Formation of a new CuII–triazole ester complex from 1,2-cyclohexanedione-bis(p-bromobenzohydrazone) compound as a consequence of copper(II)-catalyzed click reaction

• Published in: Chemical papers Vol. 75; no. 8; pp. 3901 - 3914
• Main Authors: Al-Karawi, Ahmed Jasim M., OmarAli, Al-Ameen Bariz, Dege, Necmi, Kansız, Sevgi
• Format: Journal Article
• Language: English
• Published: Warsaw Versita 01.08.2021; Springer Nature B.V
• Subjects: Acetonitrile; Biochemistry; Biotechnology; Chemical reactions; Chemistry; Chemistry and Materials Science; Chemistry/Food Science; Copper; Copper compounds; Crystallography; Hydrazones; Industrial Chemistry/Chemical Engineering; Materials Science; Medicinal Chemistry; Original Paper; Oxidation; Single crystals; Surface analysis (chemical); Triazoles; Two dimensional analysis
• ISSN: 2585-7290; 0366-6352; 1336-9075
• DOI: 10.1007/s11696-021-01614-x

Reaction of 1,2-cyclohexanedione-bis( p -bromobenzohydrazone) ( CBB ) as a bis-aroyl-hydrazone derivative with copper(II) nitrate trihydrate in acetonitrile under ambient conditions produced a mononuclear Cu(II) complex [Cu(TE)(NO 3 ) 2 ] (TE: triazole-ester) ( 1 ). TE is an intermediate which is formed in situ during the oxidation of CBB by Cu(II) ion based on so-called copper(II)-catalyzed click reaction. CBB and 1 are characterized with various techniques. On the basis of single-crystal X-ray crystallography, compound 1 is confirmed as a 4-coordinate mononuclear Cu(II) complex with a distorted square planner geometry. In this compound, copper is bound to the 1-N of two monodentate triazole ester molecules and two monodentate nitrate ions. Moreover, the antimicrobial activity of CBB and 1 against some selected pathogenic bacteria was investigated. Due to this study, these compounds showed a good antibacterial activity. In addition, the Hirshfeld surface analysis ( d norm surface and two-dimensional fingerprint plots) was performed to reveal the nature of intermolecular interactions in CBB and 1 . The most important contributions for the crystal packing of CBB are mainly from H…H (28.8%), Br…H/H…Br (23.2%) and C…H/H…C (19.5%) interactions, while the most important contributions for the crystal packing of 1 are found to be from H…H (27%), O…H/H…O (23.7%) and Br…H/H…Br (19%) interactions.