A new model for predicting solubilities and enthalpies of solution for a given solute in a series of solvents

Journal of Physical Chemistry B

Volumn 101, Issue 25, 1997, Pages 5002-5009

  Bustamante, Pilar ^a,b   Drago, Russell S ^a  

^a University of Florida ^*  (United States)

^b UNIVERSITY OF ALCALÁ   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0038518768     PISSN: 15206106     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp970521h     Document Type: Article

References (48)

1. Hidebrand, J. H.; Scott, R. L. The Solubility of Nonelectrolyies, 3rd ed.; Reinhold: New York, 1950.
2. Hildebrand, J. M.; Prausnitz, J. M.; Scott, R. L. Regular and Related Solutions; Van Nostrand Reinhold: New York, 1970; pp 21-22.
3. Chuu, M. S.; Knauss, C. J.; Ruch, R. J.; Myers, R. R. ACS Symp. Ser. 1983, 227, 141 and references therein.
4. Fowkes, F. M.; Tischler, D. O.; Wolfe, J. A.; Lannigan, L. A.; Ademu-John, C. M.; Halliwell, M.J. J. Polym. Sci, Polym, Chem. Ed. 1984, 106, 6638 and references therein.
5. (a) Bustamante, P.; Escalera, B.; Martin, A.; Selles, E. J. Pharm. Sci. 1989, 78, 567.
6. (b) Yang, S. S.; Guillory, J. K. J. Pharm. Sci. 1972, 61, 26.
7. (c) Beerbower, A.; Wu, P. L.; Martin, A. J. Pharm. Sci. 1984 73, 179.
8. (d) Martin, A.; Wu, P. L.; Beerbower, A. J. Pharm. Sci. 1984 73, 199.
9. (a) Hansen, C.; Beerbower, A. In Encyclopedia of Chemical Technology; Solubility Parameters; Suppl. 2nd ed.; Wiley: New York, 1971.
10. (b) Brandrup, J.; Immergut, E. H. Polymer Handbook, 3rd ed.; Wiley: New York, 1989.
11. Reiss, H. L. Adv. Chem Phys. 1966, 9, 1.
12. Leborvitz, J. L.; Hefland, E.; Proestgaard, J. Chem. Phys. 1965, 43, 774.
13. Tully-Smith, D. M.; Reiss, H. J. Chem. Phys. 1971 55, 1674.
14. Pierotti, R. A. Chem. Rev. (Washington, D.C.) 1976, 76, 717.
15. (a) Reichardt, C. Solvents and Solvent Effects in Organic Chemistry, 2nd ed.; VCH Publishers: Orlando, FL, 1988.
16. (b) Reichardt, C. Angew Chem., Int. Ed. Engl. 1965, 4, 29.
17. (a) Herbrandson, H. F.; Neufeld, F. R. J. Org. Chem. 1966, 31, 1140.
18. (b) Kamlet, M. J.; Abboud, J. L.; Abraham, M. H.; Taft, R. W. J. Org. Chem. 1983, 48, 2877 and references therein.
19. (a) Abraham, M. H. J. Am. Chem. Soc. 1982, 104, 2085 and references therein,
20. (b) Abraham, M. H. J. Am. Chem. Soc. 1979, 101, 5477.
21. (c) Kamlet, M. J.; Carr, P. W.; Taft, R. W.; Abraham, M. H. J. Am. Chem. Soc. 1981, 103, 6062.
22. Drago, R. S. Applications of Electrostatic-Covalent Models in Chemistry; Surfside Scientific: Gainesville, FL, 1995.
23. (a) Fowkes, F. M. Org. Coat. Plast. Chem. 1979, 40, 13.
24. (b) Fowkes, F. M. In Add - Base Interactions; Miteal, K. L., Anderson, H. R., Jr. Eds.; VSP: Utrecht, 1991.
25. Ho, N.-T. J. Phys. Chem. 1994, 98, 5362.
26. Bustamante, P.; Jimenez-Duran, M.; Escalera, B. Int. J. Pharm. 1996, 129, 283.
27. (a) Drago, R. S. J. Chem. Soc., Perkin Trans. 2 1992, 1827.
28. (b) Drago, R. S. J. Org. Chem. 1992, 57, 6547.
29. (c) Drago, R. S.; Hirsch, M. S.; Ferris, D. C; Chronister, C. W. J. Chem. Soc., Perkin Trans. 2 1994, 219.
30. (d) Drago, R. S.; Kovala-Demertzi, D.; Ferris, D. C. J. Coord. Chem. 1994, 32, 145.
31. (e) Ferris, D. C.; Drago, R. S. J. Am. Chem. Soc. 1994, 116, 7509.
32. (f) Drago, R. S.; Ferris, D. C. J. Phys. Chem. 1995, 99, 6563.
33. Substituting the value of δ = 5.9 for perfluorohexane into eq 4 leads to an S′ value of - 0.07. This should not be interpreted as a repulsion but as a problem arising from the lack of good data to clearly establish S′ = 0 in the reported unified solvation data fit. The true S′ = 0 of an adjusted scale would be even less solvating than perfluorohexane but more solvating than the gas phase.
34. (a) Spencer, J. N.; Berger, S. K.; Powell, C. R.; Henning, B. D.; Furman, G. S.; Loffredo, W. M.; Rydberg, E. M.; Neubert, R. A.; Shopp, G. E.; Blauch, D. N. J. Phys. Chem. 1981, 85, 1236.
35. (b) Spencer, J. N.; Gleim, J. E.; Blevins, C. H.; Garrett, R. C.; Mayer, F. J. J. Phys. Chem. 1979, 83, 1249.
36. Krishnan, C. V.; Friedman, H. L. J. Phys. Chem. 1971, 75, 3598.
37. (a) Catalán, J.; Gomez, J.; Saiz, J. L.; Couto, A.; Ferraris, M.; Laynez, J. J. Chem. Soc., Perkin Trans 2, in press.
38. (b) Catalán. J.; Gomez, J.; Couto, A.; Laynez, J. J. Am. Chem. Soc. 1990, 112, 1678.
39. (a) Drago, R. S.; Nozari, M. S.; Vogel, G. C. J. Am. Chem. Soc. 1972, 94, 90.
40. (b) Nozari, M. S.; Drago, R. S. J. Am. Chem. Soc.: 1972, 94, 6877.
41. (c) Nozari, M. S.; Jensen, C. D.; Drago, R. S. J. Am. Chem. Soc. 1973, 95, 3162.
42. Slejko, F. L. Ph.D. Thesis, University of Illinois, 1972.
43. Doan, P. E.; Drago, R. S. J. Am. Chem. Soc. 1984, 106, 2772.
44. 2i = 0.999.
45. (a) Abraham, M. H.; Grellier, P. L.; Nasehzadeh, A.; Walker, A. C. J. Chem. Soc., Perkin Trans. 2 1988, 1717.
46. (b) Abraham, M. H. J. Chem. Soc., Perkin Trans. 2 1972, 1343.
47. Gander, B.; Merkle, H. P.; Nguyàn, V. P.; Hô, N.-T. J. Phys. Chem. 1995, 99, 16144.
48. Arnett, E. M.; Joris, L.; Mitchell, E.; Murty, T. S. S. R.; Gorie, T. M.; Schleyer, P. V. R. J. Am. Chem. Soc: 1970, 92, 2365 and references therein.