthesis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sulfonium&action=edit&section=5" title="Edit section: Organic synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Sulfonium salts are precursor to sulfur <a href="/wiki/Ylide" title="Ylide">ylides</a>, which are useful in carbon–carbon bond-forming reactions. In a typical application, a R<sub>2</sub>S<sup>+</sup>CH<sub>2</sub>R<span class="nowrap" style="padding-left:0.05em;">′</span> center is deprotonated to give the ylide R<sub>2</sub>S<sup>+</sup>CHR<sup>−</sup>.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:TASF.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4a/TASF.png/220px-TASF.png" decoding="async" width="220" height="72" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4a/TASF.png/330px-TASF.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4a/TASF.png/440px-TASF.png 2x" data-file-width="460" data-file-height="151" /></a><figcaption>Structure of <a href="/wiki/TASF_reagent" title="TASF reagent">tris(dimethylamino)sulfonium difluorotrimethylsilicate</a>.</figcaption></figure> <p><a href="/wiki/TASF_reagent" title="TASF reagent">Tris(dimethylamino)sulfonium difluorotrimethylsilicate</a> [((CH<sub>3</sub>)<sub>2</sub>N)<sub>3</sub>S]<sup>+</sup>[F<sub>2</sub>Si(CH<sub>3</sub>)<sub>3</sub>]<sup>−</sup> is a popular fluoridation agent.<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><p>Some azo dyes are modified with sulfonium groups to give them a positive charge. The compound <a href="/wiki/Triphenylsulfonium_triflate" class="mw-redirect" title="Triphenylsulfonium triflate">triphenylsulfonium triflate</a> is a <a href="/wiki/Photoacid" title="Photoacid">photoacid</a>, a compound that under light converts to an acid.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (November 2024)">citation needed</span></a></i>]</sup> </p><p><a href="/wiki/Organic_sulfide" title="Organic sulfide">Organic sulfides</a> react with liquid <a href="/wiki/Bromine" title="Bromine">bromine</a> to give bromosulfonium bromides, i.e.:<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p> <dl><dd>RSR<span class="nowrap" style="padding-left:0.05em;">′</span> + [RR<span class="nowrap" style="padding-left:0.05em;">′</span>S<sup>+</sup>Br]Br<sup>−</sup></dd></dl> <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=Sulfonium&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/Onium_compounds" class="mw-redirect" title="Onium compounds">Onium compounds</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=Sulfonium&action=edit&section=7" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <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"><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="CITEREFKnopCameronBakshiLinden1994" class="citation journal cs1">Knop, Osvald; Cameron, T. Stanley; Bakshi, Pradip K.; Linden, Antony; Roe, Stephen P. (1994). "Crystal Chemistry of Tetraradial Species. Part 5. Interaction Between Cation Lone Pairs and Phenyl Groups in Tetraphenylborates: Crystal Structures of Me<sub>3</sub>S<sup>+</sup>, Et<sub>3</sub>S<sup>+</sup>, Me<sub>3</sub>SO<sup>+</sup>, Ph<sub>2</sub>I<sup>+</sup>, and 1-Azoniapropellane Tetraphenylborates". <i>Canadian Journal of Chemistry</i>. <b>72</b> (8): 1870–1881. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1139%2Fv94-238">10.1139/v94-238</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Canadian+Journal+of+Chemistry&rft.atitle=Crystal+Chemistry+of+Tetraradial+Species.+Part+5.+Interaction+Between+Cation+Lone+Pairs+and+Phenyl+Groups+in+Tetraphenylborates%3A+Crystal+Structures+of+Me%3Csub%3E3%3C%2Fsub%3ES%3Csup%3E%2B%3C%2Fsup%3E%2C+Et%3Csub%3E3%3C%2Fsub%3ES%3Csup%3E%2B%3C%2Fsup%3E%2C+Me%3Csub%3E3%3C%2Fsub%3ESO%3Csup%3E%2B%3C%2Fsup%3E%2C+Ph%3Csub%3E2%3C%2Fsub%3EI%3Csup%3E%2B%3C%2Fsup%3E%2C+and+1-Azoniapropellane+Tetraphenylborates&rft.volume=72&rft.issue=8&rft.pages=1870-1881&rft.date=1994&rft_id=info%3Adoi%2F10.1139%2Fv94-238&rft.aulast=Knop&rft.aufirst=Osvald&rft.au=Cameron%2C+T.+Stanley&rft.au=Bakshi%2C+Pradip+K.&rft.au=Linden%2C+Antony&rft.au=Roe%2C+Stephen+P.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASulfonium" class="Z3988"></span></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFC._J._M._Stirling1981" class="citation book cs1">C. J. M. Stirling, ed. (1981). <i>The Sulphonium Group: Part 1, Volume 1</i>. PATAI'S Chemistry of Functional Groups. John Wiley & Sons. