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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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
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author Campodónico, Paola R.
Olivares, Belén
Tapia, Ricardo A.
author_facet Campodónico, Paola R.
Olivares, Belén
Tapia, Ricardo A.
author_sort Campodónico, Paola R.
collection PubMed
description 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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spelling pubmed-73668742020-08-03 Experimental Analyses Emphasize the Stability of the Meisenheimer Complex in a S(N)Ar Reaction Toward Trends in Reaction Pathways Campodónico, Paola R. Olivares, Belén Tapia, Ricardo A. Front Chem Chemistry 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. Frontiers Media S.A. 2020-07-10 /pmc/articles/PMC7366874/ /pubmed/32754575 http://dx.doi.org/10.3389/fchem.2020.00583 Text en Copyright © 2020 Campodónico, Olivares and Tapia. http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.
spellingShingle Chemistry
Campodónico, Paola R.
Olivares, Belén
Tapia, Ricardo A.
Experimental Analyses Emphasize the Stability of the Meisenheimer Complex in a S(N)Ar Reaction Toward Trends in Reaction Pathways
title Experimental Analyses Emphasize the Stability of the Meisenheimer Complex in a S(N)Ar Reaction Toward Trends in Reaction Pathways
title_full Experimental Analyses Emphasize the Stability of the Meisenheimer Complex in a S(N)Ar Reaction Toward Trends in Reaction Pathways
title_fullStr Experimental Analyses Emphasize the Stability of the Meisenheimer Complex in a S(N)Ar Reaction Toward Trends in Reaction Pathways
title_full_unstemmed Experimental Analyses Emphasize the Stability of the Meisenheimer Complex in a S(N)Ar Reaction Toward Trends in Reaction Pathways
title_short Experimental Analyses Emphasize the Stability of the Meisenheimer Complex in a S(N)Ar Reaction Toward Trends in Reaction Pathways
title_sort experimental analyses emphasize the stability of the meisenheimer complex in a s(n)ar reaction toward trends in reaction pathways
topic Chemistry
url 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
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