Threshold collision-induced dissociation of Na+(xBA) complexes with Xe is studied using guided ion beam mass spectrometry. The xBA ligands studied include benzoic acid and all of the mono- and dihydroxy-substituted benzoic acids: 2-, 3-, and 4-hydroxybenzoic acid and 2,3-, 2,4-, 2,5-, 2,6-, 3,4-, and 3,5-dihydroxybenzoic acid. In all cases, the primary product corresponds to endothermic loss of the intact xBA ligand. The cross section thresholds are interpreted to yield 0 and 298 K bond dissociation energies (BDEs) for Na+-xBA after accounting for the effects of multiple ion-neutral collisions, internal and kinetic energy distributions of the reactants, and dissociation lifetimes. Density functional theory calculations at the B3LYP/6-31G* level of theory are used to determine the structures of these complexes and provide the molecular constants necessary for the thermodynamic analysis of the experimental data. Theoretical BDEs are determined at the B3LYP/6-311+G(2d,2p) and MP2(full)/6-311+G(2d,2p) levels using the B3LYP/6-31G* optimized geometries. The trends in the measured BDEs suggest two very different binding modes for the Na+(xBA) complexes, while theory finds four. In general, the most stable binding conformation involves the formation of a six-membered chelation ring via interaction with the carbonyl and 2-hydroxyl oxygen atoms. The ground state geometries of the Na+(xBA) complexes in which the ligand does not possess a 2-hydroxyl group generally involve binding of Na+ to either the carbonyl oxygen atom or to both oxygen atoms of the carboxylic acid group. These binding modes tend to be competitive because the enhancement in binding associated with the chelation interactions in the latter is mediated by steric repulsion between the hydroxyl and ortho hydrogen atoms. When possible, hydrogen bonding interactions with the ring hydroxyl group(s) enhance the stability of these complexes. The agreement between the theoretical and experimental BDEs is quite good for B3LYP and somewhat less satisfactory for MP2(full).