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
- Institución
- Universidad Nacional de La Plata
- OAI Identificador
- oai:sedici.unlp.edu.ar:10915/108245
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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:UNLP2025-09-29T11:24:32Zoai: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:13292025-09-29 11:24:32.869SEDICI (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 |
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article |
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publishedVersion |
dc.identifier.none.fl_str_mv |
http://sedici.unlp.edu.ar/handle/10915/108245 |
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http://sedici.unlp.edu.ar/handle/10915/108245 |
dc.language.none.fl_str_mv |
eng |
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eng |
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openAccess |
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