A kinetic model for water reactivity (avoiding activities) for hydrolyses in aqueous mixtures - Selectivities for solvolyses of 4-substituted benzyl derivatives in alcohol-water mixtures

Journal of Physical Organic Chemistry

Volumn 21, Issue 3, 2008, Pages 251-256

  Bentley, T William ^a   Koo, In Sun ^b   Choi, Hojune ^b   Llewellyn, Gareth ^a  

^a SWANSEA UNIVERSITY   (United Kingdom)

^b Gyeongsang National University   (South Korea)

Author keywords

Alcohols; Kinetics; Rate product correlation; Solvent effects; Solvent nucleophilicity; Solvolysis; Water activity

Indexed keywords

ALCOHOLS; BENZENE; CATALYST SELECTIVITY; HYDROLYSIS; KINETIC THEORY; MATHEMATICAL MODELS;

MOLAR CONCENTRATIONS; RATE PRODUCT CORRELATIONS; SOLVENT NUCLEOPHILICITY; SOLVENT POLARITY; SOLVOLYSIS; WATER ACTIVITY;

REACTION KINETICS;

EID: 40449095559     PISSN: 08943230     EISSN: 10991395     Source Type: Journal    
DOI: 10.1002/poc.1308     Document Type: Article

References (49)

1. M. J. Blandamer, J. B. F. N. Engberts, P. T. Gleeson, J. C. R. Reis, Chem. Soc. Rev. 2005, 34, 440-458.
2. T. Rispens, C. Cabaleiro-Lago, J. B. F. N. Engberts, Org. Biomol. Chem. 2005, 3, 597-602.
3. W. P. Jencks, Catalysis in Chemistry and Enzymology, McGraw Hill, New York, 1969, 599-605.
4. M. H. Abraham, M. J. Blandamer, J. Am. Chem. Soc. 2002, 124, 7853-7856.
5. G. W. Neilson, P. E. Mason, S. Ramos, D. Sullivan, Phil. Trans. R. Soc. Lond. (A) 2001, 359, 1575-1591.
6. M. C. R. Symons, Phil. Trans. R. Soc. Lond. (A) 2001, 359, 1631-1646.
7. F. Franks (Ed.), Water, a Comprehensive Treatise, Plenum Press, New York, 1979.
8. M. C. R. Symons, Ace. Chem. Res. 1981, 14, 179-187.
9. R. Ta-Shma, Z. Rappoport, Adv. Phys. Org. Chem. 1992, 27, 239-291.
10. C. K. Ingold, Structure and Mechanism in Organic Chemistry, Cornell University Press, Ithaca, New York, 1953, 346-350.
11. F. L. Schadt, T. W. Bentley, Pv. R. Schleyer, J. Am. Chem. Soc. 1976, 98, 7667-7674.
12. D. N. Kevill, H. Ren, J. Org. Chem. 1989, 54, 5654-5655.
13. D. N. Kevill, M. J. D'Souza, H. Ren, Can. J. Chem. 1998, 76, 751-757.
14. T. W. Bentley, K. Roberts, J. Chem. Soc. Perkin Trans. 2 1987, 293-299.
15. T. W. Bentley, H. C. Harris, Z. H. Ryu, G. T. Lim, D. D. Sung, S. R. Szajda, J. Org. Chem. 2005, 70, 8963-8970.
16. T. W. Bentley, R. O. Jones, J. Chem. Soc. Perkin Trans. 2 1993, 2351-2357.
17. T. W. Bentley, R. O. Jones, I. S. Koo, J. Chem. Soc. Perkin Trans. 2 1994, 753-759.
18. I. S. Koo, K. Yang, K. Kang, I. Lee, T. W. Bentley, J. Chem. Soc. Perkin Trans. 2 1998, 1179-1183.
