Micellar charge effects upon hydrolyses of substituted benzoyl chlorides. Their relation to mechanism

Langmuir

Volumn 16, Issue 23, 2000, Pages 8595-8603

  Bunton, Clifford A ^a   Gillitt, Nicholas D ^a   Mhala, Marutirao M ^a   Moffatt, John R ^a   Yatsimirsky, Anatoly K ^b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; ELECTRON TRANSITIONS; HYDROLYSIS; POSITIVE IONS; RATE CONSTANTS; SOLVENTS;

ELECTRON DONATING SUBSTITUENTS; INTERFACIAL POLARITIES; SUBSTITUTED BENZOYL CHLORIDES;

MICELLES;

EID: 0034319522     PISSN: 07437463     EISSN: None     Source Type: Journal    
DOI: 10.1021/la000109k     Document Type: Article

References (63)

1. (a) Fendler, J. H.; Fendler, E. J. Catalysis in Micellar and Macromolecular Systems; Academic Press: New York, 1975.
2. (b) Fendler, J. H. Membrane-Mimetic Chemistry; Wiley-Interscience: New York, 1982.
3. (c) Martinek, K.; Yatsimirsky, A. K.; Levashov, A. V.; Berezin, I. V. In Micellization, Solubilization and Microemulsions; Mittal, K. L., Ed.; Plenum Press, New York, 1977; Vol. 2, p 489.
4. (d) Bunton, C. A.; Savelli, G. Adv. Phys. Org. Chem. 1986, 22, 213.
5. (e) Bunton, C. A.; Nome, F.; Quina, F. H.; Romsted, L. S. Acc. Chem. Res. 1991, 24, 357.
6. (f) Tascioglu, S. Tetrahedron 1996, 52, 11113.
7. (g) Bunton, C. A. J. Mol. Liq. 1997, 72, 231.
8. (h)Romsted, L. S.; Bunton, C. A.; Yao, J. Curr. Opin. Colloid Interface Sci. 1997, 2, 622.
9. (a) Zachariasse, K. A.; Phuc, N. Y.; Kozankiewicz, B. J. Phys. Chem. 1981, 85, 2676.
10. (b) Ramachandran, C.; Pyter, R. A.; Mukerjee, P. Phys. Chem. 1982, 86, 3198.
11. (c) Novaki, L. P.; El Seoud, O. A. Phys. Chem. Chem. Phys. 1999, 1, 1957.
12. (a) Chaudhuri, A.; Loughlin, J. A.; Romsted, L. S.; Yao, J. J. Am. Chem. Soc. 1993, 115, 8351.
13. (b) Romsted, L. S.; Yao, J. Langmuir 1996, 12, 2425 and references cited therein.
14. Buurma, N. J.; Herranz, A.; Engberts, J. B. F. N. J. Chem. Soc., Perkin Trans. 2 1999, 113, and references cited therein.
15. (a) Possidonio, S.; El Seoud, O. A. J. Mol. Liq. 1999, 80, 231.
16. (b) Possidonio, S.; Siviero, F.; El Seoud, O. A. J. Phys. Org. Chem. 1999, 12, 325.
17. (a) Bunton, C. A. In Nucleophilicity; Harris, J. M., McManus, S. P., Eds.; Advances in Chemistry Series 215; American Chemical Society: Washington, D. C., 1987; Chapter 29.
18. (b) Bunton, C. A.; Mhala, M. M.; Moffatt, J. R. In Surfactants in Solution; Mittal, K. L., Bothorel, P., Eds.; Plenum Press: New York, 1986; Vol. 5, p 625.
19. Brinchi, L.; Di Profio, R.; Germani, R.; Savelli, G.; Spreti, N.; Bunton, C. A. J. Chem. Soc., Perkin Trans. 2 1998, 361.
20. Menger, F. M.; Yoshinaga, H.; Venkatasubban, K. S.; Das, A. R. J. Org. Chem. 1981, 46, 415.
21. (a) Al-Lohedan, H.; Bunton, C. A.; Mhala, M. M. J. Am. Chem. Soc. 1982, 104, 6654.
22. (b) Bunton, C. A.; Ljunggren, S. J. Chem. Soc., Perkin Trans. 2 1984, 355.
23. Ingold, C. K. Structure and Mechanism in Organic Chemistry, 2nd ed.; Cornell University Press: Ithaca, New York, 1969; Chapter 7.
24. (a) Kivinen, A. In The Chemistry of Acyl Halides; Patai, S., Ed.; Interscience: New York, 1972; Chapter 6.
25. (b) Talbot, R. J. E. In Comprehensive Chemical Kinetics; Bamford, C. H., Tipper, C. F. H., Eds.; Elsevier: New York, 1972;, Vol. 10, p 226.
