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

Autores
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
Año de publicación
2018
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
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
Materia
Química
Thiophene
o-vanillin
X-ray crystal structure
Tautomerism
Spectroscopy
DFT
Nivel de accesibilidad
acceso abierto
Condiciones de uso
http://creativecommons.org/licenses/by/4.0/
Repositorio
SEDICI (UNLP)
Institución
Universidad Nacional de La Plata
OAI Identificador
oai:sedici.unlp.edu.ar:10915/152750
Acceder
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oai_identifier_str oai:sedici.unlp.edu.ar:10915/152750
network_acronym_str SEDICI
repository_id_str 1329
network_name_str SEDICI (UNLP)
spelling Structure, tautomerism, spectroscopic and DFT study of o-vanillin derived Schiff bases containing thiophene ringRodríguez, María RosaPlá, Julián delPiro, Oscar EnriqueEcheverría, Gustavo AlbertoEspino, GustavoPis Diez, ReinaldoParajón Costa, Beatriz SusanaGonzález Baró, Ana CeciliaQuímicaThiopheneo-vanillinX-ray crystal structureTautomerismSpectroscopyDFTTwo 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 Inorgánica2018info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionArticulohttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdf381-390http://sedici.unlp.edu.ar/handle/10915/152750enginfo:eu-repo/semantics/altIdentifier/issn/0022-2860info:eu-repo/semantics/altIdentifier/doi/10.1016/j.molstruc.2018.03.120info:eu-repo/semantics/openAccesshttp://creativecommons.org/licenses/by/4.0/Creative Commons Attribution 4.0 International (CC BY 4.0)reponame:SEDICI (UNLP)instname:Universidad Nacional de La Platainstacron:UNLP2025-09-10T12:42:05Zoai:sedici.unlp.edu.ar:10915/152750Institucionalhttp://sedici.unlp.edu.ar/Universidad públicaNo correspondehttp://sedici.unlp.edu.ar/oai/snrdalira@sedici.unlp.edu.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:13292025-09-10 12:42:05.33SEDICI (UNLP) - Universidad Nacional de La Platafalse
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 Rosa
Química
Thiophene
o-vanillin
X-ray crystal structure
Tautomerism
Spectroscopy
DFT
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 Rosa
Plá, Julián del
Piro, Oscar Enrique
Echeverría, Gustavo Alberto
Espino, Gustavo
Pis Diez, Reinaldo
Parajón Costa, Beatriz Susana
González Baró, Ana Cecilia
author Rodríguez, María Rosa
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_role author
author2 Plá, Julián del
Piro, Oscar Enrique
Echeverría, Gustavo Alberto
Espino, Gustavo
Pis Diez, Reinaldo
Parajón Costa, Beatriz Susana
González Baró, Ana Cecilia
author2_role author
author
author
author
author
author
author
dc.subject.none.fl_str_mv Química
Thiophene
o-vanillin
X-ray crystal structure
Tautomerism
Spectroscopy
DFT
topic Química
Thiophene
o-vanillin
X-ray crystal structure
Tautomerism
Spectroscopy
DFT
dc.description.none.fl_txt_mv 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
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
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/10915/152750
url http://sedici.unlp.edu.ar/handle/10915/152750
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/issn/0022-2860
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.molstruc.2018.03.120
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by/4.0/
Creative Commons Attribution 4.0 International (CC BY 4.0)
eu_rights_str_mv openAccess
rights_invalid_str_mv http://creativecommons.org/licenses/by/4.0/
Creative Commons Attribution 4.0 International (CC BY 4.0)
dc.format.none.fl_str_mv application/pdf
381-390
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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