Reactions within association complexes: The reaction of imidazole with substituted phenyl acetates in the presence of detergents in aqueous solution

Journal of Organic Chemistry

Volumn 65, Issue 8, 2000, Pages 2537-2543

  Pirinccioglu, Necmettin ^a   Zaman, Flora ^a   Williams, Andrew ^a  

^a University Chemical Laboratory Canterbury   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

DETERGENT; IMIDAZOLE DERIVATIVE; PHENYLACETIC ACID DERIVATIVE;

AQUEOUS SOLUTION; ARTICLE; COMPLEX FORMATION; DISSOCIATION CONSTANT; MICELLE; REACTION ANALYSIS; SYNTHESIS;

EID: 0034697111     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991887o     Document Type: Article

References (42)

1. Fendler, J. H.; Fendler, E. J. Catalysis in Micelles and Macromolecular Systems; Academic Press: New York, 1975.
2. Cordes, E. H.; Gitler, C. Prog. Bioorg. Chem. 1973, 2, 1.
3. Menger, F. M. Acc. Chem. Res. 1979, 12, 111.
4. Kunitake, T.; Shinkai, S. Adv. Phys. Org. Chem. 1980, 17, 435.
5. Bunton, C. A.; Savelli, G. Adv. Phys. Org. Chem. 1986, 22, 213.
6. Fujita, T.; Iwasa, J.; Hansch, C J. Am. Chem. Soc. 1964, 86, 5175.
7. Leo, A. J.; Hansch, C.; Elkins, D. Chem. Rev. 1971, 71, 525.
8. Williams, A. Adv. Phys. Org. Chem. 1992, 27, 1.
9. Ba-Saif, S. A.; Colthurst, M.; Waring, M. A.; Williams, A. J. Chem. Soc., Perkin Trans. 2 1991, 1901.
10. Chattaway, F. D. J. Chem. Soc. 1931, 2495.
11. Kirsch, J. F.; Jencks, W. P. J. Am. Chem. Soc. 1964, 86, 837.
12. Williams, A.; Naylor, R. A. J. Chem. Soc. B 1971, 1967.
13. Menger, F. M.; Portnoy, C. E. J. Am. Chem. Soc. 1967, 89, 4698.
14. Bennion, B. C.; Tong, L. K. J.; Holmes, L. P.; Eyring, E. M. J. Phys. Chem. 1969, 73, 3288.
15. Rosen, M. J. Surfactants and Interfacial Phenomena, 2nd. ed.; J. Wiley and Sons: New York, 1989.
16. Takeda, K.; Yasunaga, T. J. Colloid. Interfac. Sci. 1972, 40, 127; 1973, 45, 406.
17. Takeda, K.; Yasunaga, T. J. Colloid. Interfac. Sci. 1972, 40, 127; 1973, 45, 406.
18. Tartar, H. V. J. Coll. Sci. 1959, 14, 115.
19. Tee, O. S.; Fedortchenko, A. A. Can. J. Chem. 1997, 75, 1434.
20. Al-Awadi, N.; Williams, A. J. Org. Chem. 1990, 55, 2001.
21. Al-Awadi, N.; Williams, A. J. Org. Chem. 1990, 55, 4359.
22. Almgren, M.; Rydholm, R. J. Phys. Chem. 1979, 83, 360
23. Kurz, J. L. Acc. Chem. Res. 1972, 5, 1.
24. Tee, O. S. Adv. Phys. Org. Chem. 1994, 29, 1.
25. Page, M. I.; Williams, A. Organic and Bio-organic Mechanisms; Addison-Wesley Longman: Harlow, 1997; p 74.
26. 27 was employed to calculate log P values for 4-nitrophenyl acetate (1.26), 4-nitrophenyl hexanoate (3.61), and 4-nitrophenyl dodecanoate (6.55).
27. (b) Broxton, T. J.; Christie, J. R.; Sango, X. J. Org. Chem. 1987, 52, 4814.
28. (c) Broxton, T. J.; Christie, J. R.; Chung, R. P. T. J. Org. Chem. 1988, 53, 3081.
29. The slope of a linear Hansch correlation with π may be employed as a measure of the nature of the complexation medium by comparing it with the slopes for complexation into standard media. Thus, the plot of log P versus π will have a slope of unity that is the standard for partitioning into the n-octanol phase from aqueous solution; a zero slope is obtained for the identity partitioning from water into water. The approach is the same as that employed by Leffler (see ref 24, p 52), who compared α values for rate constants with those for equilibrium constants to measure the progress of reaction as a function of reactant and product. A Hansch p value of zero for transfer between two states (such as complexed ester and complexed transition state) indicates that there is no change in microsolvation environment between the two states. A value for p of unity for transfer from water to the complexed system indicates that the medium in the complex has the attributes toward hydrophobic interactions such as n-octanol. A value of p of zero for such a system indicates that the part of the substrate where π varies resides in an aqueous environment in the complexed system.
30. Leo, A. J. Chem. Rev. 1993, 93, 1281.
31. Menger, F. M. In Surfactants in Solution (Proc. Int. Symp., 1982); Plenum Press: New York, 1984; p 347.
32. Menger, F. M. J. Phys. Chem. 1979, 83, 893.
33. Dill, K. A.; Flory, P. J. Proc. Nat. Acad. Sci. U.S.A. 1981, 78, 676.
34. Gustavsson, H.; Lindman, B. J. Am. Chem. Soc. 1975, 97, 3923.
35. Oakes, J. J. Chem. Soc., Faraday Trans. 2 1973, 69, 1321.
36. Robb, I. D.; Smith, R. J. Chem. Soc., Faraday Trans. 1 1974, 70, 287.
37. Tagaki, W.; Fakushima, D.; Eiki, T.; Yano, Y. J. Org. Chem. 1979, 44, 555.
38. Hansch, C. Accs. Chem. Res. 1969, 2, 232.
39. Kirby, A. J. Adv. Phys. Org. Chem. 1980, 17, 183.
40. Ba-Saif, S. A.; Waring, M. A.; Williams, A. J. Am. Chem. Soc. 1990, 112, 8115.
41. Bourne, N.; Chrystiuk, E.; Davis, A. M.; Williams, A. J. Am. Chem. Soc. 1988, 110, 1890.
42. Norrington, F. E.; Hyde, R. M.; Williams, S. G.; Wootton, R. J. Med. Chem. 1975, 18, 604.