Theoretical study of the antioxidant activity of vitamin E: Reactions of α-tocopherol with the hydroperoxy radical

Journal of Chemical Theory and Computation

Volumn 1, Issue 2, 2005, Pages 337-344

  Navarrete, Marta ^a   Rangel, Cipriano ^a   Espinosa García, Joaquín ^a   Corchado, José C ^a  

^a UNIVERSITY OF EXTREMADURA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 20544450729     PISSN: 15499618     EISSN: 15499626     Source Type: Journal    
DOI: 10.1021/ct0498932     Document Type: Article

References (44)

1. (a) Niki, E. Free Radical Res. 2000, 33, 693-704.
2. (b) Pryor, W. A. Free Radical Biol. Med. 2000, 28, 141-164.
3. Burton, G. W.; Ingold, K. U. Acc. Chem. Res. 1986, 19, 194-201.
4. Wang, X.; Quinn, P. J. Prog. Lipid Res. 1999, 38, 309-336.
5. Bowry, V. W.; Ingold, K. E. Acc. Chem. Res. 1999, 32, 27-34.
6. Niki, E. Client. Phys. Lipids 1987, 44, 227-253.
7. For a recent review see Niki, E.; Nogichu, N. Acc. Chem. Res. 2004, 37, 45-51, and references therein.
8. Stocker, R. Trends Biochem. Sci. 1999, 24, 219-223.
9. Ernster, L.; Dallner, G. Biochim. Biophys. Acta 1995, 1271, 195-204.
10. Forsmark-Andrée, P.; Dallner, G.; Ernster, L. Free Radical Biol. Med. 1995, 19, 749-757.
11. Wolf, G. Nutr. Rev. 1997, 55, 376-378.
12. Barclay, L. R. C. Can. J. Chem. 1993, 71, 1-16.
13. Castle, L.; Perkins, M. J. J. Am. Chem. Soc. 1986, 108, 6381-6382.
14. Pryor, W. A.; Stickland, T.; Church, D. F. J. Am. Chem. Soc. 1988, 110, 2224-2229.
15. Valgimigli, L.; Banks, J. T.; Lusztyk, J.; Ingold, K. U. J. Org. Chem. 1999, 64, 3381-3383.
16. Bowry, V. W.; Stocker, R.; Walling, C. Proc. Natl. Acad. Sci. U. S. A. 1993, 90, 45-49.
17. Espinosa-García, J.; Gutierrez-Merino, C. J. Phys. Chem. A 2003, 107, 9712-9723.
18. Espinosa-García, J. J. Am. Chem. Soc. 2004, 126, 920-927.
19. Foti, M.; Ingold, K. U.; Lusztyk, J. J. Am. Chem. Soc. 1994, 116, 9440-9447.
20. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A.; Stratman, 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.; Menucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterki, J.; Petterson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malik, D. K.; Rabuk, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, J. J.; 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.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Reploge, E. S.; Pople, J. A.; GAUSSIAN98 program, Revision A.7, Gaussian Inc., Pittsburgh, PA 1998.
21. Becke, A. D. J. Chem. Phys. 1993, 98, 1372-1377.
22. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
23. Hehre, W. J.; Ditchfield, R.; Pople, J. A. J. Chem. Phys 1972, 56, 2257-2261.
24. Fast, P. L.; Truhlar, D. G. J. Chem. Phys. 1998, 109, 3721-3729.
25. Chuang, Y.-Y.; Truhlar, D. G. J. Phys. Chem. A 1998, 102, 242-247.
26. See, for example, Truhlar, D. G.; Gordon, M. S. Science 1990, 249, 491-498, and references therein.
27. Corchado, J. C.; Coitiño, E. L.; Chuang, Y.-Y.; Fast, P. L.; Truhlar, D. G. J. Phys. Chem. A 1998, 102, 2424-2438.
28. For a recent review on these methods see Truhlar, D. G.; Gao, J.; García-Viloca, M.; Alhambra, C.; Corchado, J. C.; Sánchez, M. L.; Poulsen T. D. Int. J. Quantum Chem. 2004, 100, 1136-1152.
29. Corchado, J. C.; Chuang, Y.-Y.; Fast, P. L.; Villà, J.; Hu, W.-P.; Liu, Y.-P.; Lynch, G. C.; Nguyen, K. A.; Jackels, C. F.; Melissas, V. S.; Lynch, B. J.; Rossi, I.; Coitiño, E. L.; Fernandez-Ramos, A.; Pu, J.; Albu, T. V.; Steckler, R.; Garrett, B. C.; Isaacson, A. D.; Truhlar, D. G. POLYRATE-version 9.0, University of Minnesota, Minneapolis, 2002.
30. Corchado, J. C.; Coitiño, E. L.; Chuang, Y.-Y.; Truhlar, D. G. GAUSSRATE-version 9.0, University of Minnesota, Minneapolis, 2002.
31. Lynch, B. J.; Fast, P. L.; Harris, M.; Truhlar, D. G. J. Phys. Chem. A 2000, 104, 4811-4815.
32. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab initio Molecular Orbital Theory, Wiley: New York, 1987.
33. Fast, P. L.; Sánchez, M. L.; Truhlar, D. G. Chem. Phys. Lett 1999, 306, 407-410.
34. Chuang, Y.-Y.; Corchado, J. C.; Truhlar, D. G. J. Phys. Chem. A 1999, 103, 1140-1149.
35. Corchado, J. C.; Espinosa-García, J.; Hu, W.-P.; Rossi, I.; Truhlar, D. G. J. Phys. Chem. 1995, 99, 687-694.
36. As an example, Wayner et al. (ref 36) list an O-H bond dissociation energy for R-tocopherol of 77.3 kcal/mol, while Berkowitz et al. (ref 37) give a C-H bond dissociation energy in toluene of 88.5 kcal/mol.
37. Wayner, D. D. M.; Lusztyk, E.; Ingold, K. U.; Mulder, P. J. Org. Chem. 1996, 61, 6430-6433.
38. Berkowitz, J.; Ellison, G. B.; Gutman, D. J. Phys. Chem. 1994, 98, 2744-2765.
39. Note that the transmission coefficient κ is not only a tunneling correction but also takes into account three effects: tunneling, which tends to make κ > 1, nonclassical reflection of trajectories that classically would overcome the barrier, which tends to make κ < 1; and a better treatment of the reaction threshold than the canonical variational transition state theory, which also makes κ < 1. The net effect in the abstraction reaction is κ > 1, while in the addition reaction it is κ < 1. For a detailed description of the calculation of transmission coefficients and threshold corrections see ref 39.
40. Truhlar, D. G.; Isaacson, A. D.; Garrett, B. C. In Theory of Chemical Reaction Dynamics, Vol. 4, Baer, M., Ed. CRC Press: Boca Raton, FL, 1985; pp 65-137.
41. Koch, W.; Holthausen, M. C. A Chemist's Guide to Density Functional Theory, 2nd edition. Wiley-VCH: Weinheim (Germany), 2000.
42. Shum, L. G. S.; Benson, S. W. Int. J. Chem. Kinet. 1983, 15, 323-339.
43. Burton, G. W.; Doba, T.; Gabe, E. J.; Hughes, L.; Lee, F. L.; Prasad, L.; Ingold, K. U. J. Am. Chem. Soc. 1985, 107, 7053-7065.
44. Arudi, R. L.; Sutherland, M. W.; Bielski, B. H. J. Oxy Radicals and Their Scavenger Systems, Vol. 1, Cohen, G.; Greenwald, R. A. Eds. Elsevier: Amsterdam (The Netherlands), 1983.