Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Nucleophilic Substitution Reaction of Dansyl Chloride with Substituted Anilines$^1$

  • Published : 1985.06.20
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Abstract

Nucleophilic substitution reaction of dansyl chloride with anilines in various solvents have been investigated. The Bronsted ${\beta}$ and Hammett ${\rho}_N$ values indicated that the bond formation is advanced more than the bond breaking at the transition state. Solvatochromic correlations also predicted the importance of bond formation at the TS, showing a greater contribution of polarity (${\pi}^{\ast}$) compared to hydrogen bond donor acidity (${\alpha}$). The effect of solvent on rate was found to violate the reactivity-selectivity principle.

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References

  1. Tetrahedron v.39 Nucleophilic Displacement oat Sulfur Center I. Lee;I. S. Koo
  2. Aust. J. Chem. v.24 M. L. Tonnet;A. N. Hambly
  3. Aust. J. Chem. v.24 R. Foon;A. N. Hambly
  4. J. Korean Chem. Soc. v.25 I. Lee;I. S. Koo
  5. Bull, Korean Chem. Soc. v.2 I. Lee;I. S. Koo
  6. J. Chem. Soc. (P) O. Rogne
  7. J. Chem. Soc. (P) O. Rogne
  8. J. Chem. Soc. (P) O. Rogne
  9. J. Chem. Soc., Perkin v.2 O. Rogne
  10. Tetrahedron v.39 I. Lee;I. S. Koo
  11. Ukr. Khim. Zr. v.33 L. M. Litvinenko;A. F. Popov;V. A.Savelova
  12. Zh. Obshch. Khim. v.41 L. M. Litvinenko;N. T. Maleeva;V. A. Savelova;T. D. Kovach
  13. J. Chem. Soc. Perkin v.2 E. Ciuffarine;L. Senatore;M. Isola
  14. J. Chem. Soc. Perkin v.2 L. J. Stangeland;L. Senatore;E. Ciuffarin
  15. J. Org. Chem. v.24 A. Arcoria;E. Maccarone;G. Musumarra;C. A. Tomaselli
  16. J. Chem. Soc. Perkin v.2 A. Arcoria;P. P. Ballistreri;G. Musumarra;G. A. Tomaselli
  17. Biochemistry F. B. Armstrong
  18. J. Org. Chem. v.22 K. Massie
  19. Amer. Ind. Hyg. Assoc. J. v.23 H. F. Smith
  20. J. Gen. Chem. (U.S.S.R.) v.21 B. I. Ardashev
  21. Ber. v.75 R. Weidenhagen;G. Train
  22. J. Amer. Chem. Soc. v.73 E. C. Evers;A. G. Knox
  23. Ind. Eng. Chem. Anal., Ed. v.5 A. W. Stout;H. A. Schuette
  24. U. S. Pat. 2356689 R. J. Ozol;C. R. Materson
  25. Chem. Abs. v.39 R. J. Ozol;C. R. Materson
  26. J. Chem. Soc. J. Clarke;R. Robinson;J.C. Smith
  27. Roez. Chem. v.18 J. Timmermans;Gillo
  28. Bull. Inst. Basic Sci. Inha Uni. v.6 I. Lee;I. S. Koo;B. D. Chang;D. H. Kang
  29. Adv. Phys. Org. Chem. v.14 A. Pross
  30. Chem. Rev. v.75 C. D. Johnson
  31. Tetrahedron v.34 D. J. McLennan
  32. Acc Chem. Res. v.5 C.D. Ritchie

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