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
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/129296
Ver los metadatos del registro completo
id |
CONICETDig_716f43e8f3d545bf4131f1713085bd09 |
---|---|
oai_identifier_str |
oai:ri.conicet.gov.ar:11336/129296 |
network_acronym_str |
CONICETDig |
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 Técnicas2025-09-29T09:43:25Zoai: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:34982025-09-29 09:43:25.761CONICET 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 |
_version_ |
1844613367262609408 |
score |
13.070432 |