Structure and electronic properties of (+)-catechin : aqueous solvent effects

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We report a study of the structure of (+)-catechin, which belongs to the family of the flavan-3-ols—one of the five most widely distributed phenolic groups. The biological activities and pharmaceutical utility of these compounds are related to antioxidant activity due to their ability to scaveng...

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Autores principales: Bentz, Erika Natalia, Pomilio, Alicia Beatriz, Lobayan, Rosana María
Formato: Artículo
Lenguaje:Inglés
Publicado: Springer Nature 2026
Materias:
(+)-Catechin
Antioxidants
Density functional theory
Aqueous solvent effect
PCM model
Atoms in molecules
Natural bond orbital analysis
Molecular polarizability
Acceso en línea:http://repositorio.unne.edu.ar/handle/123456789/60078
Aporte de:
RIUNNE - Repositorio Institucional de la Universidad Nacional del Nordeste (UNNE) de Universidad Nacional del Nordeste
id I48-R184-123456789-60078
record_format dspace
spelling I48-R184-123456789-600782026-02-20T10:26:31Z Structure and electronic properties of (+)-catechin : aqueous solvent effects Bentz, Erika Natalia Pomilio, Alicia Beatriz Lobayan, Rosana María (+)-Catechin Antioxidants Density functional theory Aqueous solvent effect PCM model Atoms in molecules Natural bond orbital analysis Molecular polarizability We report a study of the structure of (+)-catechin, which belongs to the family of the flavan-3-ols—one of the five most widely distributed phenolic groups. The biological activities and pharmaceutical utility of these compounds are related to antioxidant activity due to their ability to scavenge free radicals. A breakthrough in the study of the conforma- tional space of this compound, so far absent in the literature, is presented herein. A detailed analysis of the electronic distri- bution, charge delocalization effects, and stereoelectronic ef- fects is presented following application of the theory of atoms in molecules (AIM) and natural bond orbital analysis. The stability order, and the effects of electron delocalization in the structures were analyzed in depth. The molecular electrostatic potential (MEP) was also obtained, assessing changes in the electronic distribution in aqueous solution, the effects of the solvent on the intrinsic electronic properties, and molecular geometry. The effect of the aqueous solvent on MEP was also quantified, and rationalized by charge delocalization mecha- nisms, relating them to structural changes and topological properties of the electronic charge density. To further analyze the effects of the aqueous solvent, as well as investigating the molecular and structural properties of these compounds in a biological environment, the polarizabilities for all conformers characterized were also calculated. All results were interpreted on the basis of our accumulated knowledge on (4α→6", 2α→ O→1")-phenylflavans in previous reports, thus enriching and deepening the analysis of both types of structure. 2026-02-19T13:38:40Z 2026-02-19T13:38:40Z 2014-02 Artículo Bentz, Erika Natalia, Pomilio, Alicia Beatriz y Lobayan, Rosana María, 2014. Structure and electronic properties of (+)-catechin : aqueous solvent effects. Journal of Molecular Modeling. Heidelberg: Springer Nature, vol. 20, no. 2, p. 1-13. E-ISSN 1610-2940. DOI https://doi.org/10.1007/s00894-014-2105-z 0948-5023 http://repositorio.unne.edu.ar/handle/123456789/60078 eng https://doi.org/10.1007/s00894-014-2105-z openAccess http://creativecommons.org/licenses/by-nc-nd/2.5/ar/ application/pdf p. 1-13 application/pdf Springer Nature Journal of Molecular Modeling, 2014, vol. 20, no. 2, p. 1-13.
institution Universidad Nacional del Nordeste
institution_str I-48
repository_str R-184
collection RIUNNE - Repositorio Institucional de la Universidad Nacional del Nordeste (UNNE)
language Inglés
topic (+)-Catechin
Antioxidants
Density functional theory
Aqueous solvent effect
PCM model
Atoms in molecules
Natural bond orbital analysis
Molecular polarizability
spellingShingle (+)-Catechin
Antioxidants
Density functional theory
Aqueous solvent effect
PCM model
Atoms in molecules
Natural bond orbital analysis
Molecular polarizability
Bentz, Erika Natalia
Pomilio, Alicia Beatriz
Lobayan, Rosana María
Structure and electronic properties of (+)-catechin : aqueous solvent effects
topic_facet (+)-Catechin
Antioxidants
Density functional theory
Aqueous solvent effect
PCM model
Atoms in molecules
Natural bond orbital analysis
Molecular polarizability
description We report a study of the structure of (+)-catechin, which belongs to the family of the flavan-3-ols—one of the five most widely distributed phenolic groups. The biological activities and pharmaceutical utility of these compounds are related to antioxidant activity due to their ability to scavenge free radicals. A breakthrough in the study of the conforma- tional space of this compound, so far absent in the literature, is presented herein. A detailed analysis of the electronic distri- bution, charge delocalization effects, and stereoelectronic ef- fects is presented following application of the theory of atoms in molecules (AIM) and natural bond orbital analysis. The stability order, and the effects of electron delocalization in the structures were analyzed in depth. The molecular electrostatic potential (MEP) was also obtained, assessing changes in the electronic distribution in aqueous solution, the effects of the solvent on the intrinsic electronic properties, and molecular geometry. The effect of the aqueous solvent on MEP was also quantified, and rationalized by charge delocalization mecha- nisms, relating them to structural changes and topological properties of the electronic charge density. To further analyze the effects of the aqueous solvent, as well as investigating the molecular and structural properties of these compounds in a biological environment, the polarizabilities for all conformers characterized were also calculated. All results were interpreted on the basis of our accumulated knowledge on (4α→6", 2α→ O→1")-phenylflavans in previous reports, thus enriching and deepening the analysis of both types of structure.
format Artículo
author Bentz, Erika Natalia
Pomilio, Alicia Beatriz
Lobayan, Rosana María
author_facet Bentz, Erika Natalia
Pomilio, Alicia Beatriz
Lobayan, Rosana María
author_sort Bentz, Erika Natalia
title Structure and electronic properties of (+)-catechin : aqueous solvent effects
title_short Structure and electronic properties of (+)-catechin : aqueous solvent effects
title_full Structure and electronic properties of (+)-catechin : aqueous solvent effects
title_fullStr Structure and electronic properties of (+)-catechin : aqueous solvent effects
title_full_unstemmed Structure and electronic properties of (+)-catechin : aqueous solvent effects
title_sort structure and electronic properties of (+)-catechin : aqueous solvent effects
publisher Springer Nature
publishDate 2026
url http://repositorio.unne.edu.ar/handle/123456789/60078
work_keys_str_mv AT bentzerikanatalia structureandelectronicpropertiesofcatechinaqueoussolventeffects
AT pomilioaliciabeatriz structureandelectronicpropertiesofcatechinaqueoussolventeffects
AT lobayanrosanamaria structureandelectronicpropertiesofcatechinaqueoussolventeffects
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