Molecular size-based model to describe simple organic liquids

Journal of Physical Chemistry B

Volumn 102, Issue 29, 1998, Pages 5715-5726

  Buchwald, Peter ^a   Bodor, Nicholas ^a  

^a UNIVERSITY OF FLORIDA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000339241     PISSN: 15206106     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp980643p     Document Type: Article

References (86)

1. Ben-Naim, A. J. Phys. Chem. 1978, 82, 792.
2. Ben-Naim, A. Hydrophobic Interactions; Plenum Press: New York, 1980.
3. Ben-Naim, A. Salvation Thermodynamics; Plenum Press: New York, 1987.
4. Bodor, N.; Buchwald, P. J. Phys. Chem. B 1997, 101, 3404.
5. Buchwald, P.; Bodor, N. Proteins 1998, 30, 86.
6. Bodor, N.; Buchwald, P.; Huang, M.-J. SAR QSAR Environ. Res. 1998, 8, 41.
7. Bodor, N.; Buchwald, P. Pharmacol. Ther. 1997, 76, 1.
8. Bodor, N.; Buchwald, P. Chem. Br. 1998, 34 (1), 36.
9. Hildebrand, J. H.; Scott, R. L. The Solubility of Nonelectrolytes, 3rd ed.; Reinhold Publishing Corporation: New York, 1950.
10. Alberty, R. A.; Silbey, R. J. Physical Chemistry, 2nd ed.; Wiley: New York, 1997.
11. Laidler, K. J.; Meiser, J. H. Physical Chemistry, 2nd ed.; Houghton Mifflin: Boston, MA, 1995.
12. Guggenheim, E. A. Proc. R. Soc. London, Ser. A 1932, 135, 181.
13. Luck, W. A. P. Angew. Chem., Int. Ed. Engl. 1979, 18, 350.
14. Cramer, R. D., III. J. Am. Chem. Soc. 1980, 102, 1837.
15. Grant, D. J. W.; Higuchi, T. Solubility Behavior of Organic Compounds; Wiley-Interscience: New York, 1990.
16. Hermann, R. B. J. Phys. Chem. 1972, 76, 2754.
17. Harris, M. J.; Higuchi, T.; Rytting, J. H. J. Phys. Chem. 1973, 77, 2694.
18. Amidon, G. L.; Yalkowsky, S. H.; Anik, S. T.; Valvani, S. C. J. Phys. Chem. 1975, 79, 2239.
19. Leo, A.; Hansch, C.; Jow, P. Y. C. J. Med. Chem. 1976, 19, 611.
20. Valvani, S. C.; Yalkowsky, S. H.; Amidon, G. L. J. Phys. Chem. 1976, 80, 829.
21. Ben-Naim, A.; Marcus, Y. J. Chem. Phys. 1984, 81, 2016.
22. Pearlman, R. S. In Partition Coefficient Determination and Estimation; Dunn, W. J., III, Block, J. H., Pearlman, R. S., Eds.; Pergamon: New York, 1986; p 3.
23. Silla, E.; Tunon, I.; Villar, F.; Pascual-Ahuir, J. L. J. Mol. Struct.: THEOCHEM 1992, 254, 369.
24. Ben-Naim, A.; Mazo, R. M. J. Phys. Chem. 1993, 97, 10829.
25. Ben-Naim, A. Biophys. Chem. 1994, 51, 203.
26. Ben-Naim, A.; Lovett, R. J. Phys. Chem. B 1997, 101, 10535.
27. Pierotti, R. A. Chem. Rev. 1976, 76, 717.
28. Meyer, A. Y. J. Comput. Chem. 1986, 7, 144.
29. Bader, R. F. W.; Carrol, M. T.; Cheeseman, J. R.; Chang, C. J. Am. Chem. Soc. 1987, 109, 7968.
30. Hildebrand, J. H. J. Chem. Phys. 1947, 15, 225.
31. Giesen, D. J.; Cramer, C. J.; Truhlar, D. G. J. Phys. Chem. 1994, 98, 4141.
32. Holtzer, A. Biopolymers 1992, 32, 711.
33. Holtzer, A. Biopolymers 1994, 34, 315.
34. Abraham, M. H.; Sakellariou, P. J. Chem. Soc., Perkins Trans. 2 1994, 405.
35. Sanchez-Ruiz, J. M. Eur. Biophys. J. 1996, 24, 261.
36. Sharp, K. A.; Nicholls, A.; Friedman, R.; Honig, B. Biochemistry 1991, 30, 9686.
37. Sharp, K. A.; Nicholls, A.; Fine, R. F.; Honig, B. Science 1991, 252, 106.
38. Kumar, S. K.; Szleifer, I.; Sharp, K.; Rossky, P. J.; Friedman, R.; Honig, B. J. Phys. Chem. 1995, 99, 8382.
39. Sharp, K. A.; Kumar, S.; Rossky, P. J.; Friedman, R. A.; Honig, B. J. Phys. Chem. 1996, 100, 14166.
40. Lazaridis, T.; Paulaitis, M. E. J. Phys. Chem. 1992, 96, 3847.
41. Irisa, M.; Nagayama, K.; Hirata, F. Chem. Phys. Lett. 1993, 207, 430.
42. Tuñ́on, I.; Silla, E.; Pascual-Ahuir, J. L. J. Phys. Chem. 1994, 98, 377.
43. White, S. H.; Wimley, S. C. Curr. Opin. Struct. Biol. 1994, 4, 79.
44. Chan, H. S.; Dill, K. A. J. Chem. Phys. 1994, 101, 7007.
