Ormazábal-Toledo, RodrigoContreras, RenatoCampodónico, Paola2017-04-102017-04-102013The Journal of Organic Chemistry, 2013, 78 (3):1091–1097http://hdl.handle.net/11447/1119http://dx.doi.org/10.1021/jo3025048Centro de Química MédicaWe herein report on the usefulness of the reactivity indices profiles along a reaction coordinate. The model is tested to fully describe the reaction mechanism of the title reactions. Group nucleophilicity and electrophilicity profiles help describe the bond-breaking/bond-formation processes and the intramolecular electron density reorganization. The reactivity indices’ profile analysis is consistently complemented with hydrogen bonding (HB) effects along the reaction coordinate: the final outcome of the reaction is determined by the stage at which the HB complex can be formed. Transition-state structures located for six reactions studied, including the charged nucleophile thiocyanate, show that the main stabilizing interaction is that formed between the hydrogen atom of the nucleophile and the o-NO2 group. This result discards the role of HB interaction between the nucleophile and the leaving group previously proposed in the literature.7en-USReactivity Indiceshydrogen bondingreaction coordinateArtículo