Blue-shifting hydrogen bonds

Chemical Reviews

Volumn 100, Issue 11, 2000, Pages 4253-4264

  Hobza, Pavel ^a,b   Havlas, Zdeněk ^b  

^a J HEYROVSKÝ INSTITUTE OF PHYSICAL CHEMISTRY   (Czech Republic)

^b INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

ATOMS; BENZENE; BINDING ENERGY; CARBON; CARRIER CONCENTRATION; DIMERS; ELECTRONIC STRUCTURE; MOLECULAR DYNAMICS; MOLECULAR STRUCTURE; MOLECULAR VIBRATIONS; QUANTUM THEORY;

BLUE SHIFTING HYDROGEN BOND; INTRAMOLECULAR INTERACTION; MOLECULAR ORBITALS;

HYDROGEN BONDS;

EID: 0034317323     PISSN: 00092665     EISSN: None     Source Type: Journal    
DOI: 10.1021/cr990050q     Document Type: Article

References (59)

1. Jeffrey, G. A. An Introduction to Hydrogen Bonding; Oxford University Press: New York, 1997.
2. Desiraju, G. R.; Steiner, T. The Weak Hydrogen Bond; Oxford University Press: Oxford, 1999.
3. Schemer, S. Hydrogen Bonding; Oxford University Press: New York, 1997.
4. Pauling, L. J. Am. Chem. Soc. 1931, 53, 1367.
5. Suzuki, S.; Green, P. G.; Bumgarner, R. E.; Dasgupta, S.; Goddard, W. A., III; Blake, G. A. Science 1992, 257, 942.
6. Pribble, R. N.; Garret, A. W.; Haber, K.; Zwier, T. S. J. Chem. Phys. 1995, 103, 531.
7. Djafari, S.; Lembach, G.; Barth, H.-D.; Brutschy, B. Z. Phys. Chem. 1996, 195, 253.
8. Djafari, S.; Barth, H.-D.; Buchhold, K.; Brutschy, B. J. Chem. Phys. 1997, 107, 10573.
9. Legon, A. C.; Wallwork, A. L.; Warner, H. E. Chem. Phys. Lett. 1992, 191, 97.
10. Legon, A. C.; Roberts, B. P.; Wallwork, A. L. Chem. Phys. Lett. 1990, 173, 107.
11. Steiner, T.; Desiraju, G. R. Chem Commun. 1998, 891.
12. Steiner, T.; Tamm, M.; Grzegorzewski, A.; Schulte, M.; Veldman, N.; Schreurs, A. M. M.; Kanters, J. A.; Kroon, J.; van der Maas, J. J. Chem. Soc., Perkin Trans. 2 1996, 2441.
13. Andrews, A. M.; Hillig, K. W., II.; Kuczkowski, R. L. J. Chem. Phys. 1992, 96, 1783.
14. Steiner, T.; Starikov, E. B.; Amado, A. M.; Teixeira-Dias, J. J. C. J. Chem. Soc., Perkin 2 1995, 1321.
15. Block, P. A.; Marshall, M. D.; Pedersen, L. G.; Miller, R. E. J. Chem. Phys. 1992, 96, 7321.
16. Sodupe, M.; Rios, R.; Branchadell, V.; Nicholas, T.; Oliva, A.; Danneneberg, J. J. J. Am. Chem. Soc. 1997, 119, 4232.
17. Aakeröy, C. B.; Seddon, K. R. Chem. Soc. Rev. 1993, 397.
18. Kock, U.; Popelier, P. L. A. J. Phys Chem. 1995, 99, 9747. Popelier, P. L. A. J. Phys. Chem. A 1998, 102, 1873.
19. Kock, U.; Popelier, P. L. A. J. Phys Chem. 1995, 99, 9747. Popelier, P. L. A. J. Phys. Chem. A 1998, 102, 1873.
20. Maes, G.; Smets, J.; Adamowicz, L.; McCarthy, W.; VanBael, M. K.; Houben, L.; Schoone, K. J. Mol. Struct. 1997, 410-411, 315.
21. Smets, J.; McCarthy, W.; Maes, G.; Adamowicz, L. J. Mol. Struct. 1999, 476, 27.
22. Buděšinský, M.; Fiedler, P.; Arnold, Z. Synthesis 1989, 858.
23. Keshavarz, K. M.; Cox, S. D.; Angus, R. O., Jr.; Wudl, F. Synthesis 1988, 641.
24. Boldeskul, I. E.; Tsymbal, I. F.; Ryltsev, E. V.; Latajka, Z.; Barnes, A. J. J. Mol. Struct. 1997, 436, 167.
25. Hobza, P.; Špirko, V.; Selzle, H. L.; Schlag, E. W. J. Phys. Chem. A 1998, 102, 2501.
26. Hobza, P.; Špirko, V.; Havlas, Z.; Buchhold, K.; Reimann, B.; Barth, H.-D.; Brutschy, B. Chem. Phys. Lett. 1999, 299, 180.
27. Reimann, B.; Buchhold, K.; Vaupel, S.; Brutschy, B.; Havlas, Z.; Hobza, P. J. Am. Chem. Soc., submitted for publication.
28. Hobza, P.; Havlas, Z. Chem. Phys. Lett. 1999, 303, 447.
29. Gu, Y.; Scheiner, S. J. Am. Chem. Soc. 1999, 121, 9411.
30. Kelley, J. A.; Weber, J. M.; Robertson, W. H.; Lisle, K. M.; Johnsson, M. A.; Havlas, Z.; Hobza, P. J. Am. Chem. Soc., submitted for publication.
31. Boys, S. F.; Bernardi, F. Mol. Phys. 1970, 19, 553.
