Structure of Flavones and Flavonols. Part II: Role of Position on the O-H Bond Dissociation Enthalpy


The enthalpies of bond dissociations of the hydroxyl groups, the energy of the highest occupied molecular orbitals and the corresponding radicals spin densities of all possible ten isomeric mono-hydroxyl flavones are calculated by means of 3-parameter Becke, Lee, Yang and Parr functional. The structural factors affecting these descriptors of radical-scavenging activity are outlined. The results obtained show that the hydroxyl groups in ring A and C are more involved in the process of a radical-capturing than recently believed.

Share and Cite:

M. Vakarelska-Popovska and Z. Velkov, "Structure of Flavones and Flavonols. Part II: Role of Position on the O-H Bond Dissociation Enthalpy," Computational Chemistry, Vol. 2 No. 1, 2014, pp. 1-5.
doi: 10.4236/cc.2014.21001.

Conflicts of Interest

The authors declare no conflicts of interest.


[1] Ell. Middleton Jr., Ch. Kandaswami and Th. C. Theoharides, “The Effects of Plant Flavonoids on Mammalian Cells: Implications for Inflammation, Heart Disease, and Cancer,” Pharmacological Reviews, Vol. 52, No. 4, 2000, pp. 673-751.
[2] P.-G. Pietta, “Flavonoids as Antioxidants,” Journal of Natural Products, Vol. 63, No. 7, 2000, pp. 1035-1042.
[3] A. R. Tapas, D. M. Sakarkar and R. B. Kakde, “Flavonoids as Nutraceuticals: A Review,” Tropical Journal of Pharmaceutical Research, Vol. 7, No. 3, 2008, pp. 1089-1099.
[4] P. C. H. Hollman and M. B. Katan, “Dietary Flavonoids: Intake, Health Effects and Bioavailability,” Food and Chemical Toxicology, Vol. 37, No. 9-10, 1999, pp. 937-942.
[5] B. F. Rasulev, N. Abdullaev, V. N. Syrov and J. Leszczynski, “A Quantitative Structure-Activity Relationship (QSAR) Study of the Antioxidant Activity of Flavonoids,” QSAR & Combinatorial Science, Vol. 24, No. 5, 2005, pp. 1056-1065.
[6] T. Z. Todorova, M. G. Traykov, A. V. Tadjer and Zh. A. Velkov, “Structure of Flavones and Flavonols. Part I: Role of Substituents on the Planarity of the System,” Computational and Theoretical Chemistry, Vol. 1017, 2013, pp. 85-90.
[7] D. Amic, D. Davidovic-Amic, D. Beslo and N. Trinjastic, “Structure-Radical Scavenging Activity Relationships of Flavonoids,” Croatica Chemica Acta, Vol. 76, No. 1, 2003, pp. 55-61.
[8] A. D. Y?lmaz, T. Coban and S. Suzen, “Synthesis and Antioxidant Activity Evaluations of Melatonin-Based Analogue Indole-Hydrazide/Hydrazone Derivatives,” Journal of Enzyme Inhibition and Medicinal Chemistry, Vol. 27, No. 3, 2012, pp. 428-436.
[9] H. Shirinzadeh, B. Eren, H. Gurer-Orhan, S. Suzen and S. Ozden, “Novel Indole-Based Analogs of Melatonin: Synthesis and in Vitro Antioxidant Activity Studies,” Molecules, Vol. 15, No. 4, 2010, pp. 2187-2202.
[10] S. Suzen, S. S. Cihaner and T. Coban, “Synthesis and Comparison of Antioxidant Properties of Indole-Based Melatonin Analogue Indole Amino Acid Derivatives,” Chemical Biology & Drug Design, Vol. 79, No. 1, 2012, pp. 76-83.
[11] K. R. Korzekwa, J. P. Jones and J. R. Gillette, “Theoretical Studies on Cytochrome P-450 Mediated Hydroxylation: A Predictive Model for Hydrogen Atom Abstractions,” Journal of the American Chemical Society, Vol. 112, No. 19, 1990, pp. 7042-7046.
[12] T. Koopmans, “über die Zuordnung von Wellenfunktionen und Eigenwertenzu den Einzelnen Elektroneneines Atoms,” Physica, Vol. 1, No. 1-6, 1934, pp. 104-113.
[13] Zh. Cheng, J. Ren, Y. Li, W. Chang and Zh. Chen, “Establishment of a Quantitative Structure—Activity Relationship Model for Evaluating and Predicting the Protective Potentials of Phenolic Antioxidants on Lipid Peroxidation,” Journal of Pharmaceutical Sciences, Vol. 92, No. 3, 2003, pp. 475-484.
[14] 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. M. Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Lyengar, J. Tomasi, M. Coss, 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 and D. J. Fox, Gaussian, Inc.,Wallingford CT, 2009.
[15] R. G. Parr and W. Yang, “Density-Functional Theory of Atoms and Molecules,” Oxford University Press, Oxford, 1989.
[16] K. M. Nikolic, “Theoretical Study of Phenolic Antioxidants Properties in Reaction with Oxygen-Centered Radicals,” Journal of Molecular Structure: THEOCHEM, Vol. 774, No. 1-3, 2006, pp. 95-105.
[17] S. Riahi, P. Norouzi, Ab. B. Moghaddam, M. R. Ganjali, Gh. R. Karimipour and H. Sharghi, “Theoretical and Experimental Report on the Determination of Oxidation Potentials of Hydroxyanthracene and Thioxanthene Derivatives,” Chemical Physics, Vol. 337, No. 1-3, 2007, pp. 33-38.
[18] J. B. Foresman, T. A. Keith, K. B. Wiberg, J. Snoonian and M. J. Frisch, “Solvent Effects. 5. Influence of Cavity Shape, Truncation of Electrostatics, and Electron Correlation on Ab Initio Reaction Field Calculations,” Journal of Physical Chemistry, Vol. 100, No. 40, 1996, pp. 16098-16104.
[19] M. Vakarelska-Popovska and Zh. Velkov, “Quantum-Chemical Calculation of O-H Bond Dissociation Enthalpy in Flavones,” Proceedings of the 5th International Scientific Conference, Vol. 4, 2013, pp. 10-16.
[20] S. A. B. E. van Acker, M. J. de Groot, D. J. van den Berg, M. N. J. L. Tromp, G. D. O. den Kelder and W. J. F. van der Vrjgh and A. Bast, “A Quantum Chemical Explanation of the Antioxidant Activity of Flavonoids,” Chemical Research in Toxicology, Vol. 9, No. 8, 1996, pp. 1305-1312.
[21] M. F. Triola, “Elementary Statistics,” Addison-Wesley, Boston, 2003.
[22] P. F. Kador and N. E. Sharpless, “Structure-Activity Studies of Aldose Reductase Inhibitors Containing the 4- Oxo-4H-Chromen Ring System,” Biophysical Chemistry, Vol. 8, No. 1, 1978, pp. 81-85.
[23] P. F. Kador and N. E. Sharpless, “Pharmacophor Requirements of the Aldose Reductase Inhibitor Site,” Molecular Pharmacology, Vol. 24, No. 3, 1983, pp. 521-531.

Copyright © 2023 by authors and Scientific Research Publishing Inc.

Creative Commons License

This work and the related PDF file are licensed under a Creative Commons Attribution 4.0 International License.