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KMID : 1059519880320030163
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Journal of the Korean Chemical Society
1988 Volume.32 No. 3 p.163 ~ p.170
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MO Studies on the Conformational Stabilities and the Rotational Barriers about C-N Bond in Amides
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Kim Wang-Ki
Sohn Chang-Kook
Lee Ik-Choon
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Abstract
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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.
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