Group 13 ion coordination to pyridyl models NAD reduction potentials.

-alkylation and -metallation of pyridine are explored herein to understand how metal-ligand complexes can model NAD redox chemistry. Syntheses of substituted dipyrazolylpyridine (pzP) compounds (pzP)Me (1) and (pzP)GaCl (2) are reported, and compared with (pzP)AlCl(THF) and transition element pzP complexes from previous reports. Cyclic voltammetry measurements of cationic 1 and 2 show irreversible reduction events ∼900 mV anodic those for neutral pzP complexes of divalent metals. We proposed that -metallation using Group 13 ions of 3+ charge provides an electrochemical model for -alkylated pyridyls like NAD.