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Updated: Oct 3, 2025

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How the Nature of an Alpha-Nucleophile Determines a Brønsted Type-Plot and Its Reaction Pathways. An Experimental
Paola R Campodónico1, Ricardo A Tapia2, Cristian Suárez-Rozas1
1Centro de Química Médica, Instituto de Ciencias e Innovación en Medicina, Clínica Alemana Universidad del Desarrollo, Santiago, Chile.
Abstract:
The reactions between 2-chloro-5-nitro pyrimidine with a serie of α-nucleophile derivatives were kinetically evaluated. The kinetic study was carried out in aqueous media and the data shown an unusual split on the Brønsted type-plot, opening a controversial discussion based on reactivities and possible reaction pathways. These split Brønsted type-plots are discussed over the hypothetical transition state (TS) structures associated to concerted or stepwise mechanisms with emphasis on hydrogen bond interactions between electrophile/nucleophile pair able to determine the reactivities and the plausible reaction routes.
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