Nature of H-bonding in clusters, liquids, and enzymes: An ab initio, natural bond orbital perspective

Journal of Molecular Structure: THEOCHEM

Volumn 398-399, Issue , 1997, Pages 181-197

  Weinhold, F ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

Clusters; Enzymes; H bonding; Liquids

Indexed keywords

EID: 30244443082     PISSN: 01661280     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0166-1280(96)04936-6     Document Type: Article

References (77)

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8. The following quotations from well-known General Chemistry texts are typical: "Hydrogen bonding is a special form of dipole-dipole attraction..." (Kotz and Purcell, p. 507); "The hydrogen bond is a special type of dipole-dipole interaction..." (Chang, p. 384); "Hydrogen bonds are a particularly strong form of dipole-dipole attraction..." (McQuarrie and Rock, p 475); "A hydrogen bond is a dipole-dipole force that is exceptionally strong..." (Gillespie, Humphreys, Baird, and Robinson, p. 479).
9. The following quotations from well-known General Chemistry texts are typical: "Hydrogen bonding is a special form of dipole-dipole attraction..." (Kotz and Purcell, p. 507); "The hydrogen bond is a special type of dipole-dipole interaction..." (Chang, p. 384); "Hydrogen bonds are a particularly strong form of dipole-dipole attraction..." (McQuarrie and Rock, p 475); "A hydrogen bond is a dipole-dipole force that is exceptionally strong..." (Gillespie, Humphreys, Baird, and Robinson, p. 479).
10. The following quotations from well-known General Chemistry texts are typical: "Hydrogen bonding is a special form of dipole-dipole attraction..." (Kotz and Purcell, p. 507); "The hydrogen bond is a special type of dipole-dipole interaction..." (Chang, p. 384); "Hydrogen bonds are a particularly strong form of dipole-dipole attraction..." (McQuarrie and Rock, p 475); "A hydrogen bond is a dipole-dipole force that is exceptionally strong..." (Gillespie, Humphreys, Baird, and Robinson, p. 479).
11. The following quotations from well-known General Chemistry texts are typical: "Hydrogen bonding is a special form of dipole-dipole attraction..." (Kotz and Purcell, p. 507); "The hydrogen bond is a special type of dipole-dipole interaction..." (Chang, p. 384); "Hydrogen bonds are a particularly strong form of dipole-dipole attraction..." (McQuarrie and Rock, p 475); "A hydrogen bond is a dipole-dipole force that is exceptionally strong..." (Gillespie, Humphreys, Baird, and Robinson, p. 479).
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25. Representative examples: F.H. Stillinger, A. Rahman, J. Chem. Phys. 60 (1974) 1545; S.J. Weiner, P.A. Kollman, D.T. Nguyen, D.A. Case, J. Comput. Chem. 7 (1986) 230; B.R. Brooks, R.E. Bruccoleri, B.D. Olafson, D.J. States, S. Swaminathan, M. Karplus, J. Comput. Chem. 4 (1983) 187; K.S. Kim, E. Clementi, J. Am. Chem. Soc. 107 (1985) 5504; A.D. Buckingham, P.W. Fowler, J.M. Hutson, Chem. Rev. 88 (1988) 963.
26. Representative examples: F.H. Stillinger, A. Rahman, J. Chem. Phys. 60 (1974) 1545; S.J. Weiner, P.A. Kollman, D.T. Nguyen, D.A. Case, J. Comput. Chem. 7 (1986) 230; B.R. Brooks, R.E. Bruccoleri, B.D. Olafson, D.J. States, S. Swaminathan, M. Karplus, J. Comput. Chem. 4 (1983) 187; K.S. Kim, E. Clementi, J. Am. Chem. Soc. 107 (1985) 5504; A.D. Buckingham, P.W. Fowler, J.M. Hutson, Chem. Rev. 88 (1988) 963.
27. Representative examples: F.H. Stillinger, A. Rahman, J. Chem. Phys. 60 (1974) 1545; S.J. Weiner, P.A. Kollman, D.T. Nguyen, D.A. Case, J. Comput. Chem. 7 (1986) 230; B.R. Brooks, R.E. Bruccoleri, B.D. Olafson, D.J. States, S. Swaminathan, M. Karplus, J. Comput. Chem. 4 (1983) 187; K.S. Kim, E. Clementi, J. Am. Chem. Soc. 107 (1985) 5504; A.D. Buckingham, P.W. Fowler, J.M. Hutson, Chem. Rev. 88 (1988) 963.
