Taking into account all experimental findings and with the aid of high-level quantum chemical calculations, we proposed the mechanism of electrochemical transformations of 8AQ in low and high pH regimes (see Figure ). At pH below 5, two forms of 8AQH + (2a and 2b) exist in equilibrium (vide supra). They differ significantly in oxidation potentials. Because 2a has a significantly lower oxidation potential of 1.01 V w.r.t. SHE, it will undergo oxidation under experimental conditions to form the 2aox1 dicationic radical in a single electron process. The relatively high charge accumulated in the molecule makes it prone to proton loss upon another oxidation act. The final dication 2aox2 is in equilibrium with the nitrenium dication 2box2 (70%:30%). The total process should follow the 2-electron/1-proton model assumed in the Nernst equation with a slope of 33 meV (see SI Nernst Equation).