Anion binding by catechols--an NMR, optical and electrochemical study

Organic & Biomolecular Chemistry
Keith J WinstanleyDavid K Smith

Abstract

The X-ray structure of the ClC chloride channel made it clear that O-H...chloride interactions play a key role in important biological membrane-bound systems, however, surprisingly this type of interaction has only been rarely exploited for the development of synthetic anion receptors. This paper therefore reports the anion binding strengths and selectivities of some simple commercially available bis-phenols. In particular, we compare catechol (1,2-dihydroxybenzene) and resorcinol (1,3-dihydroxybenzene) which show interesting and different selectivities between the halide anions in acetonitrile solution. Catechol binds tetrabutylammononium (TBA) chloride almost 30 times more strongly than TBA bromide, whilst for resorcinol, this difference drops to a factor of ca. 3.5. It is suggested that this is a consequence of the bite angle of the chelating hydrogen bonding groups of catechol being particularly appropriate for effective binding of the smaller anion. The oxidation of catechol to ortho-quinone is perturbed by the addition of chloride anions, as probed via cyclic voltammetry, and this compound can therefore be considered to act as an electrochemical sensor for chloride. Nitrocatechol is able to bind chloride anions more stron...Continue Reading

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Citations

May 17, 2012·Journal of Fluorescence·Kai LiuRan Huo
Feb 5, 2009·Journal of the American Chemical Society·Sofya Kostina Berezin, Jeffery T Davis
Mar 20, 2009·Journal of the American Chemical Society·Asha BrownPaul D Beer
Jul 26, 2008·Chemical Communications : Chem Comm·Jungjae JuKyu-Sung Jeong
May 14, 2009·Chemical Communications : Chem Comm·Massimo Cametti, Kari Rissanen
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May 21, 2010·Beilstein Journal of Organic Chemistry·Ajit Kumar MahapatraPrithidipa Sahoo
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