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

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dc.contributor.authorCalfuman, Karla
dc.contributor.authorGallardo, Sebastian
dc.contributor.authorContreras, Renato
dc.contributor.authorTapia, Ricardo
dc.contributor.authorCampodónico, Paola
dc.date.accessioned2018-01-18T17:04:40Z
dc.date.available2018-01-18T17:04:40Z
dc.date.issued2017
dc.description.abstractReaction 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.extent7
dc.identifier.citationNew J. Chem., 2017,41, 12671-12677
dc.identifier.urihttp://hdl.handle.net/11447/1921
dc.identifier.urihttp://dx.doi.org/10.1039/C7NJ02708G
dc.language.isoen_US
dc.publisherRoyal Society of Chemistry
dc.subjectSNAr reaction
dc.subjectatrazine
dc.subjectendogenous thiols
dc.titleMechanism for the SNAr reaction of atrazine with endogenous thiols: experimental and theoretical study
dc.typeArtículo

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