Issue 6, 2020

Co(ii) and Zn(ii) pyrazolyl-benzimidazole complexes with remarkable antibacterial activity

Abstract

Three mononuclear coordination complexes of 1-butyl-2-((5-methyl-1H-pyrazol-3-yl)methyl)-1H-benzimidazole (L), namely [CoL]Cl2 (C1), [Co2L2]Cl2·H2O (C2) and [Zn2L2]Cl2 (C3), have been synthesized and characterized spectroscopically. Their single-crystal X-ray diffraction analysis revealed that C1 and C2 display pseudopolymorphism. The presence of N–H⋯Cl and C–H⋯Cl hydrogen bonding in the crystal structure of C1 and C3 assists the formation of a 2D hydrogen bonded sheet and orthogonal packing [2D sheet + a pair of 1D chains], respectively, leading to supramolecular structures. A combination of N–H⋯Cl, C–H⋯Cl, O–H⋯Cl, and C–H⋯O interactions results however in a 2D corrugated hydrogen bonded sheet with inclusion of water molecules in C2. Hirshfeld surface analysis confirms that hydrogen bonding and π-stacking contacts stabilize the crystal structures. These metal complexes display good performance towards their antimicrobial activity against Escherichia coli, Pseudomonas aeruginosa, and Staphylococcus aureus. In particular a normalized minimum inhibitory concentration as low as 6.25 μg mL−1 for the bacterial strains was recorded for C2. Its structure–bioactivity correlation is discussed in detail.

Graphical abstract: Co(ii) and Zn(ii) pyrazolyl-benzimidazole complexes with remarkable antibacterial activity

Supplementary files

Article information

Article type
Paper
Submitted
27 Nov 2019
Accepted
02 Jan 2020
First published
14 Jan 2020

New J. Chem., 2020,44, 2210-2221

Co(II) and Zn(II) pyrazolyl-benzimidazole complexes with remarkable antibacterial activity

K. Chkirate, K. Karrouchi, N. Dege, N. Kheira Sebbar, A. Ejjoummany, S. Radi, N. N. Adarsh, A. Talbaoui, M. Ferbinteanu, E. M. Essassi and Y. Garcia, New J. Chem., 2020, 44, 2210 DOI: 10.1039/C9NJ05913J

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