Trimethylsulfoxonium (abbreviated TMSO) is a cation with a formula (CH3)3SO+ consisting of a sulfur atom attached to three methyl groups and one oxygen atom. It has a net charge of +1.
Production Refluxing dimethyl sulfoxide with methyl iodide can yield trimethylsulfoxonium iodide.
Reactions Treated with sodium hydride, trimethylsulfoxonium forms dimethylsulfoxonium methylide.
Trimethylsulfoxonium can polymerise to yield polyethylene.
Copper, zinc and palladium ions in water react with trimethylsulfoxonium and sodium hydroxide to form sulfur ylide complexes.
Properties In the chloride, the sulfur-oxygen bond length is 1.436 Å, sulfur-carbon bond is 1.742. OSC angles are 112.6°, and CSC angles are 106.2°.
List of compounds nameformulacrystal Åvolumedensitycommentreferencetrimethylsulfoxonium phthalimide[C3H9SO][C8H4NO2]orthorhombic Pnma a=8.445 b=10.958 c=12.084 Z=41118.2colourlessTrimethylsulfoxonium nitrateTrimethylsulfoxonium tetraphenylborate[(CH3)3SO]Ph4BP21/m a=9.482 b=12.790 c=9.713 β=106.48° Z=211301.177Trimethylsulfoxonium chloride[(CH3)3SO]Clwhite; sublime 227°CTrimethylsulfoxonium chromatetrimethylsulfoxonium tetrachloridocobaltate(II) [(CH3)3SO]2CoCl4monoclinic, P21/c a = 8.4397, b = 15.6692, c = 12.5989, β = 93.858°, Z = 41662.3blueTrimethylsulfoxonium bromideTrimethylsulfoxonium iodide[(CH3)3SO]Iyellow; dec 170°C[(CH3)3SO]Cu2I3Pnma[(CH3)3SO]Ag2I3Pnmatrimethyloxosulfonium trichloro-cadmate[(CH3)3SO]CdCl3orthorhombic Pnma a=6.688 b=10.147 c=13.446 Z=4912.52.270trimethyloxosulfonium tribromo-cadmate[(CH3)3SO]CdBr3orthorhombic Pnma a=6.946 b=10.543 c=13.782 Z=41009.32.928colourlessbis(trimethylsulfoxonium) catena-poly[μ2-hexabromido-indium(III)sodium(I)][(CH3)3SO]2NaInBr6orthorhombic, Pmn21, a = 10.5451, b = 7.1169, c = 13.7034, Z = 21028.42colourless[(CH3)3SO]PbBr3orthorhombic Pnma a=7.5697 b=10.7768 c=13.9143 Z=41135.093.160white[(CH3)3SO]PbI3orthorhombic Pnma a=7.8157 b=11.1996 c=14.3780 Z=41260.293.590light yellow; band gap 2.30 eV[(CH3)3SO]3Bi2Br9orthorhombic Pnma a=7.0351 b=10.6613 c=13.91901043.983.004light yellow[(CH3)3SO]3Bi2I9orthorhombic Pnma a=7.4530 b=11.2169 c=14.4009 1203.923.383red
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