Sulfine

Sulfinylmethane or sulfine is an organic compound with molecular formula H2CSO. It is the simplest sulfine. Sulfines are chemical compounds with the general structure XY=SO.[1] IUPAC considers the term 'sulfine' obsolete,[2] preferring instead thiocarbonyl S-oxide, despite this the use of the term sulfine still predominates in the chemical literature.

Sulfine
Names
IUPAC name
sulfinylmethane
Other names
sulfine
Identifiers
3D model (JSmol)
ChemSpider
Properties
CH2OS
Molar mass 62.09 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Substituted sulfines

The parent sulfine H2CSO is very labile, whereas substituted derivatives are more conveniently isolated. One example is syn-propanethial-S-oxide which is produced from allicin and is responsible for eye-watering effects of cutting onions. Another example is diphenylsulfine, obtained by oxidation of thiobenzophenone:[3]

(C6H5)2C=S + [O] → (C6H5)2C=S=O
Structure of diphenylsulfine. Selected distances and angles: rS=O = 1.468, rC=S = 1.612 Å, <C=S=O = 113.7°.

See also

References

  1. Binne Zwanenburg (1989). "Sulfine Chemistry". Phosphorus, Sulfur, and Silicon and the Related Elements. 43. doi:10.1080/10426508908040276.
  2. IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version:  (2006) "sulfines". doi:10.1351/goldbook.S06108
  3. G. Rindorf, L. Carlsen (1979). "The crystal and molecular structures of the thiobenzophenone S-oxide and thiobenzophenone". Acta Crystallogr. B35: 1179–1182. doi:10.1107/S0567740879005835.CS1 maint: uses authors parameter (link)
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