Experimental Analyses Emphasize the Stability of the Meisenheimer Complex in a S(N)Ar Reaction Toward Trends in Reaction Pathways

The mechanism of S(N)Ar reactions between 2-chloro-5-nitropyrimidine with primary and secondary alicyclic amines, respectively, have been studied by kinetic measurements. The kinetic data obtained in aqueous media opens a controversial discussion based on Brönsted-type plots analysis. The first appr...

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Detalles Bibliográficos
Autores principales: Campodónico, Paola R., Olivares, Belén, Tapia, Ricardo A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Frontiers Media S.A. 2020
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7366874/
https://www.ncbi.nlm.nih.gov/pubmed/32754575
http://dx.doi.org/10.3389/fchem.2020.00583
Descripción
Sumario:The mechanism of S(N)Ar reactions between 2-chloro-5-nitropyrimidine with primary and secondary alicyclic amines, respectively, have been studied by kinetic measurements. The kinetic data obtained in aqueous media opens a controversial discussion based on Brönsted-type plots analysis. The first approach based on the kinetic data reveals a non-catalyzed pathway. Then, the subtlety of the mathematical treatment of the kinetic data is discussed over a concerted or stepwise mechanism, respectively.

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