Abstract
BackgroundChemicals generically referred to as flavonoids belong to the group of phenolic compounds and constitute an important group of secondary metabolites due to their applications as well as their biochemical properties. Flavonoids, which share a common benzo- γ-pyrone structure, constitute a kind of compound which are highly ubiquitous in the plant kingdom.FindingsThe M06 family of density functionals has been assessed for the calculation of the molecular structure and properties of the Naringenin flavonoid. The chemical reactivity descriptors have been calculated through Conceptual DFT. The active sites for nucleophilic and electrophilic attacks have been chosen by relating them to the Fukui function indices and the dual descriptor f(2)(r). A comparison between the descriptors calculated through vertical energy values and those arising from the Koopmans’ theorem approximation have been performed in order to check for the validity of the last procedure.ConclusionsThe M06 family of density functionals (M06, M06L, M06-2X and M06-HF) used in the present work leads to the same qualitatively and quantitatively similar description of the chemistry and reactivity of the Naringenin molecule, yielding reasonable results. However, for the case of the M06-2X and M06-HF density functionals, which include a large portion of HF exchange, the calculations considering the validity of the Koopmans’ theorem lead to negative electron affinities.
Highlights
For the case of the M06-2X and M06-HF density functionals, which include a large portion of HF exchange, the calculations considering the validity of the Koopmans’ theorem lead to negative electron affinities
The validity of the Koopmans’ theorem within the DFT approximation is controversial. It has been shown [35] that the KS orbitals may differ in shape and energy from the HF orbitals, the combination of them produces Conceptual DFT reactivity descriptors that correlate quite well with the reactivity descriptors obtained through Hartree-Fock calculations
From the whole of the results presented in this contribution it has been clearly demonstrated that the sites of interaction of the Naringenin molecule can be predicted by using DFT-based reactivity descriptors such as the hardness, softness, and electrophilicity, as well as Fukui function calculations
Summary
Essentials of Computational Chemistry - Theories and Models, 2nd edition. Zhao Y, Truhlar DG: Density functionals with broad applicability in chemistry. Chemicals generically referred to as flavonoids belong to the group of phenolic compounds and constitute an important group of secondary metabolites due to their applications as well as their biochemical properties. Flavonoids, which share a common benzo-γ -pyrone structure, constitute a kind of compound which are highly ubiquitous in the plant kingdom
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