28. Representative examples: F.H. Stillinger, A. Rahman, J. Chem. Phys. 60 (1974) 1545; S.J. Weiner, P.A. Kollman, D.T. Nguyen, D.A. Case, J. Comput. Chem. 7 (1986) 230; B.R. Brooks, R.E. Bruccoleri, B.D. Olafson, D.J. States, S. Swaminathan, M. Karplus, J. Comput. Chem. 4 (1983) 187; K.S. Kim, E. Clementi, J. Am. Chem. Soc. 107 (1985) 5504; A.D. Buckingham, P.W. Fowler, J.M. Hutson, Chem. Rev. 88 (1988) 963.
29. H. Guo, M. Karplus, J. Phys. Chem. 98 (1994) 7104; P.W. Fowler, A.J. Stone, A.D. Buckingham (private communication).
30. H. Guo, M. Karplus, J. Phys. Chem. 98 (1994) 7104; P.W. Fowler, A.J. Stone, A.D. Buckingham (private communication).
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32. See e.g. J.E. Del Bene, J.A. Pople, Chem. Phys. Lett. 4, (1969) 426; P. Seiler, G.R. Weisman, E.D. Glendening, F. Weinhold, V.B. Johnson, J.D. Dunitz, Angew. Chem. Int. Ed. Engl. 26, (1987) 1175; K.B. Lipkowitz, D.B. Boyd, Reviews in Computational Chemistry, VCH, New York, 1991, vol. 2, pp. 165-218; S. Suhai, Int. J. Quantum Chem. 52 (1994) 395; L. Ojamiie, K. Hermansson, J. Phys. Chem. 98 (1994) 4271; B.F. King, F. Weinhold, J. Chem. Phys. 103 (1995) 333; A.S. Edison, F. Weinhold, J.L. Markley, J. Am. Chem. Soc. 117 (1995) 9619-9624. For experimental evidence supporting cooperativity in H-bonded systems, see e.g. H.S. Frank, W. Wen, Disc. Faraday Soc. 24 (1957) 133; P.L. Huyskens, W.A.P. Luck, T. Zeegers-Huyskens, Intermolecular Forces, Springer, Berlin, 1991, pp. 251-280; J.D. Cruzan, L.B. Braly, Kun Liu, M.G. Brown, J.G. Loeser, R.J. Saykally, Science 271 (1996) 59.
33. See e.g. J.E. Del Bene, J.A. Pople, Chem. Phys. Lett. 4, (1969) 426; P. Seiler, G.R. Weisman, E.D. Glendening, F. Weinhold, V.B. Johnson, J.D. Dunitz, Angew. Chem. Int. Ed. Engl. 26, (1987) 1175; K.B. Lipkowitz, D.B. Boyd, Reviews in Computational Chemistry, VCH, New York, 1991, vol. 2, pp. 165-218; S. Suhai, Int. J. Quantum Chem. 52 (1994) 395; L. Ojamiie, K. Hermansson, J. Phys. Chem. 98 (1994) 4271; B.F. King, F. Weinhold, J. Chem. Phys. 103 (1995) 333; A.S. Edison, F. Weinhold, J.L. Markley, J. Am. Chem. Soc. 117 (1995) 9619-9624. For experimental evidence supporting cooperativity in H-bonded systems, see e.g. H.S. Frank, W. Wen, Disc. Faraday Soc. 24 (1957) 133; P.L. Huyskens, W.A.P. Luck, T. Zeegers-Huyskens, Intermolecular Forces, Springer, Berlin, 1991, pp. 251-280; J.D. Cruzan, L.B. Braly, Kun Liu, M.G. Brown, J.G. Loeser, R.J. Saykally, Science 271 (1996) 59.
