The ligand 6,6′-dihydroxy terpyridine (dhtp) is presented as a bifunctional ligand capable of directing proton transfer events with metal-coordinated substrates. Solid-state analysis of a Ru(II)-dhtp complex reveals directed hydrogen-bonding interactions of the hydroxyl groups of dhtp with a Ru-bound chloride ligand. The utility of dhtp was demonstrated by chemoselective transfer hydrogenation of ketones.