Computational description and kinetic properties based on density functional theory methods of the key step of the addition reaction between a model nucleophile and nitroaromatic ring in positions occupied by hydrogen are presented. A wide series of DFT functionals (PBE0, B3LYP, ωB97XD, M062X, PBE1PBE-D3, B3LYP-D3 and APFD) was used to track the influence of functional groups in nitroaromatic rings on reaction activation barriers. The comparison of experimentally determined relative rates of nucleophilic addition and their calculated thermodynamic counterparts at various positions in a series of