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

Chen Lin, Vladimir Simov, and Dale G. Drueckhammer*
Department of Chemistry, Stony Brook University, Stony Brook, New York 11794
J. Org. Chem., 2007, 72 (5), pp 1742–1746
DOI: 10.1021/jo062467j
Publication Date (Web): February 8, 2007
Copyright © 2007 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, dale.drueckhammer@sunysb.edu

Abstract

Abstract Image

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.

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History

  • Published In Issue March 02, 2007
  • Received December 2, 2006

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