Z-Isomers of (4α→6′′, 2α→O→1′′)-phenylflavan substituted with R′=R=OH. Conformational properties, electronic structure and aqueous solvent effects
Procyanidins are highly hydroxylated polymers known as antioxidant compounds, thereby exhibiting benefi- cial effects. These compounds are protective agents against oxidative stress and the damage induced by free radicals in membranes and nucleic acids. This paper describes a study of the c...
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Springer Nature
2026
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I48-R184-123456789-600682026-02-19T10:22:48Z Z-Isomers of (4α→6′′, 2α→O→1′′)-phenylflavan substituted with R′=R=OH. Conformational properties, electronic structure and aqueous solvent effects Bentz, Erika Natalia Pomilio, Alicia Beatriz Lobayan, Rosana María (4α→6′′, 2α→O→1′′)- phenylflavans Antioxidants Density functional theory Aqueous solvent effect PCM model Atoms in molecules Natural bond orbital analysis Molecular polarizability Procyanidins are highly hydroxylated polymers known as antioxidant compounds, thereby exhibiting benefi- cial effects. These compounds are protective agents against oxidative stress and the damage induced by free radicals in membranes and nucleic acids. This paper describes a study of the conformational space of (4α→6′′, 2α→O→1′′)- phenylflavan substituted with R′=R=OH as part of a larger study of similar structures with different substitutions. The relationships between aqueous solution–vacuum variations of some properties were studied, as well as the stabilization and reactivity of (4α→6′′, 2α→O→1′′)-phenylflavan substituted with R′=R=H, R′=H, R=OH, R′=R=OH, and (+)- catechin. The variations in geometric parameters and electron- ic properties due to conformational changes, as well as the effects of substituents and polar solvents, were evaluated and analyzed. Bader’s theory of atoms in molecules was applied to characterize intramolecular interactions, along with a natural bond orbital analysis for each conformer described. The mo- lecular electrostatic potential was rationalized by charge delo- calization mechanisms and interatomic intramolecular interac- tions, relating them to the structural changes and topological properties of the electron charge density. Molecular polariz- ability and permanent electric dipole moment values were estimated. The results show the importance of a knowledge of the conformational space, and values for each conformer. Based on our previous results, we showed the existence of electron charge delocalization mechanisms acting coopera- tively as “delocalization routes”, showing interactions be- tween different rings not even sharing the same plane. These “delocalization routes” were more effective for (4α→6′′, 2α→O→1′′)-phenylflavan substituted with R′=R=OH than for (+)-catechin, and are proposed as adding insight into the structure–antioxidant activity relationship of flavans. 2026-02-18T14:59:29Z 2026-02-18T14:59:29Z 2016 Artículo Bentz, Erika Natalia, Pomilio, Alicia Beatriz y Lobayan, Rosana María, 2016. Z-Isomers of (4α→6′′, 2α→O→1′′)-phenylflavan substituted with R′=R=OH. Conformational properties, electronic structure and aqueous solvent effects. Journal of Molecular Modeling. Heidelberg: Springer Nature, vol. 22, no. 187, p. 1-15. E-ISSN 1610-2940. DOI https://doi.org/10.1007/s00894-016-3034-9 0948-5023 http://repositorio.unne.edu.ar/handle/123456789/60068 eng https://doi.org/10.1007/s00894-016-3034-9 openAccess http://creativecommons.org/licenses/by-nc-nd/2.5/ar/ application/pdf p. 1-15 application/pdf Springer Nature Journal of Molecular Modeling, 2016, vol. 22, no. 187, p. 1-15. |
| 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 |
(4α→6′′, 2α→O→1′′)- phenylflavans Antioxidants Density functional theory Aqueous solvent effect PCM model Atoms in molecules Natural bond orbital analysis Molecular polarizability |
| spellingShingle |
(4α→6′′, 2α→O→1′′)- phenylflavans 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 Z-Isomers of (4α→6′′, 2α→O→1′′)-phenylflavan substituted with R′=R=OH. Conformational properties, electronic structure and aqueous solvent effects |
| topic_facet |
(4α→6′′, 2α→O→1′′)- phenylflavans Antioxidants Density functional theory Aqueous solvent effect PCM model Atoms in molecules Natural bond orbital analysis Molecular polarizability |
| description |
Procyanidins are highly hydroxylated polymers
known as antioxidant compounds, thereby exhibiting benefi-
cial effects. These compounds are protective agents against
oxidative stress and the damage induced by free radicals in
membranes and nucleic acids. This paper describes a study of
the conformational space of (4α→6′′, 2α→O→1′′)-
phenylflavan substituted with R′=R=OH as part of a larger
study of similar structures with different substitutions. The
relationships between aqueous solution–vacuum variations
of some properties were studied, as well as the stabilization
and reactivity of (4α→6′′, 2α→O→1′′)-phenylflavan
substituted with R′=R=H, R′=H, R=OH, R′=R=OH, and (+)-
catechin. The variations in geometric parameters and electron-
ic properties due to conformational changes, as well as the
effects of substituents and polar solvents, were evaluated and
analyzed. Bader’s theory of atoms in molecules was applied to
characterize intramolecular interactions, along with a natural
bond orbital analysis for each conformer described. The mo-
lecular electrostatic potential was rationalized by charge delo-
calization mechanisms and interatomic intramolecular interac-
tions, relating them to the structural changes and topological
properties of the electron charge density. Molecular polariz-
ability and permanent electric dipole moment values were
estimated. The results show the importance of a knowledge
of the conformational space, and values for each conformer.
Based on our previous results, we showed the existence of
electron charge delocalization mechanisms acting coopera-
tively as “delocalization routes”, showing interactions be-
tween different rings not even sharing the same plane. These
“delocalization routes” were more effective for (4α→6′′,
2α→O→1′′)-phenylflavan substituted with R′=R=OH than
for (+)-catechin, and are proposed as adding insight into the
structure–antioxidant activity relationship of flavans. |
| 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 |
Z-Isomers of (4α→6′′, 2α→O→1′′)-phenylflavan substituted with R′=R=OH. Conformational properties, electronic structure and aqueous solvent effects |
| title_short |
Z-Isomers of (4α→6′′, 2α→O→1′′)-phenylflavan substituted with R′=R=OH. Conformational properties, electronic structure and aqueous solvent effects |
| title_full |
Z-Isomers of (4α→6′′, 2α→O→1′′)-phenylflavan substituted with R′=R=OH. Conformational properties, electronic structure and aqueous solvent effects |
| title_fullStr |
Z-Isomers of (4α→6′′, 2α→O→1′′)-phenylflavan substituted with R′=R=OH. Conformational properties, electronic structure and aqueous solvent effects |
| title_full_unstemmed |
Z-Isomers of (4α→6′′, 2α→O→1′′)-phenylflavan substituted with R′=R=OH. Conformational properties, electronic structure and aqueous solvent effects |
| title_sort |
z-isomers of (4α→6′′, 2α→o→1′′)-phenylflavan substituted with r′=r=oh. conformational properties, electronic structure and aqueous solvent effects |
| publisher |
Springer Nature |
| publishDate |
2026 |
| url |
http://repositorio.unne.edu.ar/handle/123456789/60068 |
| work_keys_str_mv |
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| _version_ |
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