A recent study investigating the stability of isomers of a related Bi(bipy)-HVI species also found that an isomer structure analogous to structure 1 is the most stable. This consistency suggests that regardless of the electronic nature of the bidentate nitrogen ligand, isomer 1 is likely lower in energy than the other possible systems. Oxidation of p-nitrophenol by Bi(bipy)-HVI. Next, we focused on understanding why Bi(4-CO2Etbipy)-HVI is a suitable reagent for oxidation of electron-deficient phenols in contrast to IBX (Table , entries 1 and 3). To this end, different mechanistic pathways were explored for the oxidation of PhOH by Bi(4-CO2Etbipy)-HVI, the results of which are given in the Supporting Information (see Figures and Figure shows the energy profile calculated for oxidative dearomatization of p-nitrophenol as a model for an electron-deficient substrate based on the mechanism outlined in Scheme 1.