Role of charge-transfer effects in regioselectivity

International Journal of Quantum Chemistry

Volumn 101, Issue 6, 2005, Pages 714-721

  Korchowiec, Jacek ^a  

^a JAGIELLONIAN UNIVERSITY   (Poland)

Author keywords

Charge transfer energy; Chemical potential; Cycloaddition reactions; Energy partitioning schemes; Fukui function; Hardness softness data; Reactivity criteria

Indexed keywords

ADDITION REACTIONS; APPROXIMATION THEORY; DEFORMATION; HARDNESS; INTEGRAL EQUATIONS; PROBABILITY DENSITY FUNCTION;

CHARGE-TRANSFER ENERGY; CHEMICAL POTENTIAL; CYCLOADDITION REACTIONS; ENERGY PARTITIONING SCHEMES; FUKUI FUNCTIONS; HARDNESS/SOFTNESS DATA; REACTIVITY CRITERIA; REGIOCHEMISTRY;

CHARGE TRANSFER;

EID: 13844276130     PISSN: 00207608     EISSN: None     Source Type: Journal    
DOI: 10.1002/qua.20328     Document Type: Conference Paper

References (57)

1. Parr, R. G.; Yang, W. Density Functional Theory of Atoms and Molecules; Oxford University Press: New York, 1989.
2. Nalewajski, R. F.; Korchowiec, J. Charge Sensitivity Approach to Electronic Structure and Chemical Reactivity, Advanced Series in Physical Chemistry, Vol. 8; World Scientific: Singapore, 1997.
3. Gázquea, J. L.; Méndez, F. J Phys Chem 1994, 98, 4591.
4. Damoun, S.; Van de Woude, G.; Méndez, F.; Gerlings, P. J Phys Chem A 1997, 101, 886.
5. Chandra, A. K.; Michalak, A.; Nguyen, M. T.; Nalewajski, R. F. J Phys Chem A 1998, 102, 10182.
6. Chandra, A. K.; Uchimaru, T.; Nguyen, M. T. J Chem Soc, Perkin Trans 1999, 2, 2117.
7. Chermette, H. J. Comp Chem 1999, 20, 129.
8. Ayers, P. W.; Parr, R. G. J Am Chem Soc 2000, 122, 2010.
9. Chattaraj, P. K. J Phys Chem A 2001, 105, 511.
10. Chandrakumar, K. R. S.; Pal, S. J Phys Chem A 2002, 106, 5737.
11. Cong, Y.; Yang, Z. Z.; Wang, C. S.; Liu, X. C.; Bao, X. H. Chem Phys Lett 2002, 357, 59.
12. Ayers, P. W.; Morrison, R. C.; Roy, R. K. J Chem Phys 2002, 116, 8731.
13. Chattaraj, P. K.; Maiti, B.; Sarkar, U. J Phys Chem A 2003, 107, 4973.
14. Perez, P. J Org Chem 2003, 68, 5886.
15. Deka, R. C.; Ajitha, D.; Hirao, K. J Phys Chem B 2003, 107, 8574.
16. Chandrakumar, K. R. S.; Pal, S. J Phys Chem A 2003, 107, 5755.
17. Vivas-Reyes, R.; De Proft, F.; Biesemans, M.; Willem, R.; Geerlings, P. Eur J Inorg Chem 2003, 7, 1315.
18. Fukui, K. Theory of Orientation and Stereoselection; Springer-Verlag: Heidelberg, Germany, 1982.
19. Kitaura, K.; Morokuma, K. Int J Quantum Chem 1976, 10, 325.
20. Stevens, W. J.; Fink, W. H. Chem Phys Lett 1987, 139, 15.
21. Reed, A. E.; Weinhold, F. J Chem Phys 1983, 78, 4066.
22. Glendening, E. D.; Streitwieser, A. J Chem Phys 1994, 100, 2900.
23. Sokalski, W. A.; Roszak, S. M. J Mol Struct (Theochem) 1991, 234, 387.
24. Szalewicz, K.; Jeziorski, B. Mol Phys 1979, 38, 191.
25. Hayes, C.; Stone, J. Mol Phys 1984, 53, 83.
26. Boys, S. F.; Bernardi, F. Mol Phys 1970, 19, 553.
27. Korchowiec, J.; Uchimaru, T. J Phys Chem A 1998, 102, 6682.
28. Korchowiec, J.; Uchimaru, T. J Chem Phys 2000, 112, 1623.
29. Szefczyk, B.; Sokalski, W. A.; Leszczyński, J. J Chem Phys 2002, 117, 6952.
30. Korchowiec, J.; Chandra, A. K.; Uchimaru, T. Theochem 2001, 572, 193.
31. Korchowiec, J. Theochem 2003, 663, 175.
32. Geerlings, P.; De Proft, F.; Langenaeker, W. Chem Rev 2003, 103, 1793.
33. Diels, O.; Alder, K. Justus Leibigs Ann Chem 1928, 460, 98.
34. Titov, Yu. A. Usp Khim 1962, 31, 267.
35. Titov, Yu. A.; Kuznecowa, A. I. Izvest Akad Nauk SSSR Otdel Khim Nauk 1960, 10, 1810.
36. Dudenskaya, A. A.; Nowikov, S. S.; Shvechgeymer, G. A. Izvest Akad Nauk SSSR 1965, 2024.
37. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; AlLaham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 98, Revision A.11.4, Gaussian, Pittsburgh, 1998.
38. Becke, A. D. J Chem Phys 1993, 98, 5648.
39. Lee, C.; Yang, W.; Parr, R. G. Phys Rev B 1988, 37, 785.
40. Miechlich, B.; Savin, A.; Stoll, H.; Preuss, H. Chem Phys Lett 1989, 157, 200.
41. Hariharan, P. C.; Pople, J. A. Theor Chim Acta 1973, 28, 213.
42. Mo, Y.; Gao, J. J Phys Chem A 2001, 105, 6530.
43. Woodward, R. B.; Hoffmann, R. Angew Chem Int Ed Engl 1969, 8, 781.
44. Fukui, K. Ace Chem Res 1971, 4, 57.
45. Sauer, J. Angew Chem Int Ed Engl 1967, 6, 16.
46. Feuer, J.; Herndon, W. C.; Hall, L. H. Tetrahedron 1968, 24, 2583.
47. Houk, K. N. J Am Chem Soc 1973, 95, 4092.
48. Alston, P. V.; Shillady, D. D. J Org Chem 1974, 39, 3402.
49. Sauer, J.; Sustmann, R. Angew Chem Int Ed Engl 1980, 19, 779.
50. Paquette, L. A.; Schaefer, A. G.; Blount, J. F. J Am Chem Soc 1983, 105, 3642.
51. Dewar, M. J. S.; Olivella, S.; Stewart, J. J. P. J Am Chem Soc 1986, 108, 5771.
52. Herndon, W. C. Chem Rev 1972, 72, 157.
53. Epiotis, N. D. J Am Chem Soc 1973, 95, 5624.
54. Kahn, S. D.; Pau, C. F.; Overman, L. E.; Hehre, W. J. J Am Chem Soc 1986, 108, 7381.
55. Nalewajski, R. F. Phys Chem Chem Phys 2002, 4, 1710.
56. Nalewajski, R. F. Chem Phys Lett 2003, 372, 28.
57. Nalewajski, R. F. J Phys Chem A 2003, 107, 3792.