NMR chemical shifts and coupling constants of various nuclei of N, N-diethylbenzenesulfenamide, N, N-diethylbenzeneseleneamide and some related sulfur amides
Abstract
The 77Se, 15N, 13C and 1H NMR parameters have been determined for N, N-diethylbenzenesulfen- and N, N-diethylbenzeneseleneamide and the 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 seleneamide 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.
- Publication:
-
Spectrochimica Acta Part A: Molecular Spectroscopy
- Pub Date:
- 1988
- DOI:
- 10.1016/0584-8539(88)80079-5
- Bibcode:
- 1988AcSpA..44.1105R