![]() ![]() It is a base, e.g., for the deprotonation of ketones to form sodium enolates, phosphonium salts to form Wittig reagents, and formamidinium salts to form diaminocarbenes. The sodium derivative of DMSO formed in this way is referred to as dimsyl sodium. Stabilization of the resultant carbanion is provided by the S(O)R group. For this reason, the basicities of many weakly basic organic compounds have been examined in this solvent.ĭeprotonation of DMSO requires strong bases like lithium diisopropylamide and sodium hydride. The methyl groups of DMSO are only weakly acidic, with a p K a = 35. I + NaH → (CH 3) 2S(CH 2)O + NaI + H 2 Acidity This salt can be deprotonated with sodium hydride to form the sulfur ylide: With methyl iodide it forms trimethylsulfoxonium iodide, I: The sulfur center in DMSO is nucleophilic toward soft electrophiles and the oxygen is nucleophilic toward hard electrophiles. Dimethyl sulfoxide is produced industrially from dimethyl sulfide, a by-product of the Kraft process, by oxidation with oxygen or nitrogen dioxide. It has a trigonal pyramidal molecular geometry consistent with other three-coordinate S(IV) compounds, with a nonbonded electron pair on the approximately tetrahedral sulfur atom.ĭimethyl sulfoxide was first synthesized in 1866 by the Russian scientist Alexander Zaytsev, who reported his findings in 1867. In terms of chemical structure, the molecule has idealized C s symmetry. DMSO has the unusual property that many individuals perceive a garlic-like taste in the mouth after DMSO makes contact with their skin. It 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. This colorless liquid is the sulfoxide most widely used commercially. Dimethyl sulfoxide ( DMSO) is an organosulfur compound with the formula ( CH 3) 2 S O. ![]()
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