A new series of 1,4 and 1,5-disubstituted-1,2,3-triazole derivatives containing a benzimidazolone moiety [(3a-3b), (4a-4b), (5a-5b) and (6a-6b)] were synthesized using 1,3-dipolar cycloaddition in toluene under thermal conditions with N-alkyl, N-propargyl- benzimidazolones as dipolarophiles and azide derivatives as dipoles. Furthermore, the 1,4-disubstituted-1,2,3-regioisomers (3a-6a) have been also obtained exclusively using click chemistry (Copper-Catalyzed Azide-Alkyne Cycloaddition). The structures of all compounds were characterized by (1) H-and C-13-NMR spectroscopy. The molecular and crystal structures of three compounds (3a, 4a, and 5a) were confirmed by single crystal X-ray crystallography. In addition, Density Functional Theory (DFT) was used to predict spectral data at the B3LYP/6-31G (d, p) level. Intermolecular interactions in the crystals of 3a, 4a, and 5a were determined by Hirshfeld surface analyses and the Monte Carlo method was used to investigate the interfacial interactions of these derivatives with iron, copper, and aluminum surfaces. Based on the Monte Carlo results, the new compounds can provide better anti-corrosion properties for iron as compared to copper and aluminum. The expected inhibition efficiency is 5a > 3a > 4a, which is attributed to the favorable effect of the lateral carbon chain of the triazole moiety in this process. The antibacterial activities of 1, 2, 3a, 3b, 4a, 5a, 5b, 6a, and 6b against Gram-positive and Gram-negative microbial strains, such as Staphylococcus aureus, Escherichia coli, and Pseudomonas aeruginosa were evaluated, and the results obtained showed antibacterial activities for all of them using a minimum inhibitory concentration (MIC) test. (C) 2021 Elsevier B.V. All rights reserved.