45. Chan, H. S.; Dill, K. A. Annu. Rev. Biophys. Biomol. Struct. 1997, 26, 425.
46. Lide, D. R., (Ed.) CRC Handbook of Chemistry and Physics, 78th ed.; CRC Press; Boca Raton, FL, 1997-1998.
47. Lide, D. R., Milne, G. W., Eds. Handbook of Data on Common Organic Compounds; CRC Press: Boca Raton, FL, 1995.
48. Hine, J.; Mookerje, P. K. J. Org. Chem. 1975, 40, 292.
49. Valvani, S. C.; Yalkowski, S. H.; Roseman, T. J. J. Pharm. Sci. 1981, 70, 502.
50. Bodor, N.; Huang, M.-J. J. Pharm. Sci. 1992, 81, 954.
51. Abraham, M. H.; Whiting, G. S.; Fuchs, R.; Chambers, E. J. J. Chem. Soc., Perkin Trans. 2 1990, 291.
52. Abraham, M. H.; Andonian-Haftvan, J.; Whiting, G. S.; Leo, A.; Taft, R. S. J. Chem. Soc., Perkin Trans. 2 1994, 1777.
53. Abraham, M. H.; Chadha, H. S.; Whiting, G. S.; Mitchell, R. C. J. Pharm. Sci. 1994, 83, 1085.
54. Hansch, C.; Leo, A. J. Substituent Constants for Correlation Analysis in Chemistry and Biology; Wiley-Interscience: New York, 1979.
55. Hansch, C.; Leo, A.; Hoekman, D. Exploring QSAR. Hydrophobic, Electronic, and Steric Constants.; American Chemical Society: Washington, DC, 1995; Vol. 2.
56. Sangster, J. J. Phys. Chem. Ref. Data 1989, 18, 1111.
57. Pollack, G. L. J. Chem. Phys. 1981, 75, 5875.
58. Pollack, G. L.; Himm, J. F. J. Chem. Phys. 1982, 77, 3221.
59. Bondi, A. J. Phys. Chem. 1964, 68, 441.
60. Motoc, I.; Marshall, R. Chem. Phys. Lett. 1985, 116, 415.
61. Cramer, R. D., III; Patterson, D. E.; Bunce, J. D. J. Am. Chem. Soc. 1988, 110, 5959.
62. Bodor, N.; Gabanyi, Z.; Wong, C.-K. J. Am. Chem. Soc. 1989, 111, 3783.
63. Nyburg, S. C.; Faerman, C. H. Acta Crystallogr. 1985, B41, 274.
64. Némethy, G.; Scheraga, H. A. J. Chem. Phys. 1962, 36, 3382.
65. Levine, I. N. Physical Chemistry, 4th ed.; McGraw-Hill: New York, 1995.
66. Abraham, M. H. J. Am. Chem. Soc. 1979, 101, 5477.
67. Ben-Naim, A.; Marcus, Y. J. Chem. Phys. 1984, 80, 4438.
68. De Young, L. R.; Dill, K. A. J. Phys. Chem. 1990, 94, 801.
69. Shinoda, K.; Hildebrand, J. H. J. Phys. Chem. 1958, 62, 292.
70. Shinoda, K.; Hildebrand, J. H. J. Phys. Chem. 1958, 62, 295.
71. Némethy, G. Angew. Chem., Int. Ed. Engl. 1967, 6, 195.
72. Franks, F. E. Water: A Comprehensive Treatise; Plenum Press; New York, 1972.
73. Taylor, P. J. In Comprehensive Medicinal Chemistry; Hansch, C., Sammes, P. G., Taylor, J. B., Eds.; Pergamon Press: New York, 1990; Vol. 4, p 241.
74. Silverstein, K. A. T.; Haymet, A. D. J.; Dill, K. A. J. Am. Chem. Soc. 1998, 120, 3166.
75. Luck, W. A. P. Acta Chim. Hung. 1986, 121, 119.
76. Cramer, R. D., III. J. Am. Chem. Soc. 1977, 99, 5408.
77. Leahy, D. E.; Morris, J. J.; Taylor, P. J.; Wait, A. R. J. Chem. Soc., Perkin Trans. 2 1992, 723.
78. Sangster, J. Octanol-Water Partition Coefficients: Fundamentals and Physical Chemistry; Wiley & Sons: Chichester, 1997.
79. Dunn, W. J., III; Grigoras, S.; Johansson, E. In Partition Coefficient Determination and Estimation; Dunn, W. J., III., Block, J. H., Pearlman, R. S., Eds.; Pergamon: New York, 1986; p 21.
80. Famini, G. R.; Penski, C. A.; Wilson, L. Y. J. Phys. Org. Chem. 1992, 5, 395.
81. El-Tayar, N.; Testa, B.; Carrupt, P.-A. J. Phys. Chem. 1992, 96, 1455.
82. Yalkowsky, S. H.; Pinal, R.; Banerjee, S. J. Pharm. Sci. 1988, 77, 74.
83. Taft, R. W.; Abraham, M. H.; Doherty, R. M.; Kamlet, M. J. Nature 1985, 313, 384.
84. Kamlet, M. J.; Doherty, R. M.; Abraham, M. H.; Marcus, Y.; Taft, R. W. J. Phys. Chem. 1988, 92, 5244.
85. Fersht, A. R.; Shi, J.-P.; Knill-Jones, J.; Lowe, D. M.; Wilkinson, A. J.; Blow, D. M.; Brick, P.; Carter, P.; Waye, M. M. Y.; Winter, G. Nature 1985, 314, 235.
86. Shirley, B. A.; Stanssens, P.; Hahn, U.; Pace, C. N. Biochemistry 1992, 31, 725.