Predicting properties of species derived from N-(1H-indol-3-ylmethyl)-N,N-dimethylamine, Gramine, a indol alkaloid.

Autores
Iramain, Maximiliano Alberto; Ruiz Hidalgo, José; Brandan, Silvia Antonia
Año de publicación
2019
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Hybrid B3LYP/6-31G* calculations were employed to study the structural, electronic,topological and vibrational properties of free base, cationic and hydrochloride species ofindol alkaloid, N-(1H-indol-3-ylmethyl)-N,N-dimethylamine known as gramine. Theexperimental available IR, Raman, 1H- and 13C-NMR spectra were compared with thecorresponding predicted showing reasonable concordanceproperties were studies with the polarized continuum (PCM) and the universal solvationmodel. The cationic species of gramine presents a corrected solvation energy ofkJ/mol slightly higher than the corresponding to cocaine (studies have evidenced higher stabilities for free base and hydrochloride species while thecomparisons of N-CH3 distances obtained for three species of gramine with similarcompounds have evidenced that the hydrochloride species of gramine in solution presentspractically the same value than the corresponding species of heroin. The frontier orbitalsstudies suggest higher reactivities for the hydrochloride species in both media due to itslow gap values while on the contrary are observed for the cationic species in both media.Furthermore, the cationic species of gramine shows global nucleophilicity andelectrophilicity indexes closer to cocaine. Probably, these results could justify why thecorrected solvation energy value observed for the cationic species is approximately closerto the value corresponding to cocaine. The harmonic force fields, force constants and thecomplete vibrational assignments for the 75, 78 and 81 normal vibration modes of freebase, cationic and hydrochloride species are reported for first time.
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: Brandan, Silvia Antonia. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; Argentina
Materia
Molecular structure
Vibrational spectra
Force field
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
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oai:ri.conicet.gov.ar:11336/118852
Acceder
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network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Predicting properties of species derived from N-(1H-indol-3-ylmethyl)-N,N-dimethylamine, Gramine, a indol alkaloid.Iramain, Maximiliano AlbertoRuiz Hidalgo, JoséBrandan, Silvia AntoniaMolecular structureVibrational spectraForce fieldhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Hybrid B3LYP/6-31G* calculations were employed to study the structural, electronic,topological and vibrational properties of free base, cationic and hydrochloride species ofindol alkaloid, N-(1H-indol-3-ylmethyl)-N,N-dimethylamine known as gramine. Theexperimental available IR, Raman, 1H- and 13C-NMR spectra were compared with thecorresponding predicted showing reasonable concordanceproperties were studies with the polarized continuum (PCM) and the universal solvationmodel. The cationic species of gramine presents a corrected solvation energy ofkJ/mol slightly higher than the corresponding to cocaine (studies have evidenced higher stabilities for free base and hydrochloride species while thecomparisons of N-CH3 distances obtained for three species of gramine with similarcompounds have evidenced that the hydrochloride species of gramine in solution presentspractically the same value than the corresponding species of heroin. The frontier orbitalsstudies suggest higher reactivities for the hydrochloride species in both media due to itslow gap values while on the contrary are observed for the cationic species in both media.Furthermore, the cationic species of gramine shows global nucleophilicity andelectrophilicity indexes closer to cocaine. Probably, these results could justify why thecorrected solvation energy value observed for the cationic species is approximately closerto the value corresponding to cocaine. The harmonic force fields, force constants and thecomplete vibrational assignments for the 75, 78 and 81 normal vibration modes of freebase, cationic and hydrochloride species are reported for first time.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: Brandan, Silvia Antonia. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; ArgentinaSJIF2019-04info: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/11336/118852Iramain, Maximiliano Alberto; Ruiz Hidalgo, José; Brandan, Silvia Antonia; Predicting properties of species derived from N-(1H-indol-3-ylmethyl)-N,N-dimethylamine, Gramine, a indol alkaloid.; SJIF; International Journal of Current Advanced Research; 8; 4; 4-2019; 18113-181242319-65052319-6475CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.24327/ijcar.2019.18124.3455info:eu-repo/semantics/altIdentifier/url/https://www.journalijcar.org/issues/predicting-properties-species-derived-n-1h-indol-3-ylmethyl-nn-dimethylamine-gramine-indolinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T15:25:45Zoai:ri.conicet.gov.ar:11336/118852instacron: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 15:25:46.191CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Predicting properties of species derived from N-(1H-indol-3-ylmethyl)-N,N-dimethylamine, Gramine, a indol alkaloid.
title Predicting properties of species derived from N-(1H-indol-3-ylmethyl)-N,N-dimethylamine, Gramine, a indol alkaloid.
spellingShingle Predicting properties of species derived from N-(1H-indol-3-ylmethyl)-N,N-dimethylamine, Gramine, a indol alkaloid.
