Selective binding of cis-1,3,5-cyclohexane tricarboxylic acid vs its epimeric trans isomer by a tripodal amidopyridine receptor; crystal structures of the 1:1 complexes.
[figure: see text] A tripodal tris-amidopyridine receptor forms a 1:1 complex with trans-1,3,5-cyclohexane tricarboxylic acid that is 1 order of magnitude less stable than the one formed with the corresponding cis-triacid epimer. The X-ray crystal structures of the complexes have been determined, confirming the binding geometry derived from NMR data in solution and force-field calculations, and its geometrical features are used to explain the observed selectivity.