From amides to thioamides: understanding enhanced anion binding in acyclic receptors

Abstract

We synthesized acyclic amide and thioamide-based receptors and evaluated their anion binding efficacy experimentally and computationally. Our study shows the receptors adopt favorable conformations upon chloride binding and confirms that the stronger NH donor ability of thioamides arises from sulfur's larger size relative to oxygen. Moreover, the anion size dictates selectivity.