Donor-acceptor interactions as descriptors of the free radical scavenging ability of flavans and catechin
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...
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todo:paper_2210271X_v1110_n_p14_Bentz2023-10-03T16:40:28Z Donor-acceptor interactions as descriptors of the free radical scavenging ability of flavans and catechin Bentz, E.N. Pomilio, A.B. Lobayan, R.M. (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 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. Fil:Pomilio, A.B. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_2210271X_v1110_n_p14_Bentz |
| institution |
Universidad de Buenos Aires |
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I-28 |
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R-134 |
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Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
(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 |
| spellingShingle |
(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 Bentz, E.N. Pomilio, A.B. Lobayan, R.M. Donor-acceptor interactions as descriptors of the free radical scavenging ability of flavans and catechin |
| topic_facet |
(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 |
| description |
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. |
| format |
JOUR |
| author |
Bentz, E.N. Pomilio, A.B. Lobayan, R.M. |
| author_facet |
Bentz, E.N. Pomilio, A.B. Lobayan, R.M. |
| author_sort |
Bentz, E.N. |
| title |
Donor-acceptor interactions as descriptors of the free radical scavenging ability of flavans and catechin |
| title_short |
Donor-acceptor interactions as descriptors of the free radical scavenging ability of flavans and catechin |
| title_full |
Donor-acceptor interactions as descriptors of the free radical scavenging ability of flavans and catechin |
| title_fullStr |
Donor-acceptor interactions as descriptors of the free radical scavenging ability of flavans and catechin |
| title_full_unstemmed |
Donor-acceptor interactions as descriptors of the free radical scavenging ability of flavans and catechin |
| title_sort |
donor-acceptor interactions as descriptors of the free radical scavenging ability of flavans and catechin |
| url |
http://hdl.handle.net/20.500.12110/paper_2210271X_v1110_n_p14_Bentz |
| work_keys_str_mv |
AT bentzen donoracceptorinteractionsasdescriptorsofthefreeradicalscavengingabilityofflavansandcatechin AT pomilioab donoracceptorinteractionsasdescriptorsofthefreeradicalscavengingabilityofflavansandcatechin AT lobayanrm donoracceptorinteractionsasdescriptorsofthefreeradicalscavengingabilityofflavansandcatechin |
| _version_ |
1807323315605340160 |