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
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/118852
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CONICET Digital (CONICET) |
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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 Técnicas2025-09-29T10:28:39Zoai: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:34982025-09-29 10:28:39.705CONICET 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 |
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CONICET Digital (CONICET) |
collection |
CONICET Digital (CONICET) |
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Consejo Nacional de Investigaciones Científicas y Técnicas |
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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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1844614290834718720 |
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13.070432 |