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

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dc.contributor.author Calfuman, Karla
dc.contributor.author Gallardo, Sebastian
dc.contributor.author Contreras, Renato
dc.contributor.author Tapia, Ricardo
dc.contributor.author Campodonico, Paola
dc.date.accessioned 2018-01-18T17:04:40Z
dc.date.available 2018-01-18T17:04:40Z
dc.date.issued 2017
dc.identifier.citation New J. Chem., 2017,41, 12671-12677
dc.identifier.uri http://hdl.handle.net/11447/1921
dc.identifier.uri http://dx.doi.org/10.1039/C7NJ02708G
dc.description.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.
dc.format.extent 7
dc.language.iso en_US
dc.publisher Royal Society of Chemistry
dc.subject SNAr reaction
dc.subject atrazine
dc.subject endogenous thiols
dc.title Mechanism for the SNAr reaction of atrazine with endogenous thiols: experimental and theoretical study
dc.type Artículo


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