Conformational and electronic (AIM/NBO) study of unsubstituted A-type dimeric proanthocyanidin

The conformational space of the unsubstituted A-type dimeric proanthocyanidin was scanned using molecular dynamics at a semiempirical level, and complemented with functional density calculations. The lowest energy conformers were obtained. Electronic distributions were analysed at a higher calculati...

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Autores principales: Lobayan, Rosana M., Jubert, Alicia Haydeé, Vitale, Martín Gustavo, Pomilio, Alicia Beatriz
Formato: Articulo
Lenguaje:Inglés
Publicado: 2008
Materias:
Química
Ciencias Exactas
Atoms in molecules
Dimeric procyanidin
Density functional theory
Nuclear magnetic resonance
Natural bond orbital analysis
Topological properties
Acceso en línea:http://sedici.unlp.edu.ar/handle/10915/141606
Aporte de:
SEDICI (UNLP) de Universidad Nacional de La Plata
id I19-R120-10915-141606
record_format dspace
institution Universidad Nacional de La Plata
institution_str I-19
repository_str R-120
collection SEDICI (UNLP)
language Inglés
topic Química
Ciencias Exactas
Atoms in molecules
Dimeric procyanidin
Density functional theory
Nuclear magnetic resonance
Natural bond orbital analysis
Topological properties
spellingShingle Química
Ciencias Exactas
Atoms in molecules
Dimeric procyanidin
Density functional theory
Nuclear magnetic resonance
Natural bond orbital analysis
Topological properties
Lobayan, Rosana M.
Jubert, Alicia Haydeé
Vitale, Martín Gustavo
Pomilio, Alicia Beatriz
Conformational and electronic (AIM/NBO) study of unsubstituted A-type dimeric proanthocyanidin
topic_facet Química
Ciencias Exactas
Atoms in molecules
Dimeric procyanidin
Density functional theory
Nuclear magnetic resonance
Natural bond orbital analysis
Topological properties
description The conformational space of the unsubstituted A-type dimeric proanthocyanidin was scanned using molecular dynamics at a semiempirical level, and complemented with functional density calculations. The lowest energy conformers were obtained. Electronic distributions were analysed at a higher calculation level, thus improving the basis set. A topological study based on Bader’s theory (AIM: atoms in molecules) and natural bond orbital (NBO) framework was performed. Furthermore, molecular electrostatic potential maps (MEPs) were obtained and analysed. NMR chemical shifts were calculated at ab initio level and further compared with previous experimental values; coupling constants were also calculated. The stereochemistry of the molecule is thoroughly discussed, revealing the key role that hyperconjugative interactions play in defining experimental trends. These results show the versatility of geminal spin–spin coupling 2J(C-1′,O) as a probe for stereochemical studies of proanthocyanidins.
format Articulo
Articulo
author Lobayan, Rosana M.
Jubert, Alicia Haydeé
Vitale, Martín Gustavo
Pomilio, Alicia Beatriz
author_facet Lobayan, Rosana M.
Jubert, Alicia Haydeé
Vitale, Martín Gustavo
Pomilio, Alicia Beatriz
author_sort Lobayan, Rosana M.
title Conformational and electronic (AIM/NBO) study of unsubstituted A-type dimeric proanthocyanidin
title_short Conformational and electronic (AIM/NBO) study of unsubstituted A-type dimeric proanthocyanidin
title_full Conformational and electronic (AIM/NBO) study of unsubstituted A-type dimeric proanthocyanidin
title_fullStr Conformational and electronic (AIM/NBO) study of unsubstituted A-type dimeric proanthocyanidin
title_full_unstemmed Conformational and electronic (AIM/NBO) study of unsubstituted A-type dimeric proanthocyanidin
title_sort conformational and electronic (aim/nbo) study of unsubstituted a-type dimeric proanthocyanidin
publishDate 2008
url http://sedici.unlp.edu.ar/handle/10915/141606
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AT vitalemartingustavo conformationalandelectronicaimnbostudyofunsubstitutedatypedimericproanthocyanidin
AT pomilioaliciabeatriz conformationalandelectronicaimnbostudyofunsubstitutedatypedimericproanthocyanidin
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