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

Enrique A. Castro, Alvaro Cañete, Paola R. Campodónico, Marjorie Cepeda, Paulina Pavez, Renato Contreras, José G. Santos

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)130-135
Number of pages6
JournalChemical Physics Letters
Volume572
DOIs
Publication statusPublished - 30 May 2013

ASJC Scopus subject areas

  • Physics and Astronomy(all)
  • Physical and Theoretical Chemistry

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