Sulfilimine

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

In chemistry, a sulfilimine (or sulfimide) is a type of chemical compound containing a sulfur-to-nitrogen bond which is often represented as a double bond (S=N). In fact, a double bond violates the octet rule, and the bond may be considered a single bond with a formal charge of +1 on the sulfur and a formal charge of −1 on the nitrogen. The parent compound is sulfilimine H2S=NH, which is mainly of theoretical interest.

Examples include S,S-diphenylsulfilimine[2] and sulfoximines [Category] such as methylphenylsulfoximine:[3] In the case of a sulfoximine, the bonds can be considered single bonds, with formal charges of −1 on both the oxygen and the nitrogen, and a formal charge of +2 on the sulfur.

Methyl-phenylsulfoximine, a sulfur(VI) compound (left), and S,S-diphenylsulfilimine, a sulfur(IV) compound (right)
  1. ^ Elsegood, Mark R. J.; Holmes, Kathryn E.; Kelly, Paul F.; Parr, Jonathan; Stonehouse, Julia M. (2002). "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". New Journal of Chemistry. 26 (2): 202–206. doi:10.1039/b103502a.
  2. ^ "S,S-Diphenylsulfilimine". Sigma-Aldrich.
  3. ^ "(R)-(−)-S-Methyl-S-phenylsulfoximine". Sigma-Aldrich.