Iramain, Maximiliano Alberto
Molecular structure
Vibrational spectra
Force field
title_short Predicting properties of species derived from N-(1H-indol-3-ylmethyl)-N,N-dimethylamine, Gramine, a indol alkaloid.
title_full Predicting properties of species derived from N-(1H-indol-3-ylmethyl)-N,N-dimethylamine, Gramine, a indol alkaloid.
title_fullStr Predicting properties of species derived from N-(1H-indol-3-ylmethyl)-N,N-dimethylamine, Gramine, a indol alkaloid.
title_full_unstemmed Predicting properties of species derived from N-(1H-indol-3-ylmethyl)-N,N-dimethylamine, Gramine, a indol alkaloid.
title_sort Predicting properties of species derived from N-(1H-indol-3-ylmethyl)-N,N-dimethylamine, Gramine, a indol alkaloid.
dc.creator.none.fl_str_mv Iramain, Maximiliano Alberto
Ruiz Hidalgo, José
Brandan, Silvia Antonia
author Iramain, Maximiliano Alberto
author_facet Iramain, Maximiliano Alberto
Ruiz Hidalgo, José
Brandan, Silvia Antonia
author_role author
author2 Ruiz Hidalgo, José
Brandan, Silvia Antonia
author2_role author
author
dc.subject.none.fl_str_mv Molecular structure
Vibrational spectra
Force field
topic Molecular structure
Vibrational spectra
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 Hybrid B3LYP/6-31G* calculations were employed to study the structural, electronic,topological and vibrational properties of free base, cationic and hydrochloride species ofindol alkaloid, N-(1H-indol-3-ylmethyl)-N,N-dimethylamine known as gramine. Theexperimental available IR, Raman, 1H- and 13C-NMR spectra were compared with thecorresponding predicted showing reasonable concordanceproperties were studies with the polarized continuum (PCM) and the universal solvationmodel. The cationic species of gramine presents a corrected solvation energy ofkJ/mol slightly higher than the corresponding to cocaine (studies have evidenced higher stabilities for free base and hydrochloride species while thecomparisons of N-CH3 distances obtained for three species of gramine with similarcompounds have evidenced that the hydrochloride species of gramine in solution presentspractically the same value than the corresponding species of heroin. The frontier orbitalsstudies suggest higher reactivities for the hydrochloride species in both media due to itslow gap values while on the contrary are observed for the cationic species in both media.Furthermore, the cationic species of gramine shows global nucleophilicity andelectrophilicity indexes closer to cocaine. Probably, these results could justify why thecorrected solvation energy value observed for the cationic species is approximately closerto the value corresponding to cocaine. The harmonic force fields, force constants and thecomplete vibrational assignments for the 75, 78 and 81 normal vibration modes of freebase, cationic and hydrochloride species are reported for first time.
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: Brandan, Silvia Antonia. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; Argentina
description Hybrid B3LYP/6-31G* calculations were employed to study the structural, electronic,topological and vibrational properties of free base, cationic and hydrochloride species ofindol alkaloid, N-(1H-indol-3-ylmethyl)-N,N-dimethylamine known as gramine. Theexperimental available IR, Raman, 1H- and 13C-NMR spectra were compared with thecorresponding predicted showing reasonable concordanceproperties were studies with the polarized continuum (PCM) and the universal solvationmodel. The cationic species of gramine presents a corrected solvation energy ofkJ/mol slightly higher than the corresponding to cocaine (studies have evidenced higher stabilities for free base and hydrochloride species while thecomparisons of N-CH3 distances obtained for three species of gramine with similarcompounds have evidenced that the hydrochloride species of gramine in solution presentspractically the same value than the corresponding species of heroin. The frontier orbitalsstudies suggest higher reactivities for the hydrochloride species in both media due to itslow gap values while on the contrary are observed for the cationic species in both media.Furthermore, the cationic species of gramine shows global nucleophilicity andelectrophilicity indexes closer to cocaine. Probably, these results could justify why thecorrected solvation energy value observed for the cationic species is approximately closerto the value corresponding to cocaine. The harmonic force fields, force constants and thecomplete vibrational assignments for the 75, 78 and 81 normal vibration modes of freebase, cationic and hydrochloride species are reported for first time.
publishDate 2019
dc.date.none.fl_str_mv 2019-04
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/11336/118852
Iramain, Maximiliano Alberto; Ruiz Hidalgo, José; Brandan, Silvia Antonia; Predicting properties of species derived from N-(1H-indol-3-ylmethyl)-N,N-dimethylamine, Gramine, a indol alkaloid.; SJIF; International Journal of Current Advanced Research; 8; 4; 4-2019; 18113-18124
2319-6505
2319-6475
CONICET Digital
CONICET
url http://hdl.handle.net/11336/118852
identifier_str_mv Iramain, Maximiliano Alberto; Ruiz Hidalgo, José; Brandan, Silvia Antonia; Predicting properties of species derived from N-(1H-indol-3-ylmethyl)-N,N-dimethylamine, Gramine, a indol alkaloid.; SJIF; International Journal of Current Advanced Research; 8; 4; 4-2019; 18113-18124
2319-6505
2319-6475
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.24327/ijcar.2019.18124.3455
info:eu-repo/semantics/altIdentifier/url/https://www.journalijcar.org/issues/predicting-properties-species-derived-n-1h-indol-3-ylmethyl-nn-dimethylamine-gramine-indol
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv SJIF
publisher.none.fl_str_mv SJIF
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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