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

[Image: see text] 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...

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Autores principales: Díaz, Jimena E., Mazzanti, Andrea, Orelli, Liliana R., Mancinelli, Michele
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2019
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6648013/
https://www.ncbi.nlm.nih.gov/pubmed/31459658
http://dx.doi.org/10.1021/acsomega.9b00192
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author Díaz, Jimena E.
Mazzanti, Andrea
Orelli, Liliana R.
Mancinelli, Michele
author_facet Díaz, Jimena E.
Mazzanti, Andrea
Orelli, Liliana R.
Mancinelli, Michele
author_sort Díaz, Jimena E.
collection PubMed
description [Image: see text] 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.
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spelling pubmed-66480132019-08-27 Conformational and Stereodynamic Behavior of Five- to Seven-Membered 1-Aryl-2-iminoazacycloalkanes Díaz, Jimena E. Mazzanti, Andrea Orelli, Liliana R. Mancinelli, Michele ACS Omega [Image: see text] 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. American Chemical Society 2019-03-04 /pmc/articles/PMC6648013/ /pubmed/31459658 http://dx.doi.org/10.1021/acsomega.9b00192 Text en Copyright © 2019 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
spellingShingle Díaz, Jimena E.
Mazzanti, Andrea
Orelli, Liliana R.
Mancinelli, Michele
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
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_short 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
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6648013/
https://www.ncbi.nlm.nih.gov/pubmed/31459658
http://dx.doi.org/10.1021/acsomega.9b00192
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