A combined study on structures and vibrational spectra of the antiviral rimantadine using SQMFF and DFT calculations

Autores
Iramain, Maximiliano Alberto; Ruiz Hidalgo, José; Sundius, Tom; Brandan, Silvia Antonia
Año de publicación
2022
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
In this research, a combined study on structures and vibrational spectra of antiviral rimantadine have been performed using hybrid B3LYP/6–311++G∗∗ calculations and the scaled quantum force field (SQMFF) procedure. Harmonic force fields and scaled force constants of Free Base (FB), Cationic (CA) and Hydrochloride (HCl) species derived from the antiviral rimantadine have been calculated in gas phase and in aqueous solution using normal internal coordinates and scaling factors. Good correlations were acquired comparing the theoretical IR, Raman, 1H– 13C-NMR and UV spectra of three species with the analogous experimental ones, suggesting probably, the presence of all them in both phases. The main force constants of three species have evidenced lower values than the corresponding to antiviral amantadine. The ionic character of N1–H33⋯Cl36 bond of HCl species in aqueous solution evidence positive Mulliken charge on N1 atom indicating that this species is as CA one. Rimantadine presents higher solvation energies in water than other antiviral species, such as chloroquin, niclosamide, cidofovir and brincidofovir. The FB and HCl species of rimantadine are slightly less reactive than the corresponding to amantadine while the opposite is observed for the CA species. The predicted ECD spectra for the FB and CA species show positive Cotton effect different from the negative observed for the HCl one. These different behaviours of three species of rimantadine could probably explain the differences observed in the intensities of bands predicted in the electronic spectra of these species.
Fil: Iramain, Maximiliano Alberto. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; Argentina
Fil: Ruiz Hidalgo, José. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; Argentina
Fil: Sundius, Tom. University of Helsinki; Finlandia
Fil: Brandan, Silvia Antonia. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; Argentina
Materia
DFT CALCULATIONS
FORCE FIELDS
RIMANTADINE
STRUCTURAL PROPERTIES
VIBRATIONAL ANALYSIS
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:11336/220735
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/220735
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling A combined study on structures and vibrational spectra of the antiviral rimantadine using SQMFF and DFT calculationsIramain, Maximiliano AlbertoRuiz Hidalgo, JoséSundius, TomBrandan, Silvia AntoniaDFT CALCULATIONSFORCE FIELDSRIMANTADINESTRUCTURAL PROPERTIESVIBRATIONAL ANALYSIShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1In this research, a combined study on structures and vibrational spectra of antiviral rimantadine have been performed using hybrid B3LYP/6–311++G∗∗ calculations and the scaled quantum force field (SQMFF) procedure. Harmonic force fields and scaled force constants of Free Base (FB), Cationic (CA) and Hydrochloride (HCl) species derived from the antiviral rimantadine have been calculated in gas phase and in aqueous solution using normal internal coordinates and scaling factors. Good correlations were acquired comparing the theoretical IR, Raman, 1H– 13C-NMR and UV spectra of three species with the analogous experimental ones, suggesting probably, the presence of all them in both phases. The main force constants of three species have evidenced lower values than the corresponding to antiviral amantadine. The ionic character of N1–H33⋯Cl36 bond of HCl species in aqueous solution evidence positive Mulliken charge on N1 atom indicating that this species is as CA one. Rimantadine presents higher solvation energies in water than other antiviral species, such as chloroquin, niclosamide, cidofovir and brincidofovir. The FB and HCl species of rimantadine are slightly less reactive than the corresponding to amantadine while the opposite is observed for the CA species. The predicted ECD spectra for the FB and CA species show positive Cotton effect different from the negative observed for the HCl one. These different behaviours of three species of rimantadine could probably explain the differences observed in the intensities of bands predicted in the electronic spectra of these species.Fil: Iramain, Maximiliano Alberto. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; ArgentinaFil: Ruiz Hidalgo, José. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; ArgentinaFil: Sundius, Tom. University of Helsinki; FinlandiaFil: Brandan, Silvia Antonia. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; ArgentinaElsevier2022-08info: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/11336/220735Iramain, Maximiliano Alberto; Ruiz Hidalgo, José; Sundius, Tom; Brandan, Silvia Antonia; A combined study on structures and vibrational spectra of the antiviral rimantadine using SQMFF and DFT calculations; Elsevier; Heliyon; 8; 8; 8-2022; 1-142405-8440CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://linkinghub.elsevier.com/retrieve/pii/S2405844022013901info:eu-repo/semantics/altIdentifier/doi/10.1016/j.heliyon.2022.e10102info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-nd/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-10T13:05:52Zoai:ri.conicet.gov.ar:11336/220735instacron: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 13:05:52.305CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv A combined study on structures and vibrational spectra of the antiviral rimantadine using SQMFF and DFT calculations
title A combined study on structures and vibrational spectra of the antiviral rimantadine using SQMFF and DFT calculations
spellingShingle A combined study on structures and vibrational spectra of the antiviral rimantadine using SQMFF and DFT calculations
