Abstract

Copper(II) complexes of benzimidazole are known to exhibit biological activity that makes them of inter-est for chemotherapeutic and other pharmaceutical uses. The complex bis-(acetato-κO){5,6-dimethyl-2-(pyridin-2-yl)-1-[(pyridin-2-yl)meth-yl]-1H-benzimidazole-κ2N2,N3}copper(II), has been prepared. The absorption spectrum has features attributed to intra-ligand and ligand-field transitions and the complex exhibits ligand-centered room-temperature luminescence in solution. The aceto-nitrile monosolvate, [Cu(C2H3O2)2(C20H18N4)]·C2H3N (1), and the ethanol hemisolvate, [Cu(C2H3O2)2(C20H18N4)]·0.5C2H6O (2), have been structurally characterized. Compound 2 has two copper(II) complexes in the asymmetric unit. In both 1 and 2, distorted square-planar N2O2 coordination geometries are observed and the Cu-N(Im) bond distance is slightly shorter than the Cu-N(py) bond distance. Inter-molecular π-π inter-actions are found in 1 and 2. A weak C-H⋯π inter-action is observed in 1.

Highlights

  • Copper(II) complexes of benzimidazole are known to exhibit biological activity that makes them of interest for chemotherapeutic and other pharmaceutical uses

  • Compound 2 has two copper(II) complexes in the asymmetric unit. In both 1 and 2, distorted square-planar N2O2 coordination geometries are observed and the Cu—N(Im) bond distance is slightly shorter than the Cu—N(py) bond distance

  • In 2, the most significant hydrogen-bonding interactions (Table 4) involve the disordered ethanol solvate molecule, which participates as donor in O—H O hydrogen bonding with the uncoordinated acetate oxygen atoms O2 and

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Summary

Chemical context

Copper(II) complexes containing benzimidazole ligands exhibit anticancer properties involving reactive oxygen species and DNA interactions (Prosser et al, 2017; Lewis et al., 2016; Mal et al, 2014). Similar complexes show antibacterial activity (Chen et al, 2012). In addition to biological applications, CuII complexes containing benzimidazole have been explored as catalysts. One complex behaves as a ring-opening polymerization catalyst (Zaca et al, 2016). Complexes of 5,6-dimethyl-2-(pyridin-2-yl)-1-[(pyridin-2-yl)methyl]-1H-benzimidazole, Me2BzImpy, that exhibit blue luminescence (DeStefano & Geiger, 2016) and a luminescent platinum(II) complex that exhibits an intermolecular anagostic interaction (DeStefano & Geiger, 2017). View of 1 showing the atom-labeling scheme. Anisotropic displacement parameters of non-H atoms are drawn at the 30% probability level

Spectroscopy
Structural commentary
Supramolecular features
Database survey
Synthesis and crystallization
Refinement
Full Text
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