32. Two procedures are free of the BSSE. The perturbation method for calculation of intermolecular interactions is, by definition, free of the BSSE but is useless for practical calculations where subsystem geometry is to be optimized. The variational chemical Hamiltonian approach developed by Mayer (Mayer, I. Int. J. Quantum Chem. 1983, 23, 341) is very promising since it eliminates the nonphysical terms of the Hamiltonian that are due to the BSSE. Unfortunately, derivations of an implementation of the chemical Hamiltonian gradient formulae at various theoretical levels (beyond Hartree-Fock) are not yet available. Much hope was given also to local MP treatments (Braneld, K.; Dasgupta, S.; Goddard, W. A., III. J. Phys. Chem. B 1997, 101, 4851) which claimed to be also BSSE free. Unfortunately, practical calculations performed in our laboratory have shown very limited use of the local MP methods for the calculations of molecular complexes. Until now, the only practically applicable approach for eliminating the BSSE is the use of the standard counterpoise procedure.
33. Two procedures are free of the BSSE. The perturbation method for calculation of intermolecular interactions is, by definition, free of the BSSE but is useless for practical calculations where subsystem geometry is to be optimized. The variational chemical Hamiltonian approach developed by Mayer (Mayer, I. Int. J. Quantum Chem. 1983, 23, 341) is very promising since it eliminates the nonphysical terms of the Hamiltonian that are due to the BSSE. Unfortunately, derivations of an implementation of the chemical Hamiltonian gradient formulae at various theoretical levels (beyond Hartree-Fock) are not yet available. Much hope was given also to local MP treatments (Braneld, K.; Dasgupta, S.; Goddard, W. A., III. J. Phys. Chem. B 1997, 101, 4851) which claimed to be also BSSE free. Unfortunately, practical calculations performed in our laboratory have shown very limited use of the local MP methods for the calculations of molecular complexes. Until now, the only practically applicable approach for eliminating the BSSE is the use of the standard counterpoise procedure.
34. Bouteiller, Y.; Behrouz, H. J. Phys. Chem. 1992, 96, 6033.
35. Simon, S.; Duran, M.; Dannenberg, J. J. J. Chem. Phys. 1996, 105, 11024.
36. Hobza, P.; Havlas, Z. Theor. Chem. Acc. 1998, 99, 372.
37. Buenker, P. R.; Jensen, P. Molecular Symmetry and Spectroscopy; NRC Researcch Press: Ottawa, 1998.
38. Hobza, P.; Bludský, O.; Suhai, S. Phys. Chem. Chem. Phys. 1999, 1, 2073.
39. Afonin, A. V.; Andriyankov, M. A. Zh. Org. Khim. 1988, 24, 1034.
40. Satonaka, H.; Abe, K.; Hirota, M. Bull. Chem. Soc. Jpn. 1987, 60, 953; 1988, 61, 2031.
41. Satonaka, H.; Abe, K.; Hirota, M. Bull. Chem. Soc. Jpn. 1987, 60, 953; 1988, 61, 2031.
42. Tufró, M. F.; Contréras, R. H.; Facelli, J. C. J. Mol. Struct. (THEOCHEM) 1992, 254, 271.
43. Angelotti, T.; Krisko, M.; O'Connor, T.; Serianni, A. S. J. Am. Chem. Soc. 1987, 109, 4464.
44. Vizioli, C.; Ruiz de Azúa, M. C.; Giribet, C. G.; Contréras, R. H.; Turi, L.; Dannenberg, J. J.; Rae, J. D.; Weigold, J. A.; Malagoli, M.; Zanosi, R.; Lazzeratti, P.; Weigold, J. A.; Malagoli, M.; Zanosi, R.; Lazzaretti, P. J. Phys. Chem. 1994, 98, 8585.
45. Giribet, C. G.; Vizioli, C. V.; Ruiz de Azúa, M. C.; Contréras, R. H.; Dannenberg, J. J.; Masunov, A. J. Chem. Soc., Faraday Trans. 1996, 92, 3029.
46. Contréras, R. H.; Peralta, J. E.; Giribet, C. G.; Ruiz de Azúa, M. C.; Facelli, J. C. Annu. Rep. NMR Spectrosc. 2000, 41, 55.
47. Popelier, P. L. A.; Bader, R. F. W. Chem. Phys. Lett. 1992, 189, 542.
48. Janda, K. C.; Hemminger, J. C.; Winn, J. S.; Novick, S. E.; Harris, S. J.; Klemperer, W. J. Chem. Phys. 1975, 63, 1419.
49. Hobza, P.; Selzle, H. L.; Schlag, E. W. Chem. Rev. 1994, 94, 1767.
50. Hunter, C. A.; Singh, J.; Thornton, J. M. J. Mol. Biol. 1991, 218, 837.
51. Dance, I.; Scudder, M. Chem. Eur. J. 1996, 5, 481.
52. Bock, H.; Havlas, Z.; Krenzel, V.; Sievert, M. Angew. Chem., submitted for publication.
53. Bock, H.; Dienelt, R.; Schoedel, H.; Havlas, Z. J. Chem. Soc., Chem. Commun. 1993, 1792.
54. 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.7; Gaussian, Inc.: Pittsburgh, PA, 1999
55. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899.
56. Caminati, W.; Melandri, S.; Moreschini, P.; Favero, P. G. Angew. Chem., Int. Ed. Engl. 1999, 38, 2924.
57. Bader, R. W. F. Atoms in Molecules. A Quantum Theory; Oxford University Press: Oxford, 1990.
58. Cubero, E.; Orozco, M.; Hobza, P.; Luque, F. J. J. Phys. Chem. A 1999, 103, 6394.
59. Cubero, E.; Orozco, M.; Luque, F. J. Chem. Phys. Lett. 1999, 310, 445.