Hydrogen bond contribution to preferential solvation in S(N)