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

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 center dot center dot center dot O, C-H center dot center dot center dot N and C-H -pi intermolecular interac-tions. 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 electro-static 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. (c) 2022 Elsevier B.V. All rights reserved.

Automated summary

A new Schiff base ligand and its zinc complex were synthesized and characterized. The crystal structure of the complex was determined by X-ray diffraction, and the intermolecular interactions and electronic properties were analyzed. Molecular docking studies were also conducted to evaluate their biological activities.