Vibrational characterization of active drug to the treatment of chagas disease, benznidazole by using force fields and internal coordinates

Autores
Iramain, Maximiliano Alberto; Manzur, Maria Eugenia; Castillo, María V.; Checa Monaldi, María Fernanda; Romano, Élida; Brandan, Silvia Antonia
Año de publicación
2023
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Two experimental structures of benznidazole active drug used to the treatment of Chagas disease have been structurally characterized and its vibrational spectra completely assigned combining B3LYP/6-311++G** calculations with the experimental FT-IR and FT-Raman spectra and the SQMFF methodology. The most stable conformer of benznidazole found in the study of the potential energy surface is in agreement with that experimentally observed by X-ray diffraction at room temperature while the other one was observed with the heating up to 195 ºC. Both differs in the positions of CH2 groups of acetamide fragment. Their structural properties in gas phase and ethanol solution were computed by using natural bond orbital (NBO), atoms in molecules (AIM), Merz-Kollman (MK) charges, molecular electrostatic potentials (MEP) and frontier orbitals calculations by using the hybrid B3LYP method and the 6-31G* and 6-311++G** basis sets. Additional WB97XD/6-311++G** calculations show that the energy values optimized for the most stable species in both media present lower values than the obtained with the B3LYP/6-31G* method. The vibrational assignments for those two conformers in both media were obtained from their corresponding harmonic force fields together with the scaled force constants.
Fil: Iramain, Maximiliano Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; Argentina. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; Argentina
Fil: Manzur, Maria Eugenia. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; Argentina
Fil: Castillo, María V.. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; Argentina
Fil: Checa Monaldi, María Fernanda. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; Argentina
Fil: Romano, Élida. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; Argentina
Fil: Brandan, Silvia Antonia. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; Argentina
Materia
BENZNIDAZOLE
VIBRATIONAL SPECTRA
MOLECULAR STRUCTURE
FORCE FIELD
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/258173
Acceder
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network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Vibrational characterization of active drug to the treatment of chagas disease, benznidazole by using force fields and internal coordinatesIramain, Maximiliano AlbertoManzur, Maria EugeniaCastillo, María V.Checa Monaldi, María FernandaRomano, ÉlidaBrandan, Silvia AntoniaBENZNIDAZOLEVIBRATIONAL SPECTRAMOLECULAR STRUCTUREFORCE FIELDhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Two experimental structures of benznidazole active drug used to the treatment of Chagas disease have been structurally characterized and its vibrational spectra completely assigned combining B3LYP/6-311++G** calculations with the experimental FT-IR and FT-Raman spectra and the SQMFF methodology. The most stable conformer of benznidazole found in the study of the potential energy surface is in agreement with that experimentally observed by X-ray diffraction at room temperature while the other one was observed with the heating up to 195 ºC. Both differs in the positions of CH2 groups of acetamide fragment. Their structural properties in gas phase and ethanol solution were computed by using natural bond orbital (NBO), atoms in molecules (AIM), Merz-Kollman (MK) charges, molecular electrostatic potentials (MEP) and frontier orbitals calculations by using the hybrid B3LYP method and the 6-31G* and 6-311++G** basis sets. Additional WB97XD/6-311++G** calculations show that the energy values optimized for the most stable species in both media present lower values than the obtained with the B3LYP/6-31G* method. The vibrational assignments for those two conformers in both media were obtained from their corresponding harmonic force fields together with the scaled force constants.Fil: Iramain, Maximiliano Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; Argentina. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; ArgentinaFil: Manzur, Maria Eugenia. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; ArgentinaFil: Castillo, María V.. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; ArgentinaFil: Checa Monaldi, María Fernanda. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; ArgentinaFil: Romano, Élida. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; ArgentinaFil: Brandan, Silvia Antonia. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; ArgentinaAMO Publisher2023-09info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/258173Iramain, Maximiliano Alberto; Manzur, Maria Eugenia; Castillo, María V.; Checa Monaldi, María Fernanda; Romano, Élida; et al.; Vibrational characterization of active drug to the treatment of chagas disease, benznidazole by using force fields and internal coordinates; AMO Publisher; European Journal of Theoretical and Applied Sciences; 1; 5; 9-2023; 64-922786-7447CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://ejtas.com/index.php/journal/article/view/261info:eu-repo/semantics/altIdentifier/doi/10.59324/ejtas.2023.1(5).07info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:05:49Zoai:ri.conicet.gov.ar:11336/258173instacron: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 10:05:50.039CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Vibrational characterization of active drug to the treatment of chagas disease, benznidazole by using force fields and internal coordinates
title Vibrational characterization of active drug to the treatment of chagas disease, benznidazole by using force fields and internal coordinates
spellingShingle Vibrational characterization of active drug to the treatment of chagas disease, benznidazole by using force fields and internal coordinates
Iramain, Maximiliano Alberto
BENZNIDAZOLE
VIBRATIONAL SPECTRA
MOLECULAR STRUCTURE
FORCE FIELD
title_short Vibrational characterization of active drug to the treatment of chagas disease, benznidazole by using force fields and internal coordinates
title_full Vibrational characterization of active drug to the treatment of chagas disease, benznidazole by using force fields and internal coordinates
title_fullStr Vibrational characterization of active drug to the treatment of chagas disease, benznidazole by using force fields and internal coordinates
title_full_unstemmed Vibrational characterization of active drug to the treatment of chagas disease, benznidazole by using force fields and internal coordinates
title_sort Vibrational characterization of active drug to the treatment of chagas disease, benznidazole by using force fields and internal coordinates
dc.creator.none.fl_str_mv Iramain, Maximiliano Alberto
Manzur, Maria Eugenia
Castillo, María V.
