Enhanced Method for the Synthesis and Comprehensive Characterization of 1‑(4-Phenylquinolin-2-yl)propan-1-one
Abstract
We present an enhanced method for synthesizing a
novel compound, 1-(4-phenylquinolin-2-yl)propan-1-one (3),
through the solvent-free Friedländer quinoline synthesis using
poly(phosphoric acid) as an assisting agent. The crystal structure of
compound 3 is analyzed using FT-IR, and the chemical shifts of its
1H- and 13C NMR spectra are measured and calculated using
B3LYP/6-311G(d,p), CAM-B3LYP/6-311G(d,p), and M06-2X/6-
311G(d,p) basis sets in the gas phase. Additionally, the optimized
geometry of quinoline 3 is compared with experimental X-ray
diffraction values. Through density functional theory calculations,
we explore various aspects of the compound’s properties, including
noncovalent interactions, Hirshfeld surface analysis, nonlinear
optical properties, thermodynamic properties, molecular electrostatic potential, and frontier molecular orbitals. These investigations
reveal chemically active sites within this quinoline derivative that contribute to its chemical reactivity.