The synthesis of novel hydrogen-bonded [2]rotaxanes employing an acylaminopyridine-containing thread as template is described. The electronic nature of the starting aroyl chloride employed as macrocycle precursor plays an important role in the formation of the hydrogen-bonding interactions of the supramolecular precursors of the interlocked architectures. Indeed, whereas the preparation of the rotaxane employing isophthaloyl chloride and the pyridine-based template was unfeasible, the introduction of nitro substituent at the position of the same precursor allowed the formation of the target amide-based rotaxane.