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F9780470771648">10.1002/9780470771648</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780470771648" title="Special:BookSources/9780470771648"><bdi>9780470771648</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Sulphonium+Group%3A+Part+1%2C+Volume+1&rft.series=PATAI%27S+Chemistry+of+Functional+Groups&rft.pub=John+Wiley+%26+Sons&rft.date=1981&rft_id=info%3Adoi%2F10.1002%2F9780470771648&rft.isbn=9780470771648&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASulfonium" class="Z3988"></span><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFC._J._M._Stirling1981" class="citation book cs1">C. J. M. Stirling, ed. (1981). <i>The Sulphonium Group: Part 2, Volume 2</i>. PATAI'S Chemistry of Functional Groups. 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Lema; Gabrielle A. Nevitt (2008-03-07). <a rel="nofollow" class="external text" href="https://digitalcommons.calpoly.edu/cgi/viewcontent.cgi?article=1339&context=bio_fac">"Dimethylsulfoniopropionate as a foraging cue for reef fishes"</a>. <i>Science</i>. <b>319</b> (5868): 1356. <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/2008Sci...319.1356D">2008Sci...319.1356D</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1126%2Fscience.1151109">10.1126/science.1151109</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/18323445">18323445</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:20782786">20782786</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Science&rft.atitle=Dimethylsulfoniopropionate+as+a+foraging+cue+for+reef+fishes&rft.volume=319&rft.issue=5868&rft.pages=1356&rft.date=2008-03-07&rft_id=info%3Adoi%2F10.1126%2Fscience.1151109&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A20782786%23id-name%3DS2CID&rft_id=info%3Apmid%2F18323445&rft_id=info%3Abibcode%2F2008Sci...319.1356D&rft.aulast=DeBose&rft.aufirst=Jennifer+L.&rft.au=Sean+C.+Lema&rft.au=Gabrielle+A.+Nevitt&rft_id=https%3A%2F%2Fdigitalcommons.calpoly.edu%2Fcgi%2Fviewcontent.cgi%3Farticle%3D1339%26context%3Dbio_fac&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASulfonium" class="Z3988"></span></span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text">March, J. "Advanced Organic Chemistry" 5th Ed. J. Wiley and Sons, 1992: New York. <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0-471-60180-2" title="Special:BookSources/0-471-60180-2">0-471-60180-2</a></span> </li> <li id="cite_note-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-6">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBarbachynJohnson1984" class="citation book cs1">Barbachyn, Michael R.; Johnson, Carl R. (1984). "Optical Activation and Utilization of Compounds Containing Chiral Sulfur Centers". <i>Asymmetric Synthesis</i>. pp. 227–261. <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%2FB978-0-12-507704-0.50007-6">10.1016/B978-0-12-507704-0.50007-6</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780125077040" title="Special:BookSources/9780125077040"><bdi>9780125077040</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Optical+Activation+and+Utilization+of+Compounds+Containing+Chiral+Sulfur+Centers&rft.btitle=Asymmetric+Synthesis&rft.pages=227-261&rft.date=1984&rft_id=info%3Adoi%2F10.1016%2FB978-0-12-507704-0.50007-6&rft.isbn=9780125077040&rft.aulast=Barbachyn&rft.aufirst=Michael+R.&rft.au=Johnson%2C+Carl+R.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASulfonium" class="Z3988"></span></span> </li> <li id="cite_note-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-7">^</a></b></span> <span class="reference-text">Layer, G.; Heinz, D. W.; Jahn, D.; Schubert, W.-D. "Structure and function of radical SAM enzymes" Current Opinion in Chemical Biology 2004, volume 8, 468-476. <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/10.1016%2Fj.cbpa.2004.08.001">10.1016/j.cbpa.2004.08.001</a></span> </li> <li id="cite_note-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-8">^</a></b></span> <span class="reference-text">Perry A. Frey, Olafur Th. Magnusson "S-Adenosylmethionine: A Wolf in Sheep's Clothing, or a Rich Man's Adenosylcobalamin?" Chem. Rev., 2003, 103 (6), pp 2129–2148. <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/10.1021%2Fcr020422m">10.1021/cr020422m</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="CITEREFMitchell_J._Bogdanowicz,_Barry_M._Trost1974" class="citation journal cs1">Mitchell J. Bogdanowicz, Barry M. Trost (1974). "Cyclopropylphenylsulfonium Tetrafluoroborate". <i><a href="/wiki/Organic_Syntheses" title="Organic Syntheses">Organic Syntheses</a></i>. <b>54</b>: 27. