Characterization of low-barrier hydrogen bonds. 6. Cavity polarity effects on the formic acid-formate anion model system. An ab initio and DFT investigation

Journal of the American Chemical Society

Volumn 120, Issue 1, 1998, Pages 166-169

  Pan, Yongping ^a   McAllister, Michael A ^a  

^a UNIVERSITY OF NORTH TEXAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FORMIC ACID;

ARTICLE; CALCULATION; CATALYSIS; COMPUTER SIMULATION; DIELECTRIC CONSTANT; ENZYME ACTIVE SITE; HYDROGEN BOND; MODEL; THEORY;

EID: 84962477135     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja972311o     Document Type: Article

References (62)

1. (a) Garcia-Viloca, M.; Gonzalez-Lafont, A.; Lluch, J. M. J. Am. Chem. Soc. 1997, 119, 1081.
2. (b) Laidig, J. A.; Platts, J. A. J. Phys. Chem. 1996, 100, 13455.
3. (c) Scheiner, S.; Yi, M. J. Phys. Chem. 1996, 100, 9235.
4. (d) Wesolowski, T.; Muller, R. P.; Warshel, A. J. Phys. Chem. 1996, 100, 15444.
5. (e) Chen, J.; McAllister, M. A.; Lee, J. K.; Houk, K. N. J. Am. Chem. Soc. Submitted for publication.
6. (f) Tuckerman, M. E.; Marx, D.; Klein, M. L.; Parrinello, M. Science, 1997, 275, 817.
7. (g) Zhao, Q.; Abeygunawardana, C.; Talalay, P.; Mildvan, A. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 8220.
8. (h) Wu, Z. R.; Ebrahimian, S.; Zawrotny, M. E.; Thornburg, L. D.; Perez-Alvarado, G. C.; Brothers, P.; Pollack, R. M.; Summers, M. F. Science 1997, 276, 415.
9. (a) Shan, S.; Herschlag, D. J. Am. Chem. Soc. 1996, 118, 5515.
10. (b) Shan, S.; Loh, S.; Herschlag, D. Science, 1996, 272, 97.
11. (c) Shan, S.; Herschlag, D. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 14474.
12. Schwartz, B.; Drueckhammer, D. G. J. Am. Chem. Soc. 1995, 117, 11902.
13. (a) Cleland, W. W.; Kreevoy, M. M. Science 1994, 264, 1927.
14. (b) Marimanikkuppam, S. S.; Lee, I.-S. H.; Binder, D. A.; Young, V. G.; Kreevoy, M. M. Croat. Chem. Acta 1996, 69, 1661.
15. (c) Gerlt, J. A.; Kreevoy, M M.; Cleland, W. W.; Frey, P. A. Chem. Biol. 1997, 4, 259.
16. Cleland, W. W. Biochemistry 1992, 31, 317.
17. (a) Gerlt, J. A.; Gassman, P. G. J. Am. Chem. Soc. 1993, 115, 11552.
18. (b) Gerlt, J. A.; Gassman, P. G. Biochemistry 1993, 32, 11943.
19. (c) Gerlt, J. A.; Gassman, P. G. J. Am. Chem. Soc. 1992, 114, 5928.
20. (a) Guthrie, J. P.; Kluger, R. J. Am. Chem. Soc. 1993, 115, 11569.
21. (b) Guthrie, J. P. Chem. Biol. 1996, 3, 163.
22. (a) Warshel, A.; Papazyan, A.; Kollman, P. A. Science 1995, 269, 102.
23. (b) Warshel, A.; Papazyan, A. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 13665.
24. Scheiner, S.; Kar, T. J. Am. Chem. Soc. 1995, 117, 6970.
25. (a) Perrin, C. L. Science 1994, 266, 1665.
26. (b) Perrin, C. L.; Thoburn, J. D. J. Am. Chem. Soc. 1992, 114, 8559.
27. (a) Frey, P. A.; Tobin, J. B.; Whitt, S. A. Science 1994, 164, 1887.
28. (b) Frey, P. A. Science 1995, 269, 104.
29. Kato, Y.; Toledo, L. M.; Rebek, J., Jr. J. Am. Chem. Soc. 1996, 118, 8575.
