Within the framework of understanding provided by scaling relations, ORR catalyst design strategies can be classified as either seeking to modify an existing catalyst to push the new catalyst closer to the optimal oxygen binding strength along the scaling relations, or to favorably break these scaling relations. Although the latter would be necessary to obtain the ideal catalyst starting from all currently known catalysts, the former method could potentially be productively applied to obtain catalysts with similar activity to state-of-the-art platinum catalysts with less expensive materials. In either case, systematically optimizing a catalyst requires a degree of synthetic tuneability generally only available to homogeneous catalysts, which are not as straightforward to separate from the reaction products and operate continuously in industrial applications. One class of catalysts that combines synthetic tuneability with the advantages of heterogeneous catalysts are graphite-conjugated catalysts (GCCs). GCCs are an advantageous model system because they enable the exploration of a large chemical space, which is relatively uncommon for heterogeneous catalysts. The chemical space of GCCs is large because there are many types of catalysts that could be conjugated directly to graphite: the actual synthesis only requires a diamine a molecule to be conjugated, with the only additional requirement being that the molecule cannot have any functional groups that will interfere with the condensation reaction. Broadly, this leads to a chemical space not dissimilar to small molecule drugs, estimated to contain on the order of 10 60 distinct systems. GCCs' chemical space is also as of this time relatively unexplored relative to the vast scale of small molecules that could be conjugated. A variety of GCCs have been developed, including both organometallic and organic catalysts designed for distinct reactions, demonstrating the value of exploring the depth of this chemical space further. This study focuses on how differences in GCC structures affect the intermediate reaction energies in ORR, with a particular focus on which kinds of modifications shift the catalyst along or cause deviations from the known scaling relations. We applied density functional theory (DFT) to calculate these reaction energies, as DFT is sufficiently inexpensive to enable the exploration of many structures. In this work we chose to consider functional group modifications of three initial GCC structures, which were each elaborations of a known GCC (Figure ). We chose the composition of these structures specifically to study how differences in the carbon scaffold around the cationic nitrogen affect the active sites. Each of these base structures has similar probable active sites, namely carbon atoms ortho to the cationic nitrogen, but we had no definite knowledge of which sites would be active prior to this study. Previous work by Lodaya et al. provided a thorough statistical analysis of ORR active sites on a variety of GCC structures, showing that cationic nitrogen typically activate secondary carbons that are an odd number of bonds away from