How short can the H⋯H intermolecular contact be? New findings that reveal the covalent nature of extremely strong interactions

Journal of Physical Chemistry A

Volumn 109, Issue 19, 2005, Pages 4331-4341

  Grabowski, Sławomir J ^a,b   Sokalski, W Andrzej ^c   Leszczynski, Jerzy ^b  

^a UNIVERSITY OF LODZ   (Poland)

^b JACKSON STATE UNIVERSITY   (United States)

^c WROCLAW UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

BERYLLIUM; BINDING ENERGY; CARRIER CONCENTRATION; DECOMPOSITION; DIMERS; ELECTROSTATICS; HYDROGEN BONDS; PROTONS;

DELOCALIZATION; ELECTROSTATIC ENERGY; INTERMOLECULAR HYDROGEN BONDS; INTERMOLECULAR INTERACTIONS;

MOLECULAR DYNAMICS;

HYDROGEN; OXYGEN; PROTON;

ARTICLE; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; DIMERIZATION; ELECTRON; HYDROGEN BOND; METHODOLOGY; NORMAL DISTRIBUTION; PHYSICAL CHEMISTRY; THEORETICAL MODEL;

CHEMISTRY, PHYSICAL; DIMERIZATION; ELECTRONS; HYDROGEN; HYDROGEN BONDING; MODELS, CHEMICAL; MODELS, MOLECULAR; MODELS, THEORETICAL; NORMAL DISTRIBUTION; OXYGEN; PROTONS;

EID: 19944414664     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp0444215     Document Type: Article

References (137)

