Structural, spectroscopic, Hirshfeld surface and charge distribution analysis of 3-(1H-imidazole-1-yl)-1-phenylpropan-1-ol complemented by molecular docking predictions: An integrated experimental and computational approach

Abstract

The optimized structure of title compound 3-(1H-imidazole-1-yl)-1-phenylpropan-1-ol (3HIP) was predicted according to the density functional theory (DFT) using the B3LYP method with 6-311G (d,p) basis set. Computed structural parameters of 3HIP were compared with X-ray diffraction data. Recorded and computed wavenumbers were assigned according to the total energy distribution (TED) using VEDA software. The natural bond orbital (NBO) analysis was used to characterize intramolecular rehybridization and delocalization of the electron density within the title molecule. Predictions of the NMR (1H and 13C) chemical shift assignments obtained by applying the gauge including atomic orbital (GIAO) approach were consistent with the corresponding experimental values. Ultraviolet-visible spectra of the title compound were simulated and validated experimentally. A molecular electrostatic potential (MEP) diagram visualized the electrophilic and nucleophilic sites of the 3HIP molecule. Hirshfeld surface analysis assessed the potential interactions of each atom inside the 3HIP molecule. Moreover, molecular docking analysis simulated the potential binding site pose of 3HIP within the active site of its target protein. The resulting 3HIP–target protein model can provide guidance for the development of new potent antifungal treatments.