Reaction enthalpies of OH bonds splitting-off in flavonoids: The role of non-polar and polar solvent

Computational and Theoretical Chemistry

Volumn 1050, Issue , 2014, Pages 31-38

  Vagánek, Adam ^a   Rimarčík, Ján ^a   Dropková, Kamila ^b   Lengyel, Jozef ^c   Klein, Erik ^a  

^a SLOVAK UNIVERSITY OF TECHNOLOGY   (Slovakia)

^b INSTITUTE OF CHEMICAL TECHNOLOGY   (Czech Republic)

^c J HEYROVSKÝ INSTITUTE OF PHYSICAL CHEMISTRY   (Czech Republic)

Author keywords

Antioxidant; DFT; Flavonoid; Polyphenol; Reaction enthalpy

Indexed keywords

EID: 84911421238     PISSN: 2210271X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.comptc.2014.10.020     Document Type: Article

References (35)

1. Rice-Evans C.A., Miller N.J., Pagana G. Structure-antioxidant activity relationships of flavonoids and phenolic acids. Free Radical Biol. Med. 1996, 20:933-956.
2. Gülçin I. Antioxidant activity of food constituents: an overview. Arch. Toxicol. 2012, 86:345-391.
3. Craft B.D., Kerrihard A.L., Amarowicz R., Pegg R.B. Phenol-based antioxidants and the in vitro methods used for their assessment. Compr. Rev. Food Sci. Food Saf. 2012, 11:148-173.
4. Procházková D., Boušová I., Wilhelmová N. Antioxidant and prooxidant properties of flavonoids. Fitoterapia 2011, 82:513-523.
5. 2+ ions: implications for their antioxidant properties. Biochem. J. 1998, 330:1173-1178.
6. Lengyel J., Rimarčík J., Vagánek A., Klein E. On the radical scavenging activity of isoflavones: thermodynamics of O-H bond cleavage. Phys. Chem. Chem. Phys. 2013, 15:10895-10903.
7. Vagánek A., Rimarčík J., Lukeš V., Klein E. On the energetics of homolytic and heterolytic O-H bond cleavage in flavonoids. Comput. Theor. Chem. 2012, 991:192-200.
8. Musialik M., Kuzmicz R., Pawlowski T.S., Litwinienko G. Acidity of hydroxyl groups: an overlooked influence on antiradical properties of flavonoids. J. Org. Chem. 2009, 74:2699-2709.
9. Foti M.C. Antioxidant properties of phenols. J. Pharm. Pharmacol. 2007, 59:1673-1685.
10. Fiorucci S., Golebiowski J., Cabrol-Bass D., Antonczak S. DFT study of quercetin activated forms involved in antiradical, antioxidant, and prooxidant biological processes. J. Agric. Food Chem. 2007, 55:903-911.
11. Sadasivam K., Kumaresan R. A comparative DFT study on the antioxidant activity of apigenin and scutallarein flavonoid compounds. Mol. Phys. 2011, 109:839-852.
12. Marković Z., Amić D., Milenković D., Dimitrić-Marković J.M., Marković S. Examination of the chemical behavior of the quercetin radical cation towards some bases. Phys. Chem. Chem. Phys. 2013, 15:7370-7378.
13. Lengyel J., Gorejová R., Herman Z., Fárník M. Proton transfer in hydrogen-bonded network of phenol molecules: intracluster formation of water. J. Phys. Chem. A 2013, 117:11225-11232.
14. Klein E., Lukeš V. DFT/B3LYP study of the substituent effect on the reaction enthalpies of the individual steps of single electron transfer-proton transfer and sequential proton loss electron transfer mechanisms of phenols antioxidant action. J. Phys. Chem. A 2006, 110:12312-12320.
15. Klein E., Lukeš V., Ilčin M. DFT/B3LYP study of tocopherols and chromans antioxidant action energetics. Chem. Phys. 2007, 336:51-57.
16. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery Jr., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, O. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, D.J. Fox, Gaussian 09 Revision C.01, Gaussian Inc, Wallingford, CT, 2010.
