Study of the structural and electronic properties Valproic Acid and new derivatives used as anticonvulsant agents

Autores
Comelli, Nieves Carolina; Lobayan, Rosana Maria; Castro, Eduardo Alberto; Jubert, Alicia Haydee
Año de publicación
2011
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The conformational and electronic characteristics of the polar O 9=C8-X10 moiety in the anticonvulsant valproic acid (Vpa) drug and some of their amides and ester derivatives are analyzed at the B3LYP level using the 6-31+G(d,p) and 6-311++G(d,p) 6d,10f basis sets. Exploring the delocalization of the electron density of the O9=C 8-X10 moiety by means of ELF, NBO, and AIM calculations, we found that the bending away from coplanarity of the atoms in O 9=C8-X10 is accompanied by a three-dimensional arrangement of donor and acceptor proton units closing nearly planar pseudorings of four, five, and six members arising from stabilizing interactions around the O9=C8-X10 backbone. From the structure-property relationship analysis, we explain the origin of the change in the structural parameters and atomic charges in the polar moiety.
Fil: Comelli, Nieves Carolina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; Argentina
Fil: Lobayan, Rosana Maria. Universidad de la Cuenca del Plata. Facultad de Ingeniería. Departamento de Ciencias Basicas; Argentina
Fil: Castro, Eduardo Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; Argentina
Fil: Jubert, Alicia Haydee. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; Argentina
Materia
VALPROIC ACID AND DERIVATIVES
DFT, NBO
ELF
AIM
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/188754
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/188754
network_acronym_str CONICETDig
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network_name_str CONICET Digital (CONICET)
spelling Study of the structural and electronic properties Valproic Acid and new derivatives used as anticonvulsant agentsComelli, Nieves CarolinaLobayan, Rosana MariaCastro, Eduardo AlbertoJubert, Alicia HaydeeVALPROIC ACID AND DERIVATIVESDFT, NBOELFAIMhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The conformational and electronic characteristics of the polar O 9=C8-X10 moiety in the anticonvulsant valproic acid (Vpa) drug and some of their amides and ester derivatives are analyzed at the B3LYP level using the 6-31+G(d,p) and 6-311++G(d,p) 6d,10f basis sets. Exploring the delocalization of the electron density of the O9=C 8-X10 moiety by means of ELF, NBO, and AIM calculations, we found that the bending away from coplanarity of the atoms in O 9=C8-X10 is accompanied by a three-dimensional arrangement of donor and acceptor proton units closing nearly planar pseudorings of four, five, and six members arising from stabilizing interactions around the O9=C8-X10 backbone. From the structure-property relationship analysis, we explain the origin of the change in the structural parameters and atomic charges in the polar moiety.Fil: Comelli, Nieves Carolina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; ArgentinaFil: Lobayan, Rosana Maria. Universidad de la Cuenca del Plata. Facultad de Ingeniería. Departamento de Ciencias Basicas; ArgentinaFil: Castro, Eduardo Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; ArgentinaFil: Jubert, Alicia Haydee. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; ArgentinaAmerican Chemical Society2011-02info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/188754Comelli, Nieves Carolina; Lobayan, Rosana Maria; Castro, Eduardo Alberto; Jubert, Alicia Haydee; Study of the structural and electronic properties Valproic Acid and new derivatives used as anticonvulsant agents; American Chemical Society; Journal of Physical Chemistry A; 115; 9; 2-2011; 1686-17001089-5639CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1021/jp1081998info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:11:41Zoai:ri.conicet.gov.ar:11336/188754instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-29 10:11:41.595CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Study of the structural and electronic properties Valproic Acid and new derivatives used as anticonvulsant agents
title Study of the structural and electronic properties Valproic Acid and new derivatives used as anticonvulsant agents
spellingShingle Study of the structural and electronic properties Valproic Acid and new derivatives used as anticonvulsant agents
Comelli, Nieves Carolina
VALPROIC ACID AND DERIVATIVES
