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Structure of (CH3)3S+. The C-S-C angles are 102° and C-S bond distance is 177 picometers.
A sulfonium ion, also known as sulphonium ion or sulfanium ion, is a positively charged ion (a "cation") featuring three organic substituents attached to sulfur. These organosulfur compounds have the formula [SR3]+. Together with a negatively charged counterion, they give sulfonium salts. They are typically colorless solids that are soluble in organic solvent.
The reaction proceeds by a nucleophilic substitution mechanism (SN2). Iodide is the leaving group departs. The rate of methylation is faster with more electrophilic methylating agents, such as methyl trifluoromethanesulfonate.
The compounds are pyramidal at sulfur. Thus, Me3S+ is isostructural and isoelectronic to trimethylphosphine. Sulfonium compounds wherein the three substituents differ are chiral and optically stable. [Me(Et)SCH2CO2H]+ is the first chiral sulfonium cation to be resolved into enantiomers.
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