30. (a) Hibbert, F.; Emsley, J. Adv. Phys. Org. Chem. 1990, 26, 255.
31. (b) Emsley, J. Chem. Soc. Rev. 1980, 9, 91.
32. Gilli, P.; Bertolasi, V.; Ferretti, V.; Gilli, G. J. Am. Chem. Soc. 1994, 116, 909.
33. Jeffrey, G. A. An Introduction to Hydrogen Bonding; Oxford University Press: New York, 1997.
34. Wenthold, P.; Squires, R. J. Phys. Chem. 1995, 99, 2002.
35. (a) Pan, Y.; McAllister, M. A. J. Am. Chem. Soc. 1997, 119, 7561.
36. (b) McAllister, M. A. Can. J. Chem. 1997, 75, 1195.
37. (c) McAllister, M. A. J. Mol. Struct. (THEOCHEM) 1998, 423, in press.
38. (d) Pan, Y.; McAllister, M. A. J. Mol. Struct. (THEOCHEM) 1998, 423, in press.
39. (e) Kumar, G. A.; Pan, Y.; Smallwood, C. J.; McAllister, M. A. J. Comput. Chem. Submitted for publication.
40. (f) Pan, Y.; McAllister, M. A. J. Org. Chem. 1997, 62, 8176.
41. (g) Smallwood, C. J.; McAllister, M. A. J. Am. Chem. Soc. 1997, 119, 11277.
42. Gaussian 94 (Revision C.1), Frisch, M. J.; Trucks, G. W.; Schlegal, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T. A.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart; J. P. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A., Gaussian, Inc.: Pittsburgh, PA, 1995.
43. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley-Interscience: New York, 1986; and references therein.
44. (a) Kohn, W.; Becke, A. D.; Parr, R. G. J. Phys. Chem. 1996, 100, 12974.
45. (b) Parr, R. G.; Yang, W. Density Functional Theory of Atoms and Molecules; Oxford University Press: New York, 1989.
46. (c) Dreizler, R. M.; Gross, E. K. V. Density Functional Theory; Springer: Berlin, 1990.
47. Becke, A. D. Phys. Rev. A 1988, 38, 3098.
48. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
49. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
50. (b) Becke, A. D. J. Chem. Phys. 1996, 104, 1040.
51. (c) Becke, A. D. In Modern Electronic Structure Theory; Yarkony, D. R., Ed.; World Scientific: Singapore, 1995.
52. Forseman, J. B.; Keith, T. A.; Wiberg, K. B.; Snoonian, J.; Frisch, M. J. J. Phys. Chem. 1996, 100, 16098.
53. Onsager, L. J. Am. Chem. Soc. 1936, 58, 1486.
54. (a) Rinaldi, D.; Ruiz-Lopez, M. F.; Rivail, J.-L. J. Chem. Phys. 1983, 78, 834.
55. (b) Chipot, C.; Rinaldi, D.; Rivail, J.-L. Chem. Phys. Lett. 1992, 191, 287.
56. (c) Rinaldi, D.; Rivail, J.-L.; Rguini, N. J. Comput. Chem. 1992, 13, 675.
57. (a) Miertus, S.; Scrocco, E.; Tomasi, J. Chem. Phys. 1981, 55, 117.
58. (b) Tomasi, J.; Bonaccorsi, R.; Cammi, R.; Valle, F. J. O. J. Mol. Struct. (THEOCHEM) 1991, 234, 401.
59. (c) Tomasi, J.; Bonnaccorsi, R. Croat. Chem. Acta 1992, 65, 29.
60. Truong, T. N.; Stefanovich, E. V. J. Phys. Chem. 1995, 99, 14700.
61. (a) Cramer, C. J.; Truhlar, D. G. J. Am. Chem. Soc. 1993, 115, 8810.
62. (b) Marten, B.; Kim, K.; Cortis, C.; Friesner, R. A.; Murphy, R. B.; Ringnalda, M. N.; Sitkoff, D.; Honig, B. J. Phys. Chem. 1996, 100, 11775.