The aromatic nucleophilic substitutions of 4-dimethylamino-3-trifluoroacetylquinoline 1 with amines, thiols, and alcohols are elucidated on the basis of DFT calculations. Our calculation results suggest that the reaction of 1 with amines giving N-N exchanged products 4 occurs via Meisenheimer type adducts V whereas the ones with thiols and alcohols proceed via the enol type adducts VII and IX to afford N-S and N-O exchanged products 8 and 9, respectively. It is also clarified that the conditions required for the successful substitution are not controlled by the activation energies on these processes, but by the energy changes on the processes from 1 to each intermediates, V, VII, and IX.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.