Bulletin of the Korean Chemical Society

  • 제16권7호
  • /
  • Pages.657-661
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  • 1995
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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Kinetics and Mechanism of the Reactions of S-Phenyl Dithiobenzoates with Benzylamines in Acetonitrile

  • 발행 : 1995.07.20
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초록

Kinetic studies are carried out on the reaction of S-phenyl dithiobenzoates with benzylamines in acetonitrile at 30.0 ℃. Small magnitude of ρX (βX) as well as ρZ (βZ) obtained suggests rate-limiting nucleophilic attack of the thiocarbonyl carbon. This is supported by the unusually small magnitude of ρXY and ρYZ, albeit their signs do not agree with those expected. Moreover, the inverse secondary kinetic isotope effects (kH/kD<1.0) involving deuterated benzylamine nucleophiles are also in line with the proposed mechanism.

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참고문헌

  1. Advanced Organic Chemistry March, J.
  2. Bioorganic Mechanisms v.1 Bruice, T. C.;Benkovic, S.
  3. The Chemistry of the Carbonyl Group v.1;2 Patai, S.
  4. Catalysis in Chemistry and Enzymology Jencks, W. P.
  5. J. Chem. Soc., Perkin Trans. 2 Bond, P. M.;Castro, E. A.;Moodie, R. B.
  6. J. Am. Chem. Soc. v.99 Gresser, M. J.;Jencks, W. P.
  7. J. Org. Chem. v.45 Castro, E. A.;Freudenberg, M.
  8. J. Org. Chem. v.46 Castro, C.;Castro, E. A.
  9. J. Chem. Soc., Perkin Trans. 2 Castro, E. A.;Steinfort, G. B.
  10. J. Org. Chem. v.50 Castro, E. A.;Santander, C. L.
  11. J. Org. Chem. v.54 Castro, E. A.;Ureta, C.
  12. J. Org. Chem. v.55 Castro, E. A.;Ureta, C.
  13. J. Chem. Soc., Perkin Trans. 2 Castro, E. A.;Ureta, C.
  14. J. Chem. Res. v.(S)56 Castro, E. A.;Ibanez, F.;Saitua, A. M.;Santos, J. G.
  15. J. Chem Soc., Perkin Trans. 2 Oh, H. K.;Shin, C. H.;Lee, I.
  16. Chem. Soc. Rev. v.19 Lee, I.
  17. Adv. Phys. Org. Chem. v.27 Lee, I.
  18. Lee, D.;Kim, C. K.;Lee, B. S.;Lee, I.
  19. J. Am. Chem. Soc. v.111 Ba-Saif, S.;Luthra, A. K.;Williams, A.
  20. J. Am. Chem. Soc. v.99 Hupe, D. J.;Jencks, W. P.
  21. J. Chem. soc. Blackwell, L. F.;Fischer, A.;Miller, I. J.;Topsom, R. D.;Vaughan, J.
  22. Dictionary of Organic Compounds(5th ed.) Chapman and Hall
  23. Bull. Korean Chem. Soc. v.15 Lee, I.
  24. Bull. Korean Chem. Soc. Koh, H. J.;Lee, H. C.;Lee, H. W.;Lee, I.
  25. New J. Chem. Lee, I.;Koh, H. J.
  26. Chem. Soc. Rev. Lee, I.
  27. Kinetics and Mechanism Moore, J. W.;Pearson, R. G.
  28. J. Am. Chem. Soc. v.94 Menger, F. M.;Smith, J. H.
  29. The Determination of Ionization(3rd ed.) Albeit, A.;Serjeant, E. P.
  30. J. Org. Chem. v.56 Castro, E. A.;Ibanez, F.;Salas, M.;Santos, J. G.
  31. J. Org. Chem. v.59 Castro, E. A.;Salas, M.;Santos, J. G.
  32. Bull. Korean Chem. Soc. v.11 Lee, I.;Koh, H. J.;Lee, B.-S.;Lee, H. W.;Choi, J. H.
  33. Phil. Mag. v.2 Guggenheim, E. A.