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

Chemical compound

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

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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: rS=O = 1.468, rC=S = 1.612 Å, <C=S=O = 113.7°.

## See also

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

## References

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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. ^ Block E., Gillies J.Z., Gillies C.W., Bazzi A.A., Putman D., Revelle L.K., Wang D., Zhang X. (1996). "Allium Chemistry: Microwave Spectroscopic Identification, Mechanism of Formation, Synthesis, and Reactions of (E,Z)-Propanethial S-Oxide, the Lachrymatory Factor of the Onion (Allium cepa)". J. Am. Chem. Soc. 118 (32): 7492–7501. doi:10.1021/ja960722j.`{{cite journal}}`: CS1 maint: multiple names: authors list (link)
4. ^ G. Rindorf; L. Carlsen (1979). "The crystal and molecular structures of the thiobenzophenone S-oxide and thiobenzophenone". Acta Crystallogr. B35 (5): 1179–1182. Bibcode:1979AcCrB..35.1179R. doi:10.1107/S0567740879005835.

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