Advanced
MO Studies on the Conformational Stabilities and the Rotational Barriers about C-N Bond in Amides
MO Studies on the Conformational Stabilities and the Rotational Barriers about C-N Bond in Amides
Journal of the Korean Chemical Society. 1988. Jun, 32(3): 163-170
  • Published : June 20, 1988
Download
PDF
Export by style
Article
Author
Metrics
Cited by
About the Authors
Kim, Wang Ki
Sohn, Chang Kook
Lee, Ikchoon

Abstract
The MNDO calculations were performed on the various rotamers of N-methyl formamide, N,N-dimethyl formamide, N-methyl acetamide, and N,N-dimethylacetamide in order to investigate the contribution of the one-electron and the steric effect on their rotational barriers about the C-N bond. Results show that while the conformational stabilities of formamides depend mainly on the one-electron factor, those of acetamides depend mainly on the steric factor. According to results obtained by calculations on the rotational barriers about C-N bond, for N-monosubstituted amides the steric effect is larger in the rotational ground state than in the transition state and for N,N-disubstituted amides the steric effect is larger in the rotational transition state.