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

Resultado de la investigación: Article

6 Citas (Scopus)

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.

Idioma originalEnglish
Páginas (desde-hasta)130-135
Número de páginas6
PublicaciónChemical Physics Letters
Volumen572
DOI
EstadoPublished - 30 may 2013

Huella dactilar

Kinetics
kinetics
4-nitrophenyl

ASJC Scopus subject areas

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

Citar esto

Castro, Enrique A. ; Cañete, Alvaro ; Campodónico, Paola R. ; Cepeda, Marjorie ; Pavez, Paulina ; Contreras, Renato ; Santos, José G. / Kinetic and theoretical study on nucleofugality in the phenolysis of 3-nitrophenyl and 4-nitrophenyl 4-cyanophenyl thionocarbonates. En: Chemical Physics Letters. 2013 ; Vol. 572. pp. 130-135.
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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.",
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Kinetic and theoretical study on nucleofugality in the phenolysis of 3-nitrophenyl and 4-nitrophenyl 4-cyanophenyl thionocarbonates. / Castro, Enrique A.; Cañete, Alvaro; Campodónico, Paola R.; Cepeda, Marjorie; Pavez, Paulina; Contreras, Renato; Santos, José G.

En: Chemical Physics Letters, Vol. 572, 30.05.2013, p. 130-135.

Resultado de la investigación: Article

TY - JOUR

T1 - Kinetic and theoretical study on nucleofugality in the phenolysis of 3-nitrophenyl and 4-nitrophenyl 4-cyanophenyl thionocarbonates

AU - Castro, Enrique A.

AU - Cañete, Alvaro

AU - Campodónico, Paola R.

AU - Cepeda, Marjorie

AU - Pavez, Paulina

AU - Contreras, Renato

AU - Santos, José G.

PY - 2013/5/30

Y1 - 2013/5/30

N2 - 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.

AB - 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.

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U2 - 10.1016/j.cplett.2013.04.002

DO - 10.1016/j.cplett.2013.04.002

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VL - 572

SP - 130

EP - 135

JO - Chemical Physics Letters

JF - Chemical Physics Letters

SN - 0009-2614

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