Interaction of Halide and Carboxylate Ions with 4,5-Diacetamidoacridine-9(10<i>H</i>)-one:  Thermodynamics of Association and Deprotonation Events

Abstract

4,5-Diacetamidoacridine-9(10H)-one was prepared, and its interactions with halide and benzoate anions were studied using a combination of NMR, fluorescence, and isothermal titration calorimetry experiments. Whereas chloride and bromide exhibited simple association, both fluoride and benzoate exhibited initial entropy-driven association followed by an enthalpically favorable deprotonation of the receptor by a second equivalent of the anion.