info:eu-repo/semantics/article
Conformational and Stereodynamic Behavior of Five to Seven-membered 1-Aryl-2-iminoazacycloalkanes
Fecha
2019-03Registro en:
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
Autor
Díaz, Jimena Estela
Mazzanti, Andrea
Orelli, Liliana Raquel
Mancinelli, Michele
Resumen
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.