1. Jeffrey, G. A.; Saenger, W. Hydrogen Bonding in Biological Structures; Springer-Verlag: Berlin, 1991.
2. Jeffrey, G. A. An Introduction to Hydrogen Bonding; Oxford University Press: New York, 1997.
3. Desiraju, G. R.; Steiner, T. The weak hydrogen bond in structural chemistry and biology; Oxford University Press: New York, 1999.
4. Pauling, L. The Nature of the Chemical Bond, 3rd ed.; Cornell University Press: Ithaca, New York, 1960.
5. AB values and the terms of the decomposition of the interaction energies are given in Tables 5-7.
6. Suttor, D. J. J. Chem. Soc. 1963, 1105.
7. Taylor, R.; Kennard, O. J. Am. Chem. Soc. 1982, 104, 5063.
8. (a) Grabowski, S. J. J Chem. Res. 1996, 534.
9. (b) Grabowski, S. J.; Wilamowski, J.; Osman, D.; Sepiol, J. J.; Rodier, N. Aust. J. Chem. 1996, 49, 951.
10. (a) Pinchas, S. Anal. Chem. 1955, 27, 2.
11. (b) Schneider, W. G.; Bernstein, H. J. Trans. Faraday Soc. 1956, 52, 13.
12. (c) Trudeau, G.; Dumas, J. M.; Dupuis, P.; Guerin, M.; Sandorfy, C. Top. Curr. Chem. 1980, 93, 91.
13. Hobza, P.; Havlas, Z.; Chem. Rev. 2000, 100, 4253 and references therein.
14. Grabowski, S. J.; Sokalski, W. A.; Leszczynski, J. J. Phys. Chem. A 2004, 108, 1806.
15. (a) Gilli, P.; Bertolasi, V.; Ferretti, V.; Gilli, G. J. Am. Chem. Soc. 1994, 116, 909.
16. (b) Gilli, G.; Gilli, P. J. Mol. Struct. 2000, 552, 1.
17. (c) Gilli, P.; Bertolasi, V.; Ferretti, V.; Gilli, G. J. Am. Chem. Soc. 2000, 122, 10405.
18. (d) Gilli, P.; Bertolasi, V.; Pretto, L.; Lyčka, A.; Gilli, G. J. Am. Chem. Soc. 2002, 124, 13554.
19. (e) Gilli, P.; Bertloasi, V.; Pretto, L.; Ferretti, V.; Gilli, G. J. Am. Chem. Soc. 2004, 126, 3845.
20. (a) Park, S.; Ramachandran, R.; Lough, A. J.; Morris, R. H. J. Chem. Soc. Chem. Commun. 1994, 2201.
21. (b) Lough, A. J.; Park, S.; Ramachandran, R.; Morris, R. H. J. Am. Chem. Soc. 1994, 116, 8356.
22. (c) Lee, J. C., Jr.; Rheingold, A. L.; Müller, B.; Pregosin, P. S.; Crabtree, R. H. J. Chem. Soc. Chem. Commun. 1994, 1021.
23. (d) Lee, J. C., Jr.; Peris, E.; Rheingold, A. L.; Crabtree, R. H. J. Am. Chem. Soc. 1994, 116, 11014.
24. (e) Peris, E.; Lee, J. C., Jr.; Crabtree, R. H. J. Chem. Soc. Chem. Commun. 1994, 2573.
25. (f) Peris, E.; Lee, J. C., Jr.; Rambo, J.; Eisenstein, O.; Crabtree, R. H. J. Am. Chem. Soc. 1995, 117, 3485.
26. (g) Peris, E.; Wessel, J.; Patel, B. P.; Crabtree, R. H. J. Chem. Soc. Chem. Commun. 1995, 2175.
27. Richardson, T. B.; de Gala, S.; Crabtree, R. H.; Siegbahn, P. E. M. J. Am. Chem. Soc. 1995, 117, 12875.
28. (a) Wessel, J.; Lee, J. C., Jr.; 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.
29. (b) Crabtree R. H.; Siegbahn, P. E.M.; Eisenstein, O.; Rheingold, A. L.; Koetzle, T. F. Acc. Chem. Res. 1996, 29, 348.
30. (c) Richardson, T. B.; Koetzle, T. F.; Crabtree, R. H. Inorg. Chim. Acta 1996, 250, 69.
31. (d) Cramer, C. J.; Gladfelter, W. L. Inorg. Chem. 1997, 36, 5358.
32. (e) Calhorda, M. J.; Costa, P. J. Cryst. Eng. Commun. 2002, 4, 368.
