Vibrational Study of Antiparasitic Nifurtimox Agent Combining Harmonic Force Fields with DFT Calculations

Autores
Iramain, Maximiliano Alberto; Guzzetti, Karina Andrea; Manzur, Maria Eugenia; Castillo Scheuermann, Maria Victoria Elizabeth; Brandan, Silvia Antonia
Año de publicación
2024
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A theoretical study has been performed on the anti-chagasic nifurtimox agent (NFX), by using the hybrid B3LYP/6-311++G** calculations in the gas phase, DMSO and aqueous solution to characterize the structures and vibrational spectra. The most stable conformer predicted by calculations is in agreement with the experimental reported by X-ray diffraction with a higher solvation energy in aqueous solution (-134.81 kJ/mol) than in DMSO solution (-90.71 kJ/mol). A higher dipole moment and contraction of volume is predicted in aqueous solution probably due to the presence of strongly acceptors SO2 and NO2 groups of H bonds associated to the higher permittivity of water. Nucleophilic sites on the SO2 and NO2 groups are revealed by the mapped MEP surfaces with a higher energy value in water. The higher stability of NFX in solution is supported by NBO calculations while the frontier orbitals show that NFX is most reactive in both solutions than in the gas phase. Here, complete vibrational assignments of FT-IR and FT-Raman spectra in the three media have been performed by using the normal internal coordinates, the scaled mechanical force field (SQMFF) methodology and the Molvib program. The predicted NMR and Uv-vis spectra show good concordances with the corresponding experimental ones.
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: Guzzetti, Karina Andrea. 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 Scheuermann, Maria Victoria Elizabeth. 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
NIFURTIMOX
DFT CALCULATIONS
MOLECULAR STRUCTURE
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:11336/258804
Acceder
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network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Vibrational Study of Antiparasitic Nifurtimox Agent Combining Harmonic Force Fields with DFT CalculationsIramain, Maximiliano AlbertoGuzzetti, Karina AndreaManzur, Maria EugeniaCastillo Scheuermann, Maria Victoria ElizabethBrandan, Silvia AntoniaNIFURTIMOXDFT CALCULATIONSMOLECULAR STRUCTUREhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A theoretical study has been performed on the anti-chagasic nifurtimox agent (NFX), by using the hybrid B3LYP/6-311++G** calculations in the gas phase, DMSO and aqueous solution to characterize the structures and vibrational spectra. The most stable conformer predicted by calculations is in agreement with the experimental reported by X-ray diffraction with a higher solvation energy in aqueous solution (-134.81 kJ/mol) than in DMSO solution (-90.71 kJ/mol). A higher dipole moment and contraction of volume is predicted in aqueous solution probably due to the presence of strongly acceptors SO2 and NO2 groups of H bonds associated to the higher permittivity of water. Nucleophilic sites on the SO2 and NO2 groups are revealed by the mapped MEP surfaces with a higher energy value in water. The higher stability of NFX in solution is supported by NBO calculations while the frontier orbitals show that NFX is most reactive in both solutions than in the gas phase. Here, complete vibrational assignments of FT-IR and FT-Raman spectra in the three media have been performed by using the normal internal coordinates, the scaled mechanical force field (SQMFF) methodology and the Molvib program. The predicted NMR and Uv-vis spectra show good concordances with the corresponding experimental ones.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: Guzzetti, Karina Andrea. 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 Scheuermann, Maria Victoria Elizabeth. 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 Publisher2024-11info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/258804Iramain, Maximiliano Alberto; Guzzetti, Karina Andrea; Manzur, Maria Eugenia; Castillo Scheuermann, Maria Victoria Elizabeth; Brandan, Silvia Antonia; Vibrational Study of Antiparasitic Nifurtimox Agent Combining Harmonic Force Fields with DFT Calculations; Amo Publisher; European Journal of Theoretical and Applied Sciences; 2; 6; 11-2024; 711-7322786-7447CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://ejtas.com/index.php/journal/article/view/1340info:eu-repo/semantics/altIdentifier/doi/10.59324/ejtas.2024.2(6).63info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T15:29:19Zoai:ri.conicet.gov.ar:11336/258804instacron: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:34982025-10-15 15:29:20.265CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Vibrational Study of Antiparasitic Nifurtimox Agent Combining Harmonic Force Fields with DFT Calculations
title Vibrational Study of Antiparasitic Nifurtimox Agent Combining Harmonic Force Fields with DFT Calculations
spellingShingle Vibrational Study of Antiparasitic Nifurtimox Agent Combining Harmonic Force Fields with DFT Calculations
Iramain, Maximiliano Alberto
NIFURTIMOX
DFT CALCULATIONS
MOLECULAR STRUCTURE
