Synthesis, Structural, Spectroscopic, Inhibitory, and biological Activity studies of a novel hybrid m-(CH2NH3)2C6H4 (HPO4)•2H2O: Experimental and quantum chemical Investigations

Abstract

This paper reports an experimental and theoretical analysis of a novel hybrid molecule, m-(CH₂NH₃)₂C₆H₄(HPO₄).2H₂O, abbreviated as m-XDMP. The synthesis was carried out at room temperature using a slow evaporation method, by the dropwise addition of m-xylylenediamine to an ethanol solution containing diluted phosphoric acid under magnetic stirring. The X-Ray diffractionprove that m-XDMP crystallizes in the monoclinic system by mean of non-centrosymmetric space group P2₁. This compound was characterized by UV–vis, infrared and differential scanning calorimetry (DSC) spectroscopies. Molecular optimization analysis was performed using quantum chemical calculations based on Density Functional Theory (DFT) with the B3LYP/6–311++G(d,p) method. The nucleophilic (oxygen atoms) and electrophilic (hydrogen atoms) sites responsible for the establishment of hydrogen bonding interactions were identified through Molecular Electrostatic Potential (MEP) surface analysis. The energy gap, global softness, and chemical hardness values confirmed the chemical stability of m-XDMP. Atoms in Molecules (AIM) analysis highlighted the formation of intramolecular hydrogen bonds, including O–H···O, O–H···N, N–H···O, N–H···H, and C–H···O interactions. In contrast, Hirshfeld surface analysis confirmed the presence of N–H···O, C–H···O, and O–H···O interactions within the crystalline arrangement of m-XDMP. In addition, molecular docking simulations were conducted to investigate the pharmacological potential of the compound. Several bacterial and fungal proteins were docked with m-XDMP. The docking results were compared to those of a standard drug, indicating the inhibitory potential of the studied compound, particularly against the 8OXI enzyme. Moreover, ADMET (Absorption, Distribution, Metabolism, Excretion, and Toxicity) properties were also evaluated.