33. (a) Liu, Q.; Hoffman, R. J. Am. Chem. Soc. 1995, 117, 10108.
34. (b) Alkorta, I.; Elguero, J.; Foces-Foces, C. Chem. Commun. 1996, 1633.
35. (c) Remko, M. Mol. Phys. 1998, 94, 839.
36. (d) Orlova, G.; Scheiner, S. J. Phys. Chem. 1998, 102, 260.
37. (e) Orlova, G.; Scheiner, S. J. Phys. Chem. 1998, 102, 4813.
38. (f) Braga, D.; DeLeonardis, P.; Grepioni, F.; Tedesco, E.; Calhorda, M. J. Inorg. Chem. 1998, 37, 3337.
39. (g) Kulkarni, S. A. J. Phys. Chem. A 1998, 102, 7704.
40. (h) Kulkarni, S. A. J. Phys. Chem. A 1999, 103, 9330.
41. (i) Kulkarni, S. A.; Srivastava, A. K. J. Phys. Chem. A 1999, 103, 2836.
42. (j) Calhorda, M. J.; Lopes, P. E. M. J. Organomet. Chem. 2000, 609, 53.
43. (a) Alkorta, I.; Rozas, I.; Elguero, J. Chem. Soc. Rev. 1998, 27, 163.
44. (b) Custelcean, R.; Jackson, J. E. Chem. Rev. 2001, 107, 1963.
45. (c) Epstein, L. M.; Shubina, E. S. Coord. Chem. Rev. 2002, 231, 165.
46. (a) Custelcean, R.; Jackson, J. E. J. Am. Chem. Soc. 1998, 120, 12935.
47. (b) Custelcean, R.; Jackson, J. E. Thermochim. Acta 2002, 388, 143.
48. Platts, J. A.; Howard, S. T.; Woźniak, K. Chem. Commun. 1996, 63.
49. Grabowski, S. J. J. Phys. Chem. A 2000, 104, 5551.
50. Grabowski, S. J. Chem. Phys. Lett. 1999, 312, 542.
51. (a) Alkorta, I.; Elguero, J.; Mo, O.; Yánez, M.; Del Bene, J. E. J. Phys. Chem. A 2002, 106, 9325.
52. (b) Del Bene, J. E.; Perera, S. A.; Bartlett, R. J.; Alkorta, I.; Elguero, J.; Mó, O.; Yänez, M. J. Phys. Chem. A 2002, 106, 9331.
53. (c) Cybulski, H.; Pecul, M.; Sadlej, J. J. Chem. Phys. 2003, 119, 5094.
54. Popelier, P. L. A. J. Phys. Chem. A 1998, 102, 1873.
55. Kar, T.; Scheiner, S. J. Chem. Phys. 2003, 119, 1473.
56. Kitaura, K.; Morokuma, K. Int. J. Quantum Chem. 1976, 10, 325.
57. (a) Chalasiński, G.; Szczȩśniak, M. M. Mol. Phys. 1988, 63, 205.
58. (b) Cybulski, S. M.; Chałasiński, G.; Mosźynski, R. J. Chem. Phys. 1990, 92, 4357.
59. (c) Chałasiński, G.; Szczȩśniak, M. M. Chem. Rev. 1994, 94, 1723.
60. Robertson, K. N.; Knop, O.; Cameron, T. S. Can. J. Chem. 2003, 81, 727.
61. Bader, R. F. W. Atoms in Molecules. A Quantum Theory; Oxford University Press: New York, 1990.
62. Coppens, P. X-ray Charge Densities and Chemical Bonding, IUCr; Oxford University Press: New York, 1997.
63. Grabowski, S. J.; Pfitzner, A.; Zabel, M.; Dubis, A. T.; Palusiak, M. J. Phys. Chem. B 2004, 108, 1831.
64. Matta, C. F.; Hernández-Trujillo, J.; Tang, T.-H.; R. F. W. Bader, Chem. Eur. J. 2003, 9, 1940.
65. Grabowski, S. J.; Sokalski, W. A.; Leszczynski, J. J. Phys. Chem. A 2004, 108, 5823.
66. Grabowski, S. J.; Robinson, T. L.; Leszczynski, J. Chem. Phys. Lett. 2004, 386, 44.
67. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.6; Gaussian, Inc.: Pittsburgh, PA, 1998.
68. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, Jr., J. A.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, revision B.03; Gaussian, Inc.: Wallingford CT, 2004.
69. Møller, C.; Plesset, M. S. Phys. Rev. 1934, 46, 618.
70. McLean, A. D.; Chandler, G. S. J. Chem. Phys. 1980, 72, 5639.