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.15227%2Forgsyn.054.0027">10.15227/orgsyn.054.0027</a></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Organic+Syntheses&rft.atitle=Cyclopropylphenylsulfonium+Tetrafluoroborate&rft.volume=54&rft.pages=27&rft.date=1974&rft_id=info%3Adoi%2F10.15227%2Forgsyn.054.0027&rft.au=Mitchell+J.+Bogdanowicz%2C+Barry+M.+Trost&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASulfonium" class="Z3988"></span>.</span> </li> <li id="cite_note-10"><span class="mw-cite-backlink"><b><a href="#cite_ref-10">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFW._J._Middleton1986" class="citation journal cs1">W. J. Middleton (1986). "Tris(dimethylamino)sulfonium difluorotrimethylsilicate". <i><a href="/wiki/Organic_Syntheses" title="Organic Syntheses">Organic Syntheses</a></i>. <b>64</b>: 221. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.15227%2Forgsyn.064.0221">10.15227/orgsyn.064.0221</a></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Organic+Syntheses&rft.atitle=Tris%28dimethylamino%29sulfonium+difluorotrimethylsilicate&rft.volume=64&rft.pages=221&rft.date=1986&rft_id=info%3Adoi%2F10.15227%2Forgsyn.064.0221&rft.au=W.+J.+Middleton&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASulfonium" class="Z3988"></span>.</span> </li> <li id="cite_note-11"><span class="mw-cite-backlink"><b><a href="#cite_ref-11">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMagee1971" class="citation book cs1">Magee, Philip S. (1971). "The Sulfur–Bromine Bond". In Senning, Alexander (ed.). <i>Sulfur in Organic and Inorganic Chemistry</i>. Vol. 1. New York: Marcel Dekker. pp. 316–321. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0-8247-1615-9" title="Special:BookSources/0-8247-1615-9"><bdi>0-8247-1615-9</bdi></a>. <a href="/wiki/LCCN_(identifier)" class="mw-redirect" title="LCCN (identifier)">LCCN</a> <a rel="nofollow" class="external text" href="https://lccn.loc.gov/70-154612">70-154612</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=The+Sulfur%26ndash%3BBromine+Bond&rft.btitle=Sulfur+in+Organic+and+Inorganic+Chemistry&rft.place=New+York&rft.pages=316-321&rft.pub=Marcel+Dekker&rft.date=1971&rft_id=info%3Alccn%2F70-154612&rft.isbn=0-8247-1615-9&rft.aulast=Magee&rft.aufirst=Philip+S.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASulfonium" class="Z3988"></span></span> </li> </ol></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Sulfonium&action=edit&section=8" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a rel="nofollow" class="external text" href="https://goldbook.iupac.org/terms/view/S06121">IUPAC definition</a> (short pdf)</li></ul>    </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" href="https://en.wikipedia.org/w/index.php?title=Sulfonium&oldid=1257287742">https://en.wikipedia.org/w/index.php?title=Sulfonium&oldid=1257287742</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Categories</a>: <ul><li><a href="/wiki/Category:Cations" title="Category:Cations">Cations</a></li><li><a href="/wiki/Category:Sulfonium_compounds" title="Category:Sulfonium compounds">Sulfonium compounds</a></li><li><a href="/wiki/Category:Sulfur_ions" title="Category:Sulfur ions">Sulfur ions</a></li></ul></div><div id="mw-hidden-catlinks" class="mw-hidden-catlinks mw-hidden-cats-hidden">Hidden categories: <ul><li><a href="/wiki/Category:Articles_with_short_description" title="Category:Articles with short description">Articles with short description</a></li><li><a href="/wiki/Category:Short_description_is_different_from_Wikidata" title="Category:Short description is different from Wikidata">Short description is different from Wikidata</a></li><li><a href="/wiki/Category:All_articles_with_unsourced_statements" title="Category:All articles with unsourced statements">All articles with unsourced statements</a></li><li><a href="/wiki/Category:Articles_with_unsourced_statements_from_November_2024" title="Category:Articles with unsourced statements from November 2024">Articles with unsourced statements from November 2024</a></li></ul></div></div> </div> </main> </div> <div class="mw-footer-container"> <footer id="footer" class="mw-footer" > <ul id="footer-info"> <li id="footer-info-lastmod"> This page was last edited on 14 November 2024, at 04:25<span class="anonymous-show"> (UTC)</span>.</li> <li id="footer-info-copyright">Text is available under the <a href="/wiki/Wikipedia:Text_of_the_Creative_Commons_Attribution-ShareAlike_4.0_International_License" title="Wikipedia:Text of the Creative Commons Attribution-ShareAlike 4.0 International License">Creative Commons Attribution-ShareAlike 4.0 License</a>; additional terms may apply. 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