Trimethylsulfoxonium (abbreviated TMSO) is a cation with a formula (CH
3)
3SO
+ consisting of a sulfur atom attached to three
methyl group
In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula (whereas normal methane has the formula ). In formulas, the group is often abbreviated a ...
s and one oxygen atom. It has a net charge of +1.
Production
Refluxing
dimethyl sulfoxide
Dimethyl sulfoxide (DMSO) is an organosulfur compound with the formula . This colorless liquid is the sulfoxide most widely used commercially. It is an important polar aprotic solvent that dissolves both polar and nonpolar compounds and is ...
with
methyl iodide
Iodomethane, also called methyl iodide, and commonly abbreviated "MeI", is the chemical compound with the formula CH3I. It is a dense, colorless, volatile liquid. In terms of chemical structure, it is related to methane by replacement of one h ...
can yield
trimethylsulfoxonium iodide
Trimethylsulfoxonium iodide is an organosulfur compound with the chemical formula . It is a sulfoxonium salt derived from dimethylsulfoxide. It is iodide salt of a common sulfoxonium cation. This compound, a colorless solid, is commercially avail ...
.
Reactions
Treated with
sodium hydride
Sodium hydride is the chemical compound with the empirical formula Na H. This alkali metal hydride is primarily used as a strong yet combustible base in organic synthesis. NaH is a saline (salt-like) hydride, composed of Na+ and H− ions, in co ...
, 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
References
{{Reflist
Organosulfur compounds
Cations
Sulfur ions