Theoretical studies and vibrational spectra of 1H -indole-3-acetic acid: Exploratory conformational analysis of dimeric species

Autores
Lobayan, Rosana M.; Pérez Schmit, María C.; Jubert, Alicia Haydeé; Vitale, Arturo Alberto
Año de publicación
2011
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Theoretical studies on 1H-indole-3-acetic acid (IAA) were performed to investigate the conformational properties of dimeric species and vibrational spectra. Experimental infrared spectra at 100 K and 297 K and Raman spectrum at 297 K were analyzed and compared against calculations performed at B3LYP/6-31G** level. A exploratory study of the conformational space of dimeric species was performed. Our analysis showed that dimeric forms predicted theoretically contribute distinctively to the assignments of experimental results. These structures are defined by the orientation of the acetyl moieties with respect to the plane of indole ring. The dimers are formed by two symmetrical IAA monomers (one of them with the acetyl moiety upward oriented, Re-face, and the other isomer having the acetyl moiety downward oriented, Si-face) in tail-to-tail way. The X-ray geometry and FTIR vibrational frequencies were compared with the results of DFT calculations. A conformational equilibrium involving the non-equivalent IAA dimers: CCT-CCT, A+A+T-A-A-T, A+A-T-A-A+T, and A+CT-A-CT was found. The relation of the conformational properties of the IAA molecule with the features of the vibrational spectra was described in detail. The band assignments were discussed as related to the conformations properties. Our analysis shows the significance of the theoretical study of the conformational space of the monomeric molecule in the rationalization of experimental results.
Centro de Química Inorgánica
Facultad de Ingeniería
Materia
Química
Density functional theory
1H-Indole-3-Acetic Acid (IAA)
Infrared spectroscopy
Raman spectroscopy
Nivel de accesibilidad
acceso abierto
Condiciones de uso
http://creativecommons.org/licenses/by-nc-sa/4.0/
Repositorio
SEDICI (UNLP)
Institución
Universidad Nacional de La Plata
OAI Identificador
oai:sedici.unlp.edu.ar:10915/132540

id SEDICI_26d3c1853474f11d273001037caa978e
oai_identifier_str oai:sedici.unlp.edu.ar:10915/132540
network_acronym_str SEDICI
repository_id_str 1329
network_name_str SEDICI (UNLP)
spelling Theoretical studies and vibrational spectra of 1H -indole-3-acetic acid: Exploratory conformational analysis of dimeric speciesLobayan, Rosana M.Pérez Schmit, María C.Jubert, Alicia HaydeéVitale, Arturo AlbertoQuímicaDensity functional theory1H-Indole-3-Acetic Acid (IAA)Infrared spectroscopyRaman spectroscopyTheoretical studies on 1H-indole-3-acetic acid (IAA) were performed to investigate the conformational properties of dimeric species and vibrational spectra. Experimental infrared spectra at 100 K and 297 K and Raman spectrum at 297 K were analyzed and compared against calculations performed at B3LYP/6-31G** level. A exploratory study of the conformational space of dimeric species was performed. Our analysis showed that dimeric forms predicted theoretically contribute distinctively to the assignments of experimental results. These structures are defined by the orientation of the acetyl moieties with respect to the plane of indole ring. The dimers are formed by two symmetrical IAA monomers (one of them with the acetyl moiety upward oriented, Re-face, and the other isomer having the acetyl moiety downward oriented, Si-face) in tail-to-tail way. The X-ray geometry and FTIR vibrational frequencies were compared with the results of DFT calculations. A conformational equilibrium involving the non-equivalent IAA dimers: CCT-CCT, A+A+T-A-A-T, A+A-T-A-A+T, and A+CT-A-CT was found. The relation of the conformational properties of the IAA molecule with the features of the vibrational spectra was described in detail. The band assignments were discussed as related to the conformations properties. Our analysis shows the significance of the theoretical study of the conformational space of the monomeric molecule in the rationalization of experimental results.Centro de Química InorgánicaFacultad de Ingeniería2011info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionArticulohttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdf1381-1392http://sedici.unlp.edu.ar/handle/10915/132540enginfo:eu-repo/semantics/altIdentifier/issn/0948-5023info:eu-repo/semantics/altIdentifier/issn/1610-2940info:eu-repo/semantics/altIdentifier/doi/10.1007/s00894-010-0833-2info:eu-repo/semantics/altIdentifier/pmid/20839020info:eu-repo/semantics/openAccesshttp://creativecommons.org/licenses/by-nc-sa/4.0/Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International (CC BY-NC-SA 4.0)reponame:SEDICI (UNLP)instname:Universidad Nacional de La Platainstacron:UNLP2025-09-29T11:32:12Zoai:sedici.unlp.edu.ar:10915/132540Institucionalhttp://sedici.unlp.edu.ar/Universidad públicaNo correspondehttp://sedici.unlp.edu.ar/oai/snrdalira@sedici.unlp.edu.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:13292025-09-29 11:32:13.135SEDICI (UNLP) - Universidad Nacional de La Platafalse
dc.title.none.fl_str_mv Theoretical studies and vibrational spectra of 1H -indole-3-acetic acid: Exploratory conformational analysis of dimeric species
title Theoretical studies and vibrational spectra of 1H -indole-3-acetic acid: Exploratory conformational analysis of dimeric species
spellingShingle Theoretical studies and vibrational spectra of 1H -indole-3-acetic acid: Exploratory conformational analysis of dimeric species
Lobayan, Rosana M.
