Synthesis, molecular structure, spectroscopic and theoretical investigation of 5-chlorosalicylaldehyde-2,4-dinitrophenylhydrazone

Autores
Gil, Diego Mauricio
Año de publicación
2020
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A new hydrazone derivative, 5-chlorosalicylaldehyde-2,4-dinitrophenylhydrazone (5Cl-DNPHZ) has been synthesized and characterized by different spectroscopic techniques such as IR, Raman and UVeVis. A combined experimental and quantum chemical approach was performed to study the structural and spectroscopic properties of the title compound. The effect of substituents (chlorine and hydroxyl) on the benzene ring on the structural and electronic properties of 5Cl-DNPHZ and a related compound DNPHZ previously reported are analysed. Natural bond orbital (NBO) analysis was performed to obtain information about the interactions that were responsible for the stability of the different conformers of the title compound. The Atoms in molecules (AIM) calculations revealed that the intramolecular hydrogen bonding interactions observed in both conformations are of core-shell in nature. The molecular electrostatic potential (MEP) surface of the most stable conformer of 5Cl-DNPHZ shows that the oxygens of the nitro groups are prone to electrophilic attack and the hydrogen of the hydrazine group is prone to nucleophilic attack indicating that the intramolecular hydrogen bonding interaction is favoured between both groups
Fil: Gil, Diego Mauricio. Universidad Nacional de Tucumán. Instituto de Biotecnología Farmacéutica y Alimentaria. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Biotecnología Farmacéutica y Alimentaria; Argentina. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica; Argentina
Materia
AIM APPROACH
DFT CALCULATIONS
HYDRAZONE DERIVATIVE
VIBRATIONAL STUDY
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/143335
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/143335
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthesis, molecular structure, spectroscopic and theoretical investigation of 5-chlorosalicylaldehyde-2,4-dinitrophenylhydrazoneGil, Diego MauricioAIM APPROACHDFT CALCULATIONSHYDRAZONE DERIVATIVEVIBRATIONAL STUDYhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A new hydrazone derivative, 5-chlorosalicylaldehyde-2,4-dinitrophenylhydrazone (5Cl-DNPHZ) has been synthesized and characterized by different spectroscopic techniques such as IR, Raman and UVeVis. A combined experimental and quantum chemical approach was performed to study the structural and spectroscopic properties of the title compound. The effect of substituents (chlorine and hydroxyl) on the benzene ring on the structural and electronic properties of 5Cl-DNPHZ and a related compound DNPHZ previously reported are analysed. Natural bond orbital (NBO) analysis was performed to obtain information about the interactions that were responsible for the stability of the different conformers of the title compound. The Atoms in molecules (AIM) calculations revealed that the intramolecular hydrogen bonding interactions observed in both conformations are of core-shell in nature. The molecular electrostatic potential (MEP) surface of the most stable conformer of 5Cl-DNPHZ shows that the oxygens of the nitro groups are prone to electrophilic attack and the hydrogen of the hydrazine group is prone to nucleophilic attack indicating that the intramolecular hydrogen bonding interaction is favoured between both groupsFil: Gil, Diego Mauricio. Universidad Nacional de Tucumán. Instituto de Biotecnología Farmacéutica y Alimentaria. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Biotecnología Farmacéutica y Alimentaria; Argentina. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica; ArgentinaElsevier2020-04info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/143335Gil, Diego Mauricio; Synthesis, molecular structure, spectroscopic and theoretical investigation of 5-chlorosalicylaldehyde-2,4-dinitrophenylhydrazone; Elsevier; Journal of Molecular Structure; 1205; 4-2020; 1-11; 1275890022-28601872-8014CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.molstruc.2019.127589info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/abs/pii/S0022286019316989info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-nd/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:07:27Zoai:ri.conicet.gov.ar:11336/143335instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-29 10:07:27.303CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis, molecular structure, spectroscopic and theoretical investigation of 5-chlorosalicylaldehyde-2,4-dinitrophenylhydrazone
title Synthesis, molecular structure, spectroscopic and theoretical investigation of 5-chlorosalicylaldehyde-2,4-dinitrophenylhydrazone
spellingShingle Synthesis, molecular structure, spectroscopic and theoretical investigation of 5-chlorosalicylaldehyde-2,4-dinitrophenylhydrazone
