Strength of the N-H⋯O=C and C-H⋯O=C bonds in formamide and N-methylacetamide dimers

Journal of Physical Chemistry A

Volumn 105, Issue 20, 2001, Pages 4963-4968

  Vargas, Rubicelia ^a   Garza, Jorge ^b   Friesner, Richard A ^c   Stern, Harry ^c   Hay, Benjamin P ^a   Dixon, David A ^a  

^a PACIFIC NORTHWEST NATIONAL LABORATORY   (United States)

^b DEPARTAMENTO DE QUÍMICA   (Mexico)

^c Columbia University ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALINITY; ELECTRONIC STRUCTURE; EXTRAPOLATION; HYDROGEN BONDS; PERTURBATION TECHNIQUES;

INTERACTION ENERGIES;

DIMERS;

EID: 0035942888     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp003888m     Document Type: Article

References (75)

1. (a) Baker, E. N.; Hubbard, R. E. Prog. Biophys. Mol. Biol. 1984, 44, 97.
2. (b) Dill, K. A. Biochemistry 1990, 29, 7133.
3. (c) Popot, J.-L.; Engelman, D. M. Biochemistry 1990, 29, 4031.
4. (d) Jeffrey, G. A.; Saenger, W. Hydrogen bonding in biological structures; Springer-Verlag: Berlin, 1991.
5. (e) Stickle, D. F.; Presta, L. G.; Dili, K. A.; Rose, G. D. J. Mol. Biol. 1992, 226, 1143.
6. (a) Halgren, A. T. J. Comput. Chem. 1996, 77, 520.
7. (b) Kong, J.; Yan., J.-M Int. J. Quantum Chem. 1993, 46, 239.
8. (c) Merz, K. M. J. Comput. Chem. 1992, 13, 749.
9. (d) Faerman, C. H.; Price, S. L. J. Am. Chem. Soc. 1990, 112, 4915.
10. (e) Spackman, M. A. J. Phys. Chem. 1987, 91, 3179.
11. (f) Sokalski, W. A.; Lowrey, A. H.; Roszack, S.; Levchenco, V.; Blaisdell, H.; Hariharan, P. C.; Kauffman, J. J. J. Comput. Chem. 1986, 7, 693.
12. (g) Weiner, S. J.; Kollman, P. A.; Nguyen, D. T.; Case, D. A. J. Comput. Chem. 1986, 7, 230.
13. (h) Hurst, G. J. B.; Fowler, P. W.; Stone, A. J.; Buckingham, A. D. Int. J. Quantum Chem. 1986, 29, 1986.
14. (i) Dykstra, C. E. Chem. Rev. 1993, 93, 2339.
15. (j) McDonald, D. Q.; Still, W. C. Tetrahedron Lett. 1992, 33, 7747.
16. (a) Møller, C.; Plesset, M. S. Phys. Rev. 1934, 46, 618.
17. (b) Pople, J. A.; Binkley, J.; Seeger, R. Int. J. Quantum Chem., Symp. 1976, 10, 1.
18. (a) Xantheas, S. S. J. Chem. Phys. 1995, 102, 4505.
19. (b) Xantheas, S. S. J. Chem. Phys. 1994, 100, 7523.
20. Sponer, J.; Leszczynski J.; Hobza, P. J. Phys. Chem. 1996, 100, 1995.
21. Feyereisen, M. W.; Feller, D.; Dixon, D. A. J. Phys. Chem. 1996, 100, 2993.
22. Kim, K.; Friesner, R. A. J. Am. Chem. Soc. 1997, 119, 12952.
23. Lii, H.-L.; Allinger, N. L. J. Comput. Chem. 1998, 19, 1001.
24. Hobza, P.; Sponer, J. J. Mol. Struct.: THEOCHEM 1996, 388, 115.
25. Dreyfus, M.; Maigret, B.; Pullman, A. Theor. Chim. Acta 1970, 17, 109.
26. Johansson, A.; Kollman, P.; Rothenberg, S.; McKelvey, J. J. Am. Chem. Soc. 1974, 96, 3794.
27. Ottersen, T. J. J. Mol. Struct. 1975, 26, 365.
28. Ottersen, T. J.; Jensen, H. H. J. Mol. Struct. 1975, 26, 335.
29. Kolaskar, A. S.; Lakshminarayanan, A. V.; Sarathy, K. P.; Sasisekharan, V. Biopolymers 1975, 14, 1081.
30. Yamabe, S.; Kitaura, K.; Nishimoto, K. Theor. Chim. Acta 1978, 47, 11.
31. Peters, D.; Peters, J. J. Mol. Struct. 1980, 68, 255.
32. Jeffrey, G. A.; Rubble, J. R. McMullan, R. K.; DeFrees, J. D. Pople, J. A. Acta Crystallogr. 1981, B37, 1885.
33. Pullman, A.; Berthord, H. Theor. Chim. Acta 1968, 10, 641.
34. Sapse, A. M.; Fugler, M.; Cowborn, D. Int. J. Quantum Chem. 1986, 29, 1241.
35. Dory, M.; Delhalle, J.; Fripiat, J. G.; Andre, J.-M. Int. J. Quantum Chem., Quantum Biol. Symp. 1987, 14, 85.
36. Wojcik, M. J.; Hirakawa, A. Y.; Tsuboi, M.; Kato, S.; Morokuma, K. Chem. Phys. Lett. 1988, 143, 450.
37. Novoa, J. J.; Whangbo, M.-H. J. Am. Chem. Soc. 1991, 113, 9017.
38. Neuheuser, T.; Hess, B. A.; Reutel, C.; Weber, R. J. Phys. Chem. 1994, 98, 6459.
