%0 Journal Article %1 castro2013kinetic %A Castro, E.A. %A Canete, A. %A Campodonico, P.R. %A Cepeda, M. %A Pavez, P. %A Contreras, R. %A Santos, J.G. %D 2013 %I 2013 Elsevier B.V. %J Chemical Physics Letters %K ability, aminolysis, carbonates, dqcauchile electronic elimination, ester geminal groups, interactions, leaving mechanism, quality, reactivity, scale %P 130-135 %R 10.1016/j.cplett.2013.04.002 %T Kinetic and Theoretical Study on Nucleofugality in the Phenolysis of 3-Nitrophenyl and 4-Nitrophenyl 4-Cyanophenyl Thionocarbonates %U /brokenurl#<Go to ISI>://WOS:000319332600025 %V 572 %X 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.

@article{castro2013kinetic, 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. }, added-at = {2019-12-04T03:57:35.000+0100}, author = {Castro, E.A. and Canete, A. and Campodonico, P.R. and Cepeda, M. and Pavez, P. and Contreras, R. and Santos, J.G.}, biburl = {https://www.bibsonomy.org/bibtex/289af2b1127d87ec1c060acb6c5ce7837/dqcauchile}, doi = {10.1016/j.cplett.2013.04.002}, interhash = {c9675681dddac022dceab4e967413f37}, intrahash = {89af2b1127d87ec1c060acb6c5ce7837}, issn = {0009-2614}, journal = {Chemical Physics Letters}, keywords = {ability, aminolysis, carbonates, dqcauchile electronic elimination, ester geminal groups, interactions, leaving mechanism, quality, reactivity, scale}, pages = {130-135}, publisher = {2013 Elsevier B.V.}, timestamp = {2019-12-04T04:29:21.000+0100}, title = {Kinetic and Theoretical Study on Nucleofugality in the Phenolysis of 3-Nitrophenyl and 4-Nitrophenyl 4-Cyanophenyl Thionocarbonates}, type = {Journal Article}, url = {/brokenurl#<Go to ISI>://WOS:000319332600025}, volume = 572, year = 2013 }