Theoretical study of Z isomers of A-type dimeric proanthocyanidins substituted with R=H, OH and OCH3 : stability and reactivity properties

The stereochemistry of A-type dimeric proantho- cyanidins was studied, focusing on the factors that determine it, and the changes that occur with R = OCH3, R′ = H, and R = OH, R′ = H as substituents, starting with the study of the conformational space of each species. Using molecular dynamics...

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Autores principales: Bentz, Erika Natalia, Jubert, Alicia Haydeé, Pomilio, Alicia Beatriz, Lobayan, Rosana María
Formato: Artículo
Lenguaje:Inglés
Publicado: Springer Nature 2026
Materias:
Dimeric proanthocyanidins
Density functional theory
Atoms in molecules
NBO analysis
Topological properties
Maps of electrostatic potential
Acceso en línea:http://repositorio.unne.edu.ar/handle/123456789/60075
Aporte de:
RIUNNE - Repositorio Institucional de la Universidad Nacional del Nordeste (UNNE) de Universidad Nacional del Nordeste
id I48-R184-123456789-60075
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spelling I48-R184-123456789-600752026-02-19T12:03:27Z Theoretical study of Z isomers of A-type dimeric proanthocyanidins substituted with R=H, OH and OCH3 : stability and reactivity properties Bentz, Erika Natalia Jubert, Alicia Haydeé Pomilio, Alicia Beatriz Lobayan, Rosana María Dimeric proanthocyanidins Density functional theory Atoms in molecules NBO analysis Topological properties Maps of electrostatic potential The stereochemistry of A-type dimeric proantho- cyanidins was studied, focusing on the factors that determine it, and the changes that occur with R = OCH3, R′ = H, and R = OH, R′ = H as substituents, starting with the study of the conformational space of each species. Using molecular dynamics at a semiempirical level, and complementing with functional density calculations, two conformers of lowest energy were characterized for R = H, eight conformers for R = OH, and three conformers for R = OCH3 . Electronic distributions were analyzed at a higher calculation level, thus improving the basis set. Intramolecular interactions were examined and characterized by the theory of atoms in molecules (AIM). Detailed natural bond orbitals (NBO) analysis allowed the description of subtle stereo- electronic aspects of fundamental importance for understand- ing the stabilization and antioxidant function of these structures. The study was enriched by a deep analysis of maps of molecular electrostatic potential (MEP). The coordinated analysis of MEP, together with the NBO and AIM results, allowed us to rationalize novel distribution aspects of the potential created in the space around a molecule. 2026-02-19T12:03:23Z 2026-02-19T12:03:23Z 2010-03-17 Artículo Bentz, Erika Natalia, et al., 2010. Theoretical study of Z isomers of A-type dimeric proanthocyanidins substituted with R=H, OH and OCH3 : stability and reactivity properties. Journal of Molecular Modeling. Heidelberg: Springer Nature, vol. 16, no. 12, p. 1895-1909. E-ISSN 0948-5023. DOI https://doi.org/10.1007/s00894-010-0682-z 1610-2940 http://repositorio.unne.edu.ar/handle/123456789/60075 eng https://doi.org/10.1007/s00894-010-0682-z openAccess http://creativecommons.org/licenses/by-nc-nd/2.5/ar/ application/pdf p. 1895-1909 application/pdf Springer Nature Journal of Molecular Modeling, 2010, vol. 16, no. 12, p. 1895-1909.
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 Dimeric proanthocyanidins
Density functional theory
Atoms in molecules
NBO analysis
Topological properties
Maps of electrostatic potential
spellingShingle Dimeric proanthocyanidins
Density functional theory
Atoms in molecules
NBO analysis
Topological properties
Maps of electrostatic potential
Bentz, Erika Natalia
Jubert, Alicia Haydeé
Pomilio, Alicia Beatriz
Lobayan, Rosana María
Theoretical study of Z isomers of A-type dimeric proanthocyanidins substituted with R=H, OH and OCH3 : stability and reactivity properties
topic_facet Dimeric proanthocyanidins
Density functional theory
Atoms in molecules
NBO analysis
Topological properties
Maps of electrostatic potential
description The stereochemistry of A-type dimeric proantho- cyanidins was studied, focusing on the factors that determine it, and the changes that occur with R = OCH3, R′ = H, and R = OH, R′ = H as substituents, starting with the study of the conformational space of each species. Using molecular dynamics at a semiempirical level, and complementing with functional density calculations, two conformers of lowest energy were characterized for R = H, eight conformers for R = OH, and three conformers for R = OCH3 . Electronic distributions were analyzed at a higher calculation level, thus improving the basis set. Intramolecular interactions were examined and characterized by the theory of atoms in molecules (AIM). Detailed natural bond orbitals (NBO) analysis allowed the description of subtle stereo- electronic aspects of fundamental importance for understand- ing the stabilization and antioxidant function of these structures. The study was enriched by a deep analysis of maps of molecular electrostatic potential (MEP). The coordinated analysis of MEP, together with the NBO and AIM results, allowed us to rationalize novel distribution aspects of the potential created in the space around a molecule.
format Artículo
author Bentz, Erika Natalia
Jubert, Alicia Haydeé
Pomilio, Alicia Beatriz
Lobayan, Rosana María
author_facet Bentz, Erika Natalia
Jubert, Alicia Haydeé
Pomilio, Alicia Beatriz
Lobayan, Rosana María
author_sort Bentz, Erika Natalia
title Theoretical study of Z isomers of A-type dimeric proanthocyanidins substituted with R=H, OH and OCH3 : stability and reactivity properties
title_short Theoretical study of Z isomers of A-type dimeric proanthocyanidins substituted with R=H, OH and OCH3 : stability and reactivity properties
title_full Theoretical study of Z isomers of A-type dimeric proanthocyanidins substituted with R=H, OH and OCH3 : stability and reactivity properties
title_fullStr Theoretical study of Z isomers of A-type dimeric proanthocyanidins substituted with R=H, OH and OCH3 : stability and reactivity properties
title_full_unstemmed Theoretical study of Z isomers of A-type dimeric proanthocyanidins substituted with R=H, OH and OCH3 : stability and reactivity properties
title_sort theoretical study of z isomers of a-type dimeric proanthocyanidins substituted with r=h, oh and och3 : stability and reactivity properties
publisher Springer Nature
publishDate 2026
url http://repositorio.unne.edu.ar/handle/123456789/60075
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AT jubertaliciahaydee theoreticalstudyofzisomersofatypedimericproanthocyanidinssubstitutedwithrhohandoch3stabilityandreactivityproperties
AT pomilioaliciabeatriz theoreticalstudyofzisomersofatypedimericproanthocyanidinssubstitutedwithrhohandoch3stabilityandreactivityproperties
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