Abstract <p>Studying Schiff bases still remains a relevant and developing field of research, since they are widely used in a variety of industries. The paper reports on the properties of Schiff bases synthesized by the condensation reaction of aromatic amines and aldehydes and representing colored crystals. Their structure is confirmed by IR spectroscopy, NMR technique, and gas chromatography–mass spectrometry. Using quantum chemical modeling, the geometric structure and energy values of the frontier orbitals of azomethine molecules have been determined. The pharmacological activity and side effects of the obtained Schiff bases have been assessed using the PASS Online tool and shown to be potentially biologically active.</p>