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Updated: Mar 7, 2026

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
NMR spectroscopic and computational analysis of E/Z isomerism in imines derived from isatin
Andrés Gonzalez-Oñate1, Diego Chaparro1, Rodolfo Quevedo1
1Departamento de Química, Universidad Nacional de Colombia, Sede Bogotá Av. Cra. 30 No. 45-03 Bogotá Colombia jialit@unal.edu.co.
Abstract:
Isatin reacts with primary amines to yield mixtures of E and Z imine stereoisomers. This study provides a detailed structural analysis of selected isatin-derived imines using 1H and 13C NMR spectroscopy, complemented by computational methods. The E/Z ratio in solution is shown to depend strongly on stabilization by solvent interactions and substituents attached to the imine nitrogen. Predominant isomer structures are typically stabilized by π-stacking between aromatic rings, highlighting the key role of non-covalent interactions in determining stereochemical products.
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