Using constrained Schrödinger equations to separate resonant and inductive substituent effects: A new methodology for parametrizing simple models in chemistry

Journal of Physical Chemistry A

Volumn 107, Issue 10, 2003, Pages 1655-1663

  Janesko, Benjamin G ^a   Gallek, Craig J ^a   Yaron, David ^a  

^a CARNEGIE MELLON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CONSTRAINED SCHRODINGER EQUATIONS; ELECTRONIC CONFIGURATION;

CALCULATIONS; ELECTRON RESONANCE; ELECTRONIC STRUCTURE; MATHEMATICAL MODELS; PARTIAL DIFFERENTIAL EQUATIONS; SET THEORY;

BENZENE;

EID: 0037435149     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp027576q     Document Type: Article

References (40)

1. Floris, F. M.; Tani, A. In Theoretical and Computational Chemistry: Molecular Dynamics from Classical to Quantum Methods; Balbuen, P. B., Seminario, J. M., Ed.; Elsevier Science B.V.: Amsterdam, 1999; Vol. 7, pp 363-429.
2. Machida, K. Principles of Molecular Mechanics; John Wiley and Sons: New York, 1999.
3. Niesar, U.; Corongiu, G.; Clementi, E.; Kneller, G.; Bhattacharya, D. J. Phys. Chem. 1990, 94, 7949-7956.
4. Vorpagel, E. R.; Streitweiser, A., Jr.; Alexandratos, S. D. J. Am. Chem. Soc. 1981, 103 (13), 3777-3781.
5. Niwa, J. Bull. Chem. Soc. Jpn. 1989, 62 (1), 226-233.
6. Tabacchi, G.; Mundy, C. J.; Hutter, J.; Parinello, M. J. Chem. Phys. 2002, 117 (4), 1416-1433.
7. Mukherji, A.; Karplus, M. J. Chem. Phys. 1963, 38, 44-48.
8. Jayatilaka, D. Phys. Rev. Lett. 1998, 80 (4), 798-801.
9. Berger, J. F.; Girod, M.; Gogny, D. Nucl. Phys. A 1989, A502, 85c-104c.
10. Dederichs, P. H.; Blügel, S.; Zeller, R.; Akai, H. Phys. Rev. Lett. 1984, 53 (26), 2512-2515.
11. Ichikawa, H.; Kagawa, H. Int. J. Quantum Chem. 1994, 52, 575-591.
12. Ichikawa, H.; Kagawa, H. Bull. Chem. Soc. Jpn. 1997, 70, 61-70.
13. Ichikawa, H.; Kagawa, H. Bull. Chem. Soc. Jpn. 1997, 70, 727-735.
14. Ohwada T.; Kagawa, H.; Ichikawa, H. Int. J. Quantum Chem. 1998, 68 (1), 65-72.
15. Meider, H.; Springborg, M. J. Phys.: Condens. Matter 1998, 10, 6953-6971.
16. Hansch, C.; Leo, A.; Unger, S. H.; Kim, K. H.; Nikaitani, D.; Lien, E. J. Med. Chem. 1973, 16 (11), 1207-1216.
17. Hammett, L. P. Trans. Faraday Soc. 1938, 34, 156-165.
18. Hansch, C.; Leo, A. Exploring QSAR; American Chemical Society: Washington, DC, 1995.
19. Swain, C. G.; Lupton, E. C., Jr. J. Am. Chem. Soc. 1968, 90 (16), 4328-4337.
20. Swain, C. G.; Unger, S. H.; Rosenquist, N. R.; Swain, M. C. J. Am. Chem. Soc. 1983, 105 (3), 492-502.
21. Szabo, A.; Ostlund, N. S. Modern Quantum Chemistry: Introduction to Advanced Electronic Structure Theory; Dover Publications: Mineola, NY, 1989.
22. Kirckwood, J. G.; Westheimer, F. H. J. Chem. Phys. 1938, 6, 506-512.
23. Derick, C. G. J. Am. Chem. Soc. 1911, 33, 1152.
24. Parr, R. G.; Yang, W. Density-Functional Theory of Atoms and Molecules; Oxford University Press: New York, 1989.
25. Application of the bond-order maximization constraint causes the π-bond order between the singly bonded bridge atoms to be essentially zero.
26. Topsom, R. D. In Progress in Physical Organic Chemistry; Taft, R. W., Ed.; John Wiley and Sons: New York, 1989; Vol. 16, pp 125-191.
27. Mulliken, R. S. J. Chem. Phys. 1955, 23, 1833-1840.
28. Schmidt, M. W.; Baldridge, K. K.; Boatz, J. A.; Elbert, S. T.; Gordon, M. S.; Jensen, J. J.; Koseki, S.; Matsunaga, N.; Nguyen, K. A.; Su, S. J.; Windus, T. L.; Dupuis, M.; Montgomery, J. A. J. Comput. Chem. 1993, 14, 1347-1363.
29. + and another charged group is discarded from all data sets, as calculations on these molecules tend to give unphysically large substituent effects.
30. The difference in the inductive-resonant correlation coefficients presented in Table 2 remains when data from any one of the substituents is remov from the correlation.
31. Hansch, C.; Leo, A. Substituent Constants for Correlation Analysis in Chemistry and Biology; John Wiley and Sons: New York, 1979.
32. Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91 (2), 165-195.
33. Exner, O.; Böhm, S. J. Org. Chem. 2002, 67 (18), 6320-6327.
34. The data for Sub=SH, Bridge=1(2-vinyl)3-benzene, RC=CHO was discarded due to an unphysically large calculated substituent effect
35. Pople, J. Rev. Modern Phys. 1999, 71 (5), 1267-1274.
36. Exner, O. J. Phys. Org. Chem. 1999, 12 (4), 265-274.
37. Charton, M. J. Phys. Org. Chem. 1999, 12 (4), 275-282.
38. Galkin, V. I. J. Phys. Org. Chem. 1999, 12 (4), 283-288.
39. Exner, O.; Charton, M.; Galkin, V. I. J. Phys. Org. Chem. 1999, 12 (4), 289.
40. Cimiraglia, R. NATO ASI Ser, Ser. B 1992, 299, 11-26.