Results from the Cassini-Huygens space mission at Enceladus revealed a substantial inventory of organic species embedded in plume and E ring ice grains originating from a global subsurface and putative habitable ocean. Compositional analysis by the Cosmic Dust Analyzer (CDA) indicated the presence of aromatic species and constrained some structural features, although their exact nature remains unclear. As indicated by many studies, among other organic species, low-mass aromatics likely played a role in the emergence of life on Earth and may be linked to potential prebiotic or biogenic chemistry on icy moons. Here, we study the behavior of single-ringed aromatic compounds – benzoic acid and two isomeric derivatives, 2,3- and 2,5-dihydroxybenzoic acid (DHBA) – using Laser-induced liquid beam ion desorption (LILBID), an analogue setup to simulate the impact ionization mass spectra of ice grains in space. These compounds share common structural features but also exhibit differences in functional groups and substituent positions. We investigate the fragmentation behavior and spectral appearance of each molecule over three simulated impact velocities, in both positive and negative ion mode. Parent compounds can be distinguished easily from their derivatives due to various spectral differences, including the (de)protonated molecular ion peaks appearing at different m/z values. We conclude that distinction between structural isomers in LILBID is more challenging, but some insights can be revealed by considering intermolecular bonding regimes. This work will guide future investigations into elucidating the composition of isomeric biosignatures in ice grains, relevant for future space missions to Enceladus and Europa.