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Ball-and-stick model of the diphenylsulfimide molecule, Ph2S=NH [1]

A sulfilimine (sulfimide) is a type of chemical compound containing a sulfur to nitrogen double bond. The parent compound is sulfilimine H2S=NH. Examples are methylphenylsulfoximine [2] and S,S-diphenylsulfilimine:[3]

Sulfilimines: methyl-phenylsulfoximine and S,S-diphenylsulfilimine

Sulfilimine bonds in proteins[edit]

Sulfilimine bonds stabilize collagen IV strands found in the extracellular matrix.[4] These bonds covalently connect hydroxylysine and methionine residues of adjacent polypeptide strands to form a larger collagen trimer.


  1. ^ 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
  2. ^ methyl-phenylsulfoximine
  3. ^ S,S-diphenylsulfilimine
  4. ^ Vanacore R, Ham AL, Voehler M, Sanders CR, Conrads TP, Veenstra TD, Sharpless KB, Dawson PE, Hudson BG (September 4, 2009). "A sulfilimine bond identified in collagen IV.". Science 325 (5945): 1230–1234. Bibcode:2009Sci...325.1230V. doi:10.1126/science.1176811. PMC 2876822. PMID 19729652.