Three new proton transfer compounds, [2-ammonio-5-methylcarboxybenzene perchlorate (1), (C₈H₁₀NO₂⁺·ClO₄⁻), 4-(ammoniomethyl)carboxybenzene nitrate (2), (C₈H₁₀NO₂⁺·NO₃⁻), and 4-(ammoniomethyl)carboxybenzene perchlorate (3), (C₈H₁₀NO₂⁺·ClO₄⁻)], have been synthesized, their IR modes of vibrations have been assigned and their crystal structures studied by means of single-crystal X-ray diffraction. Their asymmetric units consist of one cation and one anion for both compounds (1) and (2). However, the crystal structure of compound (3) is based on a pair of cations and a pair of anions in its asymmetric unit. The three-dimensional Hirshfeld surface analysis and the two-dimensional fingerprint maps revealed that the three structures are dominated by H...O/O...H and H...H contacts. The strongest hydrogen-bonding interactions are associated with O—H...O and N—H...O constituting the highest fraction of approximately 50%, followed by those of the H...H type contributing 20%. Other close contacts are also present, including weak C...H/H...C contacts (with about 10%).