34. See e.g. J.E. Del Bene, J.A. Pople, Chem. Phys. Lett. 4, (1969) 426; P. Seiler, G.R. Weisman, E.D. Glendening, F. Weinhold, V.B. Johnson, J.D. Dunitz, Angew. Chem. Int. Ed. Engl. 26, (1987) 1175; K.B. Lipkowitz, D.B. Boyd, Reviews in Computational Chemistry, VCH, New York, 1991, vol. 2, pp. 165-218; S. Suhai, Int. J. Quantum Chem. 52 (1994) 395; L. Ojamiie, K. Hermansson, J. Phys. Chem. 98 (1994) 4271; B.F. King, F. Weinhold, J. Chem. Phys. 103 (1995) 333; A.S. Edison, F. Weinhold, J.L. Markley, J. Am. Chem. Soc. 117 (1995) 9619-9624. For experimental evidence supporting cooperativity in H-bonded systems, see e.g. H.S. Frank, W. Wen, Disc. Faraday Soc. 24 (1957) 133; P.L. Huyskens, W.A.P. Luck, T. Zeegers-Huyskens, Intermolecular Forces, Springer, Berlin, 1991, pp. 251-280; J.D. Cruzan, L.B. Braly, Kun Liu, M.G. Brown, J.G. Loeser, R.J. Saykally, Science 271 (1996) 59.
35. See e.g. J.E. Del Bene, J.A. Pople, Chem. Phys. Lett. 4, (1969) 426; P. Seiler, G.R. Weisman, E.D. Glendening, F. Weinhold, V.B. Johnson, J.D. Dunitz, Angew. Chem. Int. Ed. Engl. 26, (1987) 1175; K.B. Lipkowitz, D.B. Boyd, Reviews in Computational Chemistry, VCH, New York, 1991, vol. 2, pp. 165-218; S. Suhai, Int. J. Quantum Chem. 52 (1994) 395; L. Ojamiie, K. Hermansson, J. Phys. Chem. 98 (1994) 4271; B.F. King, F. Weinhold, J. Chem. Phys. 103 (1995) 333; A.S. Edison, F. Weinhold, J.L. Markley, J. Am. Chem. Soc. 117 (1995) 9619-9624. For experimental evidence supporting cooperativity in H-bonded systems, see e.g. H.S. Frank, W. Wen, Disc. Faraday Soc. 24 (1957) 133; P.L. Huyskens, W.A.P. Luck, T. Zeegers-Huyskens, Intermolecular Forces, Springer, Berlin, 1991, pp. 251-280; J.D. Cruzan, L.B. Braly, Kun Liu, M.G. Brown, J.G. Loeser, R.J. Saykally, Science 271 (1996) 59.
36. See e.g. J.E. Del Bene, J.A. Pople, Chem. Phys. Lett. 4, (1969) 426; P. Seiler, G.R. Weisman, E.D. Glendening, F. Weinhold, V.B. Johnson, J.D. Dunitz, Angew. Chem. Int. Ed. Engl. 26, (1987) 1175; K.B. Lipkowitz, D.B. Boyd, Reviews in Computational Chemistry, VCH, New York, 1991, vol. 2, pp. 165-218; S. Suhai, Int. J. Quantum Chem. 52 (1994) 395; L. Ojamiie, K. Hermansson, J. Phys. Chem. 98 (1994) 4271; B.F. King, F. Weinhold, J. Chem. Phys. 103 (1995) 333; A.S. Edison, F. Weinhold, J.L. Markley, J. Am. Chem. Soc. 117 (1995) 9619-9624. For experimental evidence supporting cooperativity in H-bonded systems, see e.g. H.S. Frank, W. Wen, Disc. Faraday Soc. 24 (1957) 133; P.L. Huyskens, W.A.P. Luck, T. Zeegers-Huyskens, Intermolecular Forces, Springer, Berlin, 1991, pp. 251-280; J.D. Cruzan, L.B. Braly, Kun Liu, M.G. Brown, J.G. Loeser, R.J. Saykally, Science 271 (1996) 59.
37. See e.g. J.E. Del Bene, J.A. Pople, Chem. Phys. Lett. 4, (1969) 426; P. Seiler, G.R. Weisman, E.D. Glendening, F. Weinhold, V.B. Johnson, J.D. Dunitz, Angew. Chem. Int. Ed. Engl. 26, (1987) 1175; K.B. Lipkowitz, D.B. Boyd, Reviews in Computational Chemistry, VCH, New York, 1991, vol. 2, pp. 165-218; S. Suhai, Int. J. Quantum Chem. 52 (1994) 395; L. Ojamiie, K. Hermansson, J. Phys. Chem. 98 (1994) 4271; B.F. King, F. Weinhold, J. Chem. Phys. 103 (1995) 333; A.S. Edison, F. Weinhold, J.L. Markley, J. Am. Chem. Soc. 117 (1995) 9619-9624. For experimental evidence supporting cooperativity in H-bonded systems, see e.g. H.S. Frank, W. Wen, Disc. Faraday Soc. 24 (1957) 133; P.L. Huyskens, W.A.P. Luck, T. Zeegers-Huyskens, Intermolecular Forces, Springer, Berlin, 1991, pp. 251-280; J.D. Cruzan, L.B. Braly, Kun Liu, M.G. Brown, J.G. Loeser, R.J. Saykally, Science 271 (1996) 59.
