In this work, we investigated the evolution of clusters of ammonium and adipic acid under mildly activating thermodynamic conditions that might be present in typical CIMS instruments. In the cluster geometry, we have observed adipic acid serving as a stronger base than ammonia in the gas phase. This is consistent with similar suggestions of pinic acid acting as a base in pinic acid -sulfuric acid clusters and suggests that the specifics of the gas phase can complicate traditional views on relative basicity from solution-based perspectives. This dramatic change is basicity is likely driven by the conformation of the ammonium-adipic acid complex, and this type of conformational change in basicity could be present in many small clusters or potential particle surfaces. We demonstrate that the breakdown of adipic acid in the presence of an extra proton occurs via a complex set of internal hydrogen shifts, suggesting a possible new route for the formation of ELVOCs in the atmosphere and further supporting the notion that hydrogen shifts are crucial in understanding the role of organic compounds in the atmosphere. This acid-induced reactivity may be present in other particularly acidic clusters or on particle surfaces.