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CuII Pyrazolyl-Benzimidazole Dinuclear Complexes with Remarkable Antioxidant Activity |
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| Authors: | Karim Chkirate Gamal Al Ati Khalid Karrouchi Saad Fettach Hind Chakchak Joel T Mague Smaail Radi N N Adarsh My El Abbes Faouzi El Mokhtar Essassi Yann Garcia |
| Affiliation: | 1. Laboratory of Heterocyclic Organic Chemistry URAC 21, Pharmacochemistry Competence Center, Av. Ibn Battouta, BP 1014, Faculty of Sciences, Mohammed V University in Rabat, Rabat, 10010 Morocco;2. Laboratory of Analytical Chemistry and Bromatology, Faculty of Medicine and Pharmacy, Mohammed V University in Rabat (Morocco);3. Laboratory of Pharmacology and Toxicology, Biopharmaceutical and Toxicological Analysis Research Team, Faculty of Medicine and Pharmacy, Mohammed V University of Rabat (Morocco);4. Unités d'Appui Techniques À la Recherche Scientifique (UATRS), Centre National Pour la Recherche Scientifique et Technique (CNRST), Rabat, 10000 Morocco;5. Department of Chemistry, Tulane University, New Orleans, LA 70118 USA;6. LCAE, Département de Chimie, Faculté des Sciences, Université Mohamed Premier, B. P. 524, 60000 Oujda, Morocco;7. Department of Chemistry & Biomolecular Science, Clarkson University, Potsdam, NY 13699 USA;8. Institute of Condensed Matter and Nanosciences, Molecular Chemistry, Materials and Catalysis (IMCN/MOST), Université catholique de Louvain, Place L. Pasteur 1, 1348 Louvain-la-Neuve, Belgium |
| Abstract: | Three dinuclear coordination complexes generated from 1-n-butyl-2-((5-methyl-1H-pyrazole-3-yl)methyl)-1H-benzimidazole ( L ), have been synthesized and characterized spectroscopically and structurally by single crystal X-ray diffraction analysis. Reaction with iron(II) chloride and then copper(II) nitrate led to a co-crystal containing 78 % of Cu(NO3)(μ-Cl)( L’ )]2 ( C1 ) and 22 % of Cu(NO3)(μ-NO3)( L’ )]2 ( C2 ), where L was oxidized to a new ligand L’ . A mechanism is provided. Reaction with copper chloride led to the dinuclear complex Cu(Cl)(μ-Cl)( L) ]2 ( C3 ). The presence of N?H???O and C?H???O intermolecular interactions in the crystal structure of C1 and C2 , and C?H???N and C?H???Cl hydrogen bonding in the crystal structure of C3 led to supramolecular structures that were confirmed by Hirshfeld surface analysis. The ligands and their complexes were tested for free radical scavenging activity and ferric reducing antioxidant power. The complex C1 / C2 shows remarkable antioxidant activities as compared to the ligand L and reference compounds. |
| Keywords: | antioxidant activity benzimidazole copper dinuclear complexes Hirshfeld surface analysis |