19. F. A. Cotton, G. Wilkinson, Advanced Inorganic Chemistry, 4th edn. Wiley, New York, 1980, 545.
20. T. W. Bentley, I. S. Koo, S. J. Norman, J. Org. Chem. 1991, 56, 1604-1609.
21. H. Aronovitch, A. Pross, J. Chem. Soc. Perkin Trans. 2 1978, 540-545.
22. M. Fujio, T. Susuki, M. Goto, Y. Tsuji, K. Yatsugi, S. H. Kim, G. A.-W. Ahmed, Y. Tsuno, Bull. Chem. Soc. Jpn. 1995, 68, 673-682.
23. I. Lee, H. J. Koh, Y. S. Park, H. W. Lee, J. Chem. Soc. Perkin Trans. 21993, 1575-1582.
24. I. M. Gordon, H. Maskill, Chem. Soc. Perkin Trans. 2 2001, 2059-2062.
25. M. Fujio, T. Susuki, M. Goto, Y. Tsuji, K. Yatsugi, Y. Saeki, S. H. Kim, Y. Tsuno, Bull. Chem. Soc. Jpn. 1994, 67, 2233-2243.
26. A. Thibblin, J. Org. Chem. 1993, 58, 7427-7433.
27. J. B. Kyong, B.-C. Park, C.-B. Kim, D. N. Kevill, J. Org. Chem. 2000, 65, 8051-8058.
28. A. Queen, Can. J. Chem. 1979, 57, 2646-2651.
29. T. L. Amyes, J. P. Richard, J. Am. Chem. Soc. 1990, 112, 9507-9512.
30. T. W. Bentley, Z. H. Ryu, J. Chem. Soc. Perkin Trans. 2 1994, 761-767.
31. P. Dietze, W. P. Jencks, J. Am. Chem. Soc. 1989, 111, 5880-5886.
32. T. W. Bentley, H. C. Harris, I. S. Koo, J. Chem. Soc. Perkin Trans. 2 1988, 783-789.
33. For a recent discussion of rate-product correlations see T. W. Bentley, In The Investigation of Organic Reactions and Their Mechanisms (Ed.: H. Maskill) Blackwell, Oxford, 2006, Chapter 2.
34. T. W. Bentley, G. Llewellyn, Prog. Phys. Org. Chem. 1990, 17, 121 -158.
35. J. Kaspi, Z. Rappoport, Tetrahedron Lett. 1977, 2035-2038.
36. T. W. Bentley, G. E. Carter, K. Roberts, J. Org. Chem. 1984, 49, 5183-5189.
37. A. R. Olson, R. S. Halford, J. Am. Chem. Soc. 1937, 59, 2644-2647.
38. P. D. Bartlett, J. Am. Chem. Soc. 1939, 67, 1630-1635.
39. S. Winstein, J. Am. Chem. Soc. 1939, 67, 1635-1640.
40. D. N. Kevill, C.-B. Kim, Bull. Chem. Soc. France 1988, 383-390.
41. J. M. W. Scott, Can. J. Chem. 2005, 83, 1667-1719.
42. D. N. Kevill, In Advances in Quantitative Structure-Property Relationships (Ed.: M. Charton) Jai Press, Greenwich, CT, 1996, 1, 81-115.
43. S. Minegishi, S. Kobayashi, H. Mayr, J. Am. Chem. Soc. 2004, 126, 5174-5181.
44. T. W. Bentley, M. S. Garley, J. Phys. Org. Chem. 2006, 19, 341-349.
45. P. R. Luton, M. C. Whiting, J. Chem. Soc. Perkin Trans. 21979, 646-647.
46. R. C. Pemberton, C. J. Mash, J. Chem. Thermodynamics 1978, 10, 867-888.
47. K. Kurihara, T. Minoura, K. Takeda, K. Kojima, J. Chem. Eng. Data 1995, 40, 679-684.
48. S. D. Christian, E. H. Lane, E. E. Tucker, J. Soln. Chem. 1981, 10, 181-188.
49. L. Nord, E. E. Tucker, S. D. Christian, J. SoIn. Chem. 1984, 13, 849-867.