Mechanistic studies of phenolic antioxidants in reaction with nitrogen- and oxygen-centered radicals

Journal of Molecular Structure: THEOCHEM

Volumn 818, Issue 1-3, 2007, Pages 141-150

  Katarina, Nikolic M ^a  

^a UNIVERSITY OF BELGRADE   (Serbia)

Author keywords

Bond dissociation enthalpy; Molecular orbitals; Nitrogen centered radicals; Phenolic antioxidants; Transition states

Indexed keywords

EID: 34547776771     PISSN: 01661280     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.theochem.2007.05.011     Document Type: Article

References (34)

1. Aruoma O.I., Murcia A.M., Butler J., and Halliwell B. J. Agric. Food Chem. 1880 (1993) 41
2. Halliwell B., Asechbach R., Iloliger J., and Aruoma O. J. Food Chem. Toxicol. 601 (1995) 33
3. Burton G.W., Doba T., Gabe E.J., Hughes L., Lee F.L., Prasad L., and Ingold K. J. Am. Chem. Soc. 7053 (1985) 107
4. Mayer J.M., Hrovat D.A., Thomas J.L., and Borden W.T. J. Am. Chem. Soc. 11142 (2002) 124
5. DiLabio G.A., Pratt D.A., LoFaro A.D., and Wright J.S. J. Phys. Chem. A 1653 (1999) 103
6. Guo Zhang C., Nichols J.A., and Dixon D.A. J. Phys. Chem. A 4184 (2003) 107
7. Laarhoven L.J.J., Mulder P., and Wayner D.D.M. Acc. Chem. Res. 342 (1999) 32
8. Pedulli G.F., Lucarini M., and Pedrielli P. In: Minisci F. (Ed). Free Radicals in Biology and Environment (1997), Kluwer Academic Publishers, Dordrecht, The Netherelands 169
9. de Heer M.I., Korth H.G., and Mulder P. J. Org. Chem. 6969 (1999) 64
10. Lukarini M., Magnaini V., and Pedulli G.F. J. Org. Chem. 928 (2002) 67
11. Avila D.V., Ingold K., and Lusztyk J. J. Am. Chem. Soc. 2929 (1995) 117
12. Snelgrove D.W., Lusztyk J., Banks J.T., Mulder P., and Ingold K. J. Am. Chem. Soc. 469 (2001) 123
13. J.J.P. Stewart, MOPAC 2000 Version 7.0.0, Fujitsu Limited, Tokyo, Japan.
14. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, V.G. Zakrzewski, J.A. Montgomery, Jr., R.E. Stratmann, J.C. Burant, S. Dapprich, J.M. Millam, A.D. Daniels, K.N. Kudin, M.C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G.A. Petersson, P.Y. Ayala, Q. Cui, K. Morokuma, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Ortiz, A.G. Baboul, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P.M.W. Gill, B.G. Johnson, W. Chen, M.W. Wong, J.L. Andres, M. Head-Gordon, E.S. Replogle, J.A. Pople, Gaussian 98 (Revision A.7), Gaussian, Inc., Pittsburgh PA, 1998.
15. Becke A.D. J. Chem. Phys. 5648 (1993) 98
16. Lee C., Yang W., and Parr R.G. Phys. Rev. B. 785 (1988) 37
17. Fox T., and Kollman P.A. J. Phys. Chem. 2950 (1996) 100
18. DiLabio G.A., Pratt D.A., and Wright J.S. Chem. Phys. Lett. 181 (1998) 297
19. Wright J.S., Carpenter J.D., McKay D.J., and Ingold K.U. J. Am. Chem. Soc. 4245 (1997) 119
20. Wayner D.D.M., Lusztyk E., Ingold K.U., and Mulder P. J. Org. Chem. 6430 (1996) 61
21. Chipman D.M., Liu R., Zhou X., and Pulau P. J. Chem. Phys. 5023 (1994) 100
22. Nikolic K. J. Mol. Struct. 95 (2006) 774
23. Qin Y., and Wheeler R.A. J. Chem. Phys. 1689 (1995) 102
24. Costa Cabrol B.J.C., Fonseca R.G.B., and Simoes J.A.M. Chem. Phys. Lett. 436 (1996) 258
25. Larsen N.W. J. Mol. Struct. 175 (1979) 51
26. Dewar M.J.S., Zoebisch E.G., Healy E.F., and Stewart J.J.P. J. Am. Chem. Soc. 3902 (1985) 107
27. In: Lide D.R. (Ed). CRC. 75th ed. Hand Book of Chemistry and Physics (1994), CRC Press, Boca Raton FL 9-37
28. Bist H.D., Brand J.C.D., and Williams D.R. J. Mol. Spectrosc. 402 (1967) 24
29. Breneman C.M., and Wiberg K.B. J. Comput. Chem. 361 (1990) 11
30. Lucarini M., Pedulli G.F., and Cipollone M. J. Org. Chem. 5063 (1994) 59
31. Lind J., Shen X., Eriksen T.E., and Merenyi G. J. Am. Chem. Soc. 479 (1990) 112
32. Wayner D.D.M., Lusztyk E., Ingold K., and Mulder P. J. Org. Chem. 6430 (1996) 61
33. DiLabio G.A., Pratt D.A., and Wright J.S. J. Org. Chem. 2195 (2000) 65
34. Hehre W.J., Radom L., Schleyer P.v.R., and Pople J.A. Ab Initio Molecular Orbital Theory (1986), Wiley