Computational Insights on Molecular Structure, Electronic Properties, and Chemical Reactivity of (E)-3-(4-Chlorophenyl)-1-(2-Hydroxyphenyl)Prop-2-en-1-one

Abstract

In the current examination, (E)-3-(4-chlorophenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one has been studied to investigate geometrical entities, electronic properties, and chemical reactivity viewpoints. To inspect structural, spectroscopic, and chemical reactivity aspects, density functional theory method (DFT) at B3LYP/6-311G(d,p) basis set has been employed. The (E)-3-(4-chlorophenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one has been synthesized and characterized by FT-IR, 1HNMR, and 13C NMR spectral techniques. The detailed investigation of bond lengths and bond angles is discussed to comprehend the geometrical framework. To explore its chemical behaviour, Mulliken atomic charges, molecular electrostatic potential surface, and electronic parameters are introduced. The imperative exploration of the electronic properties, such as HOMO and LUMO energies, was studied by the time-dependent DFT (TD-DFT) method. The dipole moment of the title molecule is 2.57 Debye with C1 point group symmetry. The most electropositive carbon and hydrogen atoms in the title molecule are C14 and H27 respectively. Amongst aromatic C=C, the C16-C18 is the longest, and C17-C19 is the shortest bond. The molecular electrostatic potential plot predicts the positive electrostatic potential is around hydrogen atoms. The vibrational assignments were made by comparing the experimental FT-IR absorption peaks with the scaled frequencies obtained using computational work. Besides, some significant thermochemical information is obtained using the same basis set using frequencies.