Ab Initio Studies on Substituent Effects of Substituted Pyridines

치환 피리딘의 치환기 효과에 대한 Ab initio 연구

  • Lee, Gab Yong (Department of Chemistry, Catolic University of Taegu-Hyosung) ;
  • Chang, Mahn Sik (Department of Chemistry, The Third Military Academy)
  • 이갑용 (대구효성가톨릭대학교 자연대학 화학과) ;
  • 장만식 (육군제3사관학교 화학과)
  • Published : 19990800

Abstract

Ab initio calculation is performed to estimate the substituent effects for Para-substituted pyridines. Electrostatic potentials are obtained from ab initio molecular orbital wavefunctions of optimized structures for substituted pyridines. Electrostatic potentials are computed to be minimum at nitrogen atom of pyridines. The potential minima are good correlated with the substituent constants, ${\sigma}_p$ and with the ${\Delta}pKa$. It is shown that the electrostatic potential minima can be used as a measure of substituent effects.

Keywords

References

  1. J. Am. Chem. Soc. v.104 Streitwieser, A. Jr.;Grier, D. L.
  2. J. Org. Chem. v.44 Bromilow, J.;Brownlee, R. T. C.;Lopez, V. O.;Taft, R. W.
  3. Topics in Curr. Chem. v.42 Scrocco, E.;Tomasi, J.
  4. J. Phys. Chem. v.86 Politzer, P.;Landry S. J.;Warnheim, T.
  5. J. Mol. Struct. (Theochem) v.138 Naray-Szabo, G.
  6. J. Comp. Chem. v.7 de Oliveira Neto, M.
  7. Chem. Phys. Lett. v.46 Berthod, H.;Pullman, A.
  8. GAUSSIAN 92 FOR WINDOWS Frisch, M. J.;Trucks, G. W.;Head-Gordon, M.;Gill, P. M. W.;Wong, M. W.;Foresman, J. B.;Johnson, B. G.;Schlegel, H. B.;Robb, M. A.;Replogle, E. S.;Gomperts, R.;Andres, J. L.;Raghavachari, K.;Binkley, J. S.;Gonzalez, C.;Martin, R. L.;Fox, D. J.;Defres, D. J.;Baker, J.;Srewart, J. J. P.;Pople, J. A.
  9. J. Am. Chem. Soc. v.107 Dewar, M. J. S.;Zoebisch, E. G.;Healy, E. F.;Stewart, J. J. P.
  10. Toxicology Letters v.43 Politzer, P.
  11. Introduction to Organic Chemistry (2nd Ed.) Streitwieser, A. Jr.
  12. J. Chem. Ed. v.55 Rousseau, O. H.;Texier, F.
  13. Bull. Korean Chem. Soc. v.16 Cheong, D. Y.;Kweon, J. M.;Yoh, S. D.;Park, S. S.;Lee, O. S.
  14. Adv. Phys. Org. Chem. v.1 Stock, L. M.;Brown, H. C.
  15. Linear Free Energy Relationships Wells, P. R.
  16. Bull. Chem. Soc., Jpn. v.48 Tsuno, Y.;Sawada, M.;Fujii. T.;Tairaka, Y.;Yukawa, Y.
  17. Reaction Kinetics v.2 Laidler, K. J.
  18. J. Chem. Phys. v.20 Jaffe, H. H.
  19. J. Chem. Phys. v.21 Jaffe, H. H.
  20. J. Am. Chem. Soc. v.103 Vorpagel, E. R.;Streitwieser, A. Jr.;Alexandratos, S. D.
  21. HyperChem Ostlund, N.
  22. J. Comp. Chem. v.7 de Oliveira Neto, M.
  23. Chemical Physics Letters v.152 Murray, J. S.;Politzer, P.
  24. The Hammett Equations Johnson, K. F.
  25. Chem. Pharm. Bull. v.32 Komatsu, K.;Nakamura, H.;Umeyama, H.
  26. Physical Organic Chemistry(2nd Ed.) Hammett, L. P.
  27. J. Am. Chem. Soc. v.99 Kollman, P.
  28. An Introduction to Physical Organic Chemistry Kosower, E. M.
  29. J. Electron Spectry v.2 Almlof, J.;Johansen, H.;Ross, B.;Wahlgren, U.
  30. Carcinogenesis v.5 Politzer, P.;Laurence, P. R.
  31. J. Org. Chem. v.44 Bromilow, J.;Brownlee, R. T. C.
  32. Progress in Physical Organic Chemistry v.6 Wells, P. R.;Ehrenson, S.;Taft, R. W.;Taft, R. W.(Ed.)
  33. Tetrahedron v.26 Imafuku, K.;Nakama, S.;Matsumura. H.
  34. J. Org. Chem. v.45 Kemister, G.;Pross, A.;Radom, L.;Taft, R. W.
  35. The force concept in Chemistry Politzer, P.;Daiker. K. C.;Deb. B. M.(Ed.)
  36. J. Comp. Chem. v.11 Luque, F. J.;Illas, F.;Orozco, M.
  37. Chem. Revs. v.53 Jaffe, H. H.
  38. J. Am. Chem. Soc. v.107 Dewar, M. J. S.;Zoebish, E. J.;Healy, E. F.;Stewart, J. J. P.