%0 Journal Article %1 RN163 %A Ormazabal-Toledo, R. %A Santos, J.G. %A Rios, P. %A Castro, E.A. %A Campodonico, P.R. %A Contreras, R. %D 2013 %J Journal of Physical Chemistry B %K 2,4,6-trinitrophenyl acetonitrile, amines aromatic behavior, binary chemical dqcauchile ether, kinetics, mixtures, molecules, nucleophilic-substitution, piperidine, probes, solvent %N 19 %P 5908-5915 %R 10.1021/jp4005295 %T Hydrogen Bond Contribution to Preferential Solvation in Snar Reactions %U /brokenurl#<Go to ISI>://WOS:000319649800012 %V 117 %X Preferential solvation in aromatic nucleophilic substitution reactions is discussed using a kinetic study complemented with quantum chemical calculations. The model system is the reaction of a series of secondary alicyclic amines toward phenyl 2,4,6-trinitrophenyl ether in aqueous ethanol mixtures of different compositions. From solvent effect studies, it is found that only piperidine is sensitive to solvation effects, a result that may be traced to the polarity of the solvent composition in the ethanol/water mixture, which points to a specific electrophilic solvation in the aqueous phase.

@article{RN163, abstract = {Preferential solvation in aromatic nucleophilic substitution reactions is discussed using a kinetic study complemented with quantum chemical calculations. The model system is the reaction of a series of secondary alicyclic amines toward phenyl 2,4,6-trinitrophenyl ether in aqueous ethanol mixtures of different compositions. From solvent effect studies, it is found that only piperidine is sensitive to solvation effects, a result that may be traced to the polarity of the solvent composition in the ethanol/water mixture, which points to a specific electrophilic solvation in the aqueous phase.}, added-at = {2019-12-04T03:57:35.000+0100}, author = {Ormazabal-Toledo, R. and Santos, J.G. and Rios, P. and Castro, E.A. and Campodonico, P.R. and Contreras, R.}, biburl = {https://www.bibsonomy.org/bibtex/27db4fd08d6d6b24bf5b97acec7f11b49/dqcauchile}, doi = {10.1021/jp4005295}, interhash = {9b778fd53c280632446e1db123a94403}, intrahash = {7db4fd08d6d6b24bf5b97acec7f11b49}, issn = {1520-6106}, journal = {Journal of Physical Chemistry B}, keywords = {2,4,6-trinitrophenyl acetonitrile, amines aromatic behavior, binary chemical dqcauchile ether, kinetics, mixtures, molecules, nucleophilic-substitution, piperidine, probes, solvent}, number = 19, pages = {5908-5915}, timestamp = {2019-12-04T03:58:17.000+0100}, title = {Hydrogen Bond Contribution to Preferential Solvation in Snar Reactions}, type = {Journal Article}, url = {/brokenurl#<Go to ISI>://WOS:000319649800012}, volume = 117, year = 2013 }