Sulfinyl group

Sulphinyl group ( marked in blue ) as part of a sulphoxide, R ¹ and R ² are organyl radicals (alkyl radical, aryl radical, alkylaryl radical, etc.) or a thionyl halide (R ¹ = R ² = halogen atom.)

In organic chemistry, sulfinyl group is the name of the functional group –SO–. The substances of the organochemical compounds bearing sulfinyl groups are referred to as sulfoxides . The sulfinyl group is also found in N- sulfinylamines (R-HN = S = O), N- sulfinyl hydrazines (RNH-N = S = O) and sulfinyl halides (R-S (= O) -X).

Sulfinyl compounds belong to the organic derivatives of oxo acids of sulfur in which - in the case of sulfoxides - the two organic radicals R ¹ and R ² are bonded directly to the sulfur atom. Under the condition R ¹ ≠ R ² , the sulfoxides are chiral .

Sulphoxides (R ¹ ≠ R ² ) are chiral. The stereocenter of the enantiomers is on the sulfur atom of the sulfinyl group ( marked in blue )

Mesomeric stabilized polarized sulfinyl group

Sulphoxides are polar compounds and have a pronounced dipole moment with a negative charge on the oxygen atom and a positive charge on the sulfur atom. The bond character is thus similar to the P = O bond in a tertiary phosphine oxide R ₃ P = O.

Inorganic chemistry

There are also thionyl halides , e.g. B. Thionyl chloride (O = SCl ₂ ), which are called thionyl compounds in inorganic chemistry as halides of sulfurous acid .

Examples of sulfinyl compounds and their use

• Dimethyl sulfoxide solvent : CH ₃ - SO - CH ₃
• Drug esomeprazole
• Drug omeprazole
• Medicinal substance pantoprazole

Individual evidence

1. ↑ Weygand / Hilgetag: Organic Chemistry, 2nd edition, VEB Deutscher Verlag für Grundstoffindustrie, Leipzig, 1985, pp. 702–703.
2. ↑ Otto-Albrecht Neumüller (Ed.): Römpps Chemie-Lexikon. Volume 6: T-Z. 8th revised and expanded edition. Franckh'sche Verlagshandlung, Stuttgart 1988, ISBN 3-440-04516-1 , p. 4245.