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Mechanism for SNAr reaction of atrazine and endogenous thiols: Experimental and theoretical study.

Abstract

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 of numerous attempts to locate transition structures associated with the leaving group departure were unsuccessful, presumably because this step is extremely fast.

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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, Accepted Manuscript
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    Mechanism for SNAr reaction of atrazine and endogenous thiols: Experimental and theoretical study.

    K. Calfumán, S. Gallardo-Fuentes, R. Contreras, R. Tapia and P. R. Campodonico, New J. Chem., 2017, Accepted Manuscript , DOI: 10.1039/C7NJ02708G

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