Synthesis, characterization of Schiff base metal complexes and their biological investigation

• Published in: Applied organometallic chemistry Vol. 33; no. 9
• Main Authors: El‐Sonbati, A.Z., Mahmoud, W.H., Mohamed, Gehad G., Diab, M.A., Morgan, Sh.M., Abbas, S.Y.
• Format: Journal Article
• Language: English
• Published: Chichester Wiley Subscription Services, Inc 01-09-2019
• Subjects: antimicrobial activity; Bacteria; Base metal; Cadmium; Chemical analysis; Chemical synthesis; Chemistry; Chromium; Coliforms; Coordination compounds; Copper; E coli; Electronic spectra; Hydroxybenzaldehydes; Imines; Infrared spectroscopy; Ligands; Magnetic permeability; Mathematical analysis; Metal ions; Metals; Molecular docking; Nickel; Organic chemistry; Quantum chemistry; Schiff base; Stereochemistry; Thermal analysis; Thermal stability; thermogravimetric analysis; Transition metals; UV–vis spectroscopy
• ISSN: 0268-2605; 1099-0739
• DOI: 10.1002/aoc.5048

A new Schiff base ligand named (E)‐2‐(((3‐aminophenyl)imino)methyl)phenol (HL) was prepared through condensation reaction of m‐phenylenediamine and 2‐hydroxybenzaldehyde in 1:1 molar ratio. The new ligand was characterized by elemental analysis and spectral techniques. The coordination behavior of a series of transition metal ions named Cr (III), Mn (II), Fe (III), Co (II), Ni (II), Cu (II), Zn (II) and Cd (II) with the newly prepared Schiff base ligand (HL) is reported. The nature of bonding and the stereochemistry of the complexes have been deduced from elemental analyses, IR, UV–Vis, 1H NMR, mass, electronic spectra, magnetic susceptibility and conductivity measurements and further their thermal stability was confirmed by thermogravimetric analysis (TG). From IR spectra, it was observed that the ligand is a neutral tridentate ligand coordinates to the metal ions through protonated phenolic oxygen, azomethine nitrogen and nitrogen atom of NH2 group. The existence, the number and the position of the water molecules was studied by thermal analysis. The molecular structures of the Schiff base ligand (HL) and its metal complexes were optimized theoretically and the quantum chemical parameters were calculated. The synthesized ligand and its complexes were screened for antimicrobial activities against bacterial species (Staphylococcus aureus and Bacillis subtilis, (gram positive bacteria)), (Salmonella SP., Escherichia coli and Pseudomonas aeruginosa, (gram negative bacteria)) and fungi (Aspergillus fumigatus and Candida albicans). The complexes were found to possess high biological activities against different organisms. Molecular docking was used to predict the efficiency of binding between Schiff base ligand (HL) and both receptors of Escherichia coli (3 T88) and Staphylococcus aureus (3Q8U). The receptor of Escherichia coli (3 T88) showed best interaction with Schiff base ligand (HL) compared to receptor of Staphylococcus aureu (3Q8U).
Novel Schiff base and its metal complexes are prepared. Many analytical and spectroscopic tools are used for characterization of the prepared compounds. Biological activity and molecular docking are studied.