Journal of the Korean Chemical Society (대한화학회지)

Korean Chemical Society (대한화학회)
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Structure-Reactivity Relationships for the Reaction of Aryl Benzoates with Amines

Aryl Benzoates와 Amine류의 반응에 관한 구조-반응성 관계

  • Cheong, Duk-Young (Department of Chemistry Education, Kyungpook National University) ;
  • Kweon, Jeong-Min (Department of Chemistry Education, Kyungpook National University) ;
  • Yoh, Soo-Dong (Department of Chemistry Education, Kyungpook National University) ;
  • Park, Byung-Soo (Department of Chemistry, Andong National University)
  • 정덕영 (경북대학교 자연과학대학 화학교육과) ;
  • 권정민 (경북대학교 자연과학대학 화학교육과) ;
  • 여수동 (경북대학교 자연과학대학 화학교육과) ;
  • 박병수 (안동대학교 자연과학대학 화학과)
  • Published : 19950700
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Abstract

The reaction rates of aryl substituted(Z)-benzoates with amines were determined by a spectro-photometric method in acetonitrile at various temperatures. Hammett $\rho$, Bronsted ${\beta}$ values, and activation parameters were evaluated from the kinetic data. Linear free energy relationships, activation parameters, and the interpretation of M-O-F-J diagram suggested that these reactions were probably enforced an $S_AN$ mechanism.

아세토니트릴 용매계에서 aryl 치환(Z)-benzoate류와 아민류의 반응속도를 15, 25, 및 35 $^{\circ}C$에서 분광학적 방법으로 구했다. 2차 반응속도 상수로부터 Hammett $\rho$값, Bronsted ${\beta}$값, 및 활성화 parameter를 구했으며 이들값과 M-O-F-J diagram 등의 해석으로부터 본 반응은 $S_AN$ 메카니즘으로 진행됨을 알 수 있었다.

Keywords

References

  1. Structure and mechanism in Organic Chemistry(2nd Ed.) Ingold, C. K.
  2. J. Amer. Chem. Soc. v.97 Winey, D. A.;Thornton, E. R.
  3. J. Amer. Chem. Soc. v.89 Thornton, E. R.
  4. J. Amer. Chem. Soc. v.90 Jencks, W. P.;Gilchrist, M.
  5. J. Amer. Chem. Soc. v.99 Jencks, D. A.;Jencks, W. P.
  6. J. Chem. Soc. (B) More O'Ferrall, R. A.
  7. J. Amer. Chem. Soc. v.77 Hammond, G. S.
  8. J. Amer. Chem. Soc. v.114 Kim, H. J.;Hynes, J. T.
  9. J. Amer. Chem. Soc. v.106 Dubois, J. E.;Ruasse, M. F.;Argile, A.
  10. J. Amer. Chem. Soc. v.59 Hammett, L. P.
  11. J. Phys. Chem. v.78 Bronsted, J. N.;Pedersen, K. J.
  12. J. Amer. Chem. Soc. v.99 Jencks, D. A.;Jencks, W. P.
  13. J. Amer. Chem. Soc. v.111 Buncel, E.;Um, I. H.;Hoz, S.
  14. Ph.D. Dissertation, Osaka Univ. Yoh, S. D.
  15. J. Korean Chem. Soc. v.19 Yoh, S. D.
  16. J. Chem. Soc., Perkin Trans. 2 Yoh, S. D.;Tsuno, Y.;Fujio, M.;Sawada, M.;Yukawa, Y.
  17. J. Chem. Soc. Perkin Trans. 2 Yoh, S. D.;Tsuno, Y.;Fujio, M.;Sawada, M.;Yukawa, Y.
  18. Bull. Korean Chem. Soc. v.14 Yoh, S. D.;Cheong, D. Y.;Tsuno, Y.;Sawada, M.
  19. J. Chem. Soc., Chem. Comm. Lee, I.;Sohn, S. C.
  20. J. Org. Chem. v.56 Lee, I.;Lee, W. H.;Lee, H. W.
  21. J. Chem. Soc., Perkin Trans. 2 Lee, I.;Koh, H. J.;Sohn, D. S.;Lee, B. C.
  22. J. Amer. Chem. Soc. v.108 Hoffman, R. V.;Shankweiler, J. M.
  23. J. Amer. Chem. Soc. v.104 Hoffman, R. V.;Belfoure, E. L.
  24. Chem. Rev. v.72 Jencks, W. P.
  25. J. Amer. Chem. Soc. v.101 Harris, J. M.;Shafer, S. G.;Moffatt, J. R.;Becker, A. R.
  26. J. Amer. Chem. Soc. v.89 Bruice, T. C.;Donzel, A.;Hoffman, R. W.;Butler, A. R.
  27. J. Amer. Chem. Soc. v.91 Menger, F. M.;Smith, J. H.
  28. J. Amer. Chem. Soc. v.94 Menger, F. M.;Smith, J. H.
  29. J. Amer. Chem. Soc. v.87 Coetzee, J. F.;Padmanabhan, G. R.
  30. J. Amer. Chem. Soc. v.104 Hoffman, R. V.;Belfoure, E. L.
  31. J. Amer. Chem. Soc. v.108 Hoffman, R. V.;Shankweiler, J. M.