Synthetic and crystallographic studies on pyridinophanes

Article abstract of DOI:10.1016/S0040-4020(98)00385-8

Eight macrocyclic bisamides and tetramides have been synthesized by reaction of dimethyl pyridine-2,6-dicarboxylate 1 with α.ω-diaminoethers in methanol as a solvent. Relationship between structure of an amine used and a ratio of bisamide to tetramide has been investigated. The X-ray structure of macrocyclic amides 8, 9, 14 and linear amide 16 are reported. They show intramolecular hydrogen bond patterns within macrocyclic cavities involving N(Py) ··· NH(amide) and in the cases of 9.14 and 16, neutral molecules of water. Stability constants of selected ligands were measured using voltammetry.