Química
Density functional theory
1H-Indole-3-Acetic Acid (IAA)
Infrared spectroscopy
Raman spectroscopy
title_short Theoretical studies and vibrational spectra of 1H -indole-3-acetic acid: Exploratory conformational analysis of dimeric species
title_full Theoretical studies and vibrational spectra of 1H -indole-3-acetic acid: Exploratory conformational analysis of dimeric species
title_fullStr Theoretical studies and vibrational spectra of 1H -indole-3-acetic acid: Exploratory conformational analysis of dimeric species
title_full_unstemmed Theoretical studies and vibrational spectra of 1H -indole-3-acetic acid: Exploratory conformational analysis of dimeric species
title_sort Theoretical studies and vibrational spectra of 1H -indole-3-acetic acid: Exploratory conformational analysis of dimeric species
dc.creator.none.fl_str_mv Lobayan, Rosana M.
Pérez Schmit, María C.
Jubert, Alicia Haydeé
Vitale, Arturo Alberto
author Lobayan, Rosana M.
author_facet Lobayan, Rosana M.
Pérez Schmit, María C.
Jubert, Alicia Haydeé
Vitale, Arturo Alberto
author_role author
author2 Pérez Schmit, María C.
Jubert, Alicia Haydeé
Vitale, Arturo Alberto
author2_role author
author
author
dc.subject.none.fl_str_mv Química
Density functional theory
1H-Indole-3-Acetic Acid (IAA)
Infrared spectroscopy
Raman spectroscopy
topic Química
Density functional theory
1H-Indole-3-Acetic Acid (IAA)
Infrared spectroscopy
Raman spectroscopy
dc.description.none.fl_txt_mv Theoretical studies on 1H-indole-3-acetic acid (IAA) were performed to investigate the conformational properties of dimeric species and vibrational spectra. Experimental infrared spectra at 100 K and 297 K and Raman spectrum at 297 K were analyzed and compared against calculations performed at B3LYP/6-31G** level. A exploratory study of the conformational space of dimeric species was performed. Our analysis showed that dimeric forms predicted theoretically contribute distinctively to the assignments of experimental results. These structures are defined by the orientation of the acetyl moieties with respect to the plane of indole ring. The dimers are formed by two symmetrical IAA monomers (one of them with the acetyl moiety upward oriented, Re-face, and the other isomer having the acetyl moiety downward oriented, Si-face) in tail-to-tail way. The X-ray geometry and FTIR vibrational frequencies were compared with the results of DFT calculations. A conformational equilibrium involving the non-equivalent IAA dimers: CCT-CCT, A+A+T-A-A-T, A+A-T-A-A+T, and A+CT-A-CT was found. The relation of the conformational properties of the IAA molecule with the features of the vibrational spectra was described in detail. The band assignments were discussed as related to the conformations properties. Our analysis shows the significance of the theoretical study of the conformational space of the monomeric molecule in the rationalization of experimental results.
Centro de Química Inorgánica
Facultad de Ingeniería
description Theoretical studies on 1H-indole-3-acetic acid (IAA) were performed to investigate the conformational properties of dimeric species and vibrational spectra. Experimental infrared spectra at 100 K and 297 K and Raman spectrum at 297 K were analyzed and compared against calculations performed at B3LYP/6-31G** level. A exploratory study of the conformational space of dimeric species was performed. Our analysis showed that dimeric forms predicted theoretically contribute distinctively to the assignments of experimental results. These structures are defined by the orientation of the acetyl moieties with respect to the plane of indole ring. The dimers are formed by two symmetrical IAA monomers (one of them with the acetyl moiety upward oriented, Re-face, and the other isomer having the acetyl moiety downward oriented, Si-face) in tail-to-tail way. The X-ray geometry and FTIR vibrational frequencies were compared with the results of DFT calculations. A conformational equilibrium involving the non-equivalent IAA dimers: CCT-CCT, A+A+T-A-A-T, A+A-T-A-A+T, and A+CT-A-CT was found. The relation of the conformational properties of the IAA molecule with the features of the vibrational spectra was described in detail. The band assignments were discussed as related to the conformations properties. Our analysis shows the significance of the theoretical study of the conformational space of the monomeric molecule in the rationalization of experimental results.
publishDate 2011
dc.date.none.fl_str_mv 2011
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
Articulo
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://sedici.unlp.edu.ar/handle/10915/132540
url http://sedici.unlp.edu.ar/handle/10915/132540
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/issn/0948-5023
info:eu-repo/semantics/altIdentifier/issn/1610-2940
info:eu-repo/semantics/altIdentifier/doi/10.1007/s00894-010-0833-2
info:eu-repo/semantics/altIdentifier/pmid/20839020
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by-nc-sa/4.0/
Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International (CC BY-NC-SA 4.0)
eu_rights_str_mv openAccess
rights_invalid_str_mv http://creativecommons.org/licenses/by-nc-sa/4.0/
Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International (CC BY-NC-SA 4.0)
dc.format.none.fl_str_mv application/pdf
1381-1392
dc.source.none.fl_str_mv reponame:SEDICI (UNLP)
instname:Universidad Nacional de La Plata
instacron:UNLP
reponame_str SEDICI (UNLP)
collection SEDICI (UNLP)
instname_str Universidad Nacional de La Plata
instacron_str UNLP
institution UNLP
repository.name.fl_str_mv SEDICI (UNLP) - Universidad Nacional de La Plata
repository.mail.fl_str_mv alira@sedici.unlp.edu.ar
_version_ 1844616201895936000
score 13.070432