How the Nature of an Alpha-Nucleophile Determines a Brønsted Type-Plot and Its Reaction Pathways. An Experimental Study.

Front Chem

Centro de Química Médica, Instituto de Ciencias e Innovación en Medicina, Clínica Alemana Universidad del Desarrollo, Santiago, Chile.

Published: February 2022

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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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8847609PMC
http://dx.doi.org/10.3389/fchem.2021.740161DOI Listing

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