Thermodynamic studies on the cyclodextrin complexation of aromatic and aliphatic guests in water and water-urea mixtures. Experimental evidence for the interaction of urea with arene surfaces

Journal of Physical Chemistry B

Volumn 101, Issue 17, 1997, Pages 3376-3380

  Godínez, Luis A ^a   Schwartz, Lauren ^a   Criss, Cecil M ^a   Kaifer, Angel E ^a  

^a UNIVERSITY OF MIAMI   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0040893850     PISSN: 15206106     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp970359i     Document Type: Article

References (36)

1. (a) Creighton, T. E. J. Mol. Biol. 1979, 129, 235.
2. (b) Brandts, J. F.; Hunt, L. J. J. Am. Chem. Soc. 1967, 89, 4826.
3. (c) Schellman, J. A. Biopolymers 1978, 17, 1305.
4. (d) Wetlaufer, D. B.; Malik, S. K.; Stoller, L.; Coffin, R. L. J. Am. Chem. Soc. 1964, 86, 508.
5. Pranata, J. J. Phys. Chem. 1995, 99, 4855.
6. (a) Barone, G.; Giancola, C. Pure Appl. Chem. 1990, 62, 57.
7. (b) Roseman, M.; Jencks, W. P. J. Am. Chem. Soc. 1975, 97, 631.
8. (c) Åstrand, P. O.; Wallqvist, A.; Karlström, G. J. Chem. Phys. 1994, 100, 1262.
9. (d) Hoccart, X.; Turrell, G. J. Chem. Phys. 1993, 99, 8498.
10. (a) Finer, E. G.; Franks, F.; Tait, M. J. J. Am. Chem. Soc. 1972, 94, 4424.
11. (b) Barone, G.; Vitagliano, V. J. Phys. Chem. 1970, 74, 2230.
12. (c) Mukerjee, P.; Ray, A. J. Phys. Chem. 1963, 67, 190.
13. (d) Mukerjee, P.; Ghosh, A. J. Phys. Chem. 1963, 67, 193.
14. (a) Kauzmann, W. Adv. Protein Chem. 1959, 14, 1.
15. (b) Tanford, C. The Hydrophobic Effect; Wiley-Interscience: New York, 1973.
16. Breslow, R.; Guo, T. Proc. Natl. Acad. Sci. U.S.A. 1990, 87, 167.
17. Sinanoglu, O. Molecular Associations in Biology; Pullman, B., Ed.; Academic Press: New York, 1968; p 427.
18. Duffy, E. M.; Kowalczyk, P. J.; Jorgensen, W. L. J. Am. Chem. Soc. 1993, 115, 9271.
19. (a) Wenz, G. Angew. Chem., Int. Ed. Engl. 1994, 33, 803.
20. (b) Cromwell, W. C.; Byström, K.; Eftink, M. R. J. Phys. Chem. 1985, 89, 326.
21. (c) Eftink, M. R.; Andy, M. L.; Byström, K.; Perlmutter, H. D.; Kristol, D. S. J. Am. Chem. Soc. 1989, 111, 6765.
22. Harrison, J. C.; Eftink. M. R. Biopolymers 1982, 21, 1153.
23. (a) Inoue, Y.; Hakushi, T.; Liu, Y.; Tong, L.; Shen, B.; Jin, D. J. Am. Chem. Soc. 1993, 115, 475.
24. (b) Matsue, T.; Evans, D. H.; Osa, T.; Kobayashi, N. J. Am. Chem. Soc. 1985, 107, 3411.
25. (a) Breslow, R.; Halfon, S. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 6916.
26. (b) Godínez, L. A.; Patel, S.; Criss, C. M.; Kaifer, A. E. J. Phys. Chem. 1995, 99, 17449.
27. Lombardo, A.; Bieber, T. I. J. Chem. Educ. 1983, 60, 1080.
28. Sommer, H. Z.; Lipp, H. I.; Jackson, L. L. J. Org. Chem. 1971, 36, 824.
29. a values in water for the carboxylate guests 2, 4, 6, and 8 at 298 K are 4.2, 4.17, 4.9, and 4.87, respectively. These values were obtained from the following: Pendin, A. A.; Leont'evskaya, P. K.; L'vova, T. I.; Nikol'skii, B. P. Dokl. Akad. Nauk SSSR 1969, 189, 115 (for guest 2); Lide, D. R. CRC Handbook of Chemistry and Physics, 71st ed.; CRC Press: Boca Raton, FL, 1990 (for compound 4); and ref 9c (for guests 6 and 8).
30. a values in water for the carboxylate guests 2, 4, 6, and 8 at 298 K are 4.2, 4.17, 4.9, and 4.87, respectively. These values were obtained from the following: Pendin, A. A.; Leont'evskaya, P. K.; L'vova, T. I.; Nikol'skii, B. P. Dokl. Akad. Nauk SSSR 1969, 189, 115 (for guest 2); Lide, D. R. CRC Handbook of Chemistry and Physics, 71st ed.; CRC Press: Boca Raton, FL, 1990 (for compound 4); and ref 9c (for guests 6 and 8).
31. (a) Jullien, L.; Canceill, J.; Lacombe. L.; Lehn, J. J. Chem. Soc., Perkin Trans. 2 1994, 989.
32. (b) Saenger, W.; Noltemeyer, M.; Manor, P. C.; Hingerty, B.; Klar, B. Bioorg. Chem. 1976, 5, 187.
33. (a) Gelb, R. I.; Schwartz, L. M. J. Inclusion Phenom. 1989, 7, 465.
34. (b) Chervenak, M. C.; Toone, E. J. J. Am. Chem. Soc. 1994, 116, 10533.
35. Breslow, R. Acc. Chem. Res. 1991, 24, 159.
36. The molecular volumes of compounds 2, 4, 6, and 8 were calculated from the minimized structures using the PM3 semiempirical molecular orbital method with the Spartan 4.1 program (Wavefunction, Inc., Irvine, CA).