DOI QR코드

DOI QR Code

Structure-Reactivity Relationship of Benzyl Benzenesulfonates. Part 4. Application of Correlation Interaction Coefficients

  • 발행 : 1998.04.20

초록

The mechanism of nucleophilic displacement was studied by using three variable systems of ${\rho}_X,\; {\rho}_Y,\; and {\rho}_Z$ obtained from the change of substituent X, Y, and Z for the reaction of (Z)-substituted benzyl (X)-benzensulfonates with (Y)-substituted thiobenzamides in acetone at 45 ℃. The results ${\rho}_Z$<0 and ${\rho}_YZ$>${\rho}_XZ$ indicate that this reaction series proceeded via a dissociative $S_N2$ mechanism. The prediction of the movement of TS by using the sign of ${\rho}_XZ{\cdot}{\rho}_{YZ}$ accorded with the Hammond postulate.

키워드

참고문헌

  1. Ph.D. Dissertation, Osaka University Yoh, S. D.
  2. Abstract of the 28th Spring Meeting of the Chemical Society of Japan Yoh, S. D.;Tsuno, Y.;Yukawa, Y.
  3. Abstracts of 25th Symposium on Reaction Mechanisms Tsuno, Y.;Fujio, M.;Yoh, S. D.;Sawada, M.;Yukawa, Y.
  4. J. Korean Chem. Soc. v.28 Yoh, S. D.;Tsuno, Y.;Yukawa, Y.
  5. J. Korean Chem. Soc. v.19 Yoh, S. D.
  6. J. Korean Chem. Soc. v.38 Cheong, D. Y.;Park, J. H.;Kweon, J. M.;Yoh, S. D.;Shim, K. T.
  7. J. Phy. Org. Chem. v.9 Yoh, S. D.;Cheong, D. Y.
  8. Tertrahedron Letters v.28 Lee, I.;Koh, H. J.
  9. J. Phy. Org. Chem. v.2 Lee, I.;Kim, H. Y.;Lee, H. W.;Kim, I. C.
  10. J. Phy. Org. Chem. v.4 Lee, I.;Koh, H. J.;Lee, H. W.
  11. J. Phy. Org. Chem. v.8 Yoh, S. D.;Cheong, D. Y.
  12. J. Korean Chem. Soc. v.39 Cheong, D. Y.;Kweon, J. M.;Yoh, S. D.;Park, B. S.
  13. J. Chem. Soc., Perkin Trans 2 v.7 Yoh, S. D.;Tsuno, Y.;Fujio, M.;Sawada, M.;Yukawa, Y.
  14. J. Am. Chem. Soc. v.84 Swain, C. G.;Thornton, E. R.
  15. J. Am. Chem. Soc. v.89 Thornton, E. R.
  16. J. Am. Chem. Soc. v.92 Harris, J. C.;Kurz, J. L.
  17. J. Korean Chem. Soc. v.38 Cheong, D. Y.;Park, J. H.;Kweon, J. M.;Yoh, S. D.;Shim, K. T.
  18. Organic Solvents Riddick, J. A.
  19. J. Korean Chem. Soc. v.16 Hong, S. Y.;Yoh, S. D.
  20. Ph.D. Dissertation, Kyungpook National University Park, J. H.