title: Hydrogen bond contribution to preferential solvation in S(N)Ar reactions.
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.
authors.affiliation: Departamento de Química, Facultad de Ciencias, Universidad de Chile, Casilla 653, Santiago, Chile. rcontrer@uchile.cl
authors.forename: Rodrigo
authors.initials: R
authors.lastname: Ormazabal-Toledo
authors.forename: José G
authors.initials: JG
authors.lastname: Santos
authors.forename: Paulina
authors.initials: P
authors.lastname: Ríos
authors.forename: Enrique A
authors.initials: EA
authors.lastname: Castro
authors.forename: Paola R
authors.initials: PR
authors.lastname: Campodónico
authors.forename: Renato
authors.initials: R
authors.lastname: Contreras