Concentrated Salt Effects on the Solvolysis Reaction Rates in Methanol-Water Solution

Bulletin of the Chemical Society of Japan

Volumn 71, Issue 3, 1998, Pages 589-596

  Manege, Ludovick Christian ^a   Ueda, Tadaharu ^a   Hojo, Masashi ^a  

^a KOCHI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001200590     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.71.589     Document Type: Article

References (49)

1. K. S. Pitzer, J. Phys. Chem., 77, 268 (1973); K. S. Pitze and J. J. Kim, J. Am. Chem. Soc., 96, 5701 (1974).
2. K. S. Pitzer, J. Phys. Chem., 77, 268 (1973); K. S. Pitze and J. J. Kim, J. Am. Chem. Soc., 96, 5701 (1974).
3. J.-F. Chen and G. R. Choppin, J. Solution Chem., 24, 465 (1995).
4. T. E. Hogen-Esch and J. Smid, J. Am. Chem. Soc., 88, 307 and 318 (1966); T. E. Hogen-Esch and J. Plodinec, J. Am. Chem. Soc., 100, 7633 (1978); D. H. O'Brien, C. R. Russell, and A. J. Hart, J. Am. Chem. Soc., 101, 633 (1979).
5. T. E. Hogen-Esch and J. Smid, J. Am. Chem. Soc., 88, 307 and 318 (1966); T. E. Hogen-Esch and J. Plodinec, J. Am. Chem. Soc., 100, 7633 (1978); D. H. O'Brien, C. R. Russell, and A. J. Hart, J. Am. Chem. Soc., 101, 633 (1979).
6. T. E. Hogen-Esch and J. Smid, J. Am. Chem. Soc., 88, 307 and 318 (1966); T. E. Hogen-Esch and J. Plodinec, J. Am. Chem. Soc., 100, 7633 (1978); D. H. O'Brien, C. R. Russell, and A. J. Hart, J. Am. Chem. Soc., 101, 633 (1979).
7. a) M. Hojo, H. Nagai, M. Hagiwara, and Y. Imai, Anal. Chem., 59, 1770 (1987);
8. b) M. Hojo, H. Hasegawa, Y. Miyauchi, H. Moriyama, H. Yoneda, and S. Arisawa, Electrochim. Acta, 39, 629 (1994); M. Hojo, H. Hasegawa, and N. Hiura, J. Phys. Chem., 100, 891 (1996); M. Hojo and H. Moriyama, J. Solution Chem., 25, 681 (1996).
9. b) M. Hojo, H. Hasegawa, Y. Miyauchi, H. Moriyama, H. Yoneda, and S. Arisawa, Electrochim. Acta, 39, 629 (1994); M. Hojo, H. Hasegawa, and N. Hiura, J. Phys. Chem., 100, 891 (1996); M. Hojo and H. Moriyama, J. Solution Chem., 25, 681 (1996).
10. b) M. Hojo, H. Hasegawa, Y. Miyauchi, H. Moriyama, H. Yoneda, and S. Arisawa, Electrochim. Acta, 39, 629 (1994); M. Hojo, H. Hasegawa, and N. Hiura, J. Phys. Chem., 100, 891 (1996); M. Hojo and H. Moriyama, J. Solution Chem., 25, 681 (1996).
11. Z. Chen and M. Hojo, J. Phys. Chem. B, 101, 10896 (1997). Fuoss has predicted the relationship theoretically: R. M. Fuoss and F. Accascina, "Electrolytic Conductance," Interscience, New York (1959), p. 256.
12. Z. Chen and M. Hojo, J. Phys. Chem. B, 101, 10896 (1997). Fuoss has predicted the relationship theoretically: R. M. Fuoss and F. Accascina, "Electrolytic Conductance," Interscience, New York (1959), p. 256.
13. M. Hojo, T. Ueda, M. Nishimura, M. Matsui, and S. Umetani, to be published.
14. M. Hojo, H. Hasegawa, and H. Yoneda, Bull. Chem. Soc. Jpn., 69, 971 (1996).
15. M. Hojo, H. Hasegawa, and H. Yoneda, J. Chem. Soc., Perkin Trans. 2, 1994, 1855; M. Hojo, H. Hasegawa, A. Mizobe, Y. Ohkawa, and Y. Miimi, J. Phys. Chem., 99, 16609 (1995).
16. M. Hojo, H. Hasegawa, and H. Yoneda, J. Chem. Soc., Perkin Trans. 2, 1994, 1855; M. Hojo, H. Hasegawa, A. Mizobe, Y. Ohkawa, and Y. Miimi, J. Phys. Chem., 99, 16609 (1995).
17. M. Hojo, T. Ueda, H. Hasegawa, H. Tsurui, K. Kawamura, S. Minami, M. Yamasaki, and A. Mizobe, to be published; M. Hojo, T. Ueda, L. C. Manege, and M. Yamasaki, "7th Kyushu International Symposium on Physical Organic Chemistry (KISPOC-VII)," Fukuoka, Dec. 1997, Abstr. No. P12.
18. M. Hojo, T. Ueda, H. Hasegawa, H. Tsurui, K. Kawamura, S. Minami, M. Yamasaki, and A. Mizobe, to be published; M. Hojo, T. Ueda, L. C. Manege, and M. Yamasaki, "7th Kyushu International Symposium on Physical Organic Chemistry (KISPOC-VII)," Fukuoka, Dec. 1997, Abstr. No. P12.
19. E. M. Arnett, C. Petro, and P. v. R. Schleyer, J. Am. Chem. Soc., 101, 522 (1979).
20. Y. Marcus, J. Solution Chem., 13, 599 (1984).
21. J. E. Gordon, "The Organic Chemistry of Electrolyte Solutions," John Wiley, New York (1975), p. 91.
