Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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The Salt Effect on the Nucleophilic Substitution Reaction

  • Published : 1991.06.20
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Abstract

The nucleophilic substitution reactions of p-substituted benzenesulfonyl chlorides wiht p-substituted anilines were carried out in 1,1,1,3,3,3-hexafluoro-2-propanol and 2-propanol mixtures. The salt effect was observed to be inhibited by the reaction of 1,1,1,3,3,3-hexafluoro-2-propanol with nucleophiles. To investigate the effectiveness of the salt for the nucleophilic substitution reaction the relative salt effect was determined. According to the comparison with the inhibitive salt effect and the substituent effects for the substrates and nucleophiles, the reactions were predicted to be controlled by the salt effect more than substituent effect in HFP-PrOH mixtures.

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References

  1. Prog. Phys. Org. Chem. v.11 J. H. Marris
  2. Structure and Mechanism in Organic Chemistry C. K. Ingold
  3. J. Am. Chem. Soc. v.70 E. Grunwald;S. Winstein
  4. J. Am. Chem. Soc. v.98 F. L. Schadt;T. W. Bentley;P. v. R. Schleyer
  5. J. Org. Chem. v.46 M. H. Abraham;R. W. Taft;M. J. Kamlet
  6. J. Am. Chem. Soc. v.102 E. S. Lewis;S. Kukes;C. D. Slater
  7. Tetrahedron Lett. C. R. Wong;L. M. Jacksman;R. G. Portman
  8. J. Am. Chem. Soc. v.105 C. D. Richie;C. Kubistz;G. Y. Ting
  9. Tetrahedron Lett. G. A. Dafforn;A. Streitwiester, Jr.
  10. Nou. J. Chimie v.3 no.5 B. Allard;A. Casadevall;E. Casadevall;C. Largeau
  11. J. Am. Chem. Soc. v.92 P. v. R. Schleyer;J. L. Fry;L. K. M. Lam;C. J. Lancelot
  12. J. Am. Chem. Soc. v.91 J. L. Reich;A. Diaz;S. Winstein
  13. J. Am. Chem. Soc. v.93 D. J. Raber;J. M. Harris;R. E. Hall;P. v. R. Schleyer
  14. Chem. and Ind. F. L. Scott
  15. Tetrahedron Lett. W. S. Trahanovsky;M. P. Doyle
  16. Tetrahedron Lett. D. J. Raber;M. D. Dukes;J. Gregory
  17. Tetrahedron Lett. M. D. Bentley;J. A. Lacadie
  18. J. Phys. Chem. v.77 M. A. Matesich;J. Knoefel;H. Feidman;D. F. Evans
  19. J. Phys. Chem. v.75 D. F. Evans;J. A. Nadas;M. A. Matesich
  20. J. Org. Chem. v.51 S. P. McManus;A. Safavy
  21. Russ. Chem. Rev. (Engl. Transl.) v.32 R. V. Vizgert
  22. Adv. Phys. Org. Chem. v.17 J. L. Kice
  23. J. Chem. Soc. v.B O. Rogne
  24. J. Chem. Soc. v.B O. Rogne
  25. Can. J. Chem. v.62 J. F. King;J. H. Hillhouse
  26. Org. Syn. Coll. v.1 R. Adams;C. S. Marvel;H. T. Clarke;C. R. Noller;J. B. Conant;F. C. Whitmore
  27. J. Prakt. Chem. v.125 T. Curtius;G. Kraemer
  28. Beilsteins Handbuch der Organischen Chemie v.11
  29. Beilsteins handbuch der organischen Chemie v.11
  30. Pract. Org. Chem (Synth.) A. I. Vogel
  31. Ann v.74 Cahours
  32. The Merck Index 690 W. Windholz(ed.)
  33. J. Chem. Soc. v.119 Sidgwick;Rubie
  34. J. Korean Chem. Soc v.32 I. Lee;H. W. Lee;T. S. Uhm;D. D. Sung;Z. H. Ryu
  35. J. Chem. Soc. Perkin Trans. II I. Lee;D. D. Sung;T. S. Uhm; Z. H. Ryu
  36. Tetrahedron Lett. F. L. Schadt;P. v. R. Schleyer;T. W. Bentley
  37. J. Org. Chem. v.51 P.McManus;A. Safavy
  38. Nouv. J. Chemie v.3 B. Allard;A. Casadevall;E. Casadevall;C. Largeau
  39. J. Org. Chem. v.55 P. J. Smith;C. S. Wilcox
  40. Tetrahedron Lett. v.39 I. Lee;I. S. Koo