THE SUBSTITUTION EFFECT ON THE AROMATICITY OF SOME N-PHENYLACETAMIDE DERIVATIVES: A DFT STUDY

Abstract

The relative aromaticity of some N-phenylacetamide (NPA) derivatives were investigated in which the NPA was substituted by NO2, CN, CF3, Br, Cl, F, H, CH3 , and NH2 groups at two meta and para positions. For this purpose, density functional theory calculations were applied at the B3LYP/6-31+G(d,p) level to calculate the aromaticity indices including nucleus independent chemical shift (NICS), harmonic oscillator model of aromaticity (HOMA) and harmonic oscillator model of electron delocalization (HOMED). The obtained results indicated that the aromaticity of derivatives decreased in the order of NO 2 > CN > CF 3 > Br > Cl > F > H > CH 3 > NH 2 for both meta and para positions. Furthermore, the resulting order was directly related to the electron withdrawing and electron releasing strengths of the substituents. Finally, it was found that all the aromaticity indices of have a good correlation with the Hammett constant.