The nature of the C-H⋯X intermolecular interactions in molecular crystals. a theoretical perspective

Hydrogen Bonding - New Insights

Volumn , Issue , 2006, Pages 193-244

  Novoa, Juan J ^a   Mota, Fernando ^a   D'Oria, Emiliana ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

ab initio calculations; AIM theory; C H X interactions; crystal structures; Hydrogen bonds; van der Waals interactions

Indexed keywords

EID: 84890148164     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1007/978-1-4020-4853-1_5     Document Type: Chapter

References (110)

1. Israelachvili, J. (1992) Intermolecular and Surface Forces, 2nd edition, Academic, London.
2. Bernstein, J. (2002) Polymorphism in Molecular Crystals, Clarendon, Oxford.
3. Desiraju, G. R. (1989) Crystal Engineering. The Design of Organic Solids, Elsevier, Amsterdam.
4. Braga, D., Grepioni, F. and Orpen, G. (1999) Crystal Engineering: From Molecules and Crystals to Materials, Kluwer, Dordrecht.
5. Lehn, J. M. (1995) Supramolecular Chemistry. Concepts and Perspectives, VCH, Weinheim
6. Nishio, M., Hirota, M. and Umezawa, Y. (1998) The CH/p Interaction. Evidence, Nature, and Consequences, Wiley-VCH, New York.
7. Desiraju, G. R. and Steiner, T. (1999) The Weak Hydrogen Bond in Structural Chemistry and Biology, Oxford University Press, Oxford.
8. Desiraju, G. (1991) The C-H-O hydrogen bond in crystals. What is it? Acc. Chem. Res. 24, 290-296.
9. Steiner, T. (2002) The hydrogen bond in the solid state, Angew. Chem. Int. Ed. 41, 48-76.
10. Allen, F. H. (2002) The Cambridge Structural Database: a quarter of a million crystal structures and rising, Acta Crystallogr. B, 58, 380-388.
11. Calhorda, J. M. (2000) Weak hydrogen bonds: theoretical studies, Chem. Commun. 801-809.
12. Scheiner, S. (1997) Hydrogen Bonding. A Theoretical Perspective, Oxford University Press, New York.
13. Aakeroy, C. B. and Seddon, K. R. (1993) The hydrogen bond and crystal engineering, Chem. Soc. Rev. 22, 397-407.
14. Pauling, L. (1960) The Nature of the Chemical Bond, 3rd edition, Cornell University Press, Ithaca.
15. Pimentel, G. C. and McClellan, A. L. (1960) The Hydrogen Bond, W. H. Freeman, San Francisco.
16. Bader, R. F. (1990) Atoms in Molecules. A Quantum Theory, Clarendon, Oxford.
17. Braga, D., Maini, L., Grepioni, F., Mota, F., Rovira, C. and Novoa, J. J. (2000) Interanionic OH...O interactions: a solid-state study of the ring and chain motifs, Chem. Eur. J. 6, 4536-4551.
18. Dunitz, J. and Gavezzotti, A. (2005) Molecular recognition in organic crystals: directed intermolecular bonds or nonlocalized bonding? Angew. Chem. Int. Ed. 44, 1766-1787.
19. Desiraju, G. R. (2002) Hydrogen bridges in crystal engineering: interactions without borders, Acc. Chem. Res. 35, 565-573.
20. Tsirelson, V. G. and Ozerov, R. P. (1996) Institute of Physics Publishing, Bristol.
21. Alkorta, I and Elguero, J. (1999) Theoretical study of strong hydrogen bonds between neutral molecules: the case of the amine oxides and phosphine oxides as hydrogen bond acceptors, J. Phys. Chem. A 103, 272-279.
22. Espinosa, E., Molins, E. and Lecomte, C. (1998) Hydrogen bond strengths revealed by topological analyses of experimentally observed electrons densities, Chem. Phys. Lett. 285, 170-173.
23. Grabowski, S. J. (2001) Ab initio calculations on conventional and unconventional hydrogen bonds-study of the hydrogen bond strength, J. Phys. Chem. A 105, 10739-10746.
