Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Solvolysis of Phenylacetyl Chlorides in Methanol-Acetonitrile Mixtures

  • Lee Ikchoon (Department of Chemistry, Inha university) ;
  • Huh Chul (Department of Chemistry, Inha university) ;
  • Lee Hai Whang (Department of Chemistry, Inha university)
  • Published : 19890200
Download PDF
⟨ Previous Next ⟩

Abstract

The methanolysis reactions of phenylacetyl chlorides have been investigated in methanol-acetonitrile mixtures at temperatures ranging - $15.0-0.0^{\circ}C.$ Substituent and solvent effects on the rate supported an associative $S_N2$ mechanism for the solvolysis. Activation parameters indicated that the reaction is entropy controlled, while the a/s ratios of the Taft's solvactochromic correlation proved to be remarkably constant with a typical value of 0.50 that is consistent for the reactions proceeding by a typical $S_N2$ path.

Keywords

References

  1. The Chemistry of Acyl Halides A. Kivinen;S. Patai(ed.)
  2. Anal. Chem. v.42 D. E. Johnson;C. G. Enke
  3. Anal. Chem. v.45 P. H. Daum;D. F. Nelson
  4. J. Chem. Soc. Perkin v.2 D. N. Kevill;P. H. Daum;R. Sapre
  5. J. Chem. Soc. Perkin 2 W. T. Bentley;G. E. Carter;H. C. Harris
  6. J. Chem. Soc. Chem. Commun. T. W. Bentley;I. S. Koo
  7. Ph. D. Thesis, Inha University S. C. Sohn
  8. J. Am. Chem. Soc. v.98 T. W. Bentley;P. V. R. Schleyer
  9. J. Am. Chem. Soc. v.98 F. L. Schadt;T. W. Bentley;P. V. R. Schleyer
  10. J. Am. Chem. Soc. v.104 T. W. Bentley;G. E. Cartey
  11. Introduction to Physical Organic Chemistry R. D. Gilliom
  12. J. Chem. Soc. Perkin 2 I. Lee;C. S. Shim;S. Y. Chung;H. Y. Kim;H. W. Lee
  13. Bull. Korean Chem. Soc. v.3 I. Lee;I. S. Koo;S. C. Sohn;H. W. Lee
  14. Correlation Analysis of Organic Reactivity J. Shorter
  15. Prog. Phys. Org. Chem. v.13 M. J. Kamlet;J. L. Abboud;R. W. Taft
  16. Ph. D. Thesis, Inha Univ. H. K. Kang
  17. Acta Chem. Scand. v.20 E. Tommila
  18. J. Chem. Soc. Perkin v.2 D. N. Kevill;C. B. Kim
  19. Introduction to Physical Organic Chemistry R. D. Gilliom
  20. J. Korean Chem. Soc. v.7 I. Lee
  21. J. Am. Chem. Soc. v.47 L. C. Railfond;H. P. Lankelma
  22. J. Am. Chem. Soc. v.82 P. D. Bartlett;C. Ruchardt
  23. J. Org. Chem. v.10 H. P. Ward;E. F. Jenkins
  24. Phil. Mag. v.2 E. A. Guggenheim

Cited by

  1. Kinetics and mechanism of the aminolysis of benzoic anhydrides vol.7, pp.6, 1989, https://doi.org/10.1002/poc.610070602
  2. (Bromomethyl)phenylacetic Acids의 가용매 분해반응에 대한 Extended Grunwald-Winstein 식의 적용 vol.54, pp.3, 1989, https://doi.org/10.5012/jkcs.2010.54.3.354