The Role of a Short and Strong Hydrogen Bond on the Double Proton Transfer in the Formamidine-Formic Acid Complex: Theoretical Studies in the Gas Phase and in Solution

Journal of Physical Chemistry A

Volumn 103, Issue 33, 1999, Pages 6632-6637

  Kim, Yongho ^a   Lim, Sangbae ^a   Kim, Yangsoo ^a  

^a Kyung Hee University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001646493     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp990398p     Document Type: Article

References (48)

1. Bell, R. P. The Tunnel Effect in Chemistry; Chapman and Hall: New York, 1980.
2. Melander, L.; Saunders, W. H. J. Reaction Rates of Isotopic Molecules; John Wiley and Sons: New York, 1980; p 152.
3. Hibbert, F. Adv. Phys. Org. Chem. 1986, 22, 113.
4. Cleland, W. W.; Kreevoy, M. M. Science 1994, 264, 1887.
5. Gerlt, J. A.; Gassman, P. G. J. Am. Chem. Soc. 1993, 115, 11552.
6. Gerlt, J. A.; Kreevoy, M. M.; Cleland, W. W.; Frey, P. A. Chem. Biol. 1997, 4, 259.
7. Warshel, A.; Papazyan, A.; Kollman, P. A. Science 1995, 269, 102.
8. Garcia-Viloca, M.; Gelabert, R.; Gonzalez-Lafont, A.; Moreno, M.; Lluch, J. M. J. Phys. Chem, 1997, 101, 8727.
9. Perrin, C. L.; Nielson, J. B. Annu. Rev. Phys. Chem. 1997, 48, 511.
10. Schwartz, B.; Drueckhammer, D. G. J. Am. Chem. Soc. 1995, 117, 11902-905.
11. Scheiner, S.; Kar, T. J. Am. Chem. Soc. 1995, 117, 6970.
12. Usher, K. C.; Remington, S. J.; Martin, D. P.; Drueckhammer, D. G. Biochemistry 1994, 33, 7753.
13. Ash, E. L.; Sudmeier, J. L.; Fabo, E. C. D.; Bachovchin, W. L. Science 1997, 278, 1128.
14. Shan, S.-o.; Herschlag, D. J. Am. Chem. Soc. 1996, 118, 5515.
15. Shan, S.-o.; Loh, S.; Herschlag, D. Science 1996, 272, 97.
16. Frey, P. A.; White, S. A.; Tobin, J. B. Science 1994, 264, 1927.
17. Cassidy, C. S.; Lin, J.-L.; Frey, P. A. Biochemistry 1997, 36, 4576.
18. Tobin, J. B.; White, S. A.; Cassidy, C. S.; Frey, P. A. Biochemistry 1995, 34, 6919.
19. Kahyaoglu, A.; Haghjoo, K.; Guo, F.; Jordan, F.; Kettner, C.; Felfoldi, F.; Polgar, L. J. Biol. Chem. 1997, 272, 25547.
20. Halkides, C. J.; Wu, Y. Q.; Murray, C. J. Biochemistry 1996, 35, 15941.
21. Frisch, M. J.; Trucks, G. W.; Schlegel, 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.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94; Gaussian, Inc.: Pittsburgh, 1995.
22. Foresman, J. B.; Keith, T. A.; Wiberg, K. B.; Snoonian, J.; Frisch, M. J. J. Phys. Chem. 1996, 100, 16098.
23. Bader, R. F. W. Atoms in Molecules: A Quantum Theory, Oxford University Press: Oxford, U.K., 1990.
24. Ciolowski, J.; Mixon, S. T. J. Am. Chem. Soc. 1991, 113, 4142.
25. Ciolowski, J.; Nanayakkara, A. Chem. Phys. Lett. 1994, 219, 151.
26. Scheiner, S. In Calculation the Properties of Hydrogen Bonds by ab initio Methods; Lipkowitz, K. B., Boyd, D. B., Eds.; VCH: New York, 1991; Vol. 2, p 165.
27. Boys, S. F.; Bernardi, F. Mol. Phys. 1970, 19, 553.
28. Shimoni, L.; Glusker, J. P.; Bock, C. W. J. Phys. Chem. 1996, 100, 2957.
29. Cleland, W. W. Biochemistry 1992, 31, 317.
30. Agranat, I.; Riggs, N. V.; Radom, L. J. Chem. Soc., Chem. Commun. 1991, 1991, 80.
31. Zhang, Q.; Bell, R.; Truong, T. N. J. Phys. Chem. 1995, 99, 592.
32. Kim, Y. J. Am. Chem. Soc. 1996, 118, 1522.
33. Gilli, P.; Bertolasi, V.; Ferretti, V.; Gilli, G. J. Am. Chem. Soc. 1994, 116, 909.
34. Steiner, T.; Saenger, W. Acta. Crystallogr. 1994, B50, 348.
35. Steiner, T. J. Chem. Soc., Chem. Commum. 1995, 1331.
36. Benedict, H.; Limbach, H.-H.; Wehlan, M.; Fehlhammer, W.-P.; Golubev, N. S.; Janoschek, R. J. Am. Chem. Soc. 1998, 120, 2939.
37. Ramos, M.; Alkorta, I.; Elguero, J.; Golubev, N. S.; Denisov, G. S.; Benedict, H.; Limbach, H.-H. J. Phys. Chem. A 1997, 101, 9791.
38. Callender, R.; Chen, D.; Lugtenburg, J.; Martin, C.; Rhee, K. W.; Sloan, D.; Vandersteen, R.; Yue, K. T. Biochemistry 1988, 27, 3672.
39. Kim, Y.; Kim, H. D.; Lee, Y. J. Chem. Soc., Faradays Trans. 1997, 93, 99.
40. Chang, Y.-T.; Yamaguchi, Y.; Miller, W. H.; Schefer, H. F., III. J. Am. Chem. Soc. 1987, 109, 7245.
41. Nguyen, K. A.; Gordon, M. S.; Truhlar, D. G. J. Am. Chem. Soc. 1991, 113, 1596.
42. Lim, J.-H.; Lee, E. K.; Kim, Y. J. Phys. Chem. 1997, 101, 2233.
43. Anulewicz, R.; Wawer, I.; Krygowski, T. M.; Mannle, F.; Limbach, H.-H. J. Am. Chem. Soc. 1997, 119, 12223.
44. Meschede, L.; Limbach, H.-H. J. Phy. Chem. 1991, 95, 10267.
45. Hadzi, D. Pure Appl. Chem. 1965, 11, 435.
46. Speakman, J. C. J. Chem. Soc. 1949, 1949, 3357.
47. Zundel, G. In The Hydrogen Bond II; Schuster, P., Zundel, G., Sandorfy, C., Eds.; North Holland: Amsterdam, 1976; pp 683-766.
48. Pouchert, C. J. The Aldrich Library of FT-IR Spectra; Aldrich Chemical: Milwaukee, WI, 1985; Vol. 1, p 815.