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.
Diaz J.E., Mazzanti A., Orelli L.R., Mancinelli M. (2019). Conformational and Stereodynamic Behavior of Five- to Seven-Membered 1-Aryl-2-iminoazacycloalkanes. ACS OMEGA, 4(3), 4712-4720 [10.1021/acsomega.9b00192].
Conformational and Stereodynamic Behavior of Five- to Seven-Membered 1-Aryl-2-iminoazacycloalkanes
Mazzanti A.;Mancinelli M.
2019
Abstract
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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
