Structural, spectroscopic, and theoretical analysis of a molecular system based on 2-((2-(4-chlorophenylhydrazone)methyl)quinolone

A novel molecular system based on 2-((2-(4-chlorophenylhydrazone)methyl)quinoline (1-E) was synthesized. Interconversion of 1-E to its configurational isomer 1-Z was achieved using UV radiation (250 W Hg lamp). Such isomerization was monitored by 1H-NMR. The results suggest that the hydrazone deriva...

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Autores:
Chaur Valencia, Manuel Noé
Romero, Elkin Libardo
Gutierrez, Gustavo
Soto Monsalve, Mónica
D´Vries, Richard
Zuluaga, Héctor Fabio
Tipo de recurso:
Article of journal
Fecha de publicación:
2018
Institución:
Universidad Nacional de Colombia
Repositorio:
Universidad Nacional de Colombia
Idioma:
spa
OAI Identifier:
oai:repositorio.unal.edu.co:unal/66242
Acceso en línea:
https://repositorio.unal.edu.co/handle/unal/66242
http://bdigital.unal.edu.co/67266/
Palabra clave:
54 Química y ciencias afines / Chemistry
Hydrazone derivatives
configurational dynamic
single XRD
DFT calculations
electrochemistry
derivados hidrazónicos
dinámica configuracional
cristalografía de rayos X
cálculos DFT
electroquímica
derivados de hidrazonas
Dinâmica configuracional
Cristalografia de Raios-X
Cálculos DFT
Eletroquímica
Rights
openAccess
License
Atribución-NoComercial 4.0 Internacional
id UNACIONAL2_5e099f17c6ebd46b3125a686b68df218
oai_identifier_str oai:repositorio.unal.edu.co:unal/66242
network_acronym_str UNACIONAL2
network_name_str Universidad Nacional de Colombia
repository_id_str
dc.title.spa.fl_str_mv Structural, spectroscopic, and theoretical analysis of a molecular system based on 2-((2-(4-chlorophenylhydrazone)methyl)quinolone
title Structural, spectroscopic, and theoretical analysis of a molecular system based on 2-((2-(4-chlorophenylhydrazone)methyl)quinolone
spellingShingle Structural, spectroscopic, and theoretical analysis of a molecular system based on 2-((2-(4-chlorophenylhydrazone)methyl)quinolone
54 Química y ciencias afines / Chemistry
Hydrazone derivatives
configurational dynamic
single XRD
DFT calculations
electrochemistry
derivados hidrazónicos
dinámica configuracional
cristalografía de rayos X
cálculos DFT
electroquímica
derivados de hidrazonas
Dinâmica configuracional
Cristalografia de Raios-X
Cálculos DFT
Eletroquímica
title_short Structural, spectroscopic, and theoretical analysis of a molecular system based on 2-((2-(4-chlorophenylhydrazone)methyl)quinolone
title_full Structural, spectroscopic, and theoretical analysis of a molecular system based on 2-((2-(4-chlorophenylhydrazone)methyl)quinolone
title_fullStr Structural, spectroscopic, and theoretical analysis of a molecular system based on 2-((2-(4-chlorophenylhydrazone)methyl)quinolone
title_full_unstemmed Structural, spectroscopic, and theoretical analysis of a molecular system based on 2-((2-(4-chlorophenylhydrazone)methyl)quinolone
title_sort Structural, spectroscopic, and theoretical analysis of a molecular system based on 2-((2-(4-chlorophenylhydrazone)methyl)quinolone
dc.creator.fl_str_mv Chaur Valencia, Manuel Noé
Romero, Elkin Libardo
Gutierrez, Gustavo
Soto Monsalve, Mónica
D´Vries, Richard
Zuluaga, Héctor Fabio
dc.contributor.author.spa.fl_str_mv Chaur Valencia, Manuel Noé
Romero, Elkin Libardo
Gutierrez, Gustavo
Soto Monsalve, Mónica
D´Vries, Richard
Zuluaga, Héctor Fabio
dc.subject.ddc.spa.fl_str_mv 54 Química y ciencias afines / Chemistry
topic 54 Química y ciencias afines / Chemistry
Hydrazone derivatives
configurational dynamic
single XRD
DFT calculations
electrochemistry
derivados hidrazónicos
dinámica configuracional
cristalografía de rayos X
cálculos DFT
electroquímica
derivados de hidrazonas
Dinâmica configuracional
Cristalografia de Raios-X
Cálculos DFT
Eletroquímica
dc.subject.proposal.spa.fl_str_mv Hydrazone derivatives
configurational dynamic
single XRD
DFT calculations
electrochemistry
derivados hidrazónicos
dinámica configuracional
cristalografía de rayos X
cálculos DFT
electroquímica
derivados de hidrazonas
Dinâmica configuracional
Cristalografia de Raios-X
Cálculos DFT
Eletroquímica
description A novel molecular system based on 2-((2-(4-chlorophenylhydrazone)methyl)quinoline (1-E) was synthesized. Interconversion of 1-E to its configurational isomer 1-Z was achieved using UV radiation (250 W Hg lamp). Such isomerization was monitored by 1H-NMR. The results suggest that the hydrazone derivative can act as a chemical brake in solution. This molecular system was structurally (Single Crystal X-Ray diffraction and DFT calculations) and spectroscopically (NMR, UV, and IR) characterized. Electrochemical measurements showed that configurational changes induce differential redox behavior. In this regard, the reported quinoline system exhibits different dynamic absorption and electrochemical properties that are modulated by the UV-light induced configurational change. Therefore, 1-E can be regarded as potential photo-electrochemical switch.
