Conformational and Stereodynamic Behavior of Five to Seven-membered 1-Aryl-2-iminoazacycloalkanes

Autores
Díaz, Jimena Estela; Mazzanti, Andrea; Orelli, Liliana Raquel; Mancinelli, Michele
Año de publicación
2019
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The stereodynamic behavior of 1-arylpyrrolidin-2-imines, having a C aryl -N stereogenic axis, has been studied by means of dynamic nuclear magnetic resonance and density functional theory calculations, evaluating the steric effect of ortho-aryl substituents. The rotational barrier due to E/Z isomerism about the C=N-H bond was also determined. The dynamic stereochemistry of homologous six- and seven-membered iminoazacycloalkane rings and their oxo-analogues was also comparatively investigated, evidencing a ring size effect. It was found that the seven-membered heterocycle shows additional dynamic features because of ring inversion.
Fil: Díaz, Jimena Estela. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina. Universidad de Bologna; Italia
Fil: Mazzanti, Andrea. Universidad de Bologna; Italia
Fil: Orelli, Liliana Raquel. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina
Fil: Mancinelli, Michele. Universidad de Bologna; Italia
Materia
NITROGEN HETEROCYCLES
ATROPISOMERISM
DYNAMIC NMR
DFT CALCULATIONS
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:11336/129296
Acceder
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repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Conformational and Stereodynamic Behavior of Five to Seven-membered 1-Aryl-2-iminoazacycloalkanesDíaz, Jimena EstelaMazzanti, AndreaOrelli, Liliana RaquelMancinelli, MicheleNITROGEN HETEROCYCLESATROPISOMERISMDYNAMIC NMRDFT CALCULATIONShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The stereodynamic behavior of 1-arylpyrrolidin-2-imines, having a C aryl -N stereogenic axis, has been studied by means of dynamic nuclear magnetic resonance and density functional theory calculations, evaluating the steric effect of ortho-aryl substituents. The rotational barrier due to E/Z isomerism about the C=N-H bond was also determined. The dynamic stereochemistry of homologous six- and seven-membered iminoazacycloalkane rings and their oxo-analogues was also comparatively investigated, evidencing a ring size effect. It was found that the seven-membered heterocycle shows additional dynamic features because of ring inversion.Fil: Díaz, Jimena Estela. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina. Universidad de Bologna; ItaliaFil: Mazzanti, Andrea. Universidad de Bologna; ItaliaFil: Orelli, Liliana Raquel. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; ArgentinaFil: Mancinelli, Michele. Universidad de Bologna; ItaliaAmerican Chemical Society Inc2019-03info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/129296Díaz, Jimena Estela; Mazzanti, Andrea; Orelli, Liliana Raquel; Mancinelli, Michele; Conformational and Stereodynamic Behavior of Five to Seven-membered 1-Aryl-2-iminoazacycloalkanes; American Chemical Society Inc; ACS Omega; 4; 3; 3-2019; 4712-47202470-1343CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1021/acsomega.9b00192info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-22T11:12:05Zoai:ri.conicet.gov.ar:11336/129296instacron: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:34982025-10-22 11:12:06.043CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Conformational and Stereodynamic Behavior of Five to Seven-membered 1-Aryl-2-iminoazacycloalkanes
title Conformational and Stereodynamic Behavior of Five to Seven-membered 1-Aryl-2-iminoazacycloalkanes
spellingShingle Conformational and Stereodynamic Behavior of Five to Seven-membered 1-Aryl-2-iminoazacycloalkanes
Díaz, Jimena Estela
NITROGEN HETEROCYCLES
ATROPISOMERISM
DYNAMIC NMR
DFT CALCULATIONS
title_short Conformational and Stereodynamic Behavior of Five to Seven-membered 1-Aryl-2-iminoazacycloalkanes
title_full Conformational and Stereodynamic Behavior of Five to Seven-membered 1-Aryl-2-iminoazacycloalkanes
title_fullStr Conformational and Stereodynamic Behavior of Five to Seven-membered 1-Aryl-2-iminoazacycloalkanes
title_full_unstemmed Conformational and Stereodynamic Behavior of Five to Seven-membered 1-Aryl-2-iminoazacycloalkanes
title_sort Conformational and Stereodynamic Behavior of Five to Seven-membered 1-Aryl-2-iminoazacycloalkanes
dc.creator.none.fl_str_mv Díaz, Jimena Estela
Mazzanti, Andrea
Orelli, Liliana Raquel
Mancinelli, Michele
author Díaz, Jimena Estela
author_facet Díaz, Jimena Estela
Mazzanti, Andrea
Orelli, Liliana Raquel
Mancinelli, Michele
author_role author
author2 Mazzanti, Andrea
Orelli, Liliana Raquel
Mancinelli, Michele
author2_role author
author
author
dc.subject.none.fl_str_mv NITROGEN HETEROCYCLES
ATROPISOMERISM
DYNAMIC NMR
DFT CALCULATIONS
topic NITROGEN HETEROCYCLES
ATROPISOMERISM
DYNAMIC NMR
DFT CALCULATIONS
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The stereodynamic behavior of 1-arylpyrrolidin-2-imines, having a C aryl -N stereogenic axis, has been studied by means of dynamic nuclear magnetic resonance and density functional theory calculations, evaluating the steric effect of ortho-aryl substituents. The rotational barrier due to E/Z isomerism about the C=N-H bond was also determined. The dynamic stereochemistry of homologous six- and seven-membered iminoazacycloalkane rings and their oxo-analogues was also comparatively investigated, evidencing a ring size effect. It was found that the seven-membered heterocycle shows additional dynamic features because of ring inversion.
Fil: Díaz, Jimena Estela. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina. Universidad de Bologna; Italia
Fil: Mazzanti, Andrea. Universidad de Bologna; Italia
Fil: Orelli, Liliana Raquel. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina
Fil: Mancinelli, Michele. Universidad de Bologna; Italia
description The stereodynamic behavior of 1-arylpyrrolidin-2-imines, having a C aryl -N stereogenic axis, has been studied by means of dynamic nuclear magnetic resonance and density functional theory calculations, evaluating the steric effect of ortho-aryl substituents. The rotational barrier due to E/Z isomerism about the C=N-H bond was also determined. The dynamic stereochemistry of homologous six- and seven-membered iminoazacycloalkane rings and their oxo-analogues was also comparatively investigated, evidencing a ring size effect. It was found that the seven-membered heterocycle shows additional dynamic features because of ring inversion.
publishDate 2019
dc.date.none.fl_str_mv 2019-03
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/11336/129296
Díaz, Jimena Estela; Mazzanti, Andrea; Orelli, Liliana Raquel; Mancinelli, Michele; Conformational and Stereodynamic Behavior of Five to Seven-membered 1-Aryl-2-iminoazacycloalkanes; American Chemical Society Inc; ACS Omega; 4; 3; 3-2019; 4712-4720
2470-1343
CONICET Digital
CONICET
url http://hdl.handle.net/11336/129296
identifier_str_mv Díaz, Jimena Estela; Mazzanti, Andrea; Orelli, Liliana Raquel; Mancinelli, Michele; Conformational and Stereodynamic Behavior of Five to Seven-membered 1-Aryl-2-iminoazacycloalkanes; American Chemical Society Inc; ACS Omega; 4; 3; 3-2019; 4712-4720
2470-1343
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1021/acsomega.9b00192
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 American Chemical Society Inc
publisher.none.fl_str_mv American Chemical Society Inc
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 12.982451

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