Anion binding behavior of heterocycle-strapped calix[4]pyrroles.

ABSTRACT: A comparative study of the halide and benzoate anion binding properties of a series of phenyl, pyrrole, and furan-strapped calix[4]pyrroles has been carried out. These receptors, which have previously been shown to bind the chloride anion (Yoon et al., Angew. Chem., Int. Ed. 47(27):5038-5042, 2008), were found to bind bromide and benzoate anion (studied as the corresponding tetrabutyl-ammonium salts) with near equal affinity in acetonitrile, albeit less well than chloride, as determined from ITC measurements or NMR spectroscopic titrations. This stands in marked contrast to the parent octamethylcalix[4]pyrrole, where the carboxylate anion affinities are substantially higher than those for bromide anion under identical conditions. This finding is rationalized in terms of tighter binding cav

SUBMITTER: Gross DE 

PROVIDER: S-EPMC3016718 | biostudies-literature | 2010 Feb

REPOSITORIES: biostudies-literature