publishDate 2018
dc.date.issued.spa.fl_str_mv 2018-05-01
dc.date.accessioned.spa.fl_str_mv 2019-07-03T01:45:05Z
dc.date.available.spa.fl_str_mv 2019-07-03T01:45:05Z
dc.type.spa.fl_str_mv Artículo de revista
dc.type.coar.fl_str_mv http://purl.org/coar/resource_type/c_2df8fbb1
dc.type.driver.spa.fl_str_mv info:eu-repo/semantics/article
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dc.type.content.spa.fl_str_mv Text
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format http://purl.org/coar/resource_type/c_6501
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dc.identifier.issn.spa.fl_str_mv ISSN: 2357-3791
dc.identifier.uri.none.fl_str_mv https://repositorio.unal.edu.co/handle/unal/66242
dc.identifier.eprints.spa.fl_str_mv http://bdigital.unal.edu.co/67266/
identifier_str_mv ISSN: 2357-3791
url https://repositorio.unal.edu.co/handle/unal/66242
http://bdigital.unal.edu.co/67266/
dc.language.iso.spa.fl_str_mv spa
language spa
dc.relation.spa.fl_str_mv https://revistas.unal.edu.co/index.php/rcolquim/article/view/67115
dc.relation.ispartof.spa.fl_str_mv Universidad Nacional de Colombia Revistas electrónicas UN Revista Colombiana de Química
Revista Colombiana de Química
dc.relation.references.spa.fl_str_mv Chaur Valencia, Manuel Noé and Romero, Elkin Libardo and Gutierrez, Gustavo and Soto Monsalve, Mónica and D´Vries, Richard and Zuluaga, Héctor Fabio (2018) Structural, spectroscopic, and theoretical analysis of a molecular system based on 2-((2-(4-chlorophenylhydrazone)methyl)quinolone. Revista Colombiana de Química, 47 (2). pp. 63-72. ISSN 2357-3791
dc.rights.spa.fl_str_mv Derechos reservados - Universidad Nacional de Colombia
dc.rights.coar.fl_str_mv http://purl.org/coar/access_right/c_abf2
dc.rights.license.spa.fl_str_mv Atribución-NoComercial 4.0 Internacional
dc.rights.uri.spa.fl_str_mv http://creativecommons.org/licenses/by-nc/4.0/
dc.rights.accessrights.spa.fl_str_mv info:eu-repo/semantics/openAccess
rights_invalid_str_mv Atribución-NoComercial 4.0 Internacional
Derechos reservados - Universidad Nacional de Colombia
http://creativecommons.org/licenses/by-nc/4.0/
http://purl.org/coar/access_right/c_abf2
eu_rights_str_mv openAccess
dc.format.mimetype.spa.fl_str_mv application/pdf
dc.publisher.spa.fl_str_mv Universidad Nacional de Colombia - Sede Bogotá - Facultad de Ciencias - Departamento de Química
institution Universidad Nacional de Colombia
bitstream.url.fl_str_mv https://repositorio.unal.edu.co/bitstream/unal/66242/1/67115-385730-1-PB.pdf
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repository.name.fl_str_mv Repositorio Institucional Universidad Nacional de Colombia
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spelling Atribución-NoComercial 4.0 InternacionalDerechos reservados - Universidad Nacional de Colombiahttp://creativecommons.org/licenses/by-nc/4.0/info:eu-repo/semantics/openAccesshttp://purl.org/coar/access_right/c_abf2Chaur Valencia, Manuel Noé6233669e-538c-4dfb-9659-d67b72007ff3300Romero, Elkin Libardo24c01f26-db08-4088-869e-f15a6cd71d75300Gutierrez, Gustavod3cf7c21-4642-47f2-b8d9-e7b3563f27f8300Soto Monsalve, Mónicadf3c6f6c-196d-45d5-9494-34f161fc4e52300D´Vries, Richardcec23c6f-a5c9-4d29-9d32-00a2ce720336300Zuluaga, Héctor Fabio9048c60b-fabd-4b04-aa02-f968f7f01ac43002019-07-03T01:45:05Z2019-07-03T01:45:05Z2018-05-01ISSN: 2357-3791https://repositorio.unal.edu.co/handle/unal/66242http://bdigital.unal.edu.co/67266/A novel molecular system based on 2-((2-(4-chlorophenylhydrazone)methyl)quinoline (1-E) was synthesized. Interconversion of 1-E to its configurational isomer 1-Z was achieved using UV radiation (250 W Hg lamp). Such isomerization was monitored by 1H-NMR. The results suggest that the hydrazone derivative can act as a chemical brake in solution. This molecular system was structurally (Single Crystal X-Ray diffraction and DFT