The discovery of new catalysts that drive essential chemical reactions is a perpetual objective in chemistry. In light of the burgeoning availability of low cost solar electricity, a particularly timely challenge is the generation of materials that competently catalyze fuel-forming small molecule transformations which enable the storage of electricity as chemical energy. This chemical energy subsequently requires a corresponding set of materials to catalyze the conversion of this chemical energy back into electricity in a device known as a fuel cell. One of these reactions, the reduction of oxygen to water, is essential to proton exchange membrane fuel cell technologies, but significant research efforts are still required to make these technologies a reality. Platinum remains the best-in-class catalyst for O2 reduction, but its relatively high cost and low abundance are prohibitive to widespread adoption. In its place, various first-row transition metal and metal-free alternatives have been considered. Among these alternative catalyst paradigms, nitrogen-doped carbon materials stand out as durable, low-cost, high-activity and high-efficiency catalysts for oxygen reduction. These structures come in various forms, including nitrogen-doped fullerenes, carbon nanotubes, and graphene. Regardless of type, though, these materials are intrinsically heterogeneous, featuring mixtures of pyridine-like, pyrrole-like and graphitic/quaternary nitrogen sites. This has complicated the study of active sites in these catalysts, rendering the rational iteration and improvement of these materials more difficult. To address this gap, the development of "designer" nitrogen-doped materials with well-defined active sites has been pursued by multiple groups. These studies support the critical conclusion that carbons adjacent to pyridinic moieties are responsible for the oxygen reduction activity in these catalysts but raised further questions about the source of this activity. In the case of a previous study by Ricke et al. which focused on one particular nitrogen-doped graphite conjugated catalyst (N + -GCC), there was only a single carbon atom in the catalyst that would form a bond with O2. This activity could not be solely a result of the pyridinic nitrogen acting as an ortho-para activator to the aromatic system, as the alternate carbon ortho to the pyridinic nitrogen would not bind O2. This study noted that the active carbon had a significant accumulation of spin density, which the authors interpreted as indicating this site could most stably donate electron density to O2 during bond formation.