NMR detection of chirality and enantiopurity of amines by using benzene tricarboxamide-based hydrogelators as chiral solvating agents

Abstract

Enantiomeric excess of chiral compounds is a key parameter that can influence their activity or therapeutic action. Current approaches to the rapid measurement of enantiomeric excess using H-1 NMR is based on the formation of diastereomeric complexes between chiral analytes and a chiral host, leading to two species with no symmetry relationship. Here, we demonstrate that a gelator host system can provide a means to elicit distinct chemical shifts in the H-1 nuclear magnetic resonance (NMR) of a mixture of diamines or monoamines depending on the corresponding enantiomeric excess of the guest mixture of chiral amines. These gelator hosts provide a unique example of NMR based assessment of the chirality and enantiopurity of guest amines.