Quantum-chemical study of the complexation of flavonol derivatives with zinc and iron sations
DOI:
https://doi.org/10.15407/dopovidi2017.09.095Keywords:
complexation, flavonol derivatives, Gibbs free energy, metal sationsAbstract
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.
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