38. See e.g. J.E. Del Bene, J.A. Pople, Chem. Phys. Lett. 4, (1969) 426; P. Seiler, G.R. Weisman, E.D. Glendening, F. Weinhold, V.B. Johnson, J.D. Dunitz, Angew. Chem. Int. Ed. Engl. 26, (1987) 1175; K.B. Lipkowitz, D.B. Boyd, Reviews in Computational Chemistry, VCH, New York, 1991, vol. 2, pp. 165-218; S. Suhai, Int. J. Quantum Chem. 52 (1994) 395; L. Ojamiie, K. Hermansson, J. Phys. Chem. 98 (1994) 4271; B.F. King, F. Weinhold, J. Chem. Phys. 103 (1995) 333; A.S. Edison, F. Weinhold, J.L. Markley, J. Am. Chem. Soc. 117 (1995) 9619-9624. For experimental evidence supporting cooperativity in H-bonded systems, see e.g. H.S. Frank, W. Wen, Disc. Faraday Soc. 24 (1957) 133; P.L. Huyskens, W.A.P. Luck, T. Zeegers-Huyskens, Intermolecular Forces, Springer, Berlin, 1991, pp. 251-280; J.D. Cruzan, L.B. Braly, Kun Liu, M.G. Brown, J.G. Loeser, R.J. Saykally, Science 271 (1996) 59.
39. See e.g. J.E. Del Bene, J.A. Pople, Chem. Phys. Lett. 4, (1969) 426; P. Seiler, G.R. Weisman, E.D. Glendening, F. Weinhold, V.B. Johnson, J.D. Dunitz, Angew. Chem. Int. Ed. Engl. 26, (1987) 1175; K.B. Lipkowitz, D.B. Boyd, Reviews in Computational Chemistry, VCH, New York, 1991, vol. 2, pp. 165-218; S. Suhai, Int. J. Quantum Chem. 52 (1994) 395; L. Ojamiie, K. Hermansson, J. Phys. Chem. 98 (1994) 4271; B.F. King, F. Weinhold, J. Chem. Phys. 103 (1995) 333; A.S. Edison, F. Weinhold, J.L. Markley, J. Am. Chem. Soc. 117 (1995) 9619-9624. For experimental evidence supporting cooperativity in H-bonded systems, see e.g. H.S. Frank, W. Wen, Disc. Faraday Soc. 24 (1957) 133; P.L. Huyskens, W.A.P. Luck, T. Zeegers-Huyskens, Intermolecular Forces, Springer, Berlin, 1991, pp. 251-280; J.D. Cruzan, L.B. Braly, Kun Liu, M.G. Brown, J.G. Loeser, R.J. Saykally, Science 271 (1996) 59.
40. See e.g. J.E. Del Bene, J.A. Pople, Chem. Phys. Lett. 4, (1969) 426; P. Seiler, G.R. Weisman, E.D. Glendening, F. Weinhold, V.B. Johnson, J.D. Dunitz, Angew. Chem. Int. Ed. Engl. 26, (1987) 1175; K.B. Lipkowitz, D.B. Boyd, Reviews in Computational Chemistry, VCH, New York, 1991, vol. 2, pp. 165-218; S. Suhai, Int. J. Quantum Chem. 52 (1994) 395; L. Ojamiie, K. Hermansson, J. Phys. Chem. 98 (1994) 4271; B.F. King, F. Weinhold, J. Chem. Phys. 103 (1995) 333; A.S. Edison, F. Weinhold, J.L. Markley, J. Am. Chem. Soc. 117 (1995) 9619-9624. For experimental evidence supporting cooperativity in H-bonded systems, see e.g. H.S. Frank, W. Wen, Disc. Faraday Soc. 24 (1957) 133; P.L. Huyskens, W.A.P. Luck, T. Zeegers-Huyskens, Intermolecular Forces, Springer, Berlin, 1991, pp. 251-280; J.D. Cruzan, L.B. Braly, Kun Liu, M.G. Brown, J.G. Loeser, R.J. Saykally, Science 271 (1996) 59.