24. Maitland, G. C, Rigby, M., Smith, E. B. and Wakeham, W. (1981) Intermolecular Forces. Their Origin and Determination, Clarendon Oxford.
25. Stone, A. J. (1996) The Theory of Intermolecular Forces, Clarendon Oxford.
26. Hayes, I. C. and Stone, A. J. (1984) An intermolecular perturbation theory for the region of moderate overlap, J. Mol. Phys. 53, 83-105.
27. Novoa, J. J., Lafuente, P. and Mota, F. (1998) Are non-linear C-H-O contacts hydrogen bonds or van der Waals interactions? Establishing the limits between hydrogen bonds and van der Waals interactions, Chem. Phys. Lett. 290, 519-525.
28. Pimentel, G. C. and McClellan, A. L. (1971) Hydrogen bonding, Ann. Rev. Phys. Chem. 22, 347-385.
29. Hibbert, F. and Emsley, J. (1990) Hydrogen bonding and chemical reactivity, Adv. Phys. Org. Chem. 26, 255-379.
30. Jeffrey, G. A. and Saenger, W. (1991) Hydrogen Bonding in Biological Structures, Springer, Berlin.
31. Bondi, A. (1964) van der Waals volumes and radii, J. Phys. Chem. 68, 441-452.
32. Chickos, J. S. and Acree, Jr. W. E. (2002) Enthalpies of sublimation of organic and organo-metallic compounds, J. Phys. Chem. Ref Data 31, 537-698.
33. Gavezzotti, A. (1998) The crystal packing of organic molecules: challenge and fascination below 1000 Da, Cryst. Rev. 7, 5-121.
34. Szabo. A. and Ostlund, N. S. (1982) Modern Quantum Chemistry: Introduction to Advanced Electronic Structure Theory, Macmillan, New York.
35. Parr, R. G. and Yang, W. (1989) Density-Functional Theory of Atoms and Molecules, Oxford University Press, New York.
36. Jensen, F. (1998) Introduction to Computational Chemistry, John Wiley, New York.
37. Legon, A. C. and Millen, D. J. (1987) Directional character, strength, and nature of the hydrogen bond in gas-phase dimers, Acc. Chem. Res. 20, 39-46.
38. Jeffrey, G. A. (1997) An Introduction to Hydrogen Bonding, Oxford University Press, New York.
39. Hobza, P. and Havlas, Z. (2000) Blue-shifting hydrogen bonds, Chem. Rev. 100, 4253-4264.
40. Hallam, H. E. (1973) Vibrational Spectroscopy of Trapped Species, John Wiley, New York.
41. Ault, B. S., Balboa, A., Tevault, D. and Hurley, M. (2004) Matrix isolation infrared spectroscopy and theoretical study of the interaction of water and dimethyl methylphosphonate, J. Phys. Chem. A 108, 10094-10098.
42. Brunner, E. and Sternberg, U. (1998) Solid-state NMR investigations on the nature of hydrogen bonds, J. Prog. NMR Spectrosc. 32, 21-57.
43. Shenderovich, I. G., Tolstoy, P. M., Golubev, N. S., Smirnov, S. N., Denisov, G. S. and Limbach, H. H. (2003) Low-temperature NMR studies of the structure and dynamics of a novel series of acid-base complexes of HF with collidine exhibiting scalar couplings across hydrogen bonds, J. Am. Chem. Soc. 125, 11710-11720.
44. Novoa, J. J., Tarron, B., Whangbo, M.-W. and Williams, J. (1991) Interaction energies associated with short intermolecular contacts of C-H bonds. Ab initio computational study of the C-H-O contact interaction in CH4...OH2, J. Chem. Phys. 95, 5179-5186.
45. Novoa, J. J., Nobeli, I., Grepioni, F. and Braga, D. (2000) Are all short O-H-O contacts hydrogen bonds? A quantitative look at the nature of O-H-O intermolecular hydrogen bonds, New. J. Chem. 24, 5-8.
