A Computational Study of the Structure-Activity Relationships of Some p-Hydroxybenzoic Acid Antioxidants

JAOCS, Journal of the American Oil Chemists' Society

Volumn 80, Issue 12, 2003, Pages 1217-1223

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

^a ARISTOTLE UNIVERSITY OF THESSALONIKI   (Greece)

Author keywords

3,4 dihydroxybenzoic acid; 4 hydroxy 3,5 dimethoxybenzoic acid; 4 hydroxy 5 methoxybenzoic acid; Antioxidant; B3LYP; BDE; DFT; p hydroxybenzoic acid; Structure activity relationships; HOF

Indexed keywords

CARBOXYLIC ACIDS; COMPUTATIONAL METHODS; EIGENVALUES AND EIGENFUNCTIONS; HYDROGEN; MOLECULAR STRUCTURE; ORGANIC SOLVENTS;

NONPOLAR SOLVENTS;

ANTIOXIDANTS;

HOMO;

EID: 0346685898     PISSN: 0003021X     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11746-003-0845-3     Document Type: Article

References (21)

1. Bakalbassis E.G., A. Chatzopoulou, V.S. Melissas, M. Tsimidou, M. Tsolaki, and A. Vafiadis, An ab initio and a DFT Study for the Explanation of the Antioxidant Activity of Four p-Hydroxycinnamic Acid Derivatives, Lipids 36:181-190 (2001).
2. Nenadis, N., S. Boyle, E.G. Bakalbassis, and M. Tsimidou, An Experimental Approach to Structure-Activity Relationships of Caffeic and Dihydrocaffeic Acids and Related Monophenols, J. Am. Oil Chem. Soc. 80:451-458 (2003).
3. Bakalbassis E.G., N. Nenadis, and M. Tsimidou, A Density Functional Theory Study of Structure-Activity Relationships in Caffeic and Dihydrocaffeic Acids and Related Monophenols, Ibid. 80:459-466 (2003).
4. Tyrakowska, B., A.E.M.F. Soffers, H. Szymusiak, S. Boeren, M.G. Boersma, K. Lemanska, J. Vervoort, and I.M.C.M. Rietjens, TEAC Antioxidant Activity of 4-Hydroxybenzoates, Free Rad. Biol. Med. 27:1427-1436 (1999).
5. Colapietro, M., A. Domenicano, and C. Marciante, Structural Studies of Benzene Derivatives. VI. Refinement of the Crystal Structure of p-Hydroxybenzoic Acid Monohydrate, Acta Cryst. B 35:2177-2180 (1979).
6. Heath, E.A., P. Singh, and Y. Ebisuzaki, Structure of p-Hydroxybenzoic Acid and Acid-Acetone Complex (2/1), Acta Cryst. C 48:1960-1965 (1992).
7. Parr, R.G., and W. Yang, Density Functional Theory of Atoms and Molecules, Oxford University Press, New York, 1989.
8. Frisch, M.J., 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, et al., Gaussian 98, Revision A.11, Gaussian, Inc., Pittsburgh, PA, 2001.
9. Tewari, Y.B., J. Chen, M.J. Holden, K.N. Houk, and R.N. Goldberg, Thermodynamic and Quantum Chemical Study of the Conversion of Chorismate to (pyruvate + 4-hydroxybenzoate), J. Phys. Chem. B 102:8634-8639 (1998).
10. Wiberg, K.B., Substituent Effects on the Acidity of Weak Acids. 2. Calculated Gas-Phase Acidities of Substituted Benzoic Acids, J. Org. Chem. 67:4787-4794 (2002).
11. Fabian, W.M.F., AM1 Calculations of Rotation Around Essential Single Bonds and Preferred Conformations in Conjugated Molecules, J. Comput. Chem. 9:369-377 (1988).
12. Nelson, M.R., and R.F. Borkman, Internal Rotation Barriers: Ab initio Calculations on Substituted Ethyl Benzoates and Benzoic Acids as Models for Polyester Flexibility, J. Mol. Struct. THEOCHEM 432:241-255 (1998).
13. Wright, J.S., D.J. Carpenter, D.J. McKay, and K.U. Ingold, Theoretical Calculation of Substituent Effects on the O-H Bond Strength of Phenolic Antioxidants Related to Vitamin E, J. Am. Chem. Soc. 119:4245-4252 (1997).
14. Zhang, H. Y. Selection of Theoretical Parameters Characterizing Scavenging Activity of Antioxidants on Free Radicals, J. Am. Oil Chem. Soc. 75:1705-1709 (1998).
15. Bors, W., W. Heller, C. Michel, and M. Saran, Flavonoids as Antioxidants: Determination of Radical-Scavenging Efficiencies, Methods Enzymol. 186:345-355 (1990).
16. Rice-Evans, C.A., N.J. Miller, and G. Pagana, Structure-Antioxidant Activity Relationships of Flavonoids and Phenolic Acids, Free Rad. Biol. Med. 20:933-956 (1996).
17. Natella, F., M. Nardini, M. Di Felice, and C. Scaccini, Benzoic and Cinnamic Acid Derivatives as Antioxidants: Structure-Activity Relation, J. Agric. Food Chem. 47:1453-1459 (1999).
18. Wright, J.S., E.R. Jonson, and G.A. DiLabio, Predicting the Activity of Phenolic Antioxidants: Theoretical Method, Analysis of Substituent Effects, and Application to Major Families of Antioxidants, J. Am. Chem. Soc. 123:1173-1183 (2001).
19. Zhang, H.-Y., Y.-M. Sun, and X.-L. Wang, Substituent Effects on O-H Bond Dissociation Enthalpies and Ionization Potentials of Catechols: A DFT Study and Its Implications in the Rational Design of Phenolic Antioxidants and Elucidation of Structure-Activity Relationships for Flavonoid Antioxidants, Chem. Eur. J. 9:502-508 (2003).
20. Hansch, C., A. Leo, and R.W. Taft, A Survey of Hammett Substituent Constants and Resonance and Field Parameters, Chem. Rev. 91:165-195 (1991).
21. Van Acker, S.A.B.E., M.J. de Groot, D.J. van den Berg, M.N.J.L. Tromp, G.D.O. den Kelder, W.J.F. van der Vijgh, and A. Bast, A Quantum Chemical Explanation of the Antioxidant Activity of Flavonoids, Chem. Res. Toxicol. 9:1305-1312 (1996).