13C-13C spin-spin coupling constants in structural studies: XLI. Stereochemical study on N-(polychloroethylidene)arenesulfonamides and N’-arylsulfonylformimidamides

Abstract

The second-order polarization propagator approach (SOPPA) was used to calculate 13C-1H, 13C-13C, and 15N-1H coupling constants for a series of N-(polychloroethylidene)arenesulfonamides and N’-arylsulfonylformimidamides, and their configuration with respect to the C=N bond was determined by comparing the calculated data with the experimental values. All the examined compounds were found to exist in solution exclusively as the corresponding E isomers. The most favorable conformations and relative energies of the E and Z isomers in the gas phase were determined in terms of the second-order perturbation theory (MP2/6-311G**). N’-Arylsulfonylformimidamides are characterized by restricted internal rotation of the dialkylamino group about the C-N bond having an increased order.