Theoretical study of the low-barrier hydrogen bond in the hydrogen maleate anion in the gas phase. Comparison with normal hydrogen bonds

Journal of the American Chemical Society

Volumn 119, Issue 5, 1997, Pages 1081-1086

  Garcia Viloca, Mireia ^a   González Lafont, Angels ^a   Lluch, José M ^a  

^a UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; DRUG STRUCTURE; HYDROGEN BOND; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE; QUANTUM MECHANICS; THEORY; THERMODYNAMICS;

EID: 1842332702     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja962662n     Document Type: Article

References (42)

1. Gerlt, J. A.; Gassman, P. G. J. Am. Chem. Soc. 1993, 115, 11552.
2. Gerlt, J. A.; Gassman, P. G. Biochemistry 1993, 32, 11943.
3. Cleland, W. W; Kreevoy, M. M. Science 1994, 264, 1887.
4. Frey, P. A; Whitt, S. A.; Tobin, J. B. Science 1994, 264, 1927.
5. Kenyon, G. L; Gerlt, J. A.; Petsko, G. A.; Kozarich, J. W. Acc. Chem. Res. 1995, 28, 178.
6. Xiang, S.; Short, S. A.; Wolfenden, R.; Carter, C. W. Biochemistry 1995, 34, 4516.
7. Cleland, W. W.; Kreevoy, M. M. Science 1995, 269, 104.
8. Frey, P. A. Science 1995, 269, 104.
9. Cleland, W. W. Biochemistry 1992, 31, 317.
10. Perrin, C. L.; Thoburn, J. D. J. Am. Chem. Soc. 1992, 114, 8559.
11. Perrin, C. L. Science 1994, 266, 1665.
12. Warshel, A.; Naray-Szabo, G.; Sussman, F.; Hwang, J. K. Biochemistry 1989, 28, 3629.
13. Warshel, A.; Papazyan, A.; Kollman, P. A. Science 1995, 269, 102.
14. Schwartz, B.; Drueckhammer, D. G. J. Am. Chem. Soc. 1995, 117, 11902.
15. Gilli, P.; Bertolasi, V.; Ferretti, V.; Gilli, G. J.Am. Chem. Soc. 1994, 116, 909.
16. Warshel, A.; Muller, R. P. J. Phys. Chem. 1995, 99, 17516.
17. Warshel, A.; Robert, M. W. J. Am. Chem. Soc. 1980, 102, 6218.
18. Scheiner, S.; Kar, T. J. Am. Chem. Soc. 1995, 117, 6970.
19. (a) Clark, T.; Chandrasekhar, J.; Spitznagel, G. W.; Schleyer, P.v.R. J. Comput. Chem. 1983, 4, 294.
20. (b) Frisch, M. J.; Pople, J. A.; Binkley, J. S. J. Chem. Phys. 1984, 80, 3265.
21. Møller, C.; Plesset, M. S. Phys. Rev. 1934, 46, 618.
22. Binkley, J. S; Pople, J. A. Int. J. Quantum Chem. 1975, 9, 229.
23. Schlegel, H. B. J. Comput. Chem. 1982, 3, 214.
24. Bader, R. F. W.; Tal, Y.; Anderson, S. G.; Nguyen-Dang, T. T. Isr. J. Chem. 1980, 19, 8.
25. Bader, R. F. W. Acc. Chem. Res. 1985, 18, 9.
26. Bader, R. F. W.; Carroll, M. T.; Cheeseman, J. R.; Chang, C. J. Am. Chem. Soc. 1987, 109, 7968.
27. Bader, R. F. W. Atoms in Molecules. A Quantum Theory; Oxford University Press: New York, 1990.
28. Biegler-König, F. W.; Bader, R. F. W.; Tang, T.-H. J. Comput. Chem. 1982, 3, 317-328.
29. Keith, T. A.; Bader, R. F. W. Chem. Phys. Lett. 1992, 194, 1.
30. Pople, J. A.; Krishnan, A.; Schlegel, H. B.; Binkley, J. S. Int. J. Quantum Chem., Quantum Chem. Symp. 1979, 13, 225.
31. Head-Gordon, M.; Head-Gordon, T. Chem. Phys. Lett. 1994, 220, 122.
32. Trucks, G. W.; Frisch, M. J.; Andres, J. L.; Schlegel, H. B. J. Chem. Phys., submitted for publication.
33. 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.; Brinkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon. M.; Gonzalez, C.; Pople, J. A. Gaussian 94; Gaussian, Inc.: Pittsburgh, PA, 1995.
34. Ríos, M. A.; Rodríguez, J. Can. J. Chem. 1993, 71, 303 and references therein.
35. Darlow, S. F.; Cochram, W. Acta Crystallogr. 1961, 14, 1250.
36. Peterson, S. W.; Levy, H. A. J. Chem. Phys. 1958, 29, 948.
37. Olovsson, G.; Olovsson, I.; Lehmann, M. S. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1984, C40, 1521.
38. George, P. J. Phys. Chem. 1983, 87, 1839.
39. Hodošček, M.; Haži, D. J. Mol. Struct. (THEOCHEM) 1990, 209, 411.
40. Murthy, A. S. N; Bhat, S. N; Rao, C. N. R. J. Chem. Soc. A 1970, 1970, 1251.
41. Gunnarsson, G.; Wennerström, H.; Egan, W.; Forsén, S. Chem. Phys. Lett. 1976, 38, 96.
42. Brezinski, B.; Szafran, M. Org. Magn. Reson. 1981, 15, 78.