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.
%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
}