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
Preferred IUPAC name Methylidene-λ4-sulfanone
Other names sulfine
Identifiers
CAS Number	40100-16-1
3D model (JSmol)	Interactive image
ChemSpider	125626
PubChem CID	142407
CompTox Dashboard (EPA)	DTXSID20193145
InChI InChI=1S/CH2OS/c1-3-2/h1H2 Key: IWOKCMBOJXYDEE-UHFFFAOYSA-N
SMILES C=S=O
Properties
Chemical formula	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 route is a variant of ketene synthesis, in which a sulfinyl halide reacts with a hindered base. For example, syn-propanethial-S-oxide, responsible for eye-watering effects of cutting onions, is produced so from allicin.^[3]

Another route is oxidation, as with thiobenzophenone from diphenylsulfine:^[4]

(C₆H₅)₂C=S + [O] → (C₆H₅)₂C=S=O

Structure of diphenylsulfine. Selected distances and angles: r_S=O = 1.468, r_C=S = 1.612 Å, <_C=S=O = 113.7°.

See also

• Sulfene - related functional group with the formula H₂C=SO₂
• Ethenone
• Heterocumulene