To continue our investigation, we explored systems in which the tetra-bonded N atom within the scaffold corresponds to a strong hydrogen-bond donor and, therefore, facilitates the formation of a traditional hydrogen-bonding interaction. This encom-passed the study of both neutral and positively charged catalystbased systems, aiming to discern and characterize the variations between the neutral cases, and the interactions encountered in charged systems. Furthermore, various substituents, including CF 3 , CH 3 , and t Bu, were considered to account for multiple electronic and steric scenarios (Figure ). The calculated interaction energies and anion-cation distances, for both positively charged and neutral species are summarised in Table . As expected, the interaction energies obtained are all negative, indicating favourable intermolecular interactions. Notably, when comparing the neutral species (imine derivatives) to their positively charged counterparts (iminium derivatives), a significant reduction in interaction energies is observed. In terms of the different substituents studied, it is evident that CF 3 exhibits the most negative values, indicating the strongest interactions within the formed complexes. Conversely, t Bu demonstrates the weakest interaction energies. In general, the intermolecular interactions studied are more favourable when Cl -is involved as the counteranion.