Characterization of low-barrier hydrogen bonds. 3. Hydrogen maleate. An ab initio and DFT investigation

Canadian Journal of Chemistry

Volumn 75, Issue 9, 1997, Pages 1195-1202

  McAllister, Michael A ^a  

^a UNIVERSITY OF NORTH TEXAS   (United States)

Author keywords

Ab initio; Density functional theory; Hydrogen maleate; Low barrier hydrogen bonds; Short strong hydrogen bonds

Indexed keywords

CHARGE TRANSFER; COMPOSITION EFFECTS; COMPUTATIONAL METHODS; CORRELATION METHODS; HYDROGEN BONDS; SOLVENTS;

DENSITY FUNCTIONAL THEORY; HYDROGEN MALEATE; SOLVENT CAVITY METHOD; ZERO POINT VIBRATIONAL ENERGY;

CARBOXYLIC ACIDS;

EID: 0031222820     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v97-144     Document Type: Article

References (45)

1. (a) M. Garcia-Viloca, A. Gonzalez-Lafont, and J.M. Lluch. J. Am. Chem. Soc. 119, 1081 (1997);
2. (b) K.E. Laidig and J.A. Platts. J. Phys. Chem. 100, 13455 (1996);
3. (c) S. Scheiner and M. Yi. J. Phys. Chem. 100, 9235 (1996);
4. (d) T. Wesolowski, R.P. Muller, and A. Warshel. J. Phys. Chem. 100, 15444 (1996).
5. (a) S. Shan and D. Herschlag. J. Am. Chem. Soc. 118, 5515 (1996);
6. (b) S. Shan, S. Loh, and D. Herschlag. Science (Washington, D.C.), 272, 97 (1996);
7. (c) S. Shan and D. Herschlag. Proc. Natl. Acad. Sci. U.S.A. 93, 14474 (1996).
8. B. Schwartz and D.G. Drueckhammer. J. Am. Chem. Soc. 117, 11902 (1995).
9. W.W. Cleland and M.M. Kreevoy. Science (Washington, D.C.), 264, 1927 (1994).
10. W.W. Cleland. Biochemistry, 31, 317 (1992).
11. (a) J.A. Gerlt, and P.G. Gassman. J. Am. Chem. Soc. 115, 11552 (1993);
12. (b) Biochemistry 32, 11943 (1993);
13. (c) J. Am. Chem. Soc. 114, 5928 (1992).
14. (a) J.P. Guthrie and R. Kluger. J. Am. Chem. Soc. 115, 11569 (1993);
15. (b) J.P. Guthrie. Chem. Biol. 3, 163 (1996).
16. A. Warshel, A. Papazyan, and P.A. Kollman. Science (Washington, D.C.), 269, 102 (1995).
17. S. Scheiner and T. Kar. J. Am. Chem. Soc. 117, 6970 (1995).
18. (a) C.L. Perrin. Science (Washington, D.C.), 266, 1665 (1994);
19. (b) C.L. Perrin and J.D. Thoburn. J. Am. Chem. Soc. 114, 8559 (1992).
20. (a) P.A. Frey, J.B. Tobin, and S.A. Whitt. Science (Washington, D.C.), 264, 1887 (1994);
21. (b) P.A. Frey. Science (Washington, D.C.), 269, 104 (1995).
22. Y. Kato, L.M. Toledo, and J. Rebek, Jr. J. Am. Chem. Soc. 118, 8575 (1996).
23. (a) F. Hibbert and J. Emsley. Adv. Phys. Org. Chem. 26, 255 (1990);
24. (b) J. Emsley. Chem. Soc. Rev. 9, 91 (1980).
25. P. Gilli, V. Bertolasi, V. Ferretti, and G. Gilli. J. Am. Chem. Soc. 116, 909 (1994).
26. G.A. Jeffrey. An introduction to hydrogen bonding. Oxford University Press, New York. 1997.
27. P. Wenthold and R. Squires. J. Phys. Chem. 99, 2002 (1995).
28. M.J. Frisch, G.W. Trucks, H.B. Schlegel, P.M.W. Gill, B.G. Johnson, M.A. Robb, J.R. Cheeseman, T.A. Keith, G.A. Petersson, J.A. Montgomery, K. Raghavachari, M.A. Al-Laham, V.G. Zakrzewski, J.V. Ortiz, J.B. Foresman, J. Cioslowski, B.B. Stefanov, A. Nanayakkara, M. Challacombe, C.Y. Peng, P.Y. Ayala, W. Chen, M.W. Wong, J.L. Andres, E.S. Replogle, R. Gomperts, R.L. Martin, D.J. Fox, J.S. Binkley, D.J. Defrees, J. Baker, J.P. Stewart, M. Head-Gordon, C. Gonzalez, and J.A. Pople. Gaussian 94, Revision D.3. Gaussian, Inc., Pittsburgh Pa. 1996.
29. W.J. Hehre, L. Radom, P.v.R. Schleyer, and J.A. Pople. Ab Initio molecular orbital theory. Wiley-Interscience, New York. 1986, and refs. therein.
30. (a) W. Kohn, A.D. Becke, and R.G. Parr. J. Phys. Chem. 100, 12974 (1996);
31. (b) R.G. Parr and W. Yang. Density functional theory of atoms and molecules. Oxford University Press, New York. 1989;
32. (c) R.M. Dreizler and E.K.V. Gross. Density functional theory. Springer, Berlin. 1990.
33. A.D. Becke. Phys. Rev. A: At. Mol. Opt. Phys. 38, 3098 (1988).
34. C. Lee, W. Yang, and R.G. Parr. Phys. Rev. B: Condens. Matter, 37, 785 (1988).
35. (a) A.D. Becke. J. Chem. Phys. 98, 5648 (1993);
36. (b) A.D. Becke. J. Chem. Phys. 104, 1040 (1996);
37. (c) A.D. Becke. In Modern electronic structure theory. Edited by D.R. Yarkony. World Scientific, Singapore. 1995.
38. J.P. Perdew. In Electronic structure of solids. Edited by P. Ziesche and H. Eschrig. Akademie Verlag, Berlin. 1991.
39. (a) S. Miertus, E. Scrocco, and J. Tomasi. Chem. Phys. 55, 117 (1981);
40. (b) J. Tomasi, R. Bonaccorsi, R. Cammi, and F.J.O. Valle. J. Mol. Struct. (Theochem), 234, 401 (1991);
41. (c) J. Tomasi and R. Bonaccorsi. Croat. Chem. Acta, 65, 29 (1992).
42. J.B. Foresman, T.A. Keith, K.B. Wiberg, J. Snoonian, and M.J. Frisch. J. Phys. Chem. 100, 16098 (1996).
43. (a) K.B. Wiberg, T.A. Keith, M.J. Frisch, and M. Murcko. J. Phys. Chem. 99, 9072 (1995);
44. (b) K.B. Wiber, P.R. Rablen, D.J. Rush, and T.A. Keith. J. Am. Chem. Soc. 117, 4261 (1995).
45. M.E. Tuckerman, D. Marx, M.L. Klein, and M. Parrinello. Science (Washington, D.C.), 275, 817 (1997).