Abstract Heterolytic and homolytic bond dissociation energies of the C4 [BOND] H bonds in ten NADH models (seven 1, 4-dihydronicotinamide derivatives, two Hantzsch 1, 4- dihydropyridine derivatives, and 9, 10-dihydroacridine) and their radical cations in acetonitrile were evaluated by titration calorimetry and electrochemistry, according to the four thermodynamic cycles constructed from the reactions of the NADH models with N, N, ...