High-level ab initio calculations of dihydrogen-bonded complexes

Journal of Physical Chemistry A

Volumn 104, Issue 23, 2000, Pages 5551-5557

  Grabowski, Stawomir J ^a  

^a UNIVERSITY OF BIALYSTOK   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

BINDING ENERGY; CALCULATIONS; CHEMICAL BONDS; DEHYDROGENATION; ELECTRONIC DENSITY OF STATES; MOLECULAR DYNAMICS; NUMERICAL ANALYSIS; PROBABILITY DENSITY FUNCTION;

DIHYDROGEN BONDED COMPLEXES; PROTON DONATING MOLECULE;

FLUORINE COMPOUNDS;

EID: 0033685726     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp993984r     Document Type: Article

References (78)

1. (a) Desiraju, G. R. Ace. Chem. Res. 1996, 29, 441 and references therein,
2. (b) Viswamitra, M.A.; Radhakrishnan, R.; Bandekar, J.; Desiraju, G.R. J. Am. Chem. Soc. 1993, 115, 4868.
3. Steiner, T. Crystallogr. Rev. 1996, 6,1.
4. Platts, J. A.; Howard, S. T.; Wozniak, K. Chem. Commun. 1996, 63.
5. Alkorta, I.; Rozas, I.; Elguero, J. Chem. Soc. Rev. 1998, 27, 163.
6. Robinson, J. M. A.; Philp, D.; Kariuki, B. M.; Harris, K. D. M. Chem. Commun. 1999, 329.
7. Taylor, R.; Kennard, O. J. Am. Chem. Soc. 1982, 104, 5063.
8. Sumathi, R.; Chandra, A. K. Chem. Phys. Lett. 1997, 277, 287.
9. Chandra, A. K.; Nguyen, M. T. J. Chem. Res., Synop. 1997, 216.
10. Grabowski, S. J. J. Chem. Res., Synop. 1996, 534.
11. Wessel, J.; Lee, J. C.; Peris, E.; Yap, G. P. A.; Fortin, J. B.; Ricci, J. S.; Sini, G.; Albinati, A.; Koetzle, T. F.; Eisenstein, O.; Rheingold, A. L.; Crabtree, R. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2507.
12. Crabtree, R. H.; Siegbahn, P. E. M.; Eisenstein, O.; Rheingold, A. L.; Koetzle, T. F. Acc. Chem. Res. 1996, 29, 348.
13. Bosque, R.; Maseras, F.; Eisenstein, O.; Patel, B. P. P.; Yao.W.; Crabtree, R. H. Inorg.Chem. 1997, 36, 5505.
14. Richardson, T. B.; deGala, S.; Crabtree, R. H.; Siegbahn, P. E. M. J. Am. Chem. Soc. 1995, 117, 12875.
15. Siegbahn, P. E. M.; Blomberg, M. R. A.; Svensson, M. Chem. Phys. Lett. 1994, 223, 35.
16. Liu, Q.; Hoffmann, R. J. Am. Chem. Soc. 1995, 117, 10108.
17. (a) Orlova, G.; Scheiner, S. J. Phys. Chem. A 1998, 702, 260.
18. (b) Orlova, G.; Scheiner, S. J. Phys. Chem. A 1998, 702,4813.
19. Orlova, G.; Scheiner, S.; Kar, T. J. Phys. Chem. A 1999, 103, 514.
20. Remko, M. Mol. Phys. 1998, 94, 839.
21. Alkorta, I.; Elguero, J.; Foces-Foces, C. Chem. Commun. 1996, 1633.
22. Grabowski, S. J. Chem. Phys. Lett. 1999, 572, 542.
23. Rozas, I.; Alkorta, I.; Elguero, J. Chem. Phys. Lett. 1997,275,423.
24. Brown, I. D. Acta Crystallogr. 1992, B48, 553 and references therein.
25. Dunitz, J. D. X-ray Analysis and the Structure of Organic Molecules; Cornell University Press: Ithaca, NY, 1979.
26. Biirgi, H. B. Angew. Chem., Int. Ed. Engl. 1975, 14, 460.
27. (a) Grabowski, S. J.; Krygowski, T. M. Tetrahedron 1998,54,5683.
28. (b) Grabowski, S. J. Tetrahedron 1998, 54, 10153.
29. Grabowski, S. J.; Krygowski, T. M. Chem. Phys. Lett. 1999, 305, 247.
30. Bader, R. F. W. Atoms in Molecules. A Quantum Theory; Oxford University Press: New York, 1990.
31. (a) Bytheway, I.; Bacskay, G. B.; Hush, N. S. J. Phys. Chem. 1996, 100, 6023.
32. (b) Bytheway, I.; Bacskay, G. B.; Hush, N. S. J. Phys. Chem. 1996, 700, 14899.
33. Kestner, N. R. J. Chem. Phys. 1968, 48, 252.
34. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; 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.; Barker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzales, C.; Pople, J. A. Gaussian 94, revision E.3; Gaussian, Inc.: Pittsburgh, PA, 1995.
35. Moller, C.; Plesset, M. S. Phys. Rev. 1934, 46, 618.
36. Krishnan, R.; Pople, J. A. Int. J. Quantum Chem. 1978, 14, 91.
