Nucleophilic Substitution Reaction of Imidazole with Various 2-Bromo-1-arylethanone Derivatives: A Computational Study

Abstract

In this study, it was intended to investigate the reactions between imidazole and 2-bromo-1-arylethanones such as 2-bromoacetophenone, 2-bromo-1-(4-chlorophenyl)ethan-1-one, 2-bromo-1-(2,4-dichlorophenyl)ethan-1-one and 2-bromo-1-(furan-2-yl)ethan-1-one, computationally. In the study, some Density Functional Theory (DFT) calculations have been performed on the chemical species involved in the investigated chemical reactions. DFT calculations have been performed at DFT B3LYP (Becke, three-parameter, Lee-Yang-Parr) level of theory using 6-31G(d), 6-31G(d,p), 6-311G(d,p) and 6-311+G(2d,p) basis sets. Single Point Energy (SPE) calculations, geometry optimizations, vibrational analysis, Frontier Molecular Orbital (FMO) calculations, global reactivity descriptor determinations, Molecular Electrostatic Potential (MEP) map calculations and estimation of the nuclear magnetic shielding tensors have been carried out at the same levels of theory. In 1H-NMR calculations, CSGT (Continuous Set of Gauge Transformations) and GIAO (Gauge-Independent Atomic Orbital) models were used and experimental data have been compared with the computationally obtained data.