Sulfilimine
A sulfilimine (sulfimide) is a type of chemical compound containing a sulfur to nitrogen double bond. The parent compound is sulfilimine H2S=NH, which is mainly of theoretical interest. Other simple examples are methylphenylsulfoximine[2] and S,S-diphenylsulfilimine:[3]
-
File:Sulfilimines.svgMethyl-phenylsulfoximine, a sulfur(VI) compound, and S,S-diphenylsulfilimine, a sulfur(IV) compound.
Preparation
Most sulfilimines are N-substituted with electron-withdrawing groups. These compounds are typically prepared by oxidation of thioethers with electrophilic amine reagents, such as chloramine-T in the presence of a base:[4]
- R2S + ClNHTs → R2S=NTs + HCl
An alternative route involves reactions of electrophilic sulfur compounds with amines. The limidosulfonium reagents provide a source of "Me2S2+", which are attacked by amines.
Sulfilimine bonds in proteins
Sulfilimine bonds stabilize collagen IV strands found in the extracellular matrix.[5] These bonds covalently connect hydroxylysine and methionine residues of adjacent polypeptide strands to form a larger collagen trimer.
References
- ↑ The preparation and structure of novel sulfimide systems; X-ray crystal structures of 1,4-(PhS{NH})2C6H4(and dihydrate), 1,2-(PhS{NH})(PhS)C6H4·H2O and of [Ph2SNH] and its hydrate Mark R. J. Elsegood, Kathryn E. Holmes, Paul F. Kelly, Jonathan Parr and Julia M. Stonehouse New J. Chem., 2002, 26, 202 - 206. doi:10.1039/b103502a
- ↑ sigmaaldrich.com/catalog methyl-phenylsulfoximine
- ↑ sigmaaldrich.com/catalog S,S-diphenylsulfilimine
- ↑ Gilchrist, T. L.; Moody, C. J., "The chemistry of sulfilimines", Chem. Rev. 1977, 77, 409-435. doi:10.1021/cr60307a005
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
