20912-40-7Relevant academic research and scientific papers
Secondary Reactions of Sulfenes from Sulfonyl Chlorides and Tertiary Amines, 3. - Crystal Structure Analysis of Bis(trimethylammoniosulfonyl)methanide Tetraphenylborate - n-?*-Interactions (Hyperconjugation and Homohyperconjugation) in Sulfene-Amine S,N-Adducts
Opitz, Guenter,Wiehn, Walter,Ziegler, Manfred L.,Nuber, Bernhard
, p. 1621 - 1626 (2007/10/02)
Bis(trimethylammoniosulfonyl)methanide chloride (3b) could be obtained in 97percent yield by reaction of methanedisulfonyl dichloride (5) with three equivalents of trimethylamine.X-ray analysis of the tetraphenylborate 3c reveals that the conformation of the cation is determined by nC-?*S-N interactions (negative hyperconjugation) and by nC-?*N-C interactions (negative homohyperconjugation).These effects were deduced from alterations of the bond lengths within the S-N-C chains which are coplanar to the occupied pz orbital at the central C atom.Comparison with known crystal structure data shows, that sulfene-amine S,N-adducts generally have the zwitterionic ammoniosulfonylmethanide structure 3, stabilized by nC-?* interactions. Key Words: Bis(trimethylammoniosulfonyl)methanide tetraphenylborate / Sulfene-amine adducts / Hyperconjugation, negative / Homohyperconjugation, negative / n-?* interactions
