NMR chemical shifts and coupling constants of various nuclei of N,N-diethylbenzenesulfenamide, N,N-diethylbenzeneseleneamide and some related sulfur amides

Article abstract of DOI:10.1016/0584-8539(88)80079-5

The 77Se, 15N, 13C, and 1H NMR parameters have been determined for N,N-diethylbenzenesulfen- and N,N-diethylbenzeneseleneamide and 1H-13C coupling constants additionally for N,N-dimethylmethanesulfinamide, N,N-dimethylbenzenesulfinamide, N,N-dimethylmethanesulfonamide, N,N-dimethylbenzenesulfonamide and diphenylsulfone.The nitrogen-15 nucleus is slightly more shielded in the sulfenamide than in the seleneamide.Compared to sulfin- and sulfonamides the nitrogen nuclei of these amides are more shielded.The solvent effects on the chemical shift of both selenium-77 and nitrogen-15 nuclei are observable.The nitrogen-15 chemical shifts of sulfur and seleneamides are less sensitive to the solvents than those of carboxamides.This change in the nitrogen-15 chemical shift in sulfen- and selenamide is the same order of magnitude, but opposite in direction compared with that in sulfon- and sulfinamides.The 1H-13C direct aromatic coupling constants increase along with the increasing oxidation state of sulfur in sulfur amides, being greatest in sulfonamides.