71. Frisch, M. J.; Pople, J. A.; Binkley, J. S. J. Chem. Phys. 1984, 80, 3265.
72. Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650.
73. Clark, T.; Chandrasekhar, J.; Spitznagel, G. W.; Schleyer, P. V. R. J. Comput. Chem. 1983, 4, 294.
74. Woon, D. E.; Dunning, Jr., T. H. J. Chem. Phys. 1993, 98, 1358.
75. Kendall, R. E.; Dunning, T. H., Jr.; Harrison, R. J. J. Chem. Phys. 1992, 96, 6796.
76. (a) Wilson, A.; Dunning, T. H., Jr. J. Chem. Phys. 1997, 106, 8718.
77. (b) Helgaker, T.; Klopper, W.; Koch, H.; Noga, J. J. Chem. Phys. 1997, 106, 9639.
78. (c) Halkier, A.; Koch, H.; Christiansen, O.; Jorgensen, P.; Helgaker, T. J. Chem. Phys. 1997, 107, 849.
79. Boys, S. F.; Bernardi, F. Mol. Phys. 1970, 19, 553.
80. (a) Sokalski, W. A.; Roszak, S.; Pecul, K. Chem. Phys. Lett. 1988, 153, 153.
81. (b) Sokalski, W. A.; Roszak, S. J. Mol. Struct. (THEOCHEM) 1991, 234, 387.
82. (c) Gora, R. W.; Bartkowiak, W.; Roszak, S.; Leszczynski J. J. Chem. Phys. 2002, 117, 1031.
83. (d) Gora, R. W.; Bartkowiak, W.; Roszak, S.; Leszczynski J. J. Chem. Phys. 2004, 120, 2802.
84. van Lenthe, J. H.; van Duijneveldt-van de Rijdt, J. C. G. M.; van Duijneveldt, F. B. Adv. Chem. Phys. 1987, 69, 521.
85. Jeziorski, B.; Szalewicz, K.; Chałasinski, G. Int. J. Quantum Chem. 1978, 14, 271.
86. Buckingham, D. A.; Fowler, P. W. J. Chem. Phys. 1983, 79, 6426.
87. Gora, R.; Roszak, S.; Sokalski, W. A.; Leszczynski, J. Jackson State University, 1999, JSU preprint.
88. Breneman, C. M.; Wiberg, K. B. J. Comput. Chem. 1990, 11, 361.
89. Reed, A. E.; Weinstock, R. B.; Weinhold, F. J. Chem. Phys. 1985, 83, 735.
90. Szefczyk, B.; Sokalski, W. A.; Leszczynski, J. J. Chem. Phys. 2002, 117, 6952.
91. Bader, R. F. W.; MacDougall, P. J.; Lau, C. D. H. J. Am. Chem. Soc. 1984, 106, 1594.
92. Bader, R. F. W. Chem. Rev. 1991, 91, 893.
93. AIM2000 designed by Friedrich Biegler- König; University of Applied Sciences: Bielefeld, Germany, 2000.
94. Desiraju, G. R. Acc. Chem. Res. 2002, 35, 565.
95. Frish, M. J.; Del Bene, J. E.; Binkley, J. S.; Schaefer, H. F. J. Chem. Phys. 1986, 84, 2279.
96. Latajka, Z.; Bouteller, Y.; Scheiner, S. Chem. Phys. Lett. 1995, 234, 159.
97. Custelcean, R.; Vlassa, M.; Jackson, J. E. Chem. Eur. J. 2002, 8, 302.
98. Custelcean, R.; Jackson, J. E. Angew. Chem. Int. Ed. 1999, 38, 1661.
99. (a) Vanquickenborne, L. G. Quantum Chemistry of the Hydrogen Bond. In Intermolecular Forces. An Introduction to Modern Methods and Results; Huyskens, P. L., Luck, W. A. P., Zeegers-Huyskens, T., Eds.; Springer-Verlag: Berlin, 1991.
100. (b) Scheiner, S. Hydrogen Bonding: A Theoretical Perspective; Oxford University Press: New York, 1997.
101. (c) Gu, Y.; Kar, S.; Scheiner, S. J. Am. Chem. Soc. 1999, 121, 9411.
102. (a) Mo, O.; Yánez, M.; Elguero, J. J. Chem. Phys. 1992, 97, 6628.
103. (b) Mo, O.; Yánez, M.; Elguero, J. J. Mol. Struct. (THEOCHEM) 1994, 314, 73.
104. (c) Espinosa, E.; Molins, E.; Lecomte, C. Chem. Phys. Lett. 1998, 285, 170.
