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
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/162898
Ver los metadatos del registro completo
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oai:ri.conicet.gov.ar:11336/162898 |
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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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1844614522398048256 |
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13.070432 |