Hybrid density functional theory for π-stacking interactions: Application to benzenes, pyridines, and DNA bases

Journal of Computational Chemistry

Volumn 27, Issue 4, 2006, Pages 491-504

  Waller, Mark P ^a   Robertazzi, Arturo ^b   Platts, James A ^b   Hibbs, David E ^a   Williams, Peter A ^c  

^a UNIVERSITY OF SYDNEY   (Australia)

^b CARDIFF UNIVERSITY   (United Kingdom)

^c UNIVERSITY OF WESTERN SYDNEY   (Australia)

Author keywords

stacking; Atoms in molecules; Density functional theory; Electron density

Indexed keywords

BENZENE; BINDING ENERGY; CARRIER CONCENTRATION; DNA; ELECTRON GAS; POLARIZATION; POTENTIAL ENERGY; PROBABILITY DENSITY FUNCTION; QUANTUM THEORY; RNA;

Π-STACKED AROMATIC COMPLEXES; ATOMS IN MOLECULES; DIFFUSE BASIS SETS; ELECTRON GAS EXCHANGE; HYBRID DENSITY FUNCTIONAL THEORY;

AROMATIC COMPOUNDS;

BENZENE DERIVATIVE; HETEROCYCLIC COMPOUND; PURINE DERIVATIVE; PYRIDINE DERIVATIVE; PYRIMIDINE DERIVATIVE;

ALGORITHM; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMPUTER SIMULATION; ELECTRICITY; ELECTRON; HYDROGEN BOND; PHYSICAL CHEMISTRY; QUANTUM THEORY;

ALGORITHMS; BENZENE DERIVATIVES; CHEMISTRY, PHYSICAL; COMPUTER SIMULATION; ELECTRONS; ELECTROSTATICS; HETEROCYCLIC COMPOUNDS; HYDROGEN BONDING; MODELS, MOLECULAR; PURINES; PYRIDINES; PYRIMIDINES; QUANTUM THEORY;

EID: 33644897568     PISSN: 01928651     EISSN: 1096987X     Source Type: Journal    
DOI: 10.1002/jcc.20363     Document Type: Article

References (61)