Gil, Diego Mauricio
AIM APPROACH
DFT CALCULATIONS
HYDRAZONE DERIVATIVE
VIBRATIONAL STUDY
title_short Synthesis, molecular structure, spectroscopic and theoretical investigation of 5-chlorosalicylaldehyde-2,4-dinitrophenylhydrazone
title_full Synthesis, molecular structure, spectroscopic and theoretical investigation of 5-chlorosalicylaldehyde-2,4-dinitrophenylhydrazone
title_fullStr Synthesis, molecular structure, spectroscopic and theoretical investigation of 5-chlorosalicylaldehyde-2,4-dinitrophenylhydrazone
title_full_unstemmed Synthesis, molecular structure, spectroscopic and theoretical investigation of 5-chlorosalicylaldehyde-2,4-dinitrophenylhydrazone
title_sort Synthesis, molecular structure, spectroscopic and theoretical investigation of 5-chlorosalicylaldehyde-2,4-dinitrophenylhydrazone
dc.creator.none.fl_str_mv Gil, Diego Mauricio
author Gil, Diego Mauricio
author_facet Gil, Diego Mauricio
author_role author
dc.subject.none.fl_str_mv AIM APPROACH
DFT CALCULATIONS
HYDRAZONE DERIVATIVE
VIBRATIONAL STUDY
topic AIM APPROACH
DFT CALCULATIONS
HYDRAZONE DERIVATIVE
VIBRATIONAL STUDY
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv A new hydrazone derivative, 5-chlorosalicylaldehyde-2,4-dinitrophenylhydrazone (5Cl-DNPHZ) has been synthesized and characterized by different spectroscopic techniques such as IR, Raman and UVeVis. A combined experimental and quantum chemical approach was performed to study the structural and spectroscopic properties of the title compound. The effect of substituents (chlorine and hydroxyl) on the benzene ring on the structural and electronic properties of 5Cl-DNPHZ and a related compound DNPHZ previously reported are analysed. Natural bond orbital (NBO) analysis was performed to obtain information about the interactions that were responsible for the stability of the different conformers of the title compound. The Atoms in molecules (AIM) calculations revealed that the intramolecular hydrogen bonding interactions observed in both conformations are of core-shell in nature. The molecular electrostatic potential (MEP) surface of the most stable conformer of 5Cl-DNPHZ shows that the oxygens of the nitro groups are prone to electrophilic attack and the hydrogen of the hydrazine group is prone to nucleophilic attack indicating that the intramolecular hydrogen bonding interaction is favoured between both groups
Fil: Gil, Diego Mauricio. Universidad Nacional de Tucumán. Instituto de Biotecnología Farmacéutica y Alimentaria. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Biotecnología Farmacéutica y Alimentaria; Argentina. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica; Argentina
description A new hydrazone derivative, 5-chlorosalicylaldehyde-2,4-dinitrophenylhydrazone (5Cl-DNPHZ) has been synthesized and characterized by different spectroscopic techniques such as IR, Raman and UVeVis. A combined experimental and quantum chemical approach was performed to study the structural and spectroscopic properties of the title compound. The effect of substituents (chlorine and hydroxyl) on the benzene ring on the structural and electronic properties of 5Cl-DNPHZ and a related compound DNPHZ previously reported are analysed. Natural bond orbital (NBO) analysis was performed to obtain information about the interactions that were responsible for the stability of the different conformers of the title compound. The Atoms in molecules (AIM) calculations revealed that the intramolecular hydrogen bonding interactions observed in both conformations are of core-shell in nature. The molecular electrostatic potential (MEP) surface of the most stable conformer of 5Cl-DNPHZ shows that the oxygens of the nitro groups are prone to electrophilic attack and the hydrogen of the hydrazine group is prone to nucleophilic attack indicating that the intramolecular hydrogen bonding interaction is favoured between both groups
publishDate 2020
dc.date.none.fl_str_mv 2020-04
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
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://hdl.handle.net/11336/143335
Gil, Diego Mauricio; Synthesis, molecular structure, spectroscopic and theoretical investigation of 5-chlorosalicylaldehyde-2,4-dinitrophenylhydrazone; Elsevier; Journal of Molecular Structure; 1205; 4-2020; 1-11; 127589
0022-2860
1872-8014
CONICET Digital
CONICET
url http://hdl.handle.net/11336/143335
identifier_str_mv Gil, Diego Mauricio; Synthesis, molecular structure, spectroscopic and theoretical investigation of 5-chlorosalicylaldehyde-2,4-dinitrophenylhydrazone; Elsevier; Journal of Molecular Structure; 1205; 4-2020; 1-11; 127589
0022-2860
1872-8014
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1016/j.molstruc.2019.127589
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/abs/pii/S0022286019316989
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 13.070432

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