Vibrational studies of species derived from potent S(+) and R(-) ecstasy stimulant by using ab-initio calculations and the SQM approach

Autores
Guzzetti, Karina Andrea; Iramain, Maximiliano Alberto; Rudyk, Roxana Amelia; Manzur, Maria Eugenia; Brandan, Silvia Antonia
Año de publicación
2020
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
B3LYP/6-311++G** calculations and the scaled quantum mechanical force field (SQMFF) approach have been used to study the structures and vibrational spectra of three species derived from potent S(+) and R(-) ecstasy stimulant. The complete vibrational assignments of free base, cationic, and hydrochloride species of both enantiomeric forms of ecstasy have been reported by using the normal internal coordinates and the experimental available attenuated total reflectance ATR-IR and FT-Raman spectra. SQM calculations predicted that the three species could be present in the IR spectrum of hydrochloride species because the IR bands of medium intensity at 2794 cm-1 is assigned to the stretching C4-H15 and symmetric CH3 modes of the free base while the strong IR band at 1508 cm-1 is assigned easily to NH2 stretching mode of hydrochloride species and NH2 deformation modes of cationic species. The calculations reveal the same energy values for both enantiomers, indicating that both could exist simultaneously in the two media with similar corrected solvation energies in solution probably because the R(-) form is quickly converted to the S(+) one. Three types of charges studied in both media evidence higher effect on the N atoms belonging to N-CH3 groups of three species of S(+) form of ecstasy in both media than on the O atoms of R1 ring. The high gap value predicted for the hydrochloride species of S(+) form in solution supports the low reactivity of this species, in agreement to its higher stability evidenced in this medium by AIM and NBO calculations. The predicted Ultraviolet-visible and Electronic Circular Dichroism ecstasy (ECD) support the presence of both enantiomeric forms in solution while excellent concordance evidence the comparisons between the predicted1H-and13C-NMR chemical shifts for the three species of S(+) form of ecstasy with the corresponding experimental ones.
Fil: Guzzetti, Karina Andrea. Universidad Nacional de Tucumán; Argentina
Fil: Iramain, Maximiliano Alberto. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; Argentina
Fil: Rudyk, Roxana Amelia. Universidad Nacional de Tucumán; Argentina
Fil: Manzur, Maria Eugenia. Universidad Nacional de Tucumán; Argentina
Fil: Brandan, Silvia Antonia. Universidad Nacional de Tucumán; Argentina
Materia
DFT CALCULATIONS
ECSTASY
FORCE FIELDS
MOLECULAR STRUCTURE
VIBRATIONAL ANALYSIS
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
OAI Identificador
oai:ri.conicet.gov.ar:11336/162898

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network_name_str CONICET Digital (CONICET)
spelling Vibrational studies of species derived from potent S(+) and R(-) ecstasy stimulant by using ab-initio calculations and the SQM approachGuzzetti, Karina AndreaIramain, Maximiliano AlbertoRudyk, Roxana AmeliaManzur, Maria EugeniaBrandan, Silvia AntoniaDFT CALCULATIONSECSTASYFORCE FIELDSMOLECULAR STRUCTUREVIBRATIONAL ANALYSIShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1B3LYP/6-311++G** calculations and the scaled quantum mechanical force field (SQMFF) approach have been used to study the structures and vibrational spectra of three species derived from potent S(+) and R(-) ecstasy stimulant. The complete vibrational assignments of free base, cationic, and hydrochloride species of both enantiomeric forms of ecstasy have been reported by using the normal internal coordinates and the experimental available attenuated total reflectance ATR-IR and FT-Raman spectra. SQM calculations predicted that the three species could be present in the IR spectrum of hydrochloride species because the IR bands of medium intensity at 2794 cm-1 is assigned to the stretching C4-H15 and symmetric CH3 modes of the free base while the strong IR band at 1508 cm-1 is assigned easily to NH2 stretching mode of hydrochloride species and NH2 deformation modes of cationic species. The calculations reveal the same energy values for both enantiomers, indicating that both could exist simultaneously in the two media with similar corrected solvation energies in solution probably because the R(-) form is quickly converted to the S(+) one. Three types of charges studied in both media evidence higher effect on the N atoms belonging to N-CH3 groups of three species of S(+) form of ecstasy in both media than on the O atoms of R1 ring. The high gap value predicted for the hydrochloride species of S(+) form in solution supports the low reactivity of this species, in agreement to its higher stability evidenced in this medium by AIM and NBO calculations. The predicted Ultraviolet-visible and Electronic Circular Dichroism ecstasy (ECD) support the presence of both enantiomeric forms in solution while excellent concordance evidence the comparisons between the predicted1H-and13C-NMR chemical shifts for the three species of S(+) form of ecstasy with the corresponding experimental ones.Fil: Guzzetti, Karina Andrea. Universidad Nacional de Tucumán; ArgentinaFil: Iramain, Maximiliano Alberto. