A photoelectron spectroscopy study probed the microsolvation of cis-pinate, another photooxidation product of α-pinene, with various solvents and demonstrated a careful balance between solute-solvent and solvent-solvent interactions unique to the gas-phase. This suggests that the environment plays a key role in the structures and pathways of the clusters in the atmosphere and is unlike those found in the bulk. Other work has begun to explore the itermolecular interactions of organic acids in small clusters. Chemical ionization (CI) sources are common mechanisms to ionize free vapors and small particles, and are considered to be "soft" ionization sources that impart little energy into the analyte. Typically employing protonated ammonia or water clusters for analytes with basic sites and nitrate for analytes with acidic sites, ion-molecule proton transfer reactions drive the ionization process. While soft, this process may still be energetic enough to drive dissociative chemistry, and the atmospheric pressure interface of common commercial instruments have been shown to be mildly activating, suggesting that CI mass spectra may not fully represent the gas phase species being sampled. Diprotonated carboxylic acids have been observed in the presence of superacids and in the gas phase. These diprotonated species show interesting properties, for instance enhancing the reactivity of adjacent carbocationic sites and exhibit superelectrophilic reactivity. Rearrangement of the protonated carboxylic acid to produce H 2 O and an acylium ion is observed in both the condensed and gas phases. In this work, we employ collision-induced dissociation (CID) mass spectrometry to probe the behavior of adipic acid, an inexpensive analogue to pinic acid. We isolate protonated adipic acid and an adipic acid-ammonia compound in a ion trap and perform up to MS experiments to determine the decomposition products of the cluster. We then use cryogenic ion vibrational predissociation (CIVP) spectroscopy and density functional theory (DFT) calculations to determine the structure of each product, leading to a proposed mechanism describing the decomposition pathway.