Sulfine

Sulfine
Names
	IUPAC name sulfinylmethane
	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

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

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: r_S=O = 1.468, r_C=S = 1.612 Å, <_C=S=O = 113.7°.

References

^ Binne Zwanenburg (1989). "Sulfine Chemistry". Phosphorus, Sulfur, and Silicon and the Related Elements. 43. doi:10.1080/10426508908040276.
^ IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "sulfines". doi:10.1351/goldbook.S06108
^ "The crystal and molecular structures of the thiobenzophenone S-oxide and thiobenzophenone". Acta Crystallogr. B35: 1179–1182. 1979. doi:10.1107/S0567740879005835. {{cite journal}}: Cite uses deprecated parameter |authors= (help)

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[eros-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] "The crystal and molecular structures of the thiobenzophenone S-oxide and thiobenzophenone". Acta Crystallogr. B35: 1179–1182. 1979. doi:10.1107/S0567740879005835. {{cite journal}}: Cite uses deprecated parameter |authors= (help)

[1]

[2]

[3]

Substituted sulfines

See also

References