Group 13 ion coordination to pyridyl models NAD+ reduction potentials.

Abstract

N-alkylation and N-metallation of pyridine are explored herein to understand how metal-ligand complexes can model NAD+ redox chemistry. Syntheses of substituted dipyrazolylpyridine (pz2P) compounds (pz2P)Me+ (1+) and (pz2P)GaCl2+ (2+) are reported, and compared with (pz2P)AlCl2(THF)+ and transition element pz2P complexes from previous reports. Cyclic voltammetry measurements of cationic 1+ and 2+ show irreversible reduction events ∼900 mV anodic those for neutral pz2P complexes of divalent metals. We proposed that N-metallation using Group 13 ions of 3+ charge provides an electrochemical model for N-alkylated pyridyls like NAD+.