Vibrational and structural study of onopordopicrin based on the FTIR spectrum and DFT calculations

Autores
Chain, Fernando Ezequiel; Romano, Elida; Leyton, Patricio; Paipa, Carolina; Catalan, Cesar Atilio Nazareno; Fortuna, Mario; Brandán, Silvia Antonia
Año de publicación
2015
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
In the present work, the structural and vibrational properties of the sesquiterpene lactone onopordopicrin (OP) were studied by using infrared spectroscopy and density functional theory (DFT) calculations together with the 6-31G∗ basis set. The harmonic vibrational wavenumbers for the optimized geometry were calculated at the same level of theory. The complete assignment of the observed bands in the infrared spectrum was performed by combining the DFT calculations with Pulay’s scaled quantum mechanical force field (SQMFF) methodology. The comparison between the theoretical and experimental infrared spectrum demonstrated good agreement. Then, the results were used to predict the Raman spectrum. Additionally, the structural properties of OP, such as atomic charges, bond orders, molecular electrostatic potentials, characteristics of electronic delocalization and topological properties of the electronic charge density were evaluated by natural bond orbital (NBO), atoms in molecules (AIM) and frontier orbitals studies. The calculated energy band gap and the chemical potential (μ), electronegativity (χ), global hardness (η), global softness (S) and global electrophilicity index (ω) descriptors predicted for OP low reactivity, higher stability and lower electrophilicity index as compared with the sesquiterpene lactone cnicin containing similar rings.
Fil: Chain, Fernando Ezequiel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Tucumán. Instituto de Quimica del Noroeste; Argentina. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia; Argentina
Fil: Romano, Elida. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica; Argentina
Fil: Leyton, Patricio. Pontificia Universidad Catolica de Valparaiso; Chile
Fil: Paipa, Carolina. Universidad Andres Bello; Chile
Fil: Catalan, Cesar Atilio Nazareno. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Tucumán. Instituto de Quimica del Noroeste; Argentina. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia; Argentina
Fil: Fortuna, Mario. Universidad Nacional de Tucumán. Facultad de Agronomía y Zootecnia; Argentina
Fil: Brandán, Silvia Antonia. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica; Argentina
Materia
Onopordopicrin
Vibrational Spectra
Molecular Structure
Force Field
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:11336/12579
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/12579
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Vibrational and structural study of onopordopicrin based on the FTIR spectrum and DFT calculationsChain, Fernando EzequielRomano, ElidaLeyton, PatricioPaipa, CarolinaCatalan, Cesar Atilio NazarenoFortuna, MarioBrandán, Silvia AntoniaOnopordopicrinVibrational SpectraMolecular StructureForce Fieldhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1In the present work, the structural and vibrational properties of the sesquiterpene lactone onopordopicrin (OP) were studied by using infrared spectroscopy and density functional theory (DFT) calculations together with the 6-31G∗ basis set. The harmonic vibrational wavenumbers for the optimized geometry were calculated at the same level of theory. The complete assignment of the observed bands in the infrared spectrum was performed by combining the DFT calculations with Pulay’s scaled quantum mechanical force field (SQMFF) methodology. The comparison between the theoretical and experimental infrared spectrum demonstrated good agreement. Then, the results were used to predict the Raman spectrum. Additionally, the structural properties of OP, such as atomic charges, bond orders, molecular electrostatic potentials, characteristics of electronic delocalization and topological properties of the electronic charge density were evaluated by natural bond orbital (NBO), atoms in molecules (AIM) and frontier orbitals studies. The calculated energy band gap and the chemical potential (μ), electronegativity (χ), global hardness (η), global softness (S) and global electrophilicity index (ω) descriptors predicted for OP low reactivity, higher stability and lower electrophilicity index as compared with the sesquiterpene lactone cnicin containing similar rings.Fil: Chain, Fernando Ezequiel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Tucumán. Instituto de Quimica del Noroeste; Argentina. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia; ArgentinaFil: Romano, Elida. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica; ArgentinaFil: Leyton, Patricio. Pontificia Universidad Catolica de Valparaiso; ChileFil: Paipa, Carolina. Universidad Andres Bello; ChileFil: Catalan, Cesar Atilio Nazareno. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Tucumán. Instituto de Quimica del Noroeste; Argentina. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia; ArgentinaFil: Fortuna, Mario. Universidad Nacional de Tucumán. Facultad de Agronomía y Zootecnia; ArgentinaFil: Brandán, Silvia Antonia. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica; ArgentinaElsevier Science2015-11-05info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/12579Chain, Fernando Ezequiel; Romano, Elida; Leyton, Patricio; Paipa, Carolina; Catalan, Cesar Atilio Nazareno; et al.; Vibrational and structural study of onopordopicrin based on the FTIR spectrum and DFT calculations; Elsevier Science; Spectrochimica Acta Part A: Molecular And Biomolecular Spectroscopy; 150; 5-11-2015; 381-3891386-1425enginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.saa.2015.05.072info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S138614251500685Xinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-nd/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-10T13:14:16Zoai:ri.conicet.gov.ar:11336/12579instacron: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:34982025-09-10 13:14:16.925CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Vibrational and structural study of onopordopicrin based on the FTIR spectrum and DFT calculations
title Vibrational and structural study of onopordopicrin based on the FTIR spectrum and DFT calculations
