Dimethyl sulfoxide

Dimethyl sulfoxide (DMSO) is an organosulfur compound with the formula (CH₃)₂SO. This colorless liquid is an important polar aprotic solvent that dissolves both polar and nonpolar compounds and is miscible in a wide range of organic solvents as well as water.

Quotes

• Look at dimethyl sulfoxide (CH₃SOCH₃), for instance, a solvent commonly used for preserving biological cell lines at low temperature. The sulfur atom in dimethyl sulfoxide has three bonds rather than the usual two and has a formal positive charge. The oxygen atom, by contrast, has one bond rather than the usual two and has a formal negative charge. Note that an electrostatic potential map of dimethyl sulfoxide shows the oxygen as negative (red) and the sulfur as relatively positive (blue), in accordance with the formal charges. … Atomic sulfur has six valence electrons, but the dimethyl sulfoxide sulfur owns only five—one in each of the two S - C single bonds, one in the S - O single bond, and two in a lone pair. Thus, the sulfur atom has formally lost an electron and therefore has a positive charge. A similar calculation for the oxygen atom shows that it has formally gained an electron and has a negative charge.
  • John McMurry, Organic Chemistry 8th ed. (2012), Ch. 2 : Polar Covalent Bonds; Acids and Bases