17. Becke A. Density-functional thermochemistry. III. the role of exact exchange. J. Chem. Phys. 1993, 98:5648-5652.
18. Binkley J.S., Pople J.A., Hehre W.J. Self-consistent molecular orbital methods. 21. Small split-valence basis sets for first-row elements. J. Am. Chem. Soc. 1980, 102:939-947.
19. Cances E., Mennucci B., Tomasi J. A new integral equation formalism for the polarizable continuum model: theoretical background and applications to isotropic and anisotropic dielectrics. J. Chem. Phys. 1997, 107:3032-3041.
20. Cances E., Mennucci B. New applications of integral equations methods for solvation continuum models: ionic solutions and liquid crystals. J. Math. Chem. 1998, 23:309-326.
21. Tomasi J., Mennucci B., Cammi R. Quantum mechanical continuum solvation models. Chem. Rev. 2005, 105:2999-3094.
22. Bartmess J.E. Thermodynamics of the electron and the proton. J. Phys. Chem. 1994, 98:6420-6424.
23. Rimarčík J., Lukeš V., Klein E., Ilčin M. Study of the solvent effect on the enthalpies of homolytic and heterolytic N-H bond cleavage in p-phenylenediamine and tetracyano-p-phenylenediamine. J. Mol. Struct. THEOCHEM 2010, 952:25-30.
24. Rong Y.Z., Wang Z.W., Zhao B. A DFT study on structural and antioxidant properties of three flavonols. Food Biophys. 2013, 8:90-94.
25. Amić A., Marković Z., Dimitrić-Marković J.M., Stepanić V., Luči B., Amić D. Toward an improved prediction of the free radical scavenging potency of flavonoids: the significance of double PCET mechanisms. Food Chem. 2014, 152:578-585.
26. Vakarelska-Popovska M.H., Velkov Z.A. Structure of flavones and flavonols. Part II: role of position on the O-H bond dissociation enthalpy. Comput. Chem. 2014, 2:1-5.
27. Leopoldini M., Russo N., Toscano M. Gas and liquid phase acidity of natural antioxidants. J. Agric. Food Chem. 2006, 54:3078-3085.
28. Jovanovic S.V., Steenken S., Tosic M., Marjanovic M., Simic M.G. Flavonoids as antioxidants. J. Am. Chem. Soc. 1994, 116:4846-4851.
29. Dangles O., Fargeix G., Dufour C. One-electron oxidation of quercetin and quercetin derivatives in protic and non protic media. J. Chem. Soc., Perkin Trans. 1999, 2:1387-1395.
30. Torres J.L., Carreras A., Jimenez A., Brillas E., Torrelles X., Rius J., Julia L. Reducing power of simple polyphenols by electron-transfer reactions using a new stable radical of the PTM series, tris(2,3,5,6-tetrachloro-4-nitrophenyl) methyl radical. J. Org. Chem. 2007, 72:3750-3756.
31. Lemanska K., Szymusiak H., Tyrakowska B., Zielinski R., Soffers A.E.M.F., Rietjens I.M.C.M. The influence of pH on antioxidant properties and the mechanism of antioxidant action of hydroxyflavones. Free Radical Biol. Med. 2001, 31:869-881.
32. Dewar M.J.S. The Molecular Orbital Theory of Organic Chemistry 1990, McGraw-Hill, New York.
33. Najafi M., Farmanzadeh D., Klein E., Zahedi M. A Theoretical study on the enthalpies of homolytic and heterolytic N-H bond cleavage in substituted melatonins in the gas-phase and aqueous solution. Acta Chim. Slov. 2013, 60:43-55.
34. Staško A., Brezová V., Biskupič S., Mišík V. The potential pitfalls of using 1,1-diphenyl-2-picrylhydrazyl to characterize antioxidants in mixed water solvents. Free Radical Res. 2007, 41:379-390.
35. Mayer J.M., Rhile I.J. Thermodynamics and kinetics of proton-coupled electron transfer: stepwise vs. concerted pathways. Biochim. Biophys. Acta 2004, 1655:51-58.