Reactivity of the carbon-carbon double bond towards nucleophilic additions. A DFT analysis

Tetrahedron

Volumn 60, Issue 31, 2004, Pages 6585-6591

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

^a UNIVERSITY OF VALENCIA   (Spain)

^b UNIVERSIDAD ANDRÉS BELLO   (Chile)

^c UNIVERSITY OF CHILE   (Chile)

Author keywords

Density functional theory; Electrophilicity power; Michael additions

Indexed keywords

CARBON;

ANALYTIC METHOD; ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; DENSITY FUNCTIONAL THEORY; PRIORITY JOURNAL; REACTION ANALYSIS; SUBSTITUTION REACTION; THEORETICAL MODEL;

EID: 4143091851     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.06.003     Document Type: Article

References (24)

1. Mayr H., Kempf B., Ofial A.R. Acc. Chem. Res. 36:2003;66
2. Parr R.G., Szentpály L., Liu S. J. Am. Chem. Soc. 121:1999;1922
3. Mayr H., Patz M. Angew. Chem., Int. Ed. Engl. 33:1994;938
4. Legon A.C. Angew. Chem., Int. Ed. Engl. 38:1999;2686
5. Domingo L.R., Aurell M.J., Pérez P., Contreras R. Tetrahedron. 58:2002;4417
6. Pérez P., Domingo L.R., Aurell M.J., Contreras R. Tetrahedron. 59:2003;3117
7. Pérez P. J. Phys. Chem. A. 107:2003;522
8. Pérez P., Toro-Labbé A., Aizman A., Contreras R. J. Org. Chem. 67:2002;4747
9. Pérez P. J. Org. Chem. A. 68:2003;5886
10. Pérez P., Toro-Labbé A., Contreras R. J. Am. Chem. Soc. 123:2001;5527
11. Domingo L.R., Picher M.T., Zaragozá R.J. J. Org. Chem. 63:1998;9183
12. Lemek T., Mayr H. J. Org. Chem. 68:2003;6880
13. Mondal P., Hazarika K.K., Deka R.C. Phys. Chem. Commun. 6:2003;24
14. Bernasconi C.F., Killion R.B. Jr. J. Am. Chem. Soc. 110:1988;7506
15. Bernasconi C.F., Killion R.B. Jr. J. Org. Chem. 54:1989;2878
16. Bernasconi C.F., Leyes A.E., Rappoport Z. J. Org. Chem. 64:1999;2897
17. Bernasconi C.F., Ketner R.J., Chen X., Rappoport Z. J. Am. Chem. Soc. 120:1998;7461
18. Domingo L.R., Aurell M.J., Pérez P., Contreras R. J. Phys. Chem. A. 106:2002;6871
19. Domingo L.R., Aurell M.J., Pérez P., Contreras R. J. Org. Chem. 68:2003;3884
20. 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.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; W. Gill, P. M.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A.; Gaussian 98, Revision A.6 Gaussian, Inc.: Pittsburgh PA, 1998.
21. Parr R.G., Yang W. Density Functional Theory of Atoms and Molecules. 1989;Oxford University Press, New York
22. Contreras R., Fuentealba P., Galván M., Pérez P. Chem. Phys. Lett. 304:1999;405
23. Fuentealba P., Pérez P., Contreras R. J. Chem. Phys. 113:2000;2544
24. Domingo L.R., Pérez P., Contreras R. J. Org. Chem. 68:2003;6060