105. Koch, U.; Popelier, P. L. A. J. Phys. Chem. A 1995, 99, 9747.
106. Popelier, P. Atoms in Molecules. An Introduction, Prentice Hall: New York, 2000.
107. Rybarczyk-Pirek, A. J.; Grabowski, S. J.; Małecka, M.; Nawrot-Modranka, J. J. Phys. Chem. A 2002, 106, 11956.
108. Rozas, I.; Alkorta, I.; Elguero, J. J. Am. Chem. Soc. 2000, 122, 11154.
109. Gatti, C.; Cargnoni, F.; Bertini, L. J. Comput. Chem. 2003, 24, 422.
110. Grabowski, S. J. J. Chem. Phys. A 2001, 105, 10739.
111. Pauling, L. J. Am. Chem. Soc. 1947, 69, 542.
112. (a) Bürgi, H.-B. Angew. Chem., Int. Ed. 1975, 14, 460.
113. (b) Dunitz, J. D. X-ray Analysis and the Structure of Organic Molecules; Cornell University Press: Ithaca, NY, 1979.
114. (c) Brown, I. D. Chem. Soc. Rev. 1978, 7, 359.
115. (d) Brown, I. D. Acta Cryst. 1992, B48, 553.
116. (e) Brown, I. D. Altermat, D. Acta Cryst. 1985, B41, 244.
117. (f) Grabowski, S. J.; Krygowski, T. M. Molecular Geometry as a Source of Chemical Information - Application of the Bond Valence-Bond Number Models. In Advances in Quantitative Structure Property Relationships; Charton, B., Charton, M., Eds.; Elsevier Science: Amsterdam, 2002; Vol. 3, pp 27-66.
118. (a) Coulson, C. A.; Danielsson, U. Ark. Fys. 1954, 8, 239.
119. (b) Coulson, C. A.; Danielsson, U. Ark. Fys. 1954, 8, 245.
120. (c) Pimentel. G. C. J. Chem. Phys. 1951, 19, 446.
121. (d) Reid, C. J. Chem. Phys. 1959, 30, 182.
122. (e) Kollman, P. A.; Allen, L. C. J. Am. Chem. Soc. 1970, 92, 6101.
123. (f) Stevens, E. D.; Lehmann, M. S.; Coppens, P. J. Am. Chem. Soc. 1977, 99, 2829.
124. (g) Desmeules, P. J.; Allen, L. C. J. Chem. Phys. 1980, 72, 4731.
125. (a) Steiner, T.; Majerz, I.; Wilson, C. C. Angew. Chem., Int. Ed. Engl. 2001, 40, 2651.
126. (b) Vishweshwar, P.; Nangia, A.; Lynch, V. M. Chem. Commun. 2001, 179.
127. (c) Wilson, C. C. Acta Cryst. 2001, B57, 435.
128. Hunt, S. W.; Higgins, K. J.; Craddock, M. B.; Brauer, C. S.; Leopold, K. R. J. Am. Chem. Soc. 2003, 125, 13850.
129. Madsen, G. K. H.; Iversen, B. B.; Larsen, F. K.; Kapon, M.; Reisner, G. M.; Herbstein, F. H. J. Am. Chem. Soc. 1998, 120, 10040.
130. Benedict, H.; Shenderovich, I. G.; Malkina, O. L.; Malkin, V. G.; Denisov, G. S.; Golubev, N. S.; Limbach, H. H. J. Am. Chem. Soc. 2000, 122, 1979.
131. (a) Isaacs, E. D.; Shukla, A.; Platzman, P. M.; Hamann, D. R.; Barbiellini, B.; Tulk, C. A. J. Phys. Chem. Solids 2000, 61, 403.
132. (b) Isaacs, E. D.; Shukla, A.; Platzman, P. M.; Hamann, D. R.; Barbiellini, B.; Tulk, C. A. Phys. Rev. Lett. 1999, 82, 600.
133. (a) Ghanty, T. K.; Staroverov, V. N.; Koren, P. R.; Davidson, E. R. J. Am. Chem. Soc. 2000, 122, 1210.
134. (b) Martin, T. W.; Derewenda, Z. S. Nat. Struct. Biol. 1999, 6, 403.
135. (c) Dannenberg, J. J.; Haskamp, L.; Masunov, A. J. Phys. Chem. A 1999, 103, 7083.
136. (d) Guerra, C. F.; Bickelhaupt, F. M.; Snijders, J. G.; Baerends, E. J. Chem. Eur. J. 1999, 5, 3581.
137. Bukowski, R.; Jeziorski, B.; Szalewicz, K. J. Chem. Phys. 1996, 104, 3306.