Iramain, Maximiliano Alberto
DFT CALCULATIONS
FORCE FIELDS
RIMANTADINE
STRUCTURAL PROPERTIES
VIBRATIONAL ANALYSIS
title_short A combined study on structures and vibrational spectra of the antiviral rimantadine using SQMFF and DFT calculations
title_full A combined study on structures and vibrational spectra of the antiviral rimantadine using SQMFF and DFT calculations
title_fullStr A combined study on structures and vibrational spectra of the antiviral rimantadine using SQMFF and DFT calculations
title_full_unstemmed A combined study on structures and vibrational spectra of the antiviral rimantadine using SQMFF and DFT calculations
title_sort A combined study on structures and vibrational spectra of the antiviral rimantadine using SQMFF and DFT calculations
dc.creator.none.fl_str_mv Iramain, Maximiliano Alberto
Ruiz Hidalgo, José
Sundius, Tom
Brandan, Silvia Antonia
author Iramain, Maximiliano Alberto
author_facet Iramain, Maximiliano Alberto
Ruiz Hidalgo, José
Sundius, Tom
Brandan, Silvia Antonia
author_role author
author2 Ruiz Hidalgo, José
Sundius, Tom
Brandan, Silvia Antonia
author2_role author
author
author
dc.subject.none.fl_str_mv DFT CALCULATIONS
FORCE FIELDS
RIMANTADINE
STRUCTURAL PROPERTIES
VIBRATIONAL ANALYSIS
topic DFT CALCULATIONS
FORCE FIELDS
RIMANTADINE
STRUCTURAL PROPERTIES
VIBRATIONAL ANALYSIS
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 this research, a combined study on structures and vibrational spectra of antiviral rimantadine have been performed using hybrid B3LYP/6–311++G∗∗ calculations and the scaled quantum force field (SQMFF) procedure. Harmonic force fields and scaled force constants of Free Base (FB), Cationic (CA) and Hydrochloride (HCl) species derived from the antiviral rimantadine have been calculated in gas phase and in aqueous solution using normal internal coordinates and scaling factors. Good correlations were acquired comparing the theoretical IR, Raman, 1H– 13C-NMR and UV spectra of three species with the analogous experimental ones, suggesting probably, the presence of all them in both phases. The main force constants of three species have evidenced lower values than the corresponding to antiviral amantadine. The ionic character of N1–H33⋯Cl36 bond of HCl species in aqueous solution evidence positive Mulliken charge on N1 atom indicating that this species is as CA one. Rimantadine presents higher solvation energies in water than other antiviral species, such as chloroquin, niclosamide, cidofovir and brincidofovir. The FB and HCl species of rimantadine are slightly less reactive than the corresponding to amantadine while the opposite is observed for the CA species. The predicted ECD spectra for the FB and CA species show positive Cotton effect different from the negative observed for the HCl one. These different behaviours of three species of rimantadine could probably explain the differences observed in the intensities of bands predicted in the electronic spectra of these species.
Fil: Iramain, Maximiliano Alberto. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; Argentina
Fil: Ruiz Hidalgo, José. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; Argentina
Fil: Sundius, Tom. University of Helsinki; Finlandia
Fil: Brandan, Silvia Antonia. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; Argentina
description In this research, a combined study on structures and vibrational spectra of antiviral rimantadine have been performed using hybrid B3LYP/6–311++G∗∗ calculations and the scaled quantum force field (SQMFF) procedure. Harmonic force fields and scaled force constants of Free Base (FB), Cationic (CA) and Hydrochloride (HCl) species derived from the antiviral rimantadine have been calculated in gas phase and in aqueous solution using normal internal coordinates and scaling factors. Good correlations were acquired comparing the theoretical IR, Raman, 1H– 13C-NMR and UV spectra of three species with the analogous experimental ones, suggesting probably, the presence of all them in both phases. The main force constants of three species have evidenced lower values than the corresponding to antiviral amantadine. The ionic character of N1–H33⋯Cl36 bond of HCl species in aqueous solution evidence positive Mulliken charge on N1 atom indicating that this species is as CA one. Rimantadine presents higher solvation energies in water than other antiviral species, such as chloroquin, niclosamide, cidofovir and brincidofovir. The FB and HCl species of rimantadine are slightly less reactive than the corresponding to amantadine while the opposite is observed for the CA species. The predicted ECD spectra for the FB and CA species show positive Cotton effect different from the negative observed for the HCl one. These different behaviours of three species of rimantadine could probably explain the differences observed in the intensities of bands predicted in the electronic spectra of these species.
publishDate 2022
dc.date.none.fl_str_mv 2022-08
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/11336/220735
Iramain, Maximiliano Alberto; Ruiz Hidalgo, José; Sundius, Tom; Brandan, Silvia Antonia; A combined study on structures and vibrational spectra of the antiviral rimantadine using SQMFF and DFT calculations; Elsevier; Heliyon; 8; 8; 8-2022; 1-14
2405-8440
CONICET Digital
CONICET
url http://hdl.handle.net/11336/220735
identifier_str_mv Iramain, Maximiliano Alberto; Ruiz Hidalgo, José; Sundius, Tom; Brandan, Silvia Antonia; A combined study on structures and vibrational spectra of the antiviral rimantadine using SQMFF and DFT calculations; Elsevier; Heliyon; 8; 8; 8-2022; 1-14
2405-8440
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://linkinghub.elsevier.com/retrieve/pii/S2405844022013901
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.heliyon.2022.e10102
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 12.993085

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