DOI QR코드

DOI QR Code

Solvent Effect on the Reactions of DANSYL and BANSYL Chlorides with Substituted Pyridines

  • Published : 1998.05.20

Abstract

Solvent effects on the reactions of DANSYL and BANSYL chlorides with substituted pyridines have been investigated using two parameters of Taft's solvatochromic correlation and four parameters of Kirkwood-Onsager, Parker, Marcus, Hildebrand equation. The acetonitrile molecules accelerate charge separation of the reactants and stabilize the transition state. The coefficient of the solvent parameters provide a good information to predict and to analyze the reaction mechanism. The nucleophilic substitution reaction of DANSYL and BANSYL chlorides with substituted pyridines are ruled by the contribution of the change in dipole moment term and polarity-polarizability term.

Keywords

References

  1. Biochim. Biophys. Acta. v.133 Woods, K. R.;Wang, K. T.
  2. Bull. Soc. Chim. Biol. v.37 Sanger, F.
  3. Analyt. Biochim. v.65 Burzynski, S. R.
  4. Ukr. Khim. Zr. v.33 Litvinenko, L. M.;Popov. A. F.;Savelova, V. A.
  5. Zh. Obsch. Khim. v.41 Livinenko, L. M.;Maleeva, N. T.;Savelova, V. A.;Kovach, T. D.
  6. J. Chem. Soc., Perkin Trans II Ciuffarine, E.;Senatore, L.;Isola, M.
  7. J. Chem. Soc. Perkin Trans II. Arcoria, A.;Ballisteri, P. P.;Musumarra, G.;Tomaselli, G. A.
  8. Nucleophilicity King, J. F.;Skonieczny, S.;Khemani, K. C.;Lock, J. D.
  9. J. Am. Chem. Soc. v.86 Ralph, E. D.;Gilkerson, W. A.
  10. J. Chem. Soc. Kyte, C. T.;Jeffery, G. H.
  11. J. Appl. Chem. v.2 Coulson, E. A.;Ditcham, J. B.
  12. Sb. Prednasek, Semin. v.C no.A Krupicka, J.;Krystalizace, P.
  13. J. Chem. Soc., Perkin, Trans II Lee, I.;Sung, D. D.;Uhm, T. S.;Ryu, Z. H.
  14. Bull. Korean Chem. Soc. v.12 Park, H. H.;Hong, Y. S.;Sung, D. D.
  15. Philos. Mag. v.2 Guggenheim, E. A.
  16. Comprehensive Heterocyclic Chemistry v.2 Katritzky, A. FRS.;Rees, C. W. FRS.
  17. Annalen v.485 Ziegler, K.;Zeiser, H.
  18. J. Chem. Soc. Jones, A. M.;Russel, C. A.;Skidmore, S.
  19. Synthesis Beumel, O. F.;Smith, W. N.;Rybalka, B.
  20. The PMO Theory of Organic Chemistry Dewar, M. J. S.;Dougherty, R. C.
  21. Chem. Rev. v.42 Borrows, E. T.;Holland, D. O.
  22. J. Chem. Soc. v.(B) Rogne, O.
  23. Comprehensive Heterocyclic Chemistry v.2 Katritzky, A. FRS.
  24. J. Am. Chem. Soc. v.110 King, J. F.
  25. J. Org. Chem. v.53 Lee, I.;Kim, H. Y.;Kang, H. K.;Lee, H. W.
  26. J. Chem. Soc. Katritzky, A. R.;Ridgewell, B. J.
  27. J. Chem. Soc. Katritzky, A. R.;Ridgewell, B. J.
  28. Tetrahedron v.23 Adam, W.;Grimson, A.;Rodriguez, G.
  29. Prog. Phys. Org. Chem. v.13 Kamlet, M. J.;Abboud, J. L.;Taft, R. W.
  30. J. Am. Chem. Soc. v.99 Kalyanasundaram, K.;Thomas, J. K.
  31. J. Am. Chem. Soc. v.98 Taft, R. W.;Kamlet, M. J.
  32. J. Org. Chem. v.50 Mills, S. G.;Beak, P.
  33. J. Org. Chem. v.45 Beak, P.;Covington, J. B.;White, J. M.
  34. J. Chem. Phys. v.2 Kirkwood, J. G.
  35. J. Am. Chem. Soc. v.58 Onsager, L.
  36. Aust. J. Chem. v.27 Cox, B. G.;Hedwig, G. R.;Parker, A. J.;Watts, D. W.
  37. Pure Appl. Chem. v.55 Marcus, Y.
  38. Regular and Related Solutions Hildebrand, J. H.;Prausnitz, J. M.;Scott, R. L.
  39. Regular Solutions Hildebrand, J. H.;Scott, R. L.
  40. J. Org. Chem. v.57 Gajewski, J. J.
  41. J. Am. Chem. Soc. v.101 Gajewski, J. J.;Conrad, N. D.
  42. Ph. D. Thesis, Dong-A Univ. Ryu, Z. H.