As mentioned in the Kruszyk paper, ChemDraw predicts very similar chemical shifts for fluorobenzene and aniline. Since anilines are well-known to be highly reactive and fluorobenzenes generally are poor EAS substrates the impact of this ) is taken to be the bromination site in the parent compound (green circle) and corresponds to the quantitative yield obtained with NBS (black ring). b The three protonated isomers of N-methylimidazole and their PM3 free energies (kcal/mol) in chloroform. The middle isomer has a standard free energy that is within 1 kcal/mol of the left isomer, which has the lowest standard free energy. Therefore both protonated carbon atom are taken as most likely bromination sites in the parent compound (green circles). This is considered a correct prediction because one of the sites corresponds to that observed experimentally with NBS (black ring). The references to the experimental data can be found in Supplementary Information.