A protic ionic liquid, when entrapped in cationic reverse micelles, can be used as a suitable solvent for a bimolecular nucleophilic substitution reaction

CROSIO, MATÍAS A.; CORREA, N. MARIANO; SILBER, JUANA J.; FALCONE, R. DARÍO

ORGANIC & BIOMOLECULAR CHEMISTRY

ROYAL SOC CHEMISTRY

Lugar: CAMBRIDGE; Año: 2016 vol. 14 p. 3170 - 3170

1477-0520

n this work, we have explored how the confinement of the protic ionic liquid (IL) ethylammonium nitrate (EAN) inside toluene/benzyl-n-hexadecyldimethylammonium chloride (BHDC) reverse micelles (RMs) affects the Cl- nucleophilicity on the bimolecular nucleophilic substitution (SN2) reaction between this anion and dimethyl-4-nitrophenylsulfonium trifluoromethanesulfonate. To the best of our knowledge this is the first report where toluene/BHDC RMs use EAN as a polar component and it is used as a nanoreactor for carrying out kinetic experiments. Dynamic light scattering results reveal the formation of RMs containing the protic IL. The kinetic results show that upon confinement, EAN becomes a suitable solvent for the SN2 reaction while in homogeneous media it is a bad option. Entrapped in BHDC RMs, due to the strong hydrogen bond interactions, EAN behaves as an aprotic-like IL which cannot deactivate the nucleophilic power of Cl- and yet increases the substrate solubility. These facts sho