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

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 mo...

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Autores principales: Pis Diez, Reinaldo, Echeverría, Gustavo Alberto, Piro, Oscar Enrique, Jios, Jorge Luis, Parajón Costa, Beatriz Susana
Formato: Articulo
Lenguaje:Inglés
Publicado: 2016
Materias:
Química
Ciencias Exactas
Potassium salt
Crystallographic data
Acceso en línea:http://sedici.unlp.edu.ar/handle/10915/108245
Aporte de:
SEDICI (UNLP) de Universidad Nacional de La Plata
id I19-R120-10915-108245
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
Potassium salt
Crystallographic data
spellingShingle Química
Ciencias Exactas
Potassium salt
Crystallographic data
Pis Diez, Reinaldo
Echeverría, Gustavo Alberto
Piro, Oscar Enrique
Jios, Jorge Luis
Parajón Costa, Beatriz Susana
A structural, spectroscopic and theoretical study of an o-vanillin Schiff base derivative involved in enol-imine and keto-amine tautomerism
topic_facet Química
Ciencias Exactas
Potassium salt
Crystallographic data
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.
format Articulo
Articulo
author Pis Diez, Reinaldo
Echeverría, Gustavo Alberto
Piro, Oscar Enrique
Jios, Jorge Luis
Parajón Costa, Beatriz Susana
author_facet Pis Diez, Reinaldo
Echeverría, Gustavo Alberto
Piro, Oscar Enrique
Jios, Jorge Luis
Parajón Costa, Beatriz Susana
author_sort Pis Diez, Reinaldo
title A structural, spectroscopic and theoretical study of an o-vanillin Schiff base derivative involved in enol-imine and keto-amine tautomerism
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 structural, spectroscopic and theoretical study of an o-vanillin schiff base derivative involved in enol-imine and keto-amine tautomerism
publishDate 2016
url http://sedici.unlp.edu.ar/handle/10915/108245
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