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 scavenge fr...
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paper:paper_16102940_v20_n2_p_Bentz2023-06-08T16:25:06Z Structure and electronic properties of (+)-catechin: Aqueous solvent effects Pomilio, Alicia Beatriz Antioxidants Aqueous solvent effect Atoms in molecules Density functional theory Molecular polarizability Natural bond orbital analysis PCM model azadirachtin methanol absorption article carbon nuclear magnetic resonance chemical structure controlled study density functional theory dispersion Monte Carlo method priority journal proton nuclear magnetic resonance surface property ultraviolet spectroscopy 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 conformational space of this compound, so far absent in the literature, is presented herein. A detailed analysis of the electronic distribution, charge delocalization effects, and stereoelectronic effects 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 mechanisms, 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. © 2014 Springer-Verlag. Fil:Pomilio, A.B. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 2014 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_16102940_v20_n2_p_Bentz http://hdl.handle.net/20.500.12110/paper_16102940_v20_n2_p_Bentz |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
Antioxidants Aqueous solvent effect Atoms in molecules Density functional theory Molecular polarizability Natural bond orbital analysis PCM model azadirachtin methanol absorption article carbon nuclear magnetic resonance chemical structure controlled study density functional theory dispersion Monte Carlo method priority journal proton nuclear magnetic resonance surface property ultraviolet spectroscopy |
| spellingShingle |
Antioxidants Aqueous solvent effect Atoms in molecules Density functional theory Molecular polarizability Natural bond orbital analysis PCM model azadirachtin methanol absorption article carbon nuclear magnetic resonance chemical structure controlled study density functional theory dispersion Monte Carlo method priority journal proton nuclear magnetic resonance surface property ultraviolet spectroscopy Pomilio, Alicia Beatriz Structure and electronic properties of (+)-catechin: Aqueous solvent effects |
| topic_facet |
Antioxidants Aqueous solvent effect Atoms in molecules Density functional theory Molecular polarizability Natural bond orbital analysis PCM model azadirachtin methanol absorption article carbon nuclear magnetic resonance chemical structure controlled study density functional theory dispersion Monte Carlo method priority journal proton nuclear magnetic resonance surface property ultraviolet spectroscopy |
| 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 conformational space of this compound, so far absent in the literature, is presented herein. A detailed analysis of the electronic distribution, charge delocalization effects, and stereoelectronic effects 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 mechanisms, 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. © 2014 Springer-Verlag. |
| author |
Pomilio, Alicia Beatriz |
| author_facet |
Pomilio, Alicia Beatriz |
| author_sort |
Pomilio, Alicia Beatriz |
| 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 |
| publishDate |
2014 |
| url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_16102940_v20_n2_p_Bentz http://hdl.handle.net/20.500.12110/paper_16102940_v20_n2_p_Bentz |
| work_keys_str_mv |
AT pomilioaliciabeatriz structureandelectronicpropertiesofcatechinaqueoussolventeffects |
| _version_ |
1768546692368433152 |