Is an extremely low-field proton signal in the NMR spectrum conclusive evidence for a low-barrier hydrogen bond?

Journal of Physical Chemistry A

Volumn 101, Issue 46, 1997, Pages 8727-8733

  Garcia Viloca, Mireia ^a   Gelabert, Ricard ^a   González Lafont, Angels ^a   Moreno, Miquel ^a   Lluch, José M ^a  

^a UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CHARGE TRANSFER; COMPUTATIONAL METHODS; ELECTRON ENERGY LEVELS; ELECTRON TRANSITIONS; ESTERS; MOLECULAR VIBRATIONS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROBABILITY DENSITY FUNCTION; PROTONS;

CHEMICAL SHIFTS; LOW BARRIER HYDROGEN BOND (LBHB); MALEATE; MALONATE; OXALATE;

HYDROGEN BONDS;

EID: 0031275493     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp972335h     Document Type: Article

References (41)

1. Hibbert, F.; Emsley, J. Adv. Phys. Org. Chem. 1990, 26, 255.
2. Guthrie, J. P. Chem. Biol. 1996, 3, 164.
3. Warshel, A.; Papazyan, A. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 13665.
4. Cleland, W. W. Biochemistry 1992, 31, 317.
5. Gerlt, J. A.; Gassman, P. G. J. Am. Chem. Soc. 1993, 115, 11552.
6. Gerlt, J. A.; Gassman, P. G. Biochemistry 1993, 32, 11943.
7. Cleland, W. W.; Kreevoy, M. M. Science 1994, 264, 1887.
8. Frey, P. A.; Whin, S. A.; Tobin, J. B. Science 1994, 264, 1927.
9. Kenyon, G. L.; Gerlt, J. A.; Petsko, G. A.; Kozarich, J. W. Acc. Chem. Res. 1995, 28, 178.
10. Xiang, S.; Short, S. A.; Wolfenden, R.; Carter, C. W. Biochemistry 1995, 34, 4516.
11. Cleland, W. W.; Kreevoy, M. M. Science 1995, 269, 104.
12. Frey, P. A. Science 1995, 269, 104.
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. Alagona, G.; Ghio, C.; Kollman, P. A. J. Am. Chem. Soc. 1995, 117, 9855.
16. Scheiner, S.; Kar, T. J. Am. Chem. Soc. 1995, 117, 6970.
17. Tobin, J. B.; Whitt, S. A.; Cassidy, C. S.; Frey, P. A. Biochemistry 1995, 34, 6919.
18. Shan, S.-O.; Herschlag, D. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 14474.
19. Smirnov, S. N.; Golubev, N. S.; Denisov, G. S.; Benedict, H.; Schah-Mohammedi, P.; Limbach, H.-H. J. Am. Chem. Soc. 1996, 118, 4094.
20. Huskey, W. P. J. Am. Chem. Soc. 1996, 118, 1663.
21. Cassidy, C. S.; Lin, J.; Frey, P. A. Biochemistry 1997, 36, 4576.
22. Garcia-Viloca, M.; González-Lafont, A.; Lluch, J. M. J. Am. Chem. Soc. 1997, 119, 1081.
23. Garcia-Viloca, M.; González-Lafont, A.; Lluch, J. M. J. Phys. Chem. 1997, 101, 3880.
24. Kreevoy, M. M.; Liang, T. M. J. Am. Chem. Soc. 1980, 102, 3315.
25. (a) Clark, T.; Chandrasekhar, J.; Spitznagel, G. W.; Schleyer, P. v. R. J. Comput. Chem. 1983, 4, 294.
26. (b) Frisch, M. J.; Pople, J. A.; Binkley, J. S. J. Chem. Phys. 1984, 80, 3265.
27. Møller, C.; Plesset, M. S. Phys. Rev. 1934, 46, 618.
28. Binkley, J. S.; Pople, J. A. Int. J. Quantum Chem. 1975, 9, 229.
29. Schlegel, H. B J. Comput. Chem. 1982, 3, 214.
30. Ditchfield, R. Mol. Phys. 1974, 27, 789.
31. Wolinski, K.; Hinton, J. P.; Pulay, P. J. Am. Chem. Soc. 1990, 112, 8251.
32. Chesnut, D. B. Chem. Phys. 1997, 214, 73.
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.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian94; Gaussian, Inc.: Pittsburgh, PA, 1995.
34. Miller, W. H.; Ruf, B. A.; Chang, Y. J. Chem. Phys. 1988, 89, 6298.
35. (a) Hamilton, I. P.; Light, J. J. Chem. Phys. 1986, 84, 306.
36. (b) Makri, N.; Miller, W. H. J. Chem. Phys. 1987, 86, 1451.
37. Ditchfield, R. J. Chem. Phys. 1976, 65, 3123.
38. Berglund, B.; Vanghan, R. W. J. Chem. Phys. 1980, 73, 2037.
39. Jeffrey, G. A.; Yeon, Y. Acta Crystallogr. 1986, B42, 410.
40. Zheng, L.; Fishbein, K. W.; Griffin, R. G.; Herzfeld, J. J. Am. Chem. Soc. 1993, 115, 6254.
41. Altman, L. J.; Laungani, D.; Gunnarsson, G.; Wennerström, H.; Forsén, S. J. Am. Chem. Soc. 1978, 100, 8264.