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; ArgentinaFil: Rudyk, Roxana Amelia. Universidad Nacional de Tucumán; ArgentinaFil: Manzur, Maria Eugenia. Universidad Nacional de Tucumán; ArgentinaFil: Brandan, Silvia Antonia. Universidad Nacional de Tucumán; ArgentinaAMG Transcend Association2020-12info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/162898Guzzetti, Karina Andrea; Iramain, Maximiliano Alberto; Rudyk, Roxana Amelia; Manzur, Maria Eugenia; Brandan, Silvia Antonia; Vibrational studies of species derived from potent S(+) and R(-) ecstasy stimulant by using ab-initio calculations and the SQM approach; AMG Transcend Association; Biointerface Research in Applied Chemistry; 10; 6; 12-2020; 6783-68092069-5837CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.33263/BRIAC106.67836809info:eu-repo/semantics/altIdentifier/url/https://biointerfaceresearch.com/wp-content/uploads/2020/05/20695837106.67836809.pdfinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:47:45Zoai:ri.conicet.gov.ar:11336/162898instacron: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 10:47:45.516CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Vibrational studies of species derived from potent S(+) and R(-) ecstasy stimulant by using ab-initio calculations and the SQM approach
title Vibrational studies of species derived from potent S(+) and R(-) ecstasy stimulant by using ab-initio calculations and the SQM approach
spellingShingle Vibrational studies of species derived from potent S(+) and R(-) ecstasy stimulant by using ab-initio calculations and the SQM approach
Guzzetti, Karina Andrea
DFT CALCULATIONS
ECSTASY
FORCE FIELDS
MOLECULAR STRUCTURE
VIBRATIONAL ANALYSIS
title_short Vibrational studies of species derived from potent S(+) and R(-) ecstasy stimulant by using ab-initio calculations and the SQM approach
title_full Vibrational studies of species derived from potent S(+) and R(-) ecstasy stimulant by using ab-initio calculations and the SQM approach
title_fullStr Vibrational studies of species derived from potent S(+) and R(-) ecstasy stimulant by using ab-initio calculations and the SQM approach
title_full_unstemmed Vibrational studies of species derived from potent S(+) and R(-) ecstasy stimulant by using ab-initio calculations and the SQM approach
title_sort Vibrational studies of species derived from potent S(+) and R(-) ecstasy stimulant by using ab-initio calculations and the SQM approach
dc.creator.none.fl_str_mv Guzzetti, Karina Andrea
Iramain, Maximiliano Alberto
Rudyk, Roxana Amelia
Manzur, Maria Eugenia
Brandan, Silvia Antonia
author Guzzetti, Karina Andrea
author_facet Guzzetti, Karina Andrea
Iramain, Maximiliano Alberto
Rudyk, Roxana Amelia
Manzur, Maria Eugenia
Brandan, Silvia Antonia
author_role author
author2 Iramain, Maximiliano Alberto
Rudyk, Roxana Amelia
Manzur, Maria Eugenia
Brandan, Silvia Antonia
author2_role author
author
author
author
dc.subject.none.fl_str_mv DFT CALCULATIONS
ECSTASY
FORCE FIELDS
MOLECULAR STRUCTURE
VIBRATIONAL ANALYSIS
topic DFT CALCULATIONS
ECSTASY
FORCE FIELDS
MOLECULAR STRUCTURE
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 B3LYP/6-311++G** calculations and the scaled quantum mechanical force field (SQMFF) approach have been used to study the structures and vibrational spectra of three species derived from potent S(+) and R(-) ecstasy stimulant. The complete vibrational assignments of free base, cationic, and hydrochloride species of both enantiomeric forms of ecstasy have been reported by using the normal internal coordinates and the experimental available attenuated total reflectance ATR-IR and FT-Raman spectra. SQM calculations predicted that the three species could be present in the IR spectrum of hydrochloride species because the IR bands of medium intensity at 2794 cm-1 is assigned to the stretching C4-H15 and symmetric CH3 modes of the free base while the strong IR band at 1508 cm-1 is assigned easily to NH2 stretching mode of hydrochloride species and NH2 deformation modes of cationic species. The calculations reveal the same energy values for both enantiomers, indicating that both could exist simultaneously in the two media with similar corrected solvation energies in solution probably because the R(-) form is quickly converted to the S(+) one. Three types of charges studied in both media evidence higher effect on the N atoms belonging to N-CH3 groups of three species of S(+) form of ecstasy in both media than on the O atoms of R1 ring. The high gap value predicted for the hydrochloride species of S(+) form in solution supports the low reactivity of this species, in agreement to its higher stability evidenced in this medium by AIM and NBO calculations. The predicted Ultraviolet-visible and Electronic Circular Dichroism ecstasy (ECD) support the presence of both enantiomeric forms in solution while excellent concordance evidence the comparisons between the predicted1H-and13C-NMR chemical shifts for the three species of S(+) form of ecstasy with the corresponding experimental ones.
