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Interaction of halide and carboxylate ions with 4,5-diacetamidoacridine-9(10H)-one: thermodynamics of association and deprotonation events.

Lin C, Simov V, Drueckhammer DG

Department of Chemistry, Stony Brook University, Stony Brook, NY 11794, USA.

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.

Published 23 February 2007 in J Org Chem, 72(5): 1742-6.
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