Kinetic and theoretical study on nucleofugality in the phenolysis of 3-nitrophenyl and 4-nitrophenyl 4-cyanophenyl thionocarbonates

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dc.contributor.authorCastro, Enrique
dc.contributor.authorCañete, Alvaro
dc.contributor.authorCampodónico, Paola
dc.contributor.authorCepeda, Marjorie
dc.contributor.authorPavez, Paulina
dc.contributor.authorContreras, Renato
dc.contributor.authorSantos, Jose
dc.date.accessioned2017-04-10T11:52:30Z
dc.date.available2017-04-10T11:52:30Z
dc.date.issued2013
dc.descriptionCentro de Química Médica
dc.description.abstractThe phenolysis of 3-nitrophenyl 4-cyanophenyl thionocarbonate (1) and 4-nitrophenyl 4-cyanophenyl thionocarbonate (2) are subjected to a kinetic investigation in order to evaluate the nucleofugality of the corresponding leaving groups. For the reaction of 2 only 4-nitrophenoxide is obtained as leaving group. For the reaction of 1 the nucleofugality ratio 3-nitrophenoxide/4-cyanophenoxide is 1/3 from the corresponding T− intermediate. Theoretical calculations confirm the experimental results. From these results it can be concluded that the non-leaving group affects the nucleofugality ratio.
dc.format.extent6
dc.identifier.citationChemical Physics Letters Volume 572, 30 May 2013, Pages 130–135
dc.identifier.urihttp://hdl.handle.net/11447/1117
dc.identifier.urihttp://dx.doi.org/10.1016/j.cplett.2013.04.002
dc.language.isoen_US
dc.publisherElsevier
dc.subjectphenolysis
dc.subjectnucleofugality
dc.subject3-nitrophenyl
dc.subjectthionocarbonates
dc.subjectKinetic / theoretical study
dc.titleKinetic and theoretical study on nucleofugality in the phenolysis of 3-nitrophenyl and 4-nitrophenyl 4-cyanophenyl thionocarbonates
dc.typeArtículo

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