Aromatic-aromatic ring interaction revisited with model compounds of wilcox

Journal of Biomolecular Structure and Dynamics

Volumn 15, Issue 2, 1997, Pages 401-405

  Ren, Tan ^a   Jin, Yonghao ^a   Kim, Kwang S ^a   Kim, Dong H ^a  

^a Pohang University of Science and Technology (POSTECH)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUND; ORGANIC SOLVENT;

ARTICLE; CONFORMATION; DIELECTRIC CONSTANT; ENERGY; MOLECULAR INTERACTION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; TEMPERATURE; THERMODYNAMICS;

EID: 0030827417     PISSN: 07391102     EISSN: 15380254     Source Type: Journal    
DOI: 10.1080/07391102.1997.10508202     Document Type: Article

References (14)

1. Burle, S. K., and Petsko, G. A., 1985. Science, 229:23 (a) (b) J. Singh and J. M. Thornton, FEBS Lett. 191, 2 (1985). (c) R. Gould, A. M. Gray, D. Taylor, M. D. Walkinshaw, J. Am. Chem. Soc., 107, 5921 (1985). (d) S. K. Burley, A. H.-J. Wang, J. R. Votano, H. Rich, Biochem., 26, 5091 (1987). (e) C. A. Hunter, J. Singh, J. M. Thornton, J. Mol. Biol., 218, 465 (1991). (f) L. Serrano, M. Bycroft, H. R. Fersht, J. Mol. Biol., 218, 465 (1991)
2. Desraju, G. R., and Gavezzotti, A., 1988. J. Chem. Soc., Chem. Commun., 39:125 (a) (b) F. Cozzi, F. Ponzini, R. Annunziata, M. Cinguini, and J. S. Siegel, Angew. Chem. Intl. Ed., 34, 1019 (1995). (c) F. Cozzi, M. Cinguini, R. Annunziata, J. S. Siegel, J. Am. Chem. Soc., 115, 5330 (1993). (d) F. Cozzi, M. Cinguini, R. Annunziata, T. Dwyer, and J. S. Siegel, J. Am. Chem. Soc., 114, 5729 (1992). (f)T. A. Hamer, W. B. Jennings, L. D. Proctor, M. S. Tolley, D. R. Boyd, and T. Mullan, J. Chem. Soc. Perkin Trans. 2, 25 (1990)
3. Kim, D. H., Lee, S. S., Whang, D., and Kim, K., 1993. Bioorg. Med. Chem. Lett., 3:263
4. Schladetzky, K. D., Haque, T. S., and Gellman, S. H., 1995. J. Org. Chem., 60:4108
5. Newcomb, L. F., Haque, T. S., and Gellman, S. H., 1995. J. Am. Chem. Soc., 117:6509
6. Shetty, A. S., Zhang, J. S., and Moore, J. S., 1996. J. Am. Chem. Soc., 118:1019
7. Paliwal, S., Geib, S., and Wilcox, C. S., 1994. J. Am. Chem. Soc., 116:4497
8. Adams, H., Carver, F. J., Hunter, C. A., Morales, J. C., and Seward, E. M., 1996. Angew. Chem. Int. Ed. Engl., 35:1542
9. Hobza, P., Selzle, H. L., and Schlag, E. W., 1996. J. Phys. Chem., 100:18790 (a) (b) R. L. Jaffe and G. D. Smith, J. Chem. Phys. 105, 2780 (1996)
10. Jorgensen, W. J., and Severance, D. L., 1990. J. Am. Chem. Soc., 112:4768 (a) (b) C. Chipot, R. Jaffe, B. Maigret, D. A. Peralman, and P. A. Kollman, J. Am. Chem. Soc. 118, 11217 (1996)
11. Boyd, D. R., Evans, T. A., Jennings, W. B., Malone, J. F., OiSullivan, W., and Smith, A., 1996. Chem. Commun., 2269
12. Lide, D. R., ed. 1991. CRC Handbook of Chemistry and Physics, 72 ed. FL.:(CRC Press Inc. Boca Raton. 1992)
13. In bulk water, the experimental ΔG (gas => liq) is -2.1 kcal/mol, while the ΔH (gas => liq) is−10.5 kcal/mol.(12) Considering that there are four hydrogen bonds per water molecule and the double counting of number of interacting pairs, the free energy per hydrogen bond in the water solution could be approximated to be roughly ∼−1.0 kcal/mol, and the enthalpy per hydro gen bond, ∼−5 kcal/mol. This enthalpy is somewhat enhanced than that of the water dimer (∼−4 kcal/mol),(14) because the dielectric constant of the bulk water is large. Even for the phase transition of the liquid water to ice, the ΔG is only−1.4 kcal/mol. Therefore, values of−ΔG are generally much smaller than those of−ΔH. Consequently, the value of ΔG = ∼−0.7 kcal/mol should not be considered small
14. Curtiss, L. A., Frurips, D. L., and Blander, M., 1979. J. Chem. Phys., 71:2703 (a) Chem. Phys. Lett. 54, 575 (1978). (b) K. S. Kim, B. J. Mhin, U-S. Choi, and K. Lee, J. Chem. Phys. 97, 6649 (1992)