calculations) and spectroscopically (NMR, UV, and IR) characterized. Electrochemical measurements showed that configurational changes induce differential redox behavior. In this regard, the reported quinoline system exhibits different dynamic absorption and electrochemical properties that are modulated by the UV-light induced configurational change. Therefore, 1-E can be regarded as potential photo-electrochemical switch.Se sintetizó un nuevo sistema molecular basado en 2-((2-(4-chlorofenilhidrazona)metil)quinolina. Del mismo modo, se evaluó la respuesta dinámica de este compuesto a radiación ultravioleta y formación de un enlace de hidrógeno intramolecular. Los resultados muestran que este derivado de hidrazona puede actuar como freno en solución. El sistema en mención es descrito estructural (Cristalografía de Rayos X y cálculos DFT) y espectroscópicamente (RMN, UV e IR). La interconversión de este sistema entre las configuraciones 1-E y 1-Z fue mediada por radiación UV y monitoreada a través de RMN-1H. El estudio electroquímico mostró un comportamiento diferencial en función de su configuración, aspecto fundamental en el desarrollo de sistemas foto- y electroquímicamente modulados.Neste trabalho é apresentado um novo sistema molecular baseado na 2-((2-(4-clorofenilhidrazona)metil)quinolina, capaz de responder dinamicamente à radiação ultravioleta formando uma ligação de hidrogénio intramolecular que atua como um freio na solução. Este sistema é descrito estruturalmente (cristalografia de raios-X e DFT) e por diferentes técnicas espectroscópicas (RMN, de UV e de IV). Radiação UV foi usada para fazer a interconversão da hidrazona 1-E no seu isômero configuracional 1-Z. Este processo foi monitorado pelo RMN. As medidas eletroquímicas mostraram que as mudanças configuracionais entre os isômeros induzem a comportamentos redox diferentes, o que é uma caraterística chave no desenvolvimento de interruptores fotoelectroquímicos.application/pdfspaUniversidad Nacional de Colombia - Sede Bogotá - Facultad de Ciencias - Departamento de Químicahttps://revistas.unal.edu.co/index.php/rcolquim/article/view/67115Universidad Nacional de Colombia Revistas electrónicas UN Revista Colombiana de QuímicaRevista Colombiana de QuímicaChaur Valencia, Manuel Noé and Romero, Elkin Libardo and Gutierrez, Gustavo and Soto Monsalve, Mónica and D´Vries, Richard and Zuluaga, Héctor Fabio (2018) Structural, spectroscopic, and theoretical analysis of a molecular system based on 2-((2-(4-chlorophenylhydrazone)methyl)quinolone. Revista Colombiana de Química, 47 (2). pp. 63-72. ISSN 2357-379154 Química y ciencias afines / ChemistryHydrazone derivativesconfigurational dynamicsingle XRDDFT calculationselectrochemistryderivados hidrazónicosdinámica configuracionalcristalografía de rayos Xcálculos DFTelectroquímicaderivados de hidrazonasDinâmica configuracionalCristalografia de Raios-XCálculos DFTEletroquímicaStructural, spectroscopic, and theoretical analysis of a molecular system based on 2-((2-(4-chlorophenylhydrazone)methyl)quinoloneArtículo de revistainfo:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501http://purl.org/coar/resource_type/c_2df8fbb1http://purl.org/coar/version/c_970fb48d4fbd8a85Texthttp://purl.org/redcol/resource_type/ARTORIGINAL67115-385730-1-PB.pdfapplication/pdf1291275https://repositorio.unal.edu.co/bitstream/unal/66242/1/67115-385730-1-PB.pdf619f7f20ff11d017de9cd9ffea8b2fdcMD51THUMBNAIL67115-385730-1-PB.pdf.jpg67115-385730-1-PB.pdf.jpgGenerated Thumbnailimage/jpeg7258https://repositorio.unal.edu.co/bitstream/unal/66242/2/67115-385730-1-PB.pdf.jpgdfa65e3da35fd141a306c37a85204cb5MD52unal/66242oai:repositorio.unal.edu.co:unal/662422024-05-15 23:09:05.741Repositorio Institucional Universidad Nacional de Colombiarepositorio_nal@unal.edu.co

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