46. Braga, D., Grepioni, F. and Novoa, J. J. (1998) Inter-anion OH- O hydrogen bond like interactions: the breakdown of the strength-length analogy, Chem. Commun. 18, 1959-1960.
47. Feller, D. (1992) Application of systematic sequences of wavefunctions to the water dimer, J. Chem. Phys. 96, 6104-6114.
48. Chakravorty, S. J. and Davidson, E. R. (1993) The water dimer: correlation energy calculations, J. Phys. Chem. 97, 6373-6383.
49. n, n = 1-6. II. Analysis of many-body interactions, J. Chem. Phys. 100, 7523-7534.
50. Sim, F., St-Amant, A., Papai, I. and Salahub, D. R. (1992) Gaussian density functional calculations on hydrogen-bonded systems, J. Am. Chem. Soc. 114, 4391-4400.
51. Kim, K. and Jordan, K. D. (1994) Comparison of density functional and MP2 calculations on the water monomer and dimer, J. Phys. Chem. 98, 10089-10094.
52. Novoa, J. J. and Sosa, C. (1995) Evaluation of the density-functional approximation on the computation of hydrogen-bond interactions, J. Phys. Chem. 99, 15837-15845.
53. Becke, A. D. J. Chem. Phys. 98 (1993) 5648
54. Lee, C, Yang, W. and Parr, R. G, Phys. Rev. B. 37 (1988) 785.
55. Dunning, Jr. T. H. (1989) J. Chem. Phys. 90, 1007.
56. Ordutola, J. A. and Dyke, T. R. (1980) Partially deuterated water dimers: microwave spectra and structure J. Chem. Phys. 72, 5062-5070.
57. Kuchitsu, K. and Morino, Y. (1965) Estimation of anharmonic potential constants. I. linear XY2 molecules, Bull. Chem. Soc. Jpn. 38, 805-816.
58. Boys, S. F. and Bernardi, F. (1970) Calculation of small molecular interactions by differences of separate total energies-some procedures with reduced errors, Mol. Phys. 19, 553-566.
59. Novoa, J. J., Planas, M. and Whangbo, M.-H. (1994) A numerical evaluation of the counterpoise method on hydrogen bonded complexes using near complete basis sets, Chem. Phys. Lett. 225, 240-246.
60. 2O, Chem. Phys. Lett. 251, 33-46.
61. van Duijneveldt, F. B., van der Rijdt, J. G C. M. and van Lenthe, J. H. (1994) State of the art in counterpoise theory, Chem. Rev. 94, 1873-1885.
62. D'Oria, E. and Novoa, J. J. (2004) The strength-length relationship at the light of ab initio computations: does it really hold? Cryst. Eng. Comm., 64, 367-376.
63. Etter, M. C. (1990) Encoding and decoding hydrogen bond patterns of organic compounds, Acc. Chem. Res. 23, 120-126.
64. Bernstein, J., Davis, R. E., Shimoni, L. and Chang, N.-L. (1995) Patterns in hydrogen bonding: functionality and graph set analysis in crystals, Angew. Chem. Int. Ed. 34, 1555-1573.
65. Desiraju, G. R. (1995) Supramolecular synthons in crystal engineering-A new organic synthesis, Angew. Chem. Int. Ed. 34, 2311-2327.
66. Gatti, C, May, E., Destro, R. and Cargnoni, F. (2002) Fundamental properties and nature of C-H-O interactions in crystals on the basis of experimental and theoretical charge densities. The case of 3, 4-bis(dimethylamino)-3-cyclobutene-1, 2-dione (DMACB) crystal, J. Phys. Chem. A 106, 2707-2720.
67. Whalley, E. (1976) The Hydrogen Bond (Shuster, P., Zundel, G and Sandorfy, C, editors), North-Holland, Amsterdam, p. 1427).
68. Lee, C, Chen, H. and Fitzgerald, G (1995) Chemical bonding in water clusters, J. Chem. Phys. 102, 1266-1269.
69. Suhai, S. (1994) Cooperative effects in hydrogen bonding: fourth order many-body perturbation theory studies of water oligomers and of an infinite chain as a model for ice, J. Chem. Phys. 101, 9766-9782.
