Alternative probe for the determination of the hydrogen-bond acidity of ionic liquids and their aqueous solutions

Although highly relevant to a priori select adequate solvents for a given application, the determination of the hydrogen-bond acidity or proton donor ability of aqueous solutions of ionic liquids is a difficult task due to the poor solubility of the commonly used probes in aqueous media. In this work, we demonstrate the applicability of the pyridine-N-oxide probe to determine the hydrogen-bond acidity of both neat ionic liquids and their aqueous solutions, based on C-13 NMR chemical shifts, and the suitability of these values to appraise the ability of ionic liquids to form aqueous two-phase systems.