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Abstract:

Interest in food phenolics has increased in recent years largely due to their antioxidant capacity, free radical scavenging, and potential health benefits. In literature two main reaction mechanisms have been proposed for their role as free radical (FR) scavengers, i.e., the mechanism of a hydrogen atom transfer (HAT) governed by the O[sbnd]H bond dissociation enthalpy (BDE), and the mechanism of single electron transfer (SET) governed by an electron transfer process, the ionization potential (IP) playing an important role. Thirty nonplanar structures were analyzed. The study of (+)-catechin (CTQ) and (4α → 6″, 2α → O → 1″)-phenylflavans with a R′ = H, R = OH; R′ = OH, R = H, and R′ = OH, R = OH substitution is performed herein. Catechol, phenol, and resorcinol are also included as references. Results obtained with B3LYP hybrid functional with 6-311++G(d,p) and 6-31G(d,p) basis set are analyzed. Two new indicators arising from electron delocalizations are presented herein, thus showing that there is a different set of donor-acceptor interactions to explain FR scavenging mechanisms. © 2017 Elsevier B.V.

Registro:

Documento: Artículo
Título:Donor-acceptor interactions as descriptors of the free radical scavenging ability of flavans and catechin
Autor:Bentz, E.N.; Pomilio, A.B.; Lobayan, R.M.
Filiación:Departamento de Física, Facultad de Ciencias Exactas y Naturales y Agrimensura, Universidad Nacional del Nordeste, Avda. Libertad 5300, Corrientes, Argentina
Hospital de Clínicas “José de San Martín”, Departamento de Bioquímica Clínica, UBA-CONICET, Facultad de Farmacia y Bioquímica, Universidad de Buenos Aires, Av. Córdoba 2351 C1120AAF, Buenos Aires, Argentina
Palabras clave:(4α→6″, 2α → O → 1″)-phenylflavans; Antioxidants; Atoms in molecules; Bond dissociation enthalpies; Catechin; Density functional theory; Donor-acceptor interactions; Ionization potentials; Natural bond orbital analysis; Proanthocyanidins
Año:2017
Volumen:1110
Página de inicio:14
Página de fin:24
DOI: http://dx.doi.org/10.1016/j.comptc.2017.03.028
Título revista:Computational and Theoretical Chemistry
Título revista abreviado:Comput. Theor. Chem.
ISSN:2210271X
Registro:http://digital.bl.fcen.uba.ar/collection/paper/document/paper_2210271X_v1110_n_p14_Bentz

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Citas:

---------- APA ----------
Bentz, E.N., Pomilio, A.B. & Lobayan, R.M. (2017) . Donor-acceptor interactions as descriptors of the free radical scavenging ability of flavans and catechin. Computational and Theoretical Chemistry, 1110, 14-24.
http://dx.doi.org/10.1016/j.comptc.2017.03.028
---------- CHICAGO ----------
Bentz, E.N., Pomilio, A.B., Lobayan, R.M. "Donor-acceptor interactions as descriptors of the free radical scavenging ability of flavans and catechin" . Computational and Theoretical Chemistry 1110 (2017) : 14-24.
http://dx.doi.org/10.1016/j.comptc.2017.03.028
---------- MLA ----------
Bentz, E.N., Pomilio, A.B., Lobayan, R.M. "Donor-acceptor interactions as descriptors of the free radical scavenging ability of flavans and catechin" . Computational and Theoretical Chemistry, vol. 1110, 2017, pp. 14-24.
http://dx.doi.org/10.1016/j.comptc.2017.03.028
---------- VANCOUVER ----------
Bentz, E.N., Pomilio, A.B., Lobayan, R.M. Donor-acceptor interactions as descriptors of the free radical scavenging ability of flavans and catechin. Comput. Theor. Chem. 2017;1110:14-24.
http://dx.doi.org/10.1016/j.comptc.2017.03.028