Quantum-chemical study of the complexation of flavonol derivatives with zinc and iron sations

1Kazakova, OA, 1Laguta, IV, 1Stavinskaya, ON
1O. O. Chuiko Institute of Surface Chemistry of the NAS of Ukraine, Kyiv
Dopov. Nac. akad. nauk Ukr. 2017, 9:95-101
Section: Chemistry
Language: Russian

Quantum-chemical methods ab initio (6-31G(d,p) DFT (B3LYP/6-31G(d,p) and the IEF PCM (GAMESS) solvation model are used to study the formation of complexes of Zn2+ and Fe3+ cations with 3-hydroxyflavone and its three derivatives (4′-(N,N-dimethylamino)flavonol, 4′-[N,N-di(2-hydroxyethylamino)]flavonol, 3′,4′-di-(hydroxycarbonylmethoxy)flavonol. Deprotonated 3-hydroxygroups of all the molecules of flavonoles are found to be the main sites for bonding both Zn2+ and Fe3+ cations; in the case of 3′,4′-di(hydroxycarbonylmethoxy) flavonol, also the side carboxyl groups of phenyl moiety appeared to participate in the Zn2+ complexation. For both Zn2+ and Fe3+ complexation reactions, all flavonole derivatives have higher values of Gibbs free energy comparatively with an initial flavonole molecule, with the 4′-[N,N-di(2-hydroxyethylamino)]flavonol being the strongest chelating agent. For all the flavonols studied, the Gibbs free energy for the Fe3+ complexation is ∼2 times higher than for the Zn2+ complexation; this means that iron may substitute zinc in flavonol−zinc complexes. The quantum-chemical data are in good agreement with experimental results as to the Zn2+ and Fe3+ complexations, and they may be used to predict the properties of complexes.

Keywords: complexation, flavonol derivatives, Gibbs free energy, metal sations
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