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

Authors : Taner ERDOĞAN, Fatma OĞUZ ERDOĞAN

Pages : 322-332

Doi:10.16984/saufenbilder.418343

View : 24 | Download : 10

Publication Date : 2019-06-01

Article Type : Research Paper

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