39. Florian, J.; Leszcynski, J.; Johnson, B. J. Mol. Struct. 1995, 349, 421.
40. Florian, J.; Johnson, B. G. J. Phys. Chem. 1995, 99, 5899.
41. Adalsteinsson, H.; Maulitz, A. H.; Bruice, T. C. J. Am. Chem. Soc. 1996, 118, 7689.
42. Suhai, S. J. Phys. Chem. 1996, 100, 3950.
43. Bleckmann, P.; Breitenbach, P.; Dickhut, K. U., Keller, D.; Schwittek, C. Fresenius' J. Anal. Chem. 1997, 559, 115.
44. (a) Sponer, J.; Hobza, P. J. Phys. Chem. A 2000, 104, 4592.
45. e for comparison with our results, we subtracted 1.73 kcal/mol from each of the reported interaction energies.
46. Desfrancois, C.; Periquet, V.; Carles, S.; Schermann, J. P.; Andamowicz, L. Chem. Phys. 1998, 239, 475.
47. Ramachandran, G. N.; Lakshminarayanan, A. V.; Kolaskar, A. S. Biochim. Biophys. Acta 1973, 303, 8.
48. Renugopalakrishnan, V.; Rein, R. Biochim. Biophys. Acta 1976, 434, 164.
49. Cheam, T. C.; Krimm, S. J. Mol. Struct. 1986, 146, 175.
50. Guo, H.; Karplus, M. J. Phys. Chem. 1992, 96, 7273.
51. Dixon, D. A.; Dobbs, K. D.; Valentini, J. J. J. Phys. Chem. 1994, 98, 13435.
52. JAGUAR V3.0, Schrörindinger, Inc., Portland, OR, 1997.
53. (a) Dunning, T. H., Jr. J. Chem. Phys. 1989, 90, 1007.
54. (b) Kendall, R. A.; Dunning, T. H., Jr.; Harrison, R. J. J. Chem. Phys. 1992, 96, 6796.
55. (a) Woon, D. E.; Dunning, T. H., Jr. J. Chem. Phys. 1994, 101, 8877.
56. (b) Peterson, K. A.; Woon, D. E.; Dunning, T. H., Jr. J. Chem. Phys. 1994, 100, 7410.
57. Boys, S. F.; Bernardi, F. Mol. Phys. 1990, 19, 553.
58. Bernholdt, D. E.; Apra, E.; Fruchtl, H. A.; Guest, M. F.; Harrison, R. J.; Kendall, R. A.; Dutteh, R. A.; Long, X.; Nicholas, J. B.; Nichols, J. A.; Taylor, H. L.; Wong, A. T.; Fann, G. I.; Littlefield, R. J.; Nieplocha, J. Int. J. Quantum Chem., Symp. 1995, 29, 475.
59. Vargas, R.; Garza, J.; Dixon, D. A.; Hay, B. P. J. Am. Chem. Soc. 2000, 122, 4750.
60. (a) Becke, A. D. Phys. Rev. A 1988, 38, 3098.
61. (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
62. Dgauss is a program that is part of UniChem and is available from Oxford Molecular: (a) Andzelm, J.; Wimmer, E.; Salahub, D. R. In The Challenge of d and f Electrons: Theory and Computations; Salahub, D. R., Zerner, M. C., Eds.; ACS Symposium Series, No. 394; American Chemical Society: Washington, DC, 1989; p 228.
63. (b) Andzelm, J. In Density Functional Methods in Chemistry; Labanowski, J., Andzelm, J., Eds.; Springer-Verlag: New York, 1991; p. 155.
64. (c) Andzelm, J.; Wimmer, E. J. Chem. Phys. 1992, 96, 1280.
65. Godbout, N.; Salahub, D. R.; Andzelm, J.; Wimmer, E. Can. J. Chem. 1992, 70, 560.
66. e values (kcal/mol) for dimers 1-5 at the BLYP/TZVP(A2) level of theory are (1) -13.22, (2) -8.40, (3) -5.70, (4) -5.95, and (5) -3.40. These association energies are 0.8-1.6 kcal/mol weaker than the estimated MP2/CBS values given in Table 2.
67. Clement, O.; Rapko, B. M.; Hay, B. P. Coord. Chem. Rev. 1998, 170, 203.
68. Drakenberg, T.; Forsen, S. J. Chem. Soc., Chem. Commun. 1971, 1404.
69. Taft, R. W. Prog. Phys. Org. Chem. 1987, 76, 1.
70. Decouzon, M.; Exner, O.; Gal, J.-F.; Maria, P. C. J. Org. Chem. 1990, 55, 3980.
71. Hunter, E. P. L.; Lias, S. G. J. Phys. Chem. Ref. Data 1998, 27, 413.
72. Stern, H. A.; Kaminski, G. A.; Banks, J. L.; Zhou, R. H.; Berne, B. J.; Friesner, R. A. J. Phys. Chem. B 1999, 103, 4730.
73. Banks, J. L.; Kaminski, G. A.; Zhou, R. H.; Mainz, D. T.; Berne, B. J.; Friesner, R. A. J. Chem. Phys. 1999, 110, 741.
74. Liu, Y. P.; Kim, K.; Berne, B. J.; Friesner, R. A.; Rick, S. W. J. Chem. Phys. 1998, 108, 4739.
75. Murphy, R. B.; Beachy, M. D.; Friesner, R. A.; Ringnalda, M. N. J. Chem. Phys. 1995, 103, 1481.