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. 2022 Feb 14;12(9):5324-5339.
doi: 10.1039/d1ra09027e. eCollection 2022 Feb 10.

Coordination complexes constructed from pyrazole-acetamide and pyrazole-quinoxaline: effect of hydrogen bonding on the self-assembly process and antibacterial activity

Karim Chkirate  1 , Khalid Karrouchi  2 , Hind Chakchak  3 , Joel T Mague  4 , Smaail Radi  5 , N N Adarsh  6 , Weiyang Li  7 , Ahmed Talbaoui  8 , El Mokhtar Essassi  1 , Yann Garcia  7
Affiliations

Coordination complexes constructed from pyrazole-acetamide and pyrazole-quinoxaline: effect of hydrogen bonding on the self-assembly process and antibacterial activity

Karim Chkirate et al. RSC Adv. .

Abstract

Two mononuclear coordination complexes of N-(2-aminophenyl)-2-(5-methyl-1H-pyrazol-3-yl)acetamide (L1), namely [Cd(L1)2Cl2] (C1) and [Cu(L1)2(C2H5OH)2](NO3)2 (C2) and one mononuclear complex [Fe(L2)2(H2O)2](NO3)2·2H2O (C3), obtained after in situ oxidation of L1, have been synthesized and characterized spectroscopically. As revealed by single-crystal X-ray diffraction, each coordination sphere made of two heterocycles is completed either by two chloride anions (in C1), two ethanol molecules (in C2) or two water molecules (in C3). The crystal packing analysis of C1, C2 and C3, revealed 1D and 2D supramolecular architectures, respectively, via various hydrogen bonding interactions, which are discussed in detail. Furthermore, evaluation in vitro of the ligands and their metal complexes for their antibacterial activity against Escherichia coli (ATCC 4157), Pseudomonas aeruginosa (ATCC 27853), Staphylococcus aureus (ATCC 25923) and Streptococcus fasciens (ATCC 29212) strains of bacteria, revealed outstanding results compared to chloramphenicol, a well-known antibiotic, with a normalized minimum inhibitory concentration as low as 5 μg mL-1.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Fig. 1
Fig. 1. Structures of N-(2-aminophenyl)-2-(5-methyl-1H-pyrazol-3-yl)acetamide (L1) and 3-(5-methyl-1H-pyrazol-3-yl)quinoxalin-2(1H)-one (L2).
Scheme 1
Scheme 1. Synthetic route for preparation of L1.
Scheme 2
Scheme 2. Plausible reaction mechanism for the formation of L2.
Fig. 2
Fig. 2. Asymmetric unit of C1 (a), C2 (b) and C3 (c). Color codes: C – orange, N – blue, H – white, Cd – Magenta, Cu – dark orange, Fe – green, O – red, Cl – green.
Fig. 3
Fig. 3. Crystal structure illustration of C1, (a) 1D hydrogen bonded chains (black dotted lines represent the N–H⋯Cl interactions), (b) parallel packing of 1D chains (view along crystallographic axis ‘b’), (c) TOPOS view of the parallel packing of 1D chains.
Fig. 4
Fig. 4. Crystal structure illustration of C2, (a) the N–H⋯O and O–H⋯O hydrogen bonding in C2 displaying the R21(9) ring, (b) various hydrogen bonding and the view of R21(11), R21(9) and R21(8) rings, (c) TOPOS view of 2D hydrogen bonded sheet, (d) the stacking of 2D layers along crystallographic axis ‘a’ (adjacent 2D layers are shown in orange, green and magenta).
Fig. 5
Fig. 5. Crystal structure illustration of C3, (a) 1D chain self-assembly of C3 through R44(12) rings via various hydrogen bonding, (b) 2D hydrogen bonded assembly, (c) TOPOS view of 2D hydrogen bonded network, (d) 3D hydrogen bonded network, (e) TOPOS view of 3D [32·6-c]-connected net.
Fig. 6
Fig. 6. The dnorm Hirshfeld surfaces of C1 (a), C2 (b), and C3 (c) displaying hydrogen bonding interactions.
Fig. 7
Fig. 7. 2D Fingerprint plots derived from the Hirshfeld surfaces displaying various intermolecular interactions.
Fig. 8
Fig. 8. 57Fe Mössbauer spectrum of C3 recorded at 298 K. The half width of the lines Γ/2 = 0.23(1) mm s−1.
Fig. 9
Fig. 9. XRPD pattern of the black powder issued from the synthesis of C3 compared to the computed XPRD pattern obtained from the cif file of C3.
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