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
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/143335
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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 Técnicas2025-09-03T09:58:53Zoai: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:34982025-09-03 09:58:53.565CONICET 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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1842269548537970688 |
score |
13.13397 |