Synthesis and Characterization with Computational Studies of Metal Complexes of Methyl 2-((4-cyanophenyl)(hydroxy) methyl)acrylate: A New Biologically Active Multi-Functional Adduct

Abstract

The title ligand (L”x), methyl 2-((4-cyanophenyl)(hydroxy)methyl)acrylate was synthesized following the Morita-Baylis-Hillman reaction scheme. Spectroscopic techniques such as: UV- Visible, FT-IR, ESI-MS, and 1H NMR helped in characterization of the L”x. Complexes of Cr3+, Co3+, Ni2+, Mn2+, Cu2+ with L”x were prepared and characterized by UV- Visible, FT-IR and powder-XRD. FTIR spectrum of the L”x generated through DFT B3LYP method and 6-311++ G (d,p) basis set was found in good agreement with experimental spectrum. Additionally, the semi-empirical PM6 method optimization helped propose the most suitable geometries of the complexes with Cr3+, Co3+ possessing octahedral, Ni2+ square planner, Mn2+ and Cu2+ tetrahedral geometries. Powder-XRD patterns of the complexes have revealed cubic crystal class for Cr3+ and Co3+, whereas hexagonal, orthorhombic, and monoclinic for Ni2+, Mn2+, and Cu2+ complexes were observed, respectively. In addition, the nano-particle size was found in the range of 8.2560–4.5316 nm for complexes. Antibacterial activity against S. aureus, E. coli, B. pumilis and S. typhi confirmed a substantially high potential, as endorsed by their Molecular docking studies, of Ni2+ and Cu2+ complexes against each bacterial strain. Moreover, all compounds exhibited positive antioxidant activities, but have no antifungal potential except L”x. The current study demonstrates the usefulness of these novel transition metal complexes as possible potent antibacterial and antioxidant agents.

Keywords

• Morita-Baylis-Hillman
• XRD
• biological assays
• PM6 method
• molecular docking