DFT, NBO
ELF
AIM
title_short Study of the structural and electronic properties Valproic Acid and new derivatives used as anticonvulsant agents
title_full Study of the structural and electronic properties Valproic Acid and new derivatives used as anticonvulsant agents
title_fullStr Study of the structural and electronic properties Valproic Acid and new derivatives used as anticonvulsant agents
title_full_unstemmed Study of the structural and electronic properties Valproic Acid and new derivatives used as anticonvulsant agents
title_sort Study of the structural and electronic properties Valproic Acid and new derivatives used as anticonvulsant agents
dc.creator.none.fl_str_mv Comelli, Nieves Carolina
Lobayan, Rosana Maria
Castro, Eduardo Alberto
Jubert, Alicia Haydee
author Comelli, Nieves Carolina
author_facet Comelli, Nieves Carolina
Lobayan, Rosana Maria
Castro, Eduardo Alberto
Jubert, Alicia Haydee
author_role author
author2 Lobayan, Rosana Maria
Castro, Eduardo Alberto
Jubert, Alicia Haydee
author2_role author
author
author
dc.subject.none.fl_str_mv VALPROIC ACID AND DERIVATIVES
DFT, NBO
ELF
AIM
topic VALPROIC ACID AND DERIVATIVES
DFT, NBO
ELF
AIM
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The conformational and electronic characteristics of the polar O 9=C8-X10 moiety in the anticonvulsant valproic acid (Vpa) drug and some of their amides and ester derivatives are analyzed at the B3LYP level using the 6-31+G(d,p) and 6-311++G(d,p) 6d,10f basis sets. Exploring the delocalization of the electron density of the O9=C 8-X10 moiety by means of ELF, NBO, and AIM calculations, we found that the bending away from coplanarity of the atoms in O 9=C8-X10 is accompanied by a three-dimensional arrangement of donor and acceptor proton units closing nearly planar pseudorings of four, five, and six members arising from stabilizing interactions around the O9=C8-X10 backbone. From the structure-property relationship analysis, we explain the origin of the change in the structural parameters and atomic charges in the polar moiety.
Fil: Comelli, Nieves Carolina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; Argentina
Fil: Lobayan, Rosana Maria. Universidad de la Cuenca del Plata. Facultad de Ingeniería. Departamento de Ciencias Basicas; Argentina
Fil: Castro, Eduardo Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; Argentina
Fil: Jubert, Alicia Haydee. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; Argentina
description The conformational and electronic characteristics of the polar O 9=C8-X10 moiety in the anticonvulsant valproic acid (Vpa) drug and some of their amides and ester derivatives are analyzed at the B3LYP level using the 6-31+G(d,p) and 6-311++G(d,p) 6d,10f basis sets. Exploring the delocalization of the electron density of the O9=C 8-X10 moiety by means of ELF, NBO, and AIM calculations, we found that the bending away from coplanarity of the atoms in O 9=C8-X10 is accompanied by a three-dimensional arrangement of donor and acceptor proton units closing nearly planar pseudorings of four, five, and six members arising from stabilizing interactions around the O9=C8-X10 backbone. From the structure-property relationship analysis, we explain the origin of the change in the structural parameters and atomic charges in the polar moiety.
publishDate 2011
dc.date.none.fl_str_mv 2011-02
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/188754
Comelli, Nieves Carolina; Lobayan, Rosana Maria; Castro, Eduardo Alberto; Jubert, Alicia Haydee; Study of the structural and electronic properties Valproic Acid and new derivatives used as anticonvulsant agents; American Chemical Society; Journal of Physical Chemistry A; 115; 9; 2-2011; 1686-1700
1089-5639
CONICET Digital
CONICET
url http://hdl.handle.net/11336/188754
identifier_str_mv Comelli, Nieves Carolina; Lobayan, Rosana Maria; Castro, Eduardo Alberto; Jubert, Alicia Haydee; Study of the structural and electronic properties Valproic Acid and new derivatives used as anticonvulsant agents; American Chemical Society; Journal of Physical Chemistry A; 115; 9; 2-2011; 1686-1700
1089-5639
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1021/jp1081998
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv American Chemical Society
publisher.none.fl_str_mv American Chemical Society
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
_version_ 1844614017678573568
score 13.070432

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