Journal
JOURNAL OF MOLECULAR STRUCTURE
Volume 1242, Issue -, Pages -Publisher
ELSEVIER
DOI: 10.1016/j.molstruc.2021.130719
Keywords
Benzimidazolone; 1,2,3-triazole; X-ray diffraction; Hirshfeld surface; DFT; Monte Carlo; Antibacterial activities
Categories
Funding
- Tulane University
Ask authors/readers for more resources
A new series of triazole derivatives containing a benzimidazolone moiety were synthesized using 1,3-dipolar cycloaddition and click chemistry, with their structures characterized and confirmed by spectroscopy and X-ray crystallography. The compounds showed promising anti-corrosion properties for iron and exhibited antibacterial activities against various microbial strains.
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.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available