Anion binding to monotopic and ditopic macrocyclic amides

[Structure: see text] Binding of fluoride anion as well as carboxylic acid tetraalkylammonium salts by macrocyclic compounds of different size was studied by NMR in DMSO-d6. It has been found that at least a 15-membered ring is necessary for successful recognition of fluoride. Larger macrocycles obtained in a [2+2] cyclization were shown to bind dicarboxylic acid salts. Effects of binding topicity are discussed.