Importance of charge-transfer effects in [4 + 2] cycloaddition reaction

Journal of Molecular Structure: THEOCHEM

Volumn 663, Issue 1-3, 2003, Pages 175-185

  Korchowiec, Jacek ^a  

^a JAGIELLONIAN UNIVERSITY   (Poland)

Author keywords

Charge transfer energy; Chemical potential and hardness data; Cycloaddition reactions; Energy partitioning schemes; Fukui function; Reactivity criteria; Substituent effect

Indexed keywords

1,3 BUTADIENE DERIVATIVE; ALKADIENE; ETHYLENE DERIVATIVE;

ARTICLE; CYCLOADDITION; DIELS ALDER REACTION; ELECTRICITY; ELECTRON TRANSPORT; GEOMETRY; MATHEMATICAL ANALYSIS; POLARIZATION; SUBSTITUTION REACTION;

EID: 0344442265     PISSN: 01661280     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.theochem.2003.08.125     Document Type: Article

References (33)

1. O. Diels, K. Alder, Justus. Leibigs Ann. Chem. 460 (1928) 98.
2. N.L. Baud, J. Am. Chem. Soc. 114 (1992) 5800.
3. K. Fukui, Theory of Orientation and Stereoselection, Springer, Heidelberg, 1982.
4. R.B. Woodward, R. Hoffmann, The Conservation of Orbital Symmetry, Academic Press, New York, 1969.
5. Yu.A. Titov, Usp. Khim. 31 (1962) 267.
6. Yu.A. Titov, A.I. Kuznecowa, Izvest. Akad. Nauk SSSR Otdel. Khim. Nauk 10 (1960) 1810.
7. A.A. Dudenskaya, S.S. Nowikov, G.A. Shvechgeymer, Izvest. Akad. Nauk SSSR (1965) 2024.
8. R.B. Woodward, R. Hoffmann, Angew. Chem. Int. Ed. Engl. 8 (1969) 781.
9. K. Fukui, Acc. Chem. Res. 4 (1971) 57.
10. J. Sauer, Angew. Chem., Int. Ed. Engl. 6 (1967) 16.
11. J. Feuer, W.C. Herndon, L.H. Hall, Tetrahedron 24 (1968) 2583.
12. K.N. Houk, J. Am. Chem. Soc. 95 (1973) 4092.
13. P.V. Alston, D.D. Shillady, J. Org. Chem. 39 (1974) 3402.
14. J. Sauer, R. Sustmann, Angew. Chem. Int. Ed. Engl. 19 (1980) 779.
15. L.A. Paquette, A.G. Schaefer, J.F. Blount, J. Am. Chem. Soc. 105 (1983) 3642.
16. M.J.S. Dewar, S. Olivella, J.J.P. Stewart, J. Am. Chem. Soc. 108 (1986) 5771.
17. W.C. Herndon, Chem. Rev. 72 (1972) 157.
18. N.D. Epiotis, J. Am. Chem. Soc. 95 (1973) 5624.
19. S.D. Kahn, C.F. Pau, L.E. Overman, W.J. Hehre, J. Am. Chem. Soc. 108 (1986) 7381.
20. S. Damoun, G. Van de Woude, F. Mendez, P. Geerlings, J. Phys. Chem. A 101 (1997) 886.
21. J. Korchowiec, A.K. Chandra, T. Uchimaru, Theochem 572 (2001) 193.
22. J. Korchowiec, T. Uchimaru, J. Chem. Phys. 112 (2000) 1623.
23. J. Korchowiec, T. Uchimaru, J. Phys. Chem. A 102 (1998) 10167.
24. M.J. Frisch, G.W. Trucks, H.B. Schlegel, P.M.W. Gill, B.G. Johnson, M.A. Robb, J.R. Cheeseman, T. Keith, G.A. Petersson, J.A. Montgomery, K. Raghavachari, M.A. Al-Laham, V.G. Zakrzewski, J.V. Ortiz, J.B. Foresman, J. Cioslowski, B.B. Stefanov, A. Nanayakkara, M. Challacombe, C.Y. Peng, P.Y. Ayala, W. Chen, M.W. Wong, J.L. Andres, E.S. Replogle, R. Gomperts, R.L. Martin, D.J. Fox, J.S. Binkley, D.J. Defrees, J. Baker, J.P. Stewart, M. Head-Gordon, C. Gonzalez, J.A. Pople, Gaussian, Inc.: Pittsburgh PA, 1998.
25. A.D. Becke, J. Chem. Phys. 98 (1993) 5648.
26. C. Lee, W. Yang, R.G. Parr, Phys. Rev. B 37 (1988) 785.
27. B. Miechlich, A. Savin, H. Stoll, H. Preuss, Chem. Phys. Lett. 157 (1989) 200.
28. P.C. Hariharan, J.A. Pople, Theor. Chim. Acta 28 (1973) 213.
29. C.M. Breneman, K. Wiberg, J. Comput. Chem. 11 (1990) 361.
30. R.F. Nalewajski, J. Korchowiec, Charge Sensitivity Approach to Electronic Structure and Chemical Reactivity, Advanced Series in Physical Chemistry, vol. 8, Word Scientific, Singapore, 1997.
31. B. Szefczyk, W.A. Sokalski, J. Leszczyński, J. Chem. Phys. 117 (2002) 6952.
32. Y. Mo, J. Gao, J. Phys. Chem. A 105 (2001) 6530.
33. J.F. Janak, Phys. Rev. B 18 (1978) 7165.