Characterization of low-barrier hydrogen bonds. 1. Microsolvation effects. An ab initio and DFT investigation

Journal of the American Chemical Society

Volumn 119, Issue 32, 1997, Pages 7561-7566

  Pan, Yongping ^a   McAllister, Michael A ^a  

^a UNIVERSITY OF NORTH TEXAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; CALCULATION; ENZYME ACTIVE SITE; HYDROGEN BOND; PROTON TRANSPORT; THEORY; THERMODYNAMICS;

EID: 0030843208     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9709684     Document Type: Article

References (57)

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. (d) Chen, J.; McAllister, M. A.; Lee, J. K.; Houk, K. N. J. Am. Chem. Soc., submitted for publication.
6. (e) Ganeshkumar, A.; McAllister, M. A. Manuscript in preparation.
7. (f) Pan, Y.; McAllister, M. A. Manuscript in preparation.
8. (g) Speakman, J. C. J. Chem. Soc. 1949, 3357.
9. (h) Hadzi, D. Pure Appl. Chem. 1965, 11, 435.
10. (i) Gerlt, J. A.; Kreevoy, M M.; Cleland, W. W.; Frey, P. A. Chem. Biol., in press.
11. (a) Shan, S.; Herschlag, D. J. Am. Chem. Soc. 1996, 118, 5515.
12. (b) Shan, S.; Loh, S.; Herschlag, D. Science 1996, 272, 97.
13. (c) Shan, S.; Herschlag, D. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 14474.
14. Schwartz, B.; Drueckhammer, D. G. J. Am. Chem. Soc. 1995, 117, 11902.
15. Warshel, A.; Papazyan, A.; Kollman, P. A. Science 1995, 269, 102.
16. Frey, P. A. Science 1995, 269, 104.
17. (a) Scheiner, S.; Kar, T. J. Am. Chem. Soc. 1995, 117, 6970.
18. (b) Guthrie, J. P.; Kluger, R. J. Am. Chem. Soc. 1993, 115, 11569.
19. (c) Guthrie, J. P. Chem. Biol. 1996, 3, 163.
20. (a) Perrin, C. L. Science 1994, 266, 1665.
21. (b) Perrin, C. L.; Thoburn, J. D. J. Am. Chem. Soc. 1992, 114, 8559.
22. Kato, Y.; Toledo, L. M.; Rebek, Jr., J. J. Am. Chem. Soc. 1996, 118, 8575.
23. (a) Gerlt, J. A.; Gassman, P. G. J. Am. Chem. Soc. 1993, 115, 11552.
24. (b) Gerlt, J. A.; Gassman, P. G. Biochemistry 1993, 32, 11943.
25. (c) Gerlt, J. A.; Gassman, P. G. J. Am. Chem. Soc. 1992, 114, 5928.
26. (a) Cleland, W. W.; Kreevoy, M. M. Science 1994, 264, 1927.
27. (b) Marimanikkuppam, S. S.; Lee, I.-S. H.; Binder, D. A.; Young, V. G.; Kreevoy, M. M. Croat. Chem. Acta 1996, 69, 1661.
28. Cleland, W. W. Biochemistry 1992, 31, 317.
29. (a) Hibbert, F.; Emsley, J. Adv. Phys. Org. Chem. 1990, 26, 255.
30. (b) Emsley, J. Chem. Soc. Rev. 1980, 9, 91.
31. Frey, P. A.; Tobin, J. B.; Whitt, S. A. Science 1994, 164, 1887.
32. Jeffrey, G. A. An Introduction to Hydrogen Bonding; Oxford University Press: New York, 1997.
33. 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.
34. (a) Ding, Y.; Bernardo, D. N.; Levy, R. M. J. Phys. Chem. 1995, 99, 11575.
35. (b) Morgantini, P.-Y.; Kollman, P. J. Am. Chem. Soc. 1995, 117, 6057.
36. (c) Tannor, D. J.; Marten, B.; Murphy, R.; Friesner, R. A.; Sitkoff, D.; Nicholls, A.; Ringnalda, M.; Goddard, W. A. III; Honig, B. J. Am. Chem. Soc. 1994, 116, 11875.
37. (d) Meng, E. C.; Kollman, P. A. J. Phys. Chem. 1996, 100, 11460.
38. (e) Meng, E. C.; Caldwell, J. W.; Kollman, P. A. J. Phys. Chem. 1996, 100, 2367.
39. (f) Gao, J.; Pavelitee, J. J.; Habibollazadeh, D. J. Phys. Chem. 1996, 100, 2689.
40. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley-Interscience: New York, 1986; see also references therein.
41. (a) Kohn, W.; Becke, A. D.; Parr, R. G. J. Phys. Chem. 1996, 100, 12974.
42. (b) Parr, R. G.; Yang, W. Density Functional Theory of Atoms and Molecules; Oxford University Press: New York, 1989.
43. (c) Dreizler, R. M.; Gross, E. K. V. Density Functional Theory; Springer: Berlin, 1990.
44. Becke, A. D. Phys. Rev. A 1988, 38, 3098.
45. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
46. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
47. (b) Becke, A. D. J. Chem. Phys. 1996, 104, 1040.
48. (c) Becke, A. D. In Modem Electronic Structure Theory; Yarkony, D. R., Ed.; World Scientific: Singapore, 1995.
49. 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.
50. Tuckerman, M. E.; Marx, D.; Klein, M. L.; Parrinello, M. Science 1997, 275, 817.
51. Gilli, P.; Bertolasi, V.; Ferretti, V., Gilli, G. J. Am. Chem. Soc. 1994, 116, 909.
52. (a) Kuliopulos, A.; Mullen, G. P.; Xue, L.; Mildvan, S. Biochemistry 1991, 30, 3169.
53. (b) Zhao, Q.; Abeygunawardana, C.; Talalay, P.; Mildvan, A. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 8220.
54. (c) 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.
55. Li, Y.-K.; Kuliopulos, A.; Mildvan, S.; Talalay, P. Biochemistry 1993, 32, 1816.
56. Zeng, B.; Pollack, R. M. J. Am. Chem. Soc. 1991, 113, 3838.
57. a matching in the nonpolar enzyme active site will be crucial to efficient catalysis.