Synthesis, Crystal Structure, Hirshfeld Surface Analysis, Spectral Characterization, and Quantum Computational Evaluation of (E)-2

Abstract

A newly synthesized compound, (E)-2-(((4-bromophenyl)imino)methyl)-6-methylphenol (C14H12BrNO), is analyzed in detail for structural clarification by experimental X-ray, Fourier transform IR, H-1 and C-13 NMR, and UV-vis spectral data along with theoretical quantum chemical computations. For the theoretical computations, the density functional theory B3LYP functional and 6-311++G (d,p) basis set were used in the gas phase, and the harmonic vibrational wavenumbers were assigned with the help of the potential energy distribution. The theoretical NMR spectra were obtained with the gauge-including atomic orbital (GIAO) method and for the UV-vis spectrum time-dependent density functional theory based on the integral equation formalism polarizable continuum model (IEFPCM) was used. By Hirshfeld surface analysis, the most important contributions were obtained for the crystal packing, and the possible contact points were determined. In addition, frontier molecular orbital (highest occupied molecular orbital-lowest unoccupied molecular orbital), molecular electrostatic potential, and nonlinear optical analyses were performed for the calculated optimized structure. Finally, molecular docking between (E)-2-(((4-bromophenyl)imino)methyl)-6-methylphenol and two different receptors (ubiquinolcytochrome c reductase [Protein Data Bank ID 1BE3] and glucan endo-1,6-beta-glucosidase [Protein Data Bank ID5NGL]) was studied. From the results, (E)-2-(((4-bromophenyl)imino)methyl)-6-methylphenol was determined to be a good ubiquinol-cytochrome c reductase inhibitor because of its binding energy and affinity for protein active sites.