Calfuman, KarlaGallardo, SebastianContreras, RenatoTapia, RicardoCampodónico, Paola2018-01-182018-01-182017New J. Chem., 2017,41, 12671-12677http://hdl.handle.net/11447/1921http://dx.doi.org/10.1039/C7NJ02708GReaction mechanism in aromatic nucleophilic substitution reactions is discussed using kinetic study complemented with quantum chemical calculations. The model system is the reaction of a series of biothiols toward atrazine (ATZ) in aqueous media. The proposed reaction mechanism discloses a non-catalyzed pathway and the presence of a deprotonated (thiolate) nucleophile in water suggests that the reaction mechanism is borderline between a stepwise route and a concerted process. The full analysis of the potential energy surface reinforces the addition/elimination mechanism. Despite of numerous attempts to locate transition structures associated with the leaving group departure were unsuccessful, presumably because this step is extremely fast.7en-USSNAr reactionatrazineendogenous thiolsMechanism for the SNAr reaction of atrazine with endogenous thiols: experimental and theoretical studyArtÃculo