Synthesis and characterization of Zinc(II) complex with ONO donor type new phenylpropanehydrazide based ligand: Crystal structure, Hirshfeld surface analysis, DFT, energy frameworks and molecular docking

Abstract

A new Schiff base ligand N'-(3-methyl-2-hydroxybenzylidene)-3-phenylpropanehydrazide (LH) and its zinc complex [ZnL2] were synthesized and characterized by elemental and spectroscopic (IR, UV-visible and 1H-NMR) analyses. The crystal structure of [ZnL2] was determined by single crystal X-ray diffraction method and revealed that the Zn(II) ion is fitted with N2O4 compartment of two molecules of LH with distorted octahedral geometry. The complex shows C-H⋯O, C-H⋯N and C-H⋯π intermolecular interactions. The graphical approach of the intermolecular interactions was obtained from the Hirshfeld surface analysis and 2D fingerprint plots was employed to quantifies various interactions. DFT was performed to outline the optimized structure, frontier molecular orbitals, reactive parameters, and molecular electrostatic potential (MEP) of LH and [ZnL2]. Natural bonding orbitals (NBO) analysis was carried out to study the donor-acceptor atom interactions contributing to the crystal structure stabilization, further the charge transfer was evident as decrease in the charge on the Zn(II) atom. The distorted octahedral geometry due to the Jahn-Teller effect was substantiated by the NBO analysis. The topology analysis (QTAIM and NCI) gave further insights into understanding of the attractive and repulsive types of interactions in [ZnL2]. The strained metal coordination sphere was corroborated by the presence of the red regions that exist between the oxygen and nitrogen atoms. The molecular docking study was performed to understand the effective binding interactions of LH and [ZnL2] on active site of GlcN-6-P synthase and EGFR tyrosine kinase and the resulted data correlated to the experimental approach of antimicrobial and anticancer activity.