1. Hunter, C. A.; Sanders, J. K. M. J Am Chem Soc 1990, 112, 5525.
2. Burley, S. K.; Petsko, G. A. Science 1985, 229, 23.
3. Hunter, C. A.; Singh, J.; Thornton, J. M. J Mol Biol 1991, 218, 837.
4. Meyer, E. A.; Castellano, R. K.; Diederich, F. Angew Chem-Int Edit 2003, 42, 1210.
5. Claessens, C. G.; Stoddart, J. F. J Phys Org Chem 1997, 10, 254.
6. Fyfe, M. C. T.; Stoddart, J. F. Ace Chem Res 1997, 30, 393.
7. Askew, B.; Ballester, P.; Buhr, C.; Jeong, K. S.; Jones, S.; Parris, K.; Williams, K.; Rebek, J. J Am Chem Soc 1989, 111, 1082.
8. Smithrud, D. B.; Diederich, F. J Am Chem Soc 1990, 112, 339.
9. Hunter, C. A. Chem Soc Rev 1994, 23, 101.
10. Rebek, J. Chem Soc Rev 1996, 25, 255.
11. McGaughey, G. B.; Gagne, M.; Rappe, A. K. J Biol Chem 1998, 273, 15458.
12. Watson, J. D.; Crick, H. C. D. Nature 1953, 171, 737.
13. Tsuzuki, S.; Uchimaru, T.; Tanabe, K. J Mol Struct (Theochem) 1994, 113, 107.
14. Tsuzuki, S.; Luthi, H. P. J Chem Phys 2001, 114, 3949.
15. Kim, K. S.; Tarakeshwar, P.; Lee, J. Y. Chem Rev 2000, 100, 4145.
16. Steed, J. M.; Dixon, T. A.; Klemperer, W. J Chem Phys 1979, 70, 4940.
17. Arunan, E.; Gutowsky, H. S. J Chem Phys 1993, 98, 4294.
18. Sinnokrot, M. O.; Valeev, E. F.; Sherrill, C. D. J Am Chem Soc 2002, 124, 10887.
19. Hobza, P.; Spirko, V.; Selzle, H. L.; Schlag, E. W. J Phys Chem A 1998, 102, 2501.
20. Hobza, P.; Selzle, H. L.; Schlag, E. W. J Phys Chem 1996, 100, 18790.
21. Jaffe, R. L.; Smith, G. D. J Chem Phys 1996, 105, 2780.
22. Grover, J. R.; Walters, E. A.; Hui, E. T. J Phys Chem 1987, 91, 3233.
23. Sinnokrot, M. O.; Sherrill, C. D. J Am Chem Soc 2004, 126, 7697.
24. Mignon, P.; Loverix, S.; De Proft, F.; Geerlings, P. J Phys Chem A 2004, 108, 6038.
25. Hobza, P.; Selzle, H. L.; Schlag, E. W. J Am Chem Soc 1994. 116, 3500.
26. Jurecka, P.; Hobza, P. J Am Chem Soc 2003, 125, 15608.
27. Sponer, J.; Gabb, H. A.; Leszczynski, J.; Hobza, P. Biophys J 1997, 73, 76.
28. Reha, D.; Kabelac, M.; Ryjacek, F.; Sponer, J.; Sponer, J. E.; Elstner, M.; Suhai, S.; Hobza, P. J Am Chem Soc 2002, 124, 3366.
29. Hobza, P.; Kabelac, M.; Sponer, J.; Mejzlik, P.; Vondrasek, J. J Cornput Chem 1997, 18, 1136.
30. Grimme, S. J Comput Chem 2004, 25, 1463.
31. von Lilienfeld, O. A.; Tavernelli, I.; Rothlisberger, U.; Sebastiani, D. Phys Rev Lett 2004, 93, art. no.-153004.
32. Meijer, E. J.; Sprik, M. J Chem Phys 1996, 105, 8684.
33. Ye, X. Y.; Li, Z. H.; Wang, W. N.; Fan, K. N.; Xu, W.; Hua, Z. Y. Chem Phys Lett 2004, 397, 56.
34. Johnson, E. R.; Wolkow, R. A.; DiLabio, G. A. Chem Phys Lett 2004, 394, 334.
35. Xu, X.; Goddard, W. A. Proc Natl Acad Sci USA 2004, 101, 2673.
36. Cerny, J.; Hobza, P. Phys Chem Chem Phys 2005, 7, 1624.
37. Perez-Jorda, J. M.; San-Fabian, E.; Perez-Jimenez, A. J. J Chem Phys 1999, 110, 1916.
38. Walsh, T. R. Phys Chem Chem Phys 2005, 7, 443.
39. Frisch, M. J. Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; 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.; 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.; and Pople, J. A. Gaussian, Inc.: Pittsburgh, PA, 2003.
40. Becke, A. D. J Chem Phys 1993, 98, 1372.
41. Lee. C. T.; Yang, W. T.: Parr, R. G. Phys Rev B 1988, 37, 785.
42. Perezjorda, J. M.; Becke, A. D. Chem Phys Lett 1995, 233, 134.
43. Hehre, W. J.; Ditchfie, R.; Pople, J. A. J Chem Phys 1972, 56, 2257.
44. Frisch, M. J.; Pople, J. A.; Binkley, J. S. J Chem Phys 1984, 80, 3265.
45. Woon, D. E.; Dunning, T. H., Jr. J Chem Phys 1993, 98, 1358.
46. Kendall, R. A. Dunning, T. H., Jr.; Harrison, R. J. J Chem Phys 1992, 96, 6796.
47. Bernardi, F.; Boys, S. F. Mol Phys 1970, 19, 553.
48. Bader, R. F. W. Atoms in Molecules - A Quantum Theory, Oxford University Press: Oxford, 1990.
49. Popelier, P. L. A. Atoms in Molecules: An Introduction, Pearson Education: Harlow. 2000.
50. Friedrich Biegler-König, J. S. J Comp Chem 2002, 23, 1489.
51. Bader, R. F. W.; Essen, H. J Chem Phys 1984, 80, 1943.
52. Hobza, P.; Sponer, J. J Am Chem Soc 2002, 124, 11802.
53. Leininger, M. L.; Nielsen, I. M. B.; Colvin, M. E.; Janssen, C. L. J Phys Chem A 2002, 106, 3850.
54. Pettersson, I.; Liljefors, T. J Comput Chem 1987, 8, 1139.
55. Cubero, E.; Orozco, M.; Luque, F. J. J Phys Chem A 1999, 103, 315.
56. Zhikol, O. A.; Shishkin, O. V.; Lyssenko, K. A.; Leszczynski, J. J Chem Phys 2005, 122, art. no. 144104.
57. London, F. Zeitschrift fur Physik 1930, 63, 1842.
58. Hobza, P.; Sponer. J. Chem Phys Lett 1998, 288(1), 7-14.
59. Sponer, J.: Leszczynski, J.; Hobza, P. J Mol Struct (Theochem) 2001, 573, 43.
60. Robertazzi, A.; Platts, J. A. Inorg Chem 2005, 44, 267.
61. Guerra, C. F.; Bickelhaupt, F. M.; Snijders, J. G.; Baerends, E. J. J Am Chem Soc 2000, 122, 4117.