37. (a) Trucks, G. W.; Salter, E. A.; Sosa, C.; Bartlett, R. J. Chem. Phys. Lett. 1988, 747, 359.
38. (b) Trucks, G. W.; Watts, J. D.; Salter, E. A.; Bartlett, R. J. Chem. Phys. Lett. 1988, 753, 490.
39. Pople, J. A.; Head-Gordon, M.; Raghavachari, K. J. Chem. Phys. 1987, 87, 5968.
40. Boys, S. F.; Bernardi, F. Mol. Phys. 1970, 79, 553.
41. Seiler, P.; Weisman, G. R.; Glendening, E. D.; Weinhold, F.; Johnson, V. B.; Dunitz, J. D. Angew. Chem., Int. Ed. Engl. 1987,26, 1175.
42. Gu, Y.; Kar, T.; Scheiner, S. J. Am. Chem. Soc. 1999, 727, 9411.
43. Kazarian, S. G.; Hamley, P. A.; Poliakoff, H. J. Am. Chem. Soc. 1993, 115, 9069.
44. Shubina, E. S.; Belkova, N. V.; Krylov, A. N.; Vorontsov, E. V.; Epstein, L. M.; Gusev, D. G.; Niedermann, M.; Berke, H. J. Am. Chem. Soc. 1996, 118, 1105.
45. Larson, J. W.; McMahon, T. B. J. Am. Chem. Soc. 1983, 105,2944.
46. Larson, J. W.; McMahon, T. B. /. Am. Chem. Soc. 1984, 700,517.
47. Scheiner, S. Anna. Rev. Phys. Chem. 1994, 45, 23.
48. Meot-Ner (Mautner), M.; Deakyne, C. A. J. Am. Chem. Soc. 1985, 707, 469.
49. Deakyne, C. A.; Meot-Ner (Mautner), M. J. Ain. Chem. Soc. 1985, 107, 474.
50. (a) Olovsson, I.; Jönsson, P.-G. The Hydrogen Bond; Schuster, P., Zundel, G., Sandorfy, C., Eds.; North-Holland: Amsterdam, The Netherlands, 1976; Vol. II, Chapter 8.
51. (b) Ichikawa, M. Ada Crysmllogr. 1978, B34, 2074.
52. Jeffrey, G. A.; Saenger, W. Hydrogen Bonding in Biological Structures; Springer: Berlin, 1991; p 51.
53. (a) Scheiner, S.; Kar, T. J. Am. Chem. Soc. 1995, 777, 6970.
54. (b) Garcia-Viloca, M.; González-Lafont, A.; Lluch, J. M. J. Am. Chem. Soc. 1997, 779, 1081.
55. Garcia-Viloca, M.; Gelabert, R.; González-Lafont, A.; Moreno, M.; Lluch, J. M. J. Phys. Chem. A 1997, 101, 8727.
56. Smallwood, C. J.; McAllister, M. A. J. Am. Chem. Soc. 1997, 779, 11277.
57. (e) Pan, Y.; McAHister, M. A. J. Am. Chem. Soc. 1998, 720, 166.
58. (a) Meot-Ner (Mautner), M. J. Am. Chem. Soc. 1984, 700, 1257.
59. (b) Meot-Ner (Mautner), M.; Sieck, L.W. J. Am. Chem. Soc. 1986, 108, 7625.
60. (a) Allen, F. H.; Bellard, S.; Brice, M. D.; Cartwright, B. A.; Doubleday, A.; Higgs, H.; Hummelink, T. W. A.; Hummelink-Peters, B. G. M. C.; Kennard, O.; Motherwell, W. D. S.; Rodgers, J. R.; Watson, D. G. Acta Crystallogr. 1979, B35,2331.
61. (b) Allen, F. H.; Davies, J. E.; Galloy, J. E.; Johnson, J. J.; Kennard, O.; Macrae, C. F.; Mitchell, E. M.; Mitchell, G. F.; Smith, J. M.; Watson, D. G. J. Chem. Inf. Comput. Sci. 1991, 31, 187.
62. (a) Brown, I. D.; Shannon, R. D. Acta Crystallogr. 1973, A29,266.
63. (b) Biirgi, H.-B.; Dunitz, J. D. J. Am. Chem. Soc. 1987, 709, 2924.
64. Grabowski, S. J. Croat. Chem. Acta 1988, 67, 815.
65. 0 = 0.917 and B = 0.307.
66. Pauling, L. J. Am. Chem. Soc. 1947, 69, 542.
67. Bader, R. W. F.; Tang, T. H.; Tal,' Y.; Biegler-König, F. W. J. Am. Chem. Soc. 1984, 104, 946.
68. Mallison, P. R.; Woźniak, K.; Smith, G. T.; McCormack, K. L. J. Am. Chem. Soc. 1997, 119, 11502.
69. Alkorta, I.; Elguero, J. J. Phys. Chem. 1996, 700, 19367.
70. Espinosa, E.; Souhassou, M.; Lachekar, H.; Lecomte, C. Acta Crystallogr. 1999, B55, 563.
71. (a) Cioslowski, J.; Nanayakkara, A.; Challacombe, M. Chem. Phys. Lett. 1993, 203, 137.
72. (b) Cioslowski, J.; Surjan, P. R. J. Mol. Struct. 1992, 255, 9.
73. Cioslowski, J.; Stefanov, B. B. Mol. Phys. 1995, 84, 707.
74. Stefanov, B. B.; Cioslowski, J. R. J. Comput. Chem. 1995, 16, 1394.
75. (a) Cioslowski, J. Int. J. Quantum Chem., Quantum Chem. Symp. 1990, 24, 15.
76. (b) Cioslowski, J.; Mixon, S. T. J. Am. Chem. Soc. 1991, 113, 4142.
77. Cioslowski, J. Chem. Phys. Lett. 1992, 194, 73.
78. Cioslowski, J. Chem. Phys. Lett. 1992, 219, 151.