%0 Journal Article %1 RN377 %A Calfuman, K. %A Gallardo-Fuentes, S. %A Contreras, R. %A Tapia, R.A. %A Campodonico, P.R. %D 2017 %J New Journal of Chemistry %K acetonitrile, aromatic-substitution dqcauchile ions, path protein, reactions, rings, sites, %N 21 %P 12671-12677 %R 10.1039/c7nj02708g %T Mechanism for the Snar Reaction of Atrazine with Endogenous Thiols: Experimental and Theoretical Study %U /brokenurl#<Go to ISI>://WOS:000413526200036 %V 41 %X 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.

@article{RN377, 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.}, added-at = {2019-12-04T03:57:35.000+0100}, author = {Calfuman, K. and Gallardo-Fuentes, S. and Contreras, R. and Tapia, R.A. and Campodonico, P.R.}, biburl = {https://www.bibsonomy.org/bibtex/27e142f4850abef7196f0f23966336cb0/dqcauchile}, doi = {10.1039/c7nj02708g}, interhash = {4d5999fc52ea5e8485bcddc603ed78c5}, intrahash = {7e142f4850abef7196f0f23966336cb0}, issn = {1144-0546}, journal = {New Journal of Chemistry}, keywords = {acetonitrile, aromatic-substitution dqcauchile ions, path protein, reactions, rings, sites,}, number = 21, pages = {12671-12677}, timestamp = {2019-12-04T03:58:17.000+0100}, title = {Mechanism for the Snar Reaction of Atrazine with Endogenous Thiols: Experimental and Theoretical Study}, type = {Journal Article}, url = {/brokenurl#<Go to ISI>://WOS:000413526200036}, volume = 41, year = 2017 }