Structure, tautomerism, spectroscopic and DFT study of o-vanillin derived Schiff bases containing thiophene ring

Two Schiff bases derived from o-vanillin (o-HVA), a well-known antioxidant hydroxo aldehyde, have been obtained from condensation with 2-thiophenecarboxilic acid hydrazide (TPNNH) and 2- thiophenemethylamine (TPNH2), respectively. The inclusion of thiophene is based on its significance in the develo...

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Detalles Bibliográficos
Autores principales: Rodríguez, María Rosa, Plá, Julián del, Piro, Oscar Enrique, Echeverría, Gustavo Alberto, Espino, Gustavo, Pis Diez, Reinaldo, Parajón Costa, Beatriz Susana, González Baró, Ana Cecilia
Formato: Articulo
Lenguaje:Inglés
Publicado: 2018
Materias:
Química
Thiophene
o-vanillin
X-ray crystal structure
Tautomerism
Spectroscopy
DFT
Acceso en línea:http://sedici.unlp.edu.ar/handle/10915/152750
Aporte de:
SEDICI (UNLP) de Universidad Nacional de La Plata
id I19-R120-10915-152750
record_format dspace
spelling I19-R120-10915-1527502023-05-11T04:06:41Z http://sedici.unlp.edu.ar/handle/10915/152750 issn:0022-2860 Structure, tautomerism, spectroscopic and DFT study of o-vanillin derived Schiff bases containing thiophene ring Rodríguez, María Rosa Plá, Julián del Piro, Oscar Enrique Echeverría, Gustavo Alberto Espino, Gustavo Pis Diez, Reinaldo Parajón Costa, Beatriz Susana González Baró, Ana Cecilia 2018 2023-05-10T18:30:20Z en Química Thiophene o-vanillin X-ray crystal structure Tautomerism Spectroscopy DFT Two Schiff bases derived from o-vanillin (o-HVA), a well-known antioxidant hydroxo aldehyde, have been obtained from condensation with 2-thiophenecarboxilic acid hydrazide (TPNNH) and 2- thiophenemethylamine (TPNH2), respectively. The inclusion of thiophene is based on its significance in the development of effective therapeutic agents. The study of the compounds oVATPNNH and oVATPNH2 includes solid state structural and spectroscopic analysis by single-crystal X-ray diffraction and vibrational spectroscopy (FTIR and Raman). The crystal structure of oVATPNH2 shows a peculiar rotational disorder in the heterocycle. Tautomeric equilibria in solution, which depends on the molecule structure and the nature of the solvent, were analysed by means of 1H and 13C{1H} NMR along with electronic spectroscopy. Tautomerism plays an important role not only in the molecular interactions but also in the behaviour of the Schiff base when acting as a ligand in coordination compounds. Results obtained from DFT calculations were used in the interpretation of the experimental data and in the spectral assignments. Centro de Química Inorgánica Articulo Articulo http://creativecommons.org/licenses/by/4.0/ Creative Commons Attribution 4.0 International (CC BY 4.0) application/pdf 381-390
institution Universidad Nacional de La Plata
institution_str I-19
repository_str R-120
collection SEDICI (UNLP)
language Inglés
topic Química
Thiophene
o-vanillin
X-ray crystal structure
Tautomerism
Spectroscopy
DFT
spellingShingle Química
Thiophene
o-vanillin
X-ray crystal structure
Tautomerism
Spectroscopy
DFT
Rodríguez, María Rosa
Plá, Julián del
Piro, Oscar Enrique
Echeverría, Gustavo Alberto
Espino, Gustavo
Pis Diez, Reinaldo
Parajón Costa, Beatriz Susana
González Baró, Ana Cecilia
Structure, tautomerism, spectroscopic and DFT study of o-vanillin derived Schiff bases containing thiophene ring
topic_facet Química
Thiophene
o-vanillin
X-ray crystal structure
Tautomerism
Spectroscopy
DFT
description Two Schiff bases derived from o-vanillin (o-HVA), a well-known antioxidant hydroxo aldehyde, have been obtained from condensation with 2-thiophenecarboxilic acid hydrazide (TPNNH) and 2- thiophenemethylamine (TPNH2), respectively. The inclusion of thiophene is based on its significance in the development of effective therapeutic agents. The study of the compounds oVATPNNH and oVATPNH2 includes solid state structural and spectroscopic analysis by single-crystal X-ray diffraction and vibrational spectroscopy (FTIR and Raman). The crystal structure of oVATPNH2 shows a peculiar rotational disorder in the heterocycle. Tautomeric equilibria in solution, which depends on the molecule structure and the nature of the solvent, were analysed by means of 1H and 13C{1H} NMR along with electronic spectroscopy. Tautomerism plays an important role not only in the molecular interactions but also in the behaviour of the Schiff base when acting as a ligand in coordination compounds. Results obtained from DFT calculations were used in the interpretation of the experimental data and in the spectral assignments.
format Articulo
Articulo
author Rodríguez, María Rosa
Plá, Julián del
Piro, Oscar Enrique
Echeverría, Gustavo Alberto
Espino, Gustavo
Pis Diez, Reinaldo
Parajón Costa, Beatriz Susana
González Baró, Ana Cecilia
author_facet Rodríguez, María Rosa
Plá, Julián del
Piro, Oscar Enrique
Echeverría, Gustavo Alberto
Espino, Gustavo
Pis Diez, Reinaldo
Parajón Costa, Beatriz Susana
González Baró, Ana Cecilia
author_sort Rodríguez, María Rosa
title Structure, tautomerism, spectroscopic and DFT study of o-vanillin derived Schiff bases containing thiophene ring
title_short Structure, tautomerism, spectroscopic and DFT study of o-vanillin derived Schiff bases containing thiophene ring
title_full Structure, tautomerism, spectroscopic and DFT study of o-vanillin derived Schiff bases containing thiophene ring
title_fullStr Structure, tautomerism, spectroscopic and DFT study of o-vanillin derived Schiff bases containing thiophene ring
title_full_unstemmed Structure, tautomerism, spectroscopic and DFT study of o-vanillin derived Schiff bases containing thiophene ring
title_sort structure, tautomerism, spectroscopic and dft study of o-vanillin derived schiff bases containing thiophene ring
publishDate 2018
url http://sedici.unlp.edu.ar/handle/10915/152750
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