70. Donohue, J. (1968) in Structural Chemistry and Molecular Biology (Rich, A. and Davidson, N., editors), W. H. Freeman, San Francisco, pp. 459-463.
71. Allerhand, A. and Schleyer, P. v. R. (1963) A survey of C-H groups as proton donors in hydrogen bonding, J. Am. Chem. Soc. 85, 1715-1723.
72. Green, R. D. (1974) Hydrogen Bonding by C-H groups, MacMillan, London.
73. Taylor, R. and Kennard, O. (1982) Crystallographic evidence for the existence of C-H-O, C-H-N and C-H-Cl hydrogen bonds, J. Am. Chem. Soc. 104, 5063-5070.
74. Desiraju, G R. (1991) The C-H-O hydrogen bond in crystals: what is it? Acc. Chem. Res. 24, 290-296.
75. Steiner, T. (1997) Unrolling the hydrogen bond properties of C-H-O interactions, Chem. Commun. 727-734.
76. 3) hydrogen bond can be? Chem. Phys. Lett. 266, 23-30.
77. Vargas, R., Garza, J., Friesner, R. A., Stern, H, Hay, B. P. and Dixon, D. A. (2001) Strength of the N-H-O=C and C-H-O=C bonds in formamide and N-methylacetamide dimers, J. Am. Chem. Soc. 105, 4863-4968.
78. Turi, L. and Dannenberg, J. J. (1993) Molecular orbital studies of C-H-O H-bonded complexes, J. Phys. Chem. 97, 7899-7909.
79. Gu, Y., Tar, T. and Scheiner, S. (1999) Fundamental properties of the C-H-O interaction: is it a true hydrogen bond? J. Am. Chem. Soc. 121, 9411-9422.
80. Mizuno, K., Ochi, T. and Shindo, Y. (1998) Hydrophobic hydration of acetone probed by nuclear magnetic resonance and infrared: evidence for the interaction C-H...OH2, J. Chem. Phys. 109, 9502-9507.
81. Steiner, T. and Saenger, W. (1992) Geometry of C-H-O hydrogen bonds in carbohydrate crystal structures. Analysis of neutron diffraction data, J. Am. Chem. Soc. 114, 10146-10154.
82. Novoa, J. J., Whangbo, M.-H. and Williams, J. M. (1991) Interaction energies associated with short intermolecular contacts of C-H bonds. II Ab initio computational study of the C-H- H-C interactions in methane dimer, J. Chem. Phys. 94, 4835-4841.
83. Koch, U. and Popelier, P. L. A. (1995) Characterization of C-H-O hydrogen bonds on the basis of the charge density, J. Phys. Chem. 99, 9747-9754.
84. Spackman, M. A. (1999) Hydrogen bond energetics from topological analysis of experimental electron densities: recognizing the importance of the promolecule, Chem. Phys. Lett. 301, 425-429.
85. +[Cr(OCH3)] and the breakdown of the length/strength analogy, New. J. Chem. 22, 755-757.
86. Braga, D., Bazzi, C, Grepioni, F. and Novoa, J. J. (1999) Electrostatic compression on non-covalent interactions: the case of p stacks involving ions, New. J. Chem. 23, 577-579.
87. Braga, D., Maini, L., Grepioni, F., Mota, F., Rovira, C. and Novoa, J. J. (2000) Interanionic O-H...O interactions: a solid-state and computational study of the ring and chain motifs, Chem. Eur. J. 6, 4536-4551.
88. Braga, D., Novoa, J. J. and Grepioni, F. (2001) On the charge delocalization in partially deprotonated polycarboxylic acid anions and zwitterions forming O-H...O interactions in the solid state, New. J. Chem. 25, 226-230.
89. Braga, D., D'Oria, E., Grepioni, F., Mota, F., Novoa, J. J. and Rovira, C. (2002) O-H-O interactions involving doubly charged anions: charge-compression in carbonate-bicarbonate crystals, Chem. Eur. J. 8, 1173-1180.
