Experimental Analyses Emphasize the Stability of the Meisenheimer Complex in a SNAr Reaction Toward Trends in Reaction Pathways
The mechanism of SNAr 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 approa...
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Frontiers Media S.A.
2020-07-01
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| Series: | Frontiers in Chemistry |
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| Online Access: | https://www.frontiersin.org/article/10.3389/fchem.2020.00583/full |
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doaj-1cfe589ed919453b993c89327c9e83432020-11-25T02:59:55ZengFrontiers Media S.A.Frontiers in Chemistry2296-26462020-07-01810.3389/fchem.2020.00583488016Experimental Analyses Emphasize the Stability of the Meisenheimer Complex in a SNAr Reaction Toward Trends in Reaction PathwaysPaola R. Campodónico0Belén Olivares1Ricardo A. Tapia2Centro de Química Médica, Facultad de Medicina, Clínica Alemana Universidad del Desarrollo, Santiago, ChileCentro de Química Médica, Facultad de Medicina, Clínica Alemana Universidad del Desarrollo, Santiago, ChileFacultad de Química y Farmacia, Pontificia Universidad Católica de Chile, Santiago, ChileThe mechanism of SNAr 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.https://www.frontiersin.org/article/10.3389/fchem.2020.00583/fullSNAr reactionreaction mechanismBrönsted-type plotsborder mechanismsMeisenheimer complex |
| collection |
DOAJ |
| language |
English |
| format |
Article |
| sources |
DOAJ |
| author |
Paola R. Campodónico Belén Olivares Ricardo A. Tapia |
| spellingShingle |
Paola R. Campodónico Belén Olivares Ricardo A. Tapia Experimental Analyses Emphasize the Stability of the Meisenheimer Complex in a SNAr Reaction Toward Trends in Reaction Pathways Frontiers in Chemistry SNAr reaction reaction mechanism Brönsted-type plots border mechanisms Meisenheimer complex |
| author_facet |
Paola R. Campodónico Belén Olivares Ricardo A. Tapia |
| author_sort |
Paola R. Campodónico |
| title |
Experimental Analyses Emphasize the Stability of the Meisenheimer Complex in a SNAr Reaction Toward Trends in Reaction Pathways |
| title_short |
Experimental Analyses Emphasize the Stability of the Meisenheimer Complex in a SNAr Reaction Toward Trends in Reaction Pathways |
| title_full |
Experimental Analyses Emphasize the Stability of the Meisenheimer Complex in a SNAr Reaction Toward Trends in Reaction Pathways |
| title_fullStr |
Experimental Analyses Emphasize the Stability of the Meisenheimer Complex in a SNAr Reaction Toward Trends in Reaction Pathways |
| title_full_unstemmed |
Experimental Analyses Emphasize the Stability of the Meisenheimer Complex in a SNAr Reaction Toward Trends in Reaction Pathways |
| title_sort |
experimental analyses emphasize the stability of the meisenheimer complex in a snar reaction toward trends in reaction pathways |
| publisher |
Frontiers Media S.A. |
| series |
Frontiers in Chemistry |
| issn |
2296-2646 |
| publishDate |
2020-07-01 |
| description |
The mechanism of SNAr 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. |
| topic |
SNAr reaction reaction mechanism Brönsted-type plots border mechanisms Meisenheimer complex |
| url |
https://www.frontiersin.org/article/10.3389/fchem.2020.00583/full |
| work_keys_str_mv |
AT paolarcampodonico experimentalanalysesemphasizethestabilityofthemeisenheimercomplexinasnarreactiontowardtrendsinreactionpathways AT belenolivares experimentalanalysesemphasizethestabilityofthemeisenheimercomplexinasnarreactiontowardtrendsinreactionpathways AT ricardoatapia experimentalanalysesemphasizethestabilityofthemeisenheimercomplexinasnarreactiontowardtrendsinreactionpathways |
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