MO Studies on the Conformational Stabilities and the Rotational Barriers about C-N Bond in Amides

Amide류에서 형태안정화와 C-N결합의 회전장벽에 관한 분자궤도론적 연구

  • Wang Ki Kim (Department of Chemistry Education, Chonnam National University) ;
  • Chang Kook Sohn (Department of Chemistry Education, Chonnam National University) ;
  • Ikchoon Lee (Department of Chemistry, Inha University)
  • 김왕기 (전남대학교 사범대학 화학교육과) ;
  • 손창국 (전남대학교 사범대학 화학교육과) ;
  • 이익춘 (인하대학교 이과대학 화학과)
  • Published : 1988.06.20


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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