title_short Vibrational Study of Antiparasitic Nifurtimox Agent Combining Harmonic Force Fields with DFT Calculations
title_full Vibrational Study of Antiparasitic Nifurtimox Agent Combining Harmonic Force Fields with DFT Calculations
title_fullStr Vibrational Study of Antiparasitic Nifurtimox Agent Combining Harmonic Force Fields with DFT Calculations
title_full_unstemmed Vibrational Study of Antiparasitic Nifurtimox Agent Combining Harmonic Force Fields with DFT Calculations
title_sort Vibrational Study of Antiparasitic Nifurtimox Agent Combining Harmonic Force Fields with DFT Calculations
dc.creator.none.fl_str_mv Iramain, Maximiliano Alberto
Guzzetti, Karina Andrea
Manzur, Maria Eugenia
Castillo Scheuermann, Maria Victoria Elizabeth
Brandan, Silvia Antonia
author Iramain, Maximiliano Alberto
author_facet Iramain, Maximiliano Alberto
Guzzetti, Karina Andrea
Manzur, Maria Eugenia
Castillo Scheuermann, Maria Victoria Elizabeth
Brandan, Silvia Antonia
author_role author
author2 Guzzetti, Karina Andrea
Manzur, Maria Eugenia
Castillo Scheuermann, Maria Victoria Elizabeth
Brandan, Silvia Antonia
author2_role author
author
author
author
dc.subject.none.fl_str_mv NIFURTIMOX
DFT CALCULATIONS
MOLECULAR STRUCTURE
topic NIFURTIMOX
DFT CALCULATIONS
MOLECULAR STRUCTURE
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 theoretical study has been performed on the anti-chagasic nifurtimox agent (NFX), by using the hybrid B3LYP/6-311++G** calculations in the gas phase, DMSO and aqueous solution to characterize the structures and vibrational spectra. The most stable conformer predicted by calculations is in agreement with the experimental reported by X-ray diffraction with a higher solvation energy in aqueous solution (-134.81 kJ/mol) than in DMSO solution (-90.71 kJ/mol). A higher dipole moment and contraction of volume is predicted in aqueous solution probably due to the presence of strongly acceptors SO2 and NO2 groups of H bonds associated to the higher permittivity of water. Nucleophilic sites on the SO2 and NO2 groups are revealed by the mapped MEP surfaces with a higher energy value in water. The higher stability of NFX in solution is supported by NBO calculations while the frontier orbitals show that NFX is most reactive in both solutions than in the gas phase. Here, complete vibrational assignments of FT-IR and FT-Raman spectra in the three media have been performed by using the normal internal coordinates, the scaled mechanical force field (SQMFF) methodology and the Molvib program. The predicted NMR and Uv-vis spectra show good concordances with the corresponding experimental ones.
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: Guzzetti, Karina Andrea. 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 Scheuermann, Maria Victoria Elizabeth. 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 A theoretical study has been performed on the anti-chagasic nifurtimox agent (NFX), by using the hybrid B3LYP/6-311++G** calculations in the gas phase, DMSO and aqueous solution to characterize the structures and vibrational spectra. The most stable conformer predicted by calculations is in agreement with the experimental reported by X-ray diffraction with a higher solvation energy in aqueous solution (-134.81 kJ/mol) than in DMSO solution (-90.71 kJ/mol). A higher dipole moment and contraction of volume is predicted in aqueous solution probably due to the presence of strongly acceptors SO2 and NO2 groups of H bonds associated to the higher permittivity of water. Nucleophilic sites on the SO2 and NO2 groups are revealed by the mapped MEP surfaces with a higher energy value in water. The higher stability of NFX in solution is supported by NBO calculations while the frontier orbitals show that NFX is most reactive in both solutions than in the gas phase. Here, complete vibrational assignments of FT-IR and FT-Raman spectra in the three media have been performed by using the normal internal coordinates, the scaled mechanical force field (SQMFF) methodology and the Molvib program. The predicted NMR and Uv-vis spectra show good concordances with the corresponding experimental ones.
publishDate 2024
dc.date.none.fl_str_mv 2024-11
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/11336/258804
Iramain, Maximiliano Alberto; Guzzetti, Karina Andrea; Manzur, Maria Eugenia; Castillo Scheuermann, Maria Victoria Elizabeth; Brandan, Silvia Antonia; Vibrational Study of Antiparasitic Nifurtimox Agent Combining Harmonic Force Fields with DFT Calculations; Amo Publisher; European Journal of Theoretical and Applied Sciences; 2; 6; 11-2024; 711-732
2786-7447
CONICET Digital
CONICET
url http://hdl.handle.net/11336/258804
identifier_str_mv Iramain, Maximiliano Alberto; Guzzetti, Karina Andrea; Manzur, Maria Eugenia; Castillo Scheuermann, Maria Victoria Elizabeth; Brandan, Silvia Antonia; Vibrational Study of Antiparasitic Nifurtimox Agent Combining Harmonic Force Fields with DFT Calculations; Amo Publisher; European Journal of Theoretical and Applied Sciences; 2; 6; 11-2024; 711-732
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/1340
info:eu-repo/semantics/altIdentifier/doi/10.59324/ejtas.2024.2(6).63
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
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 13.22299

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