spellingShingle Vibrational and structural study of onopordopicrin based on the FTIR spectrum and DFT calculations
Chain, Fernando Ezequiel
Onopordopicrin
Vibrational Spectra
Molecular Structure
Force Field
title_short Vibrational and structural study of onopordopicrin based on the FTIR spectrum and DFT calculations
title_full Vibrational and structural study of onopordopicrin based on the FTIR spectrum and DFT calculations
title_fullStr Vibrational and structural study of onopordopicrin based on the FTIR spectrum and DFT calculations
title_full_unstemmed Vibrational and structural study of onopordopicrin based on the FTIR spectrum and DFT calculations
title_sort Vibrational and structural study of onopordopicrin based on the FTIR spectrum and DFT calculations
dc.creator.none.fl_str_mv Chain, Fernando Ezequiel
Romano, Elida
Leyton, Patricio
Paipa, Carolina
Catalan, Cesar Atilio Nazareno
Fortuna, Mario
Brandán, Silvia Antonia
author Chain, Fernando Ezequiel
author_facet Chain, Fernando Ezequiel
Romano, Elida
Leyton, Patricio
Paipa, Carolina
Catalan, Cesar Atilio Nazareno
Fortuna, Mario
Brandán, Silvia Antonia
author_role author
author2 Romano, Elida
Leyton, Patricio
Paipa, Carolina
Catalan, Cesar Atilio Nazareno
Fortuna, Mario
Brandán, Silvia Antonia
author2_role author
author
author
author
author
author
dc.subject.none.fl_str_mv Onopordopicrin
Vibrational Spectra
Molecular Structure
Force Field
topic Onopordopicrin
Vibrational Spectra
Molecular Structure
Force Field
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv In the present work, the structural and vibrational properties of the sesquiterpene lactone onopordopicrin (OP) were studied by using infrared spectroscopy and density functional theory (DFT) calculations together with the 6-31G∗ basis set. The harmonic vibrational wavenumbers for the optimized geometry were calculated at the same level of theory. The complete assignment of the observed bands in the infrared spectrum was performed by combining the DFT calculations with Pulay’s scaled quantum mechanical force field (SQMFF) methodology. The comparison between the theoretical and experimental infrared spectrum demonstrated good agreement. Then, the results were used to predict the Raman spectrum. Additionally, the structural properties of OP, such as atomic charges, bond orders, molecular electrostatic potentials, characteristics of electronic delocalization and topological properties of the electronic charge density were evaluated by natural bond orbital (NBO), atoms in molecules (AIM) and frontier orbitals studies. The calculated energy band gap and the chemical potential (μ), electronegativity (χ), global hardness (η), global softness (S) and global electrophilicity index (ω) descriptors predicted for OP low reactivity, higher stability and lower electrophilicity index as compared with the sesquiterpene lactone cnicin containing similar rings.
Fil: Chain, Fernando Ezequiel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Tucumán. Instituto de Quimica del Noroeste; Argentina. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia; Argentina
Fil: Romano, Elida. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica; Argentina
Fil: Leyton, Patricio. Pontificia Universidad Catolica de Valparaiso; Chile
Fil: Paipa, Carolina. Universidad Andres Bello; Chile
Fil: Catalan, Cesar Atilio Nazareno. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Tucumán. Instituto de Quimica del Noroeste; Argentina. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia; Argentina
Fil: Fortuna, Mario. Universidad Nacional de Tucumán. Facultad de Agronomía y Zootecnia; Argentina
Fil: Brandán, Silvia Antonia. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica; Argentina
description In the present work, the structural and vibrational properties of the sesquiterpene lactone onopordopicrin (OP) were studied by using infrared spectroscopy and density functional theory (DFT) calculations together with the 6-31G∗ basis set. The harmonic vibrational wavenumbers for the optimized geometry were calculated at the same level of theory. The complete assignment of the observed bands in the infrared spectrum was performed by combining the DFT calculations with Pulay’s scaled quantum mechanical force field (SQMFF) methodology. The comparison between the theoretical and experimental infrared spectrum demonstrated good agreement. Then, the results were used to predict the Raman spectrum. Additionally, the structural properties of OP, such as atomic charges, bond orders, molecular electrostatic potentials, characteristics of electronic delocalization and topological properties of the electronic charge density were evaluated by natural bond orbital (NBO), atoms in molecules (AIM) and frontier orbitals studies. The calculated energy band gap and the chemical potential (μ), electronegativity (χ), global hardness (η), global softness (S) and global electrophilicity index (ω) descriptors predicted for OP low reactivity, higher stability and lower electrophilicity index as compared with the sesquiterpene lactone cnicin containing similar rings.
publishDate 2015
dc.date.none.fl_str_mv 2015-11-05
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/11336/12579
Chain, Fernando Ezequiel; Romano, Elida; Leyton, Patricio; Paipa, Carolina; Catalan, Cesar Atilio Nazareno; et al.; Vibrational and structural study of onopordopicrin based on the FTIR spectrum and DFT calculations; Elsevier Science; Spectrochimica Acta Part A: Molecular And Biomolecular Spectroscopy; 150; 5-11-2015; 381-389
1386-1425
url http://hdl.handle.net/11336/12579
identifier_str_mv Chain, Fernando Ezequiel; Romano, Elida; Leyton, Patricio; Paipa, Carolina; Catalan, Cesar Atilio Nazareno; et al.; Vibrational and structural study of onopordopicrin based on the FTIR spectrum and DFT calculations; Elsevier Science; Spectrochimica Acta Part A: Molecular And Biomolecular Spectroscopy; 150; 5-11-2015; 381-389
1386-1425
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1016/j.saa.2015.05.072
info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S138614251500685X
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
dc.publisher.none.fl_str_mv Elsevier Science
publisher.none.fl_str_mv Elsevier Science
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 12.993085

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