A structural, spectroscopic and theoretical study of an o-vanillin Schiff base derivative involved in enol-imine and keto-amine tautomerism

Autores
Pis Diez, Reinaldo; Echeverría, Gustavo Alberto; Piro, Oscar Enrique; Jios, Jorge Luis; Parajón Costa, Beatriz Susana
Año de publicación
2016
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The potassium salt of the Schiff base obtained by condensation of 2-hydroxy-3-methoxybenzaldehyde (o-vanillin) and 2-aminoethanesulfonic acid (taurine) in a methanol potassium hydroxide solution was characterized by crystallographic, spectroscopic and DFT methods. The compound crystallizes in the monoclinic C2/c space group with a = 37.539(4), b = 5.9129(4), c = 26.321(5) Å, β = 121.10(2)° and Z = 8 molecules per unit cell. The crystallographic data reveal that two different anionic molecules, which constitute a tautomeric pair, coexist in the crystal. This finding is supported by FTIR, Raman and electronic measurements in methanol solution. The main crystallographic differences between the bonding structures occur along the shortest chemical path linking the oxygen and the nitrogen atom of the OH and CN group. Both tautomeric forms are stabilized by strong O–H⋯N and N–H⋯O intramolecular hydrogen bonds. Optimized geometrical parameters and calculated spectroscopic features obtained by DFT calculations show a very good agreement with the experimental data. Moreover, 1H NMR, 13C NMR and electronic measurements in DMSO solution show the prevalence of the enol-imine tautomer in this solvent.
Centro de Química Inorgánica
Instituto de Física La Plata
Materia
Química
Ciencias Exactas
Potassium salt
Crystallographic data
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:10915/108245
Acceder
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oai_identifier_str oai:sedici.unlp.edu.ar:10915/108245
network_acronym_str SEDICI
repository_id_str 1329
network_name_str SEDICI (UNLP)
spelling A structural, spectroscopic and theoretical study of an o-vanillin Schiff base derivative involved in enol-imine and keto-amine tautomerismPis Diez, ReinaldoEcheverría, Gustavo AlbertoPiro, Oscar EnriqueJios, Jorge LuisParajón Costa, Beatriz SusanaQuímicaCiencias ExactasPotassium saltCrystallographic dataThe potassium salt of the Schiff base obtained by condensation of 2-hydroxy-3-methoxybenzaldehyde (o-vanillin) and 2-aminoethanesulfonic acid (taurine) in a methanol potassium hydroxide solution was characterized by crystallographic, spectroscopic and DFT methods. The compound crystallizes in the monoclinic C2/c space group with a = 37.539(4), b = 5.9129(4), c = 26.321(5) Å, β = 121.10(2)° and Z = 8 molecules per unit cell. The crystallographic data reveal that two different anionic molecules, which constitute a tautomeric pair, coexist in the crystal. This finding is supported by FTIR, Raman and electronic measurements in methanol solution. The main crystallographic differences between the bonding structures occur along the shortest chemical path linking the oxygen and the nitrogen atom of the OH and CN group. Both tautomeric forms are stabilized by strong O–H⋯N and N–H⋯O intramolecular hydrogen bonds. Optimized geometrical parameters and calculated spectroscopic features obtained by DFT calculations show a very good agreement with the experimental data. Moreover, <sup>1</sup>H NMR, <sup>13</sup>C NMR and electronic measurements in DMSO solution show the prevalence of the enol-imine tautomer in this solvent.Centro de Química InorgánicaInstituto de Física La Plata2016info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionArticulohttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdf2730--2740http://sedici.unlp.edu.ar/handle/10915/108245enginfo:eu-repo/semantics/altIdentifier/issn/1369-9261info:eu-repo/semantics/altIdentifier/doi/10.1039/c5nj01039jinfo: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:UNLP2025-10-22T17:05:26Zoai:sedici.unlp.edu.ar:10915/108245Institucionalhttp://sedici.unlp.edu.ar/Universidad públicaNo correspondehttp://sedici.unlp.edu.ar/oai/snrdalira@sedici.unlp.edu.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:13292025-10-22 17:05:26.612SEDICI (UNLP) - Universidad Nacional de La Platafalse
dc.title.none.fl_str_mv A structural, spectroscopic and theoretical study of an o-vanillin Schiff base derivative involved in enol-imine and keto-amine tautomerism
title A structural, spectroscopic and theoretical study of an o-vanillin Schiff base derivative involved in enol-imine and keto-amine tautomerism
spellingShingle A structural, spectroscopic and theoretical study of an o-vanillin Schiff base derivative involved in enol-imine and keto-amine tautomerism