41. See e.g. J.E. Del Bene, J.A. Pople, Chem. Phys. Lett. 4, (1969) 426; P. Seiler, G.R. Weisman, E.D. Glendening, F. Weinhold, V.B. Johnson, J.D. Dunitz, Angew. Chem. Int. Ed. Engl. 26, (1987) 1175; K.B. Lipkowitz, D.B. Boyd, Reviews in Computational Chemistry, VCH, New York, 1991, vol. 2, pp. 165-218; S. Suhai, Int. J. Quantum Chem. 52 (1994) 395; L. Ojamiie, K. Hermansson, J. Phys. Chem. 98 (1994) 4271; B.F. King, F. Weinhold, J. Chem. Phys. 103 (1995) 333; A.S. Edison, F. Weinhold, J.L. Markley, J. Am. Chem. Soc. 117 (1995) 9619-9624. For experimental evidence supporting cooperativity in H-bonded systems, see e.g. H.S. Frank, W. Wen, Disc. Faraday Soc. 24 (1957) 133; P.L. Huyskens, W.A.P. Luck, T. Zeegers-Huyskens, Intermolecular Forces, Springer, Berlin, 1991, pp. 251-280; J.D. Cruzan, L.B. Braly, Kun Liu, M.G. Brown, J.G. Loeser, R.J. Saykally, Science 271 (1996) 59.
42. F. Weinhold (in prep.); see [23-29] below.
43. J.W. Gibbs, Elementary Principles in Statistical Mechanics, Developed with Especial Reference to the Rational Foundations of Thermodynamics, Yale U. Press, New Haven, 1902.
44. E. Silla, I. Tunon, J.L. Pascual-Ahuir, J. Comput. Chem. 12 (1991) 1077.
45. W.G. Hehre, L. Radom, P.V.R. Schleyer, J.A. Pople, Ab Initio Molecular Orbital Theory, Wiley, New York, 1986, p. 229ff. This reference should be consulted for standard basis set designations and theoretical methods used herein.
46. S.F. Boys, F. Bernardi, Mol. Phys. 19 (1970) 553.
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52. J.A. Bohmann, Ph. D. Thesis, U. Wisconsin, Madison, 1996.
53. J.A. Bohmann, M. Wendt, F. Weinhold, T.C. Farrar (in prep).
54. P.T. Lee, F. Weinhold, T.C. Farrar (in prep.).
55. M. Wendt, D. Sykes, F. Weinhold, T.C. Farrar (in prep.).
56. R. Ludwig, F. Weinhold, T.C. Farrar (in prep.).
57. As in other aspects of general acid-base chemistry, the Lewis (electronic) perspective affords greater generality than the Brønsted (protonic) perspective, and we accordingly employ the terms "donor" and "acceptor" in the electron-pair sense, contrary to more conventional H-bond usage.
58. -1, of deleting the 〈n|ℱ̂|σ*〉 matrix element and recalculating the SCF energy; [7].
59. Even the sign of the CH bond dipole moment is disputed [K.B. Wibert, J.J. Wendolski, J. Phys. Chem. 88 (1984) 586; A.E. Reed, F. Weinhold, J. Chem. Phys. 84 (1986) 2428], and its value is commonly set to zero in empirical bond dipole assignments [O. Exner, Dipole Moments in Organic Chemistry, George Thieme, Stuttgart, 1975].
60. Even the sign of the CH bond dipole moment is disputed [K.B. Wibert, J.J. Wendolski, J. Phys. Chem. 88 (1984) 586; A.E. Reed, F. Weinhold, J. Chem. Phys. 84 (1986) 2428], and its value is commonly set to zero in empirical bond dipole assignments [O. Exner, Dipole Moments in Organic Chemistry, George Thieme, Stuttgart, 1975].
61. Even the sign of the CH bond dipole moment is disputed [K.B. Wibert, J.J. Wendolski, J. Phys. Chem. 88 (1984) 586; A.E. Reed, F. Weinhold, J. Chem. Phys. 84 (1986) 2428], and its value is commonly set to zero in empirical bond dipole assignments [O. Exner, Dipole Moments in Organic Chemistry, George Thieme, Stuttgart, 1975].
62. L.A. Curtiss, D.J. Pochatko, A.E. Reed, F. Weinhold, J. Chem. Phys. 82 (1985) 2679.
63. H, polarized toward H.
64. B increases.
65. A.E. Reed, F. Weinhold, L.A. Curtiss, D. Pochatko, J. Chem. Phys. 84 (1986) 5687.
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