Applied Chemical Engineering

Logical Design, construction, and Computational Characterization of Transition-Metal Complexes Resulting from a Novel Cyclohexenone Ligand

Sarab Alazawi

Department of Chemistry, College of Science, Mustansiriyah University, Baghdad, 10001, Iraq

Rasha Wali Mohi Al-saedi

Department of Chemistry, College of Science, Mustansiriyah University, Baghdad, 10001, Iraq

Wasan M. Alwan

Department of Chemistry, College of Education for Pure Science (Ibn Al-Haitham), University of Baghdad, Baghdad, 10001, Iraq

Anaam Majeed Rasheed

Department of Chemistry, College of Science, Mustansiriyah University, Baghdad, 10001, Iraq

Sinan Midhat AL-Bayati

Department of Chemistry, College of Science, Mustansiriyah University, Baghdad, 10001, Iraq

DOI: https://doi.org/10.59429/ace.v9i1.5881

Keywords: cyclohexenone derivatives; michael addition; theoretical study; antibacterial

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Abstract

Cyclohexenone derivatives have more significant attention in the last current years owing to its varied range of applications in various subject, including medicinal chemistry, materials science, and organic synthesis. A derivative of cyclohexanone was prepared by condensation of chalcone derivative with acetylacetone and ethylacetoacetate to produce new ligands with titles L1 and L2, respectively, via Michael's reaction. The Newly complexes were synthesized by coordination of L1 with transition metals (CrCl₃• 6H₂O, CuCl₂•2H₂O) and L2 with (CoCl₂ • 6H₂O, NiCl₂ • 6H₂O), and characterized by ¹H NMR and LC-MS mass spectral analysis, UV and IR spectroscopy, also the magnetic susceptibility studies, molar conductivity study, C, H, N, and atomic absorption analysis. The results confirmed that both new ligands act as bidentate ligands, coordinating with metal ions through the oxygen atoms of both the ketone and hydroxide groups for L1. In contrast, L2 coordinates through two oxygen atoms of the ketone groups to form complexes with an octahedral geometry. The antibacterial capability of new compound and corresponding metal complexes was investigated against the two kinds of pathogenic bacteria microorganisms (Escherichia còli) and (Stāphylocòccus aureus) compare with the standard drug (Cephalexin), and the results showed that the ligands and their complexes activities ranged from weak to moderately to highly active against the two categories of bacteria compared with the standard drug Cephalexin. Consequently, these complexes show potential as therapeutic agents and may emerge as strong competitors to currently available pharmaceuticals. A comprehensive theoretical investigation of the ligand and its metal complexes was conducted by density functional theory (DFT) at the B3LYP level with the 3-21G basis set to provide a consistent correlation with the experimental findings, and shows that L2 and corresponding complexes are more stable compared with L1and its complexes. L2 and its complexes exhibit the highest energy gaps and chemical hardness, confirming their kinetic stability and reduced reactivity compared to other complexes.

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