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 develop...

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Autores: Rodríguez, María R., Plá, Julián del, Piro, Oscar Enrique, Echeverría, Gustavo A., Espino Ordóñez, Gustavo, Pis Diez, Reinaldo, Parajón Costa, Beatriz S., González Baró, Ana C.
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2018
País:España
Institución:Universidad de Burgos (UBU)
Repositorio:Repositorio Institucional de la Universidad de Burgos (RIUBU)
OAI Identifier:oai:riubu.ubu.es:10259/4786
Acceso en línea:http://hdl.handle.net/10259/4786
Access Level:acceso abierto
Palabra clave:Thiophene
o-vanillin
X-ray crystal structure
Tautomerism
Spectroscopy
DFT
Chemistry, Inorganic
Química inorgánica
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spelling Structure, tautomerism, spectroscopic and DFT study of o-vanillin derived Schiff bases containing thiophene ringRodríguez, María R.Plá, Julián delPiro, Oscar EnriqueEcheverría, Gustavo A.Espino Ordóñez, GustavoPis Diez, ReinaldoParajón Costa, Beatriz S.González Baró, Ana C.Thiopheneo-vanillinX-ray crystal structureTautomerismSpectroscopyDFTChemistry, InorganicQuímica inorgánicaTwo 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.CONICET and UNLP, Argentina and by Ministerio de Economía y Competitividad Español (CTQ2014-58812-C2-1-R, CTQ2015-70371-REDT)Elsevier201820182020info:eu-repo/semantics/articleinfo:eu-repo/semantics/acceptedVersionapplication/pdfhttp://hdl.handle.net/10259/4786reponame:Repositorio Institucional de la Universidad de Burgos (RIUBU)instname:Universidad de Burgos (UBU)InglésJournal of Molecular Structure. 2018, V. 1165, p. 381-390https://doi.org/10.1016/j.molstruc.2018.03.120info:eu-repo/grantAgreement/MINECO/CTQ2014-58812-C2-1-R/info:eu-repo/grantAgreement/MINECO/CTQ2015-70371-REDT/Attribution-NonCommercial-NoDerivatives 4.0 Internationalhttp://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccessoai:riubu.ubu.es:10259/47862026-05-28T07:56:11Z
dc.title.none.fl_str_mv Structure, tautomerism, spectroscopic and DFT study of o-vanillin derived Schiff bases containing thiophene ring
title Structure, tautomerism, spectroscopic and DFT study of o-vanillin derived Schiff bases containing thiophene ring
spellingShingle Structure, tautomerism, spectroscopic and DFT study of o-vanillin derived Schiff bases containing thiophene ring
Rodríguez, María R.
Thiophene
o-vanillin
X-ray crystal structure
Tautomerism
Spectroscopy
DFT
Chemistry, Inorganic
Química inorgánica
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
dc.creator.none.fl_str_mv Rodríguez, María R.
Plá, Julián del
Piro, Oscar Enrique
Echeverría, Gustavo A.
Espino Ordóñez, Gustavo
Pis Diez, Reinaldo
Parajón Costa, Beatriz S.
González Baró, Ana C.
author Rodríguez, María R.
author_facet Rodríguez, María R.
Plá, Julián del
Piro, Oscar Enrique
Echeverría, Gustavo A.
Espino Ordóñez, Gustavo
Pis Diez, Reinaldo
Parajón Costa, Beatriz S.
González Baró, Ana C.
author_role author
author2 Plá, Julián del
Piro, Oscar Enrique
Echeverría, Gustavo A.
Espino Ordóñez, Gustavo
Pis Diez, Reinaldo
Parajón Costa, Beatriz S.
González Baró, Ana C.
author2_role author
author
author
author
author
author
author
dc.subject.none.fl_str_mv Thiophene
o-vanillin
X-ray crystal structure
Tautomerism
Spectroscopy
DFT
Chemistry, Inorganic
Química inorgánica
topic Thiophene
o-vanillin
X-ray crystal structure
Tautomerism
Spectroscopy
DFT
Chemistry, Inorganic
Química inorgánica
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.
publishDate 2018
dc.date.none.fl_str_mv 2018
2018
2020
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10259/4786
url http://hdl.handle.net/10259/4786
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv Journal of Molecular Structure. 2018, V. 1165, p. 381-390
https://doi.org/10.1016/j.molstruc.2018.03.120
info:eu-repo/grantAgreement/MINECO/CTQ2014-58812-C2-1-R/
info:eu-repo/grantAgreement/MINECO/CTQ2015-70371-REDT/
dc.rights.none.fl_str_mv Attribution-NonCommercial-NoDerivatives 4.0 International
http://creativecommons.org/licenses/by-nc-nd/4.0/
info:eu-repo/semantics/openAccess
rights_invalid_str_mv Attribution-NonCommercial-NoDerivatives 4.0 International
http://creativecommons.org/licenses/by-nc-nd/4.0/
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
dc.source.none.fl_str_mv reponame:Repositorio Institucional de la Universidad de Burgos (RIUBU)
instname:Universidad de Burgos (UBU)
instname_str Universidad de Burgos (UBU)
reponame_str Repositorio Institucional de la Universidad de Burgos (RIUBU)
collection Repositorio Institucional de la Universidad de Burgos (RIUBU)
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15.300719

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