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Issue 21, 2017
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Mechanism for the SNAr reaction of atrazine with endogenous thiols: experimental and theoretical study

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Abstract

The reaction mechanism in aromatic nucleophilic substitution reactions is discussed using kinetic study complemented with quantum chemical calculations. The model system is the reaction of a series of biothiols toward atrazine (ATZ) in aqueous media. The proposed reaction mechanism discloses a non-catalyzed pathway and the presence of a deprotonated (thiolate) nucleophile in water suggests that the reaction mechanism is borderline between a stepwise route and a concerted process. The full analysis of the potential energy surface reinforces the addition/elimination mechanism. Despite numerous attempts to locate transition structures associated with the leaving group departure, they were unsuccessful, presumably because this step is extremely fast.

Graphical abstract: Mechanism for the SNAr reaction of atrazine with endogenous thiols: experimental and theoretical study

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Publication details

The article was received on 24 Jul 2017, accepted on 12 Sep 2017 and first published on 13 Sep 2017


Article type: Paper
DOI: 10.1039/C7NJ02708G
Citation: New J. Chem., 2017,41, 12671-12677
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    Mechanism for the SNAr reaction of atrazine with endogenous thiols: experimental and theoretical study

    K. Calfumán, S. Gallardo-Fuentes, R. Contreras, R. A. Tapia and P. R. Campodónico, New J. Chem., 2017, 41, 12671
    DOI: 10.1039/C7NJ02708G

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