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

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.

SUBMITTER: Campodonico PR

PROVIDER: S-EPMC8847609 | biostudies-literature | 2021

REPOSITORIES: biostudies-literature

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

Campodónico Paola R PR Tapia Ricardo A RA Suárez-Rozas Cristian C

Frontiers in chemistry 20220202

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 bon ...[more]

PMID: 35186890

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