Checa Monaldi, María Fernanda
Romano, Élida
Brandan, Silvia Antonia
author Iramain, Maximiliano Alberto
author_facet Iramain, Maximiliano Alberto
Manzur, Maria Eugenia
Castillo, María V.
Checa Monaldi, María Fernanda
Romano, Élida
Brandan, Silvia Antonia
author_role author
author2 Manzur, Maria Eugenia
Castillo, María V.
Checa Monaldi, María Fernanda
Romano, Élida
Brandan, Silvia Antonia
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv BENZNIDAZOLE
VIBRATIONAL SPECTRA
MOLECULAR STRUCTURE
FORCE FIELD
topic BENZNIDAZOLE
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 Two experimental structures of benznidazole active drug used to the treatment of Chagas disease have been structurally characterized and its vibrational spectra completely assigned combining B3LYP/6-311++G** calculations with the experimental FT-IR and FT-Raman spectra and the SQMFF methodology. The most stable conformer of benznidazole found in the study of the potential energy surface is in agreement with that experimentally observed by X-ray diffraction at room temperature while the other one was observed with the heating up to 195 ºC. Both differs in the positions of CH2 groups of acetamide fragment. Their structural properties in gas phase and ethanol solution were computed by using natural bond orbital (NBO), atoms in molecules (AIM), Merz-Kollman (MK) charges, molecular electrostatic potentials (MEP) and frontier orbitals calculations by using the hybrid B3LYP method and the 6-31G* and 6-311++G** basis sets. Additional WB97XD/6-311++G** calculations show that the energy values optimized for the most stable species in both media present lower values than the obtained with the B3LYP/6-31G* method. The vibrational assignments for those two conformers in both media were obtained from their corresponding harmonic force fields together with the scaled force constants.
Fil: Iramain, Maximiliano Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; Argentina. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; Argentina
Fil: Manzur, Maria Eugenia. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; Argentina
Fil: Castillo, María V.. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; Argentina
Fil: Checa Monaldi, María Fernanda. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; Argentina
Fil: Romano, Élida. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; Argentina
Fil: Brandan, Silvia Antonia. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; Argentina
description Two experimental structures of benznidazole active drug used to the treatment of Chagas disease have been structurally characterized and its vibrational spectra completely assigned combining B3LYP/6-311++G** calculations with the experimental FT-IR and FT-Raman spectra and the SQMFF methodology. The most stable conformer of benznidazole found in the study of the potential energy surface is in agreement with that experimentally observed by X-ray diffraction at room temperature while the other one was observed with the heating up to 195 ºC. Both differs in the positions of CH2 groups of acetamide fragment. Their structural properties in gas phase and ethanol solution were computed by using natural bond orbital (NBO), atoms in molecules (AIM), Merz-Kollman (MK) charges, molecular electrostatic potentials (MEP) and frontier orbitals calculations by using the hybrid B3LYP method and the 6-31G* and 6-311++G** basis sets. Additional WB97XD/6-311++G** calculations show that the energy values optimized for the most stable species in both media present lower values than the obtained with the B3LYP/6-31G* method. The vibrational assignments for those two conformers in both media were obtained from their corresponding harmonic force fields together with the scaled force constants.
publishDate 2023
dc.date.none.fl_str_mv 2023-09
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/11336/258173
Iramain, Maximiliano Alberto; Manzur, Maria Eugenia; Castillo, María V.; Checa Monaldi, María Fernanda; Romano, Élida; et al.; Vibrational characterization of active drug to the treatment of chagas disease, benznidazole by using force fields and internal coordinates; AMO Publisher; European Journal of Theoretical and Applied Sciences; 1; 5; 9-2023; 64-92
2786-7447
CONICET Digital
CONICET
url http://hdl.handle.net/11336/258173
identifier_str_mv Iramain, Maximiliano Alberto; Manzur, Maria Eugenia; Castillo, María V.; Checa Monaldi, María Fernanda; Romano, Élida; et al.; Vibrational characterization of active drug to the treatment of chagas disease, benznidazole by using force fields and internal coordinates; AMO Publisher; European Journal of Theoretical and Applied Sciences; 1; 5; 9-2023; 64-92
2786-7447
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://ejtas.com/index.php/journal/article/view/261
info:eu-repo/semantics/altIdentifier/doi/10.59324/ejtas.2023.1(5).07
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv AMO Publisher
publisher.none.fl_str_mv AMO Publisher
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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