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

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.

Keywords

References

  1. Progress in Stereochemistry v.4 H. C. Watson
  2. J. Am. Chem. Soc. v.95 E. Noe;M. Raban
  3. J. Chem. Res.(s) G. Tetu;J. -C. Duplan;N. Pellissier;E. Laurent
  4. J. Am. Chem. Soc. v.95 L. L. Shipman;R. E. Chritoffersen
  5. Biopolymers v.15 A. T. Halger;A. Lapiccirella
  6. Bull. Korean Chem. Soc. v.1 I. Lee;G. B. Rhyu
  7. J. Korean Chem. Soc. v.24 I. Lee;B. Lee
  8. Principle of Organic Stereochemistry B. Testa
  9. Trans. Faraday Soc. v.64 J. Bailey;A. M. North
  10. J. Am. Chem. Soc. v.95 E. D. Epiotis
  11. J. Chem. Phys. v.25 H. S. Gutowsky;C. M. Holm
  12. Topic in Current Chemistry 70 Structural Theory of Organic Chemistry N. D. Epiotis;W. R. Cherry;S. Shaik;R. Yates;F. Bernardi
  13. Topics in Sterochemistry v.5 E. Wyn-Jones;R. A. Pethrick