Kinetic and theoretical study on nucleofugality in the phenolysis of 3-nitrophenyl and 4-nitrophenyl 4-cyanophenyl thionocarbonates
Date
2013
Type:
Artículo
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6
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ORCID:
Journal Title
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Volume Title
Publisher
Elsevier
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Abstract
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.
Description
Centro de Química Médica
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Citation
Chemical Physics Letters Volume 572, 30 May 2013, Pages 130–135
Keywords
phenolysis, nucleofugality, 3-nitrophenyl, thionocarbonates, Kinetic / theoretical study