Tuning Supramolecular Selectivity for Hydrosulfide: Linear Free Energy Relationships Reveal Preferential C-H Hydrogen Bond Interactions.

ABSTRACT: Supramolecular anion receptors can be used to study the molecular recognition properties of the reactive yet biologically critical hydrochalcogenide anions (HCh^-). Achieving selectivity for HCh^- over the halides is challenging but necessary for not only developing future supramolecular probes for HCh^- binding and detection, but also for understanding the fundamental properties that govern these binding and recognition events. Here we demonstrate that linear free energy relationships (LFERs)-including Hammett and Swain-Lupton plots-reveal a clear difference in sensitivity to the polarity of an aryl C-H hydrogen bond (HB) donor for HS^- over other HCh^- and halides. Analysis using electrostatic potential maps highlights that this differenc

SUBMITTER: Fargher HA 

PROVIDER: S-EPMC7392143 | biostudies-literature | 2020 May

REPOSITORIES: biostudies-literature