Sulfine

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Sulfine
Sulfinylmethane.svg
Names
Preferred IUPAC name
Methylidene-λ4-sulfanone
Other names
sulfine
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/CH2OS/c1-3-2/h1H2
    Key: IWOKCMBOJXYDEE-UHFFFAOYSA-N
  • C=S=O
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).

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.

Substituted sulfines[edit]

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[edit]

References[edit]

  1. ^ Binne Zwanenburg (1989). "Sulfine Chemistry". Phosphorus, Sulfur, and Silicon and the Related Elements. 43 (1–2): 1–24. 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 (5): 1179–1182. doi:10.1107/S0567740879005835.{{cite journal}}: CS1 maint: uses authors parameter (link)