22. E. H. Oelkers and H. C. Helgeson, Science, 261, 888 (1993).
23. T. M. Bentley and P.v. R. Schleyer, "Advances in Physical Organic Chemistry." ed by V. Gold and D. Bethell, Academic, London (1977), Vol. 14, p. 2; D. J. Raber, J. M. Harris, and P. v. R. Schleyer, "Ions and Ion Pairs in Organic Reactions," ed by M. Szwarc, John Wiley, New York (1974), Vol. 2. Chap. 3.
24. T. M. Bentley and P.v. R. Schleyer, "Advances in Physical Organic Chemistry." ed by V. Gold and D. Bethell, Academic, London (1977), Vol. 14, p. 2; D. J. Raber, J. M. Harris, and P. v. R. Schleyer, "Ions and Ion Pairs in Organic Reactions," ed by M. Szwarc, John Wiley, New York (1974), Vol. 2. Chap. 3.
25. a) A. Loupy and B. Tchoubar, "Salt Effects in Organic and Organometallic Chemistry," VCH, Weinheim (1992);
26. b) A. Loupy, B. Tchoubar, and D. Astruc, Chem. Rev., 1992, 1141.
27. S. Winstein, E. Clippinger, A. H. Fainberg, and G. C. Robinson, J. Am. Chem. Soc., 76, 2597 (1954); A. H. Fainberg and S. Winstein, J. Am. Chem. Soc., 78, 2767 (1956); S. Winstein, P. E. Klinedinst, Jr., and G. C. Robinson, J. Am. Chem. Soc., 83, 885 (1961).
28. S. Winstein, E. Clippinger, A. H. Fainberg, and G. C. Robinson, J. Am. Chem. Soc., 76, 2597 (1954); A. H. Fainberg and S. Winstein, J. Am. Chem. Soc., 78, 2767 (1956); S. Winstein, P. E. Klinedinst, Jr., and G. C. Robinson, J. Am. Chem. Soc., 83, 885 (1961).
29. S. Winstein, E. Clippinger, A. H. Fainberg, and G. C. Robinson, J. Am. Chem. Soc., 76, 2597 (1954); A. H. Fainberg and S. Winstein, J. Am. Chem. Soc., 78, 2767 (1956); S. Winstein, P. E. Klinedinst, Jr., and G. C. Robinson, J. Am. Chem. Soc., 83, 885 (1961).
30. A. D. Allen, T. T. Tidwell, and O. S. Tee, J. Am. Chem. Soc., 115, 10091 (1993).
31. G. A. Clarke and R. W. Taft, J. Am. Chem. Soc., 84, 2295 (1962).
32. J. P. Richard and P. E. Yeary, J. Am. Chem. Soc., 115, 1739 (1993).
33. C. A. Bunton, T. W. D. Pesco, A. M. Dunlop, and K.-U. Yang. J. Org. Chem., 36, 887 (1971).
34. D. J. Raber, R. C. Bingham, J. M. Harris, J. L. Fry, and P. v. R. Schleyer, J. Am. Chem. Soc., 92, 5977 (1970).
35. T. W. Bently and G. E. Carter, J. Am. Chem. Soc., 104, 5741 (1982).
36. A. A. Frost and R. G. Pearson, "Kinetics and Mechanism," 2nd ed, John Wiley, New York (1961), p. 152.
37. V. Gutman. "The Donor-Acceptor Approach to Molecular Interactions," Plenum, New York (1978), Chap. 2.
38. R. H. Erlich, E. Roach, and A. I. Popov, J. Am. Chem. Soc., 92, 4989 (1970).
39. L. C. Bateman, M. G. Church, E. D. Hughes, C. K. Ingold, and N. A. Taher, J. Chem. Soc., 1940, 979.
40. E. S. Rudakov and I. V. Kozhevnikov, Tetrahedron Lett., 1971, 1333.
41. a) E. Grunwald and S. Winstein, J. Am. Chem. Soc., 70, 846 (1948);
42. b) S. Winstein, E. Grunwald, and H. W. Jones, J. Am. Chem. Soc., 73, 2700 (1951);
43. c) A. H. Fainberg and S. Winstein, J. Am. Chem. Soc., 78, 2770 (1956). The m and Y values are defined as follows; log(k/k°)=mY where k is the first-order rate constant in any solvent. k° is the corresponding rate constant in a standard solvent (80% ethanol-20% water), m is a parameter characteristic of the alkyl halide or ester, and Y is a parameter characteristic of the solvent. Values of Y were determined for the different solvents by choosing t-butyl chloride as a standard compound for which m was taken as 1.00 at 25°C.
44. Cl scale depending upon 1-adamantyl chloride, cf., Ref. 22.
45. e.g., R. T. Morrison and R. N. Boyd, "Organic Chemistry," 6th ed, Prentice-Hall, New York (1992). Chap. 5.
46. S. Winstein, A. H. Fairberg, and E. Grunwald, J. Am. Chem. Soc., 79, 4146 (1957).
47. A. H. Fainberg and S. Winstein, J. Am. Chem. Soc., 79, 1608 (1957).
48. V. V. Zamashchikov, T. V. Bezbozhnaya, and I. R. Chanysheva, Zh. Org. Khim., 22, 1145 (1986); cf., Ref. 15 a). p. 23.
49. V. V. Zamashchikov, T. V. Bezbozhnaya, and I. R. Chanysheva, Zh. Org. Khim., 22, 1145 (1986); cf., Ref. 15 a). p. 23.