Kinetic and theoretical study on nucleofugality in the phenolysis of 3-nitrophenyl and 4-nitrophenyl 4-cyanophenyl thionocarbonates
No hay miniatura disponible
Fecha
2013
Autores
Castro, Enrique
Cañete, Alvaro
Campodónico, Paola
Cepeda, Marjorie
Pavez, Paulina
Contreras, Renato
Santos, Jose
Título de la revista
ISSN de la revista
Título del volumen
Editor
Elsevier
Resumen
The 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.
Descripción
Centro de Química Médica
Palabras clave
phenolysis , nucleofugality , 3-nitrophenyl , thionocarbonates , Kinetic / theoretical study
Citación
Chemical Physics Letters Volume 572, 30 May 2013, Pages 130–135