Bulletin of the Korean Chemical Society

  • 제6권2호
  • /
  • Pages.99-102
  • /
  • 1985
  • /
  • 0253-2964(pISSN)
  • /
  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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Studies on the Quaternization of Tertiary Amines (Ⅳ). Kinetics and Mechanism for the Reaction of Substituted Phenacyl Tosylates with Substituted Pyridines

  • Lee, Oh-Seuk (Department of Chemistry, Teacher's College, Kyungpook National University) ;
  • Yoh, Soo-Dong (Department of Chemistry, Teacher's College, Kyungpook National University)
  • 발행 : 1985.04.20
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초록

Substituent effects of substrate and nucleophile for the reaction of substituted phenacyl tosylates with pyridines were determined conductometrically in acetonitrile. Activation parameters for these reactions were also calculated. The substituent effects in nucleophile were increased with electron-donating power of pyridines and Br${\o}$nsted linear relationship was shown. Rate constant was increased by both electron-donating and electron-attracting groups in the substrate. It seems that dissociative S$_{N}$2 ("loose" transition state) mechanism is operating in the case of electron-donating substituents while associative S$_{N}$2 ("tight" transition state) mechanism is operative in the case of electron-attracting substituents.

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참고문헌

  1. J. Chem. Soc. Pickel;Hinshelwood
  2. J. Org. Chem. v.28 J. D. Reinheimer;J. D. Harley
  3. Nippon Kakaku Kaishi v.93 M. Tsuruta;K. Marai;T. Sato;C. Kimura
  4. J. Chem. Soc. Perkin II Abraham;Grellier
  5. J. Chem. Soc. Perkin II W. Forster;R. M. Laird
  6. J. Korean Chem. Soc. v.21 W. B. Lee;S. D. Yoh
  7. J. Korean Chem. Soc. v.23 K. A. Lee;K. T. Howang;S. D. Yoh
  8. J. Korean Chem. Soc. v.26 S. D. Yoh;K. A. Lee;S. S. Park
  9. J. Chem. Soc. A. Slater;D. F. Twisse
  10. J. Amer. Chem. Soc. v.74 R. G. Pearson;S. H. Langer;F. V. Williams
  11. J. Amer. Chem. Soc. v.80 P. D. Bartiett;E. N. Trachtenberg
  12. J. Org. Chem. v.32 J. Pasto;K. Graves;M. P. Serve
  13. J. Korean Chem. Soc. v.25 S. D. Yoh;K. T. Shim;K. A. Lee
  14. J. Chem. Soc. Perkin II P. A. Nadar;C. Gnanasekaran
  15. J. Chem. v.16B P. A. Nadar;C. Gnanasekaran Indian
  16. J. Chem. Soc. Perkin II P. A. Nadar;Gnanasekaran
  17. Organic Synthesis v.1 R. M. Cowper;L. H. Davidson
  18. Beilstein Organishe Chemie v.VII Bernhard Prager;Paul Jacobson
  19. J. Chem. Soc. v.75 W. D. Emmons;A. F. Ferris
  20. J. Korean Chem. Soc. v.16 S. Y. Hong;S. D. Yoh
  21. J. Chem. Soc. (B) O. Rogne
  22. The Theory of Rate Process S. Glasson;K. J. Laidler;H. Eyring
  23. Advanced Organic Chemistry Francis A. Carey;Richard J. Sundberg
  24. J. Physik. Chem. v.108 J. N. Br${\o}$nsted;K. J. Pederson
  25. Prog. Phys. Org. Chem. v.10 O. Exner
  26. J. Korean Chem. Soc. v.28 C. S. Kim;S. Y. Hong
  27. J. Amer. Chem. Soc. v.86 F. G. Bordwell
  28. Trans. Fraday Soc. v.37 J. W. Baker
  29. J. Amer. Chem. Soc. v.73 C. G. Swain

피인용 문헌

  1. Mechanism of nucleophilic substitutions at phenacyl bromides with pyridines. A computational study of intermediate and transition state vol.21, pp.11, 1985, https://doi.org/10.1002/poc.1412