26. Kevill, D. N.; Wang, W. F. K. J. Chem. Soc., Perkin Trans. 2 1998, 2631 and references cited therein.
27. Menger, F. M.; Portnoy, C. E. J. Am. Chem. Soc. 1967, 89, 4698.
28. (a) Romsted, L. S. In Micellization, Solubilization and Microemulsions; Mittal, K. L., Ed.; Plenum Press: New York, 1977; Vol. 2, p 509.
29. (b) Romsted, L. S. In Surfactants in Solution; Mittal K. L., Lindman, B., Eds.; Plenum Press: New York, 1984; vol. 2, p 1015.
30. Coetzee, J. F.; Cunningham, G. P.; McGuire, D. K; Padnambham, G. R. Anal. Chem. 1962, 34, 1139.
31. Mukerjee, P.; Mysels, K. J. Critical Micelle Concentrations of Aqueous Surfactant Systems; National Bureau of Standards: Washington, D. C., 1971.
32. Bentley, T. W.; Carter, G. E.; Harris, H. C. J. Chem Soc., Chem. Commun. 1984, 398.
33. (a) Fainberg, A. H.; Winstein, S. J. Am. Chem. Soc. 1956, 78, 2770.
34. (b) Bentley, T. W.; Schleyer, P. v. R. Adv. Phys. Org. Chem. 1977, 14, 1.
35. Bunton, C. A.; Mhala, M. M.; Moffatt, J. R. J. Org. Chem. 1984, 49, 3637.
36. (a) Ikeda, S.; Hayashi, S.; Imae, T. J. Phys. Chem. 1981, 85, 106.
37. (b) Porte, G.; Appell, J. J. Phys. Chem. 1981, 85, 2511.
38. (a) Sepulveda, L.; Lissi, E.; Quina, F. Adv. Colloid Interface Sci. 1986, 25, 7.
39. (b) Quina, F. H.; Alonso, E. O.; Farah, J. P. S. J. Phys. Chem. 1995, 99, 11708.
40. (c) Abraham, M. H.; Chadha, H. C.; Dixon, J. P.; Rafols, C.; Treiner, C. J. Chem. Soc., Perkin Trans. 2 1995, 887.
41. Hall, D.G. J. Phys. Chem. 1987, 91, 4287.
42. Lopez-Cornejo, P. L.; Jimenez, R.; Moya, M. L.; Sanchez, F.; Burgess, J. Langmuir 1998, 12, 4981.
43. Bunton, C. A.; Robinson, L. J. Am. Chem. Soc. 1968, 90, 5972.
44. Lowry, T. H.; Richardson, K. S. Mechanism and Theory in Organic Chemistry, 3rd ed.; Harper and Row: New York, 1987; Chapter 4.
45. Song, B. D.; Jencks, W. P. J. Am. Chem. Soc. 1989, 111, 8470.
46. (a) More O'Ferrall, R. A. J. Chem. Soc. B 1970, 274.
47. (b) Jencks, W. P. Chem. Rev. 1972, 72, 705.
48. (c) Harris, J. M.; Shafer, S. G.; Moffatt, J. R.; Becker, A. R. J. Am. Chem. Soc. 1979, 101, 3295.
49. Bunton, C. A.; Mhala, M. M.; Moffatt, J. R. J. Org. Chem. 1985, 50, 4921.
50. Kevill, D. M.; D'Souza, M. J. J. Chem. Soc., Perkin Trans. 2 1997, 1721 and references cited therein.
51. (a) Brown, D. A.; Hudson, R. F. J. Chem. Soc. 1953, 3352.
52. (b) Grunden, E. W.; Hudson, R. F. J. Chem. Soc. 1956, 501.
53. Johnson, S. L. Adv. Phys. Org. Chem. 1967, 5, 237.
54. Fry, A. In Isotope Effects in Chemical Reactions; Collins, C. J., Bowman, N. S., Eds.; Van Nostrand Reinhold: New York, 1970; pp 379-380, 402.
55. Reference 25, Chapter 2.
56. Garcia-Rio, L.; Lets, J. R. Chem. Commun. 2000, 455.
57. (a) Gunnarsson, G.; Jonsson, B.; Wennerstrom, H. J. Phys. Chem. 1980, 84, 3114.
58. (b) Bunton, C. A.; Moffatt, J. R. J. Phys. Chem. 1986, 90, 538.
59. (c) Bunton, C. A.; Mhala, M. M.; Moffatt, J. R. J. Phys. Chem. 1989, 93, 7851.
60. (d) Rodenas, E.; Ortega, F. J. Phys. Chem. 1987, 91, 837.
61. Fernandez, M. S.; Fromherz, P. J. Phys. Chem. 1977, 81, 1755.
62. (a) Almgren, M.; Rydholm, R. J. Phys. Chem. 1979, 83, 360.
63. (b) Drummond, C. J.; Grieser, F.; Healy, T. W. J. Chem. Soc., Faraday Trans. 1 1989, 85, 537 and references cited therein.