A DFT study on the deprotonation antioxidant mechanistic step of ortho-substituted phenolic cation radicals

Chemical Physics

Volumn 316, Issue 1-3, 2005, Pages 195-204

  Vafiadis, Anastasios P ^a   Bakalbassis, Evangelos G ^a  

^a ARISTOTLE UNIVERSITY OF THESSALONIKI   (Greece)

Author keywords

Antioxidant mechanism; Density functional theory; Electronic effect; Hydrogen bonding; Phenolic cation radicals; Proton dissociation enthalpy

Indexed keywords

EID: 24344457135     PISSN: 03010104     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chemphys.2005.05.015     Document Type: Article

References (41)

1. J.S. Wright, E.R. Johnson, and G.A. DiLabio J. Am. Chem. Soc. 123 2001 1173
2. H.-Y. Zhang, Y.-M. Sun, and X.-L. Wang J. Org. Chem. 67 2002 2709
3. H.-Y. Zhang, X.-L. Wang, and Y.-M. Sun Internet Elect. J. Mol. Design 2 2003 262
4. G.W. Burton, Y. Le Page, E.J. Gabe, and K.U. Ingold J. Am. Chem. Soc. 102 1980 7791
5. G.W. Burton, T. Doba, E.J. Gabe, L. Hughes, F.L. Lee, L. Prasad, and K.U. Ingold J. Am. Chem. Soc. 107 1985 7053
6. M.I. de Heer, P. Mulder, H.-G. Korth, K.U. Ingold, and J. Lusztyk J. Am. Chem. Soc. 122 2000 2355
7. S. Nagaoka, A. Kuranaka, H. Tsuboi, U. Hagashima, and K. Mukai J. Phys. Chem. 96 1992 2754
8. R. Hermann, S. Naumov, G.R. Mahalaxmi, and O. Brede Chem. Phys. Lett. 324 2000 265
9. F.G. Bordwell, and J.P. Cheng J. Am. Chem. Soc. 113 1991 1736
10. R. Hermann, S. Naumov, and O. Brede J. Mol. Struct. (Theochem.) 532 2000 69
11. M.R. Ganapathi, R. Hermann, S. Naumov, and O. Brede Phys. Chem. Chem. Phys. 2 2000 4947
12. O. Brede, S. Kapoor, T. Mukherjee, R. Hermann, and S. Naumov Phys. Chem. Chem. Phys. 4 2002 5096
13. O. Brede, R. Hermann, W. Naumann, and S. Naumov J. Phys. Chem. 106 2002 1398
14. E.G. Bakalbassis, A. Chatzopoulou, V.S. Melissas, M. Tsimidou, M. Tsolaki, and A. Vafiadis Lipids 36 2001 181
15. E.G. Bakalbassis, N. Nenadis, and M. Tsimidou J. Am. Oil Chem. Soc. 80 2003 459
16. A.P. Vafiadis, and E.G. Bakalbassis J. Am. Oil Chem. Soc. 80 2003 1217
17. A.T. Lithoxoidou, and E.G. Bakalbassis J. Am. Oil Chem. Soc. 81 2004 799
18. E.G. Bakalbassis, A.T. Lithoxoidou, and A.P. Vafiadis J. Phys. Chem. 107 2003 8594
19. R.G. Parr, and W. Yang Density Functional Theory of Atoms and Molecules 1989 Oxford University press New York
20. M.J. Frisch Gaussian 98 Revision A.11 2001 Gaussian Inc. Pittsburgh, PA
21. C. Lee, W. Yang, and R.G. Parr Phys. Rev. B 37 1988 785
22. A.D. Becke J. Chem. Phys. 98 1993 1372
23. P.J. Stevens, F.J. Devlin, C.F. Chabalowski, and M.J. Frisch J. Phys. Chem. 98 1994 11623
24. Y.D. Wu, and D.K.W. Lai J. Org. Chem. 61 1996 7904
25. H.-Y. Zhang, Y.M. Sun, and D.Z. Chen Quant. Struct. Act. Relat. 20 2001 148
26. H.G. Korth, M.I. de Heer, and P. Mulder J. Phys. Chem. 106 2002 8779
27. M. Jonsson, J. Lind, T.E. Eriksen, and G. Merényi J. Chem. Soc., Perkin Trans. II 1993 1567
28. For all substituents, values are taken from C. Hansch, A. Leo, and R.W. Taft Chem. Rev. 91 1991 165 for σ p + (OH ) = - 0. 78. The originally proposed value of -0.92 is almost certainly too large to be applicable with the calculated, gas-phase ΔPDEs, see:
29. D.A. Pratt, M.I. de Heer, P. Mulder, and K.U. Ingold J. Am. Chem. Soc. 123 2001 5518 for σ p + (CHO ) = - 0. 47 see:
30. C.D. Selassie, A.J. Shuterman, S. Kapur, R.P. Verma, L. Zhang, and C. Hanch Chem. Soc., Perkin Trans. II 1999 2729
31. T. Brinck, M. Haeberline, and M. Jonsson J. Am. Chem. Soc. 119 1997 4239
32. J.S. Wright, D.J. Carpenter, D.J. Mckay, and K.U. Ingold J. Am. Chem. Soc. 119 1997 4245
33. N.W. Larsen J. Mol. Struct. 51 1979 175
34. I. Vedernikova, E. Proynov, D. Salahub, and A. Haemers Int. J. Quantum Chem. 77 2000 161
35. In the global minimum conformer of the 3-OH group, the substituent H atom is pointing toward the phenolic H atom; in the 3-COOH one, the phenolic H atom is pointing toward the OH moiety of COOH.
36. N.S. Isaacs Physical Organic Chemistry 1995 Wiley and Sons New York
37. F.G. Bordwell, X.-M. Zhang, A.V. Satish, and J.P. Cheng J. Am. Chem. Soc. 116 1994 6605
38. G.A. DiLabio, D.A. Pratt, A.D. LoFaro, and J.S. Wright J. Phys. Chem. A 103 1999 1653
39. T. Brinck, H.N. Lee, and M. Jonsson J. Phys. Chem. A 103 1999 7094
40. D.A. Pratt, G.A. Dilabio, P. Mulder, and K.U. Ingold Acc. Chem. Res. 37 2004 334
41. 2 ΔPDE from the correlation, the corresponding coefficient is increased to -0.9625.