Fil: Guzzetti, Karina Andrea. Universidad Nacional de Tucumán; Argentina
Fil: Iramain, Maximiliano Alberto. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; Argentina
Fil: Rudyk, Roxana Amelia. Universidad Nacional de Tucumán; Argentina
Fil: Manzur, Maria Eugenia. Universidad Nacional de Tucumán; Argentina
Fil: Brandan, Silvia Antonia. Universidad Nacional de Tucumán; Argentina
description B3LYP/6-311++G** calculations and the scaled quantum mechanical force field (SQMFF) approach have been used to study the structures and vibrational spectra of three species derived from potent S(+) and R(-) ecstasy stimulant. The complete vibrational assignments of free base, cationic, and hydrochloride species of both enantiomeric forms of ecstasy have been reported by using the normal internal coordinates and the experimental available attenuated total reflectance ATR-IR and FT-Raman spectra. SQM calculations predicted that the three species could be present in the IR spectrum of hydrochloride species because the IR bands of medium intensity at 2794 cm-1 is assigned to the stretching C4-H15 and symmetric CH3 modes of the free base while the strong IR band at 1508 cm-1 is assigned easily to NH2 stretching mode of hydrochloride species and NH2 deformation modes of cationic species. The calculations reveal the same energy values for both enantiomers, indicating that both could exist simultaneously in the two media with similar corrected solvation energies in solution probably because the R(-) form is quickly converted to the S(+) one. Three types of charges studied in both media evidence higher effect on the N atoms belonging to N-CH3 groups of three species of S(+) form of ecstasy in both media than on the O atoms of R1 ring. The high gap value predicted for the hydrochloride species of S(+) form in solution supports the low reactivity of this species, in agreement to its higher stability evidenced in this medium by AIM and NBO calculations. The predicted Ultraviolet-visible and Electronic Circular Dichroism ecstasy (ECD) support the presence of both enantiomeric forms in solution while excellent concordance evidence the comparisons between the predicted1H-and13C-NMR chemical shifts for the three species of S(+) form of ecstasy with the corresponding experimental ones.
publishDate 2020
dc.date.none.fl_str_mv 2020-12
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/11336/162898
Guzzetti, Karina Andrea; Iramain, Maximiliano Alberto; Rudyk, Roxana Amelia; Manzur, Maria Eugenia; Brandan, Silvia Antonia; Vibrational studies of species derived from potent S(+) and R(-) ecstasy stimulant by using ab-initio calculations and the SQM approach; AMG Transcend Association; Biointerface Research in Applied Chemistry; 10; 6; 12-2020; 6783-6809
2069-5837
CONICET Digital
CONICET
url http://hdl.handle.net/11336/162898
identifier_str_mv Guzzetti, Karina Andrea; Iramain, Maximiliano Alberto; Rudyk, Roxana Amelia; Manzur, Maria Eugenia; Brandan, Silvia Antonia; Vibrational studies of species derived from potent S(+) and R(-) ecstasy stimulant by using ab-initio calculations and the SQM approach; AMG Transcend Association; Biointerface Research in Applied Chemistry; 10; 6; 12-2020; 6783-6809
2069-5837
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.33263/BRIAC106.67836809
info:eu-repo/semantics/altIdentifier/url/https://biointerfaceresearch.com/wp-content/uploads/2020/05/20695837106.67836809.pdf
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
dc.publisher.none.fl_str_mv AMG Transcend Association
publisher.none.fl_str_mv AMG Transcend Association
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