90. Steiner. T. (1999) Inter-anion O-H-O interactions are classical hydrogen bonds, Chem. Commun. 2299-2300.
91. Mascal, M., Marajo, C. E. and Blake, A. J. (2000) Breakdown of the hydrogen bond strength-length analogy: a revision, Chem. Commun. 1591-1592.
92. Macchi, P., Iversen, B. B., Sironi, A., Chokoumakas, B. C. and Larsen, F. K. (2000) Breakdown of the hydrogen bond strength-length analogy: a revision Angew. Chem. Int. Ed. 39, 2719-2722.
93. 2, Angew. Chem. Int. Ed. 40, 2540-2545.
94. 2 dimers found ionic crystals, Cyrst. Eng. Comm. 4, 373-377.
95. 2 dimers: two-electron, four-center cation-mediated CC bonding interactions involving p* electrons, Chem. Eur. J. 8, 4894-4908.
96. White-Morris, R. L., Olmstead, M. M., Jiang, F., Tinti, D. S. and Balch, A. L. (2002) Remarkable variations in the luminescence of frozen solutions of [Au{C(NHMe)2}2](PF6)' 0. 5(acetone). Structural and spectroscopic studies of the effects of anions and solvents on Gold(I) carbene complexes, J. Am. Chem. Soc. 124, 2327-2336.
97. Schmidbaur, H. (1995) High-carat gold compounds, Chem. Soc. Rev. 391-400.
98. D'Oria, E., Braga, D., Grepioni, F. and Novoa J. J. Unpublished results.
99. Williams, J. M, Ferraro, J. R., Thorn, R. J., Carlson, K. D., Geiser, U., Wang, H. H. Kini, A. M. and Whangbo, M.-H. (1992) Organic Superconductors (Including Fullerenes). Synthesis, Structure, Properties, and Theory, Prentice Hall, Englewood Cliffs.
100. Ishiguro, T. and Yamaji, K. (1990) Organic Superconductors, Springer-Verlag, Berlin.
101. Novoa, J. J., Rovira, M. C, Rovira, C, Veciana, J. and Tarres, J. (1995) C-H-S and S-S: two major forces in organic conductors, Adv. Mater. 7, 233-237.
102. 2S- CH4 model complex, Chem. Phys. Lett. 279, 140-150.
103. Aldritch, P. D., Kukolich, S. G. and Campbell, E. J. (1983) The structure and molecular properties of the acetylene-HCN complex as determined from rotational spectra, J. Chem. Phys. 78, 3521-3530.
104. Fraser, G. T., Suenram, R. D., Lovas, F. J., Pine, A. S., Hougen, J. T., Leferty, W. J. and Muenter, J. S. (1988) Infrared and microwave investigations of interconversion tunneling in the acetylene dimer, J. Chem. Phys. 89, 6028-6045.
105. 2, J. Chem. Phys. 88, 3811-3816.
106. Novoa, J. J. and Mota, F. (2000) The C-H-p bonds: strength, identification and hydrogen-bonded nature. A theoretical study, Chem. Phys. Lett. 318, 345-354.
107. Fan, M.-F., Lin, Z., McGrady, J. E. and Mingos, D. M. P. (1996) Novel intermolecular C-H-p interactions. Ab initio and density functional theory study, J. Chem. Soc. Perkin Trans. 2, 563-568.
108. Steiner, T., Starikov, E. B. and Tamm, M. (1996) Weak hydrogen bonding. Part 3. A benzyl group accepting equally strong hydrogen bonds from O-H and C-H donors. 5-Ethynyl-5-H-dibenzo[a, d]cyclohepten-5-ol, J. Chem. Soc. Perkin Trans. 2, 67-71.
109. Umezawa, Y. and Nishio, M. (1998) CH=p interactions as demonstrated in the crystal structure of the guanine-nucleotide binding proteins src homology-2 domains and human growth hormone in complex with their specific ligands, Bioorg. Med. Chem. 6, 493-504.
110. Dance, I. and Scudder, M. (1995) The sextuple phenyl embrace, a ubiquituous concerted supramolecular motif, Chem. Commun. 1039-1040.