Sulfine

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

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 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°.

References

^ Binne Zwanenburg (1989). "Sulfine Chemistry". Phosphorus, Sulfur, and Silicon and the Related Elements. 43 (1–2): 1–24. 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
^ 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)
^ 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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[eros-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.

[1]

[2]

[3]

[4]

Substituted sulfines

See also

References