Quantitative characterization of the local electrophilicity of organic molecules. Understanding the regioselectivity on Diels-Alder reactions

Journal of Physical Chemistry A

Volumn 106, Issue 29, 2002, Pages 6871-6875

  Domingo, Luis R ^a   Aurell, M José ^a   Pérez, Patricia ^b   Contreras, Renato ^c  

^a UNIVERSITY OF VALENCIA   (Spain)

^b UNIVERSIDAD ANDRÉS BELLO   (Chile)

^c UNIVERSITY OF CHILE   (Chile)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; AROMATIC COMPOUNDS; ELECTRON TRANSITIONS; PROBABILITY DENSITY FUNCTION;

ELECTROPHILICITY;

MOLECULAR DYNAMICS;

EID: 0037173332     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp020715j     Document Type: Article

References (35)

1. Carruthers, W. Some Modern Methods of Organic Synthesis, 2nd ed.; Cambridge University Press: Cambridge, 1978.
2. Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon Press: Oxford, 1990.
3. Fleming, I. Perieyclic Reaction; Oxford University Press: Oxford, 1999.
4. Holmes, H.L. Organic Reactions; John Wiley & Sons: New York, 1948; Vol. 4, p 60.
5. Oppolzer, W. Comprehensive Organic Synthesis; Trost, B.M., Fleming, I., Paquette, L.A., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, p 315.
6. Kumar, A. Chem Rev. 2001, 101, 1.
7. Damoun, S.; Van de Woude, G.; Méndez, F.; Geertings, P. J. Phys. Chem. A 1997, 101, 886.
8. Chandra, A.K.; Nguyen, M.T. J. Phys. Chem. A 1998, 102, 6181.
9. Ponti, A. J. Phys. Chem. A 2000, 104, 8843.
10. Domingo, L.R.; Aurell, M.; Contreras, R.; Pérez, P. Tetrahedron 2002, 58, 4417.
11. Domingo, L.R.; Arnó, M.; Contreras, R.; Pérez, P. J. Phys. Chem. A 2002, 106, 952.
12. Domingo, L.R.; Aurell, M.J. J. Org. Chem. 2002, 67, 959.
13. Domingo, L.R. Tetrahedron 2002, 58, 3765.
14. Domingo, L.R.; Asensio, A.; Arroyo, P. J. Phys. Org. Chem., in press.
15. Parr, R.G.; von Szentpaly, L.; Liu, S. J. Am. Chem. Soc. 1999, 121, 1922.
16. Cedillo, A.; Contreras, R. J. Phys. Chem. A., submitted for publication, 2002.
17. Ayers, P.W.; Parr, R.G. J. Am. Chem. Soc. 2000, 122, 2010.
18. Parr, R.G.; Yang, W. J. Am. Chem. Soc. 1984, 106, 4049.
19. Pérez, P.; Toro-Labbé, A.; Contreras, R. J. Phys. Chem. A 2000, 104, 11993.
20. Pérez, P. J. Phys. Chem. A 2001, 105, 6182.
21. Parr, R.G.; Yang, W. Density Functional Theory of Atoms and Molecules; Oxford University Press: New York, 1989.
22. Parr, R.G.; Pearson, R.G. J. Am. Chem. Soc. 1983, 105, 7512.
23. Pearson, R.G. Chemical Hardness: Applications from Molecules to Solids; Wiley-VHC: Weinheim, 1997.
24. Parr, R.G.; Pearson, R.G. J. Am. Chem. Soc. 1983, 105, 7512.
25. Roy, R.K.; Krishnamurti, S.; Geerlings, P.; Pal, S. J. Phys. Chem. A 1998, 102, 3746.
26. Roy, R.K.; Pal, S.; Hirao, K. J. Chem. Phys. 1999, 110, 8236.
27. Becke, A.D. J. Chem. Phys. 1993, 98, 5648.
28. Lee, C.; Yang, W.; Parr, R.G. Phys. Rev. B 1988, 37, 785.
29. 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.; Keitb, 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.6; Gaussian, Inc.: Pittsburgh, PA, 1998.
30. Contreras, R.; Fuentealba, P.; Galván, M.; Pérez, P. Chem. Phys. Lett. 1999, 304, 405.
31. Fuentealba, P.; Pérez, P.; Contreras, R. J. Chem. Phys. 2000, 113, 2544.
32. Domingo, L.R.; Oliva, M.; Andrés, J. J. Org. Chem. 2001, 66, 6151.
33. Domingo, L.R.; Arnó, M.; Andrés, J. J. Org. Chem. 1999, 64, 5867.
34. Sustmann, R.; Sicking, W. J. Am. Chem. Soc. 1996, 118, 12562.
35. Jung, M.E.; McCombs, C.A. Tetrahedron Lett. 1976, 34, 2935.