Journal of the Korean Chemical Society (대한화학회지)

Korean Chemical Society (대한화학회)
권호 표지

MO Studies on Nicotine (I)

니코틴의 배치와 형태에 관한 분자궤도론적 연구 (제1보)

  • Ikchoon Lee (Department of Chemistry, College of Science, Inha University) ;
  • Dong Hwan Park (Department of Chemistry, College of Science, Inha University)
  • 이익춘 (인하대학교 이과대학 화학과) ;
  • 박동환 (인하대학교 이과대학 화학과)
  • Published : 1978.08.30
Download PDF
⟨ Previous Next ⟩

Abstract

Configuration and conformation of nicotine and its protonated form have been studied by MO theoretically using EHT and CNDO/2 methods. The form with angle of rotation ${\theta}\;=\;280^{\circ}$ of pyrrolidine ring was shown to be most stable and this was interpreted in terms of conjugative, electrostatic and seric effects. It was predicted that protonation occurs on the nitrogen atom of pyridine ring and forms a ${\pi}$-complex.

니코틴과 그 양성자 부가물의 배치 및 형태를 분자궤도론으로 EHT와 CNDO/2방법을 써서 연구하였다. 가장 안정한 형태는 피롤리딘 고리가 $280^{\circ}$회전된 꼴임을 알았으며 이것을 콘쥬게이션, 정전기적 및 입체효과로서 설명하였다. 양성자의 부가는 피리딘 고리에 일어나며 일종의 ${\pi}$-착물이 형성됨을 알았다.

Keywords

References

  1. Mol. Pharm. v.4 L.B. Kier
  2. Proc. Nat. Acad. Sci. v.65 C. Clothia;P. Pauling
  3. Mol. Pharm. v.7 B. Pullman;ph. Courrierer;J.L. Coubeils
  4. J. Organic. Chem. v.41 J. F. Seeman;J. I. Seeman
  5. J. Organic. Chem. v.41 J.I. Seeman;J.F. Whidby
  6. J. Korean Chem. Soc. v.21 Ikchoon Lee
  7. Approximate MO theory J.A. Pople;P.L. Beveridge
  8. J. Korean Chem. Soc. v.9 C.H. Koo;H.S. Kim
  9. J. Amer. Chem. Soc. v.95 R.J. Radna;D.L. Beveridge;A.L. Bender
  10. Tetrahedron Letter G.P. Newssoroff;S. Sternheell
  11. Mol. Pharm. v.9 K.R. Chynoweth;B. Ternai;L.S. Simeral;G.E. Maciel
  12. Mol. Pharm. v.9 B. Testa;P. Jenner
  13. J. Korean Chem. Soc. v.21 Ikchoon Lee;Shi Choon Kim
  14. J. Korean Chem. Soc. v.22 Ikchoon Lee;Suk Kee Lee;Shi Choon Kim;Young Gu Jeon
  15. J. Phys. Chem. v.76 T. Drakenberg;K. Dahlqvist;S. Farsen
  16. J. Chem. Soc. v.406 M.J.S. Dewar
  17. Ber. Bunsenges. Phys. Chem. v.68 H.H. Perkamus;E. Baumgarten
  18. J. Chem. Soc. V. Gold;F.L. Tye
  19. Molecular Physics v.1 G. Dallinga;E. Machorand L.;A. Verrijin Stuart
  20. Molecular Physics v.1 C. Maclean;J.H. van der Waals;E.L. Machor
  21. J. Amer. Chem. Soc. v.92 G.L. Olah;R.H. Schlosberg;D.P. Kelly;G.D. Mateescu
  22. J. Amer. Chem. Soc. v.94 G.L. Olah;R.H. Schlosberg;D.P. Kelly;G.D. Mateescu
  23. Ikchoon Lee;Dong Hwan Park;Yong Jong Lee;Hyo Won Bae
  24. J. Chem. Ed. v.45 R.G. Pearson
  25. Int. J. Quantum Chem. v.9 D. Heidrich;M. Grimmer
  26. Accounts Chem. Res. v.4 G.A. Olah
  27. J. Chem. Phys. v.46 Fink;Allen
  28. J. Chem. Phys. v.46 Pederson;Morukuma
  29. J. Amer. Chem. Soc. v.97 J.E. Eilers;A. Liberles