The Hammett equation and micellar effects on SN2 reactions of methyl benzenesulfonates - The role of micellar polarity

European Journal of Organic Chemistry

Volumn , Issue 23, 2000, Pages 3849-3854

  Brinchi, Lucia ^a   Di Profio, Pietro ^a   Germani, Raimondo ^a   Savelli, Gianfranco ^a   Spreti, Nicoletta ^b   Bunton, Clifford A ^c  

^a UNIVERSITY OF PERUGIA   (Italy)

^b UNIVERSITY OF L'AQUILA   (Italy)

^c UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Hammett equation; Kinetics; Micelles; Nucleophilic substitution

Indexed keywords

AMMONIUM DERIVATIVE; BENZENESULFONIC ACID DERIVATIVE; BROMINE; CATION; HYDROXYL GROUP; METHYLBENZENESULFONATE; SURFACTANT; TOLUENESULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG; WATER;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL REACTION; MICELLE;

EID: 0033675413     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200012)2000:23<3849::AID-EJOC3849>3.0.CO;2-P     Document Type: Article

References (46)

1. [1a] L. S. Romsted, in: Surfactants in Solution (Eds.: K. L. Mittal, B. Lindman), Plenum Press, New York, 1984, Vol. 2, p. 1015.
2. [1b] C. A. Bunton, G. Savelli, Adv. Phys. Org. Chem. 1986, 22, 213-309.
3. [1c] C. A. Bunton, F. Nome, L. S. Romsted, F. H. Quina, Acc. Chem. Res. 1991, 24, 357-363.
4. [1d] L. S. Romsted, C. A. Bunton, J. Yao, Curr. Opin. Colloid Interface Sci. 1997, 2, 622-628.
5. [le] L. P. Novaki, O. A. El Seoud, Phys. Chem. Chem. Phys. 1999, 1, 1957-1964.
6. K. Martinek, A. K. Yatsimirski, A. V. Levashov, I. V. Berezin, in: Micellization, Solubilization and Microemulsions (Ed.: K. L. Mittal), Plenum Press, New York, 1977, vol. 2. p. 489.
7. [3a] A. chaudhuri, L. S. Romsted, J. Am. Chem. Soc. 1991, 113, 5052-5053.
8. [3b] A. Chaudhuri, J. A. Loughlin, L. S. Romsted, J. Yao, J. Am. Chem. Soc. 1993, 115, 8351-3861.
9. [3c] A. Blaskò, C. A. Bunton, G. Cericheili, D. C. McKenzie, J. Phys. Chem. 1993, 97, 11324-11331.
10. F. M. Menger, C. E. Portnoy, J. Am. Chem. Soc. 1967, 89, 4698-4703.
11. L. Sepulveda, E. Lissi, F. H. Quina, Adv. Colloid Interface Sci. 1986, 25, 1-57.
12. [6a] C. A. Bunton, J. R. Moffatt, J. Phys. Chem. 1986, 90, 538-541.
13. [6b] C. A. Bunton, J. R. Moffatt, J. Phys. Chem. 1988, 93, 2896-2902.
14. [6c] F. Ortega, E. Rodenas, J. Phys. Chem. 1987, 91, 837-840.
15. [7a] C. A. Bunton, L.-H. Gan, J. R. Moffatt, L. S. Romsted, G. Savelli, J. Phys. Chem. 1981, 85, 4118-4125.
16. [7b] E. Rodenas, S. Vera, J. Phys. Chem. 1985, 89, 513-516.
17. C. A. Bunton, L.-H. Gan, J. R. Moffatt, J. Phys. Chem. 1983, 87, 336-341.
18. [9a] C. Bonan, R. Germani, G. Savelli, G. Cerichelli, R. Bacaloglu, C. A. Bunton, J. Phys. Chem. 1990, 94, 5331-5336.
19. [9b] R. Germani, G. Savelli, T. Romeo, N. Spreti, G. Cerichelli, C. A. Bunton, Langmuir 1993, 9, 55-60.
20. R. Germani, P. P. Ponti, T. Romeo, G. Savelli, N. Spreti, G. Cerichelli, L. Luchetti, G. Mancini, C. A. Bunton, J. Phys. Org. Chem. 1989, 2, 553-558.
21. nd edn., 1970, ch. 11.
22. [11b] H. H. Jaffé, Chem. Rev. 1953, 53, 191-261.
23. [11c] J. Shorter, N. B. Chapman, Correlation Analysis in Chemistry: Recent Advances, Plenum Press, New York, 1978, ch. 10.
24. rd edn. 1987, ch. 2.2.
25. [12a] V. R. Correia, I. M. Cuccovia, H. Chaimovich, J. Phys. Org. Chem. 1991, 4, 13-18.
26. [12b] V. R. Correia, I. M. Cuccovia, H. Chaimovich, J. Phys. Org. Chem. 1993, 6, 7-14.
27. [12c] A. Bartoletti, S. Bartolini, R. Germani, G. Savelli, C. A. Bunton, J. Chem. Soc., Perkin Trans. 2 1994, 723.
28. L. Brinchi, P. Di Profio, R. Germani, G. Savelli, C. A. Bunton, Langmuir 1997, 17, 4583-4587.
29. nd ed. 1962, p. 182 and ref cited.
30. D. N. Kevill, W. F. K. Wang, J. Chem. Soc., Perkin Trans. 2 1998, 2631-2637.
31. C. A. Bunton, M. M. Mhala, J. R. Moffatt, J. Org. Chem. 1985, 50, 4921-4924.
32. [17a] W. P. Jencks, Catalysis in Chemistry and Enzymology, McGraw-Hill, New York, 1969, ch. 10.
33. [17b] S. L. Johnson, Adv. Phys Org Chem. 1967, 5, 237-330.
34. [17c] C. A. Bunton, N. D. Gillitt, M. M. Mhala, J. R. Moffatt, A. K. Yatsimirsky, Langmuir, in press.
35. [18a] R. E. Robertson, Can. J. Chem. 1953, 31, 589-601.
36. [18b] R. E. Robertson, Prog. Phys. Org. Chem. 1967, 4, 213-280.
37. H. Al-Lohedan, C. A. Bunton, M. M. Mhala, J. Am. Chem. Soc. 1982, 104, 6654-6660.
38. [20a] N. J. Buurma, A. M. Herranz, J. B. F. N. Engberts, J. Chem. Soc., Perkin Trans. 2 1999, 113-119.
39. [21a] G. Porte, J. Appell, in: Surfactant in Solution (Eds.: K. L. Mittal, B. Lindman), Plenum Press, New York, 1984, vol. 2, p. 805-823.
40. [21b] V. Soldi, J. Keiper, L. S. Romsted, I. M. Cuccovia, H. Chaimovich, Langmuir 2000, 16, 59-71.
41. Y. Yukawa, Y. Tsuno, J. Am. Chem. Soc. 1959, 81, 2007-2012.
42. [23a] R. Bacaloglu, J. Prakt. Chem. 1975, 317, 62-65.
43. [23b] A. R. Butler, I. H. Robertson, R. Bacaloglu, J. Chem. Soc., Perkin Trans. 2 1974, 1733-1736.
44. [24a] R. A. More O' Ferrall, J. Chem. Soc. B 1970, 274-277.
45. [24b] W. P. Jencks, Chem. Rev. 1972, 72, 705-718.
46. [24c] J. M. Harris, S. G. Schafer, J. R. Moffatt, A. R. Becker, J. Am. Chem. Soc. 1979, 101, 3295-3299.