Zinc(II)‐facilitated nucleophilic addition on N‐(4‐chlorophenyl) carbon hydrazonoyl dicyanide and hybrid complex formation: X‐ray, spectral characteristics, DFT, molecular docking, and biological studies

• Published in: Applied organometallic chemistry Vol. 36; no. 9
• Main Authors: Elbadawy, Hemmat A., Ali, Ali El‐Dissouky, Elkashef, Amany Assem, Foro, Sabine, El‐Sayed, Doaa S.
• Format: Journal Article
• Language: English
• Published: Chichester Wiley Subscription Services, Inc 01.09.2022
• Subjects: Anticancer properties; antioxidant; Antioxidants; Aqueous solutions; azo‐hydrazo; Cancer; Chemical analysis; Chemistry; Complex formation; E coli; Ethanol; Mathematical analysis; Molecular docking; NMR; Nuclear magnetic resonance; Scavenging; single‐crystal X‐ray analysis; tetrahedral zinc complex; X ray photoelectron spectroscopy; Zinc compounds
• ISSN: 0268-2605; 1099-0739
• DOI: 10.1002/aoc.6793

The isolated crystalline, N‐(4‐chlorophenyl) carbonohydrazonoyl dicyanide, NCCD, showed a unique behavior in the presence of zinc ions, ethanol, and H2O. The product was proved to be a two‐unit complex consisting of coordinated zinc(II) complex part, bis‐(1‐(4‐chlorophenyl)‐2‐(1‐cyano‐2‐ethoxy‐2‐iminoethylidene)hydrazin‐1‐ide)zinc(II), Zn (CEIH)2, and a coupled modified organic part, 4‐amino‐N‐(4‐chlorophenyl)‐5‐((4‐chlorophenyl)diazen‐yl)‐6‐ethoxypyrimidine‐2‐carbohydrazonoyl cyanide (ACDPC). Such behavior may be attributed to the activity of nitrile groups in NCCD and the zinc(II) catalytic power in aqueous media. The structures of the products were confirmed by elemental analysis and single‐crystal X‐ray analysis. The spectral properties were analyzed by studying FTIR, UV–Visible, 1H NMR, 13C NMR, and XPS. Moreover, computational calculations including DFT were applied to the synthesized compounds to estimate their optimized structure and deduce some quantum parameters. The FTIR, UV–Visible, and NMR data were compared with the calculated results, showing a good agreement. Molecular docking was applied to study the interaction of NCCD and GNB‐selected protein targets for Escherichia coli (ID: 5I39) and Proteus vagaries (ID: 6QF6). The isolated compounds were investigated as antibacterial, antioxidant, and anticancer agents showing variable activities. The NCCD showed a higher impact as an antimicrobial and anticancer agent, whereas the zinc complex showed better antioxidant behavior using DPPH radical scavenging activity test. A novel hybrid Zinc complex was isolated from simple reflux of ethanolic solutions of N‐(4‐chlorophenyl) carbonohydrazonoyl dicyanide, NCCD, and Zn(II) ions. SXRD and other spectral methods characterized the products. XPS of the product showed the Zn2p3/2 and Zn2p1/2 binding peaks. MEP of the NCCD and Zn(II) complex interpret that the most electronegative sites are located in nitrile groups. Molecular docking and biological activities were studied.