Pis Diez, Reinaldo
Química
Ciencias Exactas
Potassium salt
Crystallographic data
title_short A structural, spectroscopic and theoretical study of an o-vanillin Schiff base derivative involved in enol-imine and keto-amine tautomerism
title_full A structural, spectroscopic and theoretical study of an o-vanillin Schiff base derivative involved in enol-imine and keto-amine tautomerism
title_fullStr A structural, spectroscopic and theoretical study of an o-vanillin Schiff base derivative involved in enol-imine and keto-amine tautomerism
title_full_unstemmed A structural, spectroscopic and theoretical study of an o-vanillin Schiff base derivative involved in enol-imine and keto-amine tautomerism
title_sort A structural, spectroscopic and theoretical study of an o-vanillin Schiff base derivative involved in enol-imine and keto-amine tautomerism
dc.creator.none.fl_str_mv Pis Diez, Reinaldo
Echeverría, Gustavo Alberto
Piro, Oscar Enrique
Jios, Jorge Luis
Parajón Costa, Beatriz Susana
author Pis Diez, Reinaldo
author_facet Pis Diez, Reinaldo
Echeverría, Gustavo Alberto
Piro, Oscar Enrique
Jios, Jorge Luis
Parajón Costa, Beatriz Susana
author_role author
author2 Echeverría, Gustavo Alberto
Piro, Oscar Enrique
Jios, Jorge Luis
Parajón Costa, Beatriz Susana
author2_role author
author
author
author
dc.subject.none.fl_str_mv Química
Ciencias Exactas
Potassium salt
Crystallographic data
topic Química
Ciencias Exactas
Potassium salt
Crystallographic data
dc.description.none.fl_txt_mv The potassium salt of the Schiff base obtained by condensation of 2-hydroxy-3-methoxybenzaldehyde (o-vanillin) and 2-aminoethanesulfonic acid (taurine) in a methanol potassium hydroxide solution was characterized by crystallographic, spectroscopic and DFT methods. The compound crystallizes in the monoclinic C2/c space group with a = 37.539(4), b = 5.9129(4), c = 26.321(5) Å, β = 121.10(2)° and Z = 8 molecules per unit cell. The crystallographic data reveal that two different anionic molecules, which constitute a tautomeric pair, coexist in the crystal. This finding is supported by FTIR, Raman and electronic measurements in methanol solution. The main crystallographic differences between the bonding structures occur along the shortest chemical path linking the oxygen and the nitrogen atom of the OH and CN group. Both tautomeric forms are stabilized by strong O–H⋯N and N–H⋯O intramolecular hydrogen bonds. Optimized geometrical parameters and calculated spectroscopic features obtained by DFT calculations show a very good agreement with the experimental data. Moreover, <sup>1</sup>H NMR, <sup>13</sup>C NMR and electronic measurements in DMSO solution show the prevalence of the enol-imine tautomer in this solvent.
Centro de Química Inorgánica
Instituto de Física La Plata
description The potassium salt of the Schiff base obtained by condensation of 2-hydroxy-3-methoxybenzaldehyde (o-vanillin) and 2-aminoethanesulfonic acid (taurine) in a methanol potassium hydroxide solution was characterized by crystallographic, spectroscopic and DFT methods. The compound crystallizes in the monoclinic C2/c space group with a = 37.539(4), b = 5.9129(4), c = 26.321(5) Å, β = 121.10(2)° and Z = 8 molecules per unit cell. The crystallographic data reveal that two different anionic molecules, which constitute a tautomeric pair, coexist in the crystal. This finding is supported by FTIR, Raman and electronic measurements in methanol solution. The main crystallographic differences between the bonding structures occur along the shortest chemical path linking the oxygen and the nitrogen atom of the OH and CN group. Both tautomeric forms are stabilized by strong O–H⋯N and N–H⋯O intramolecular hydrogen bonds. Optimized geometrical parameters and calculated spectroscopic features obtained by DFT calculations show a very good agreement with the experimental data. Moreover, <sup>1</sup>H NMR, <sup>13</sup>C NMR and electronic measurements in DMSO solution show the prevalence of the enol-imine tautomer in this solvent.
publishDate 2016
dc.date.none.fl_str_mv 2016
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/10915/108245
url http://sedici.unlp.edu.ar/handle/10915/108245
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/issn/1369-9261
info:eu-repo/semantics/altIdentifier/doi/10.1039/c5nj01039j
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
2730--2740
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
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score 12.982451

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