Structure and electronic properties of (+)-catechin : aqueous solvent effects
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: | , , |
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| Formato: | Artículo |
| Lenguaje: | Inglés |
| Publicado: |
Springer Nature
2026
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| Materias: | |
| Acceso en línea: | http://repositorio.unne.edu.ar/handle/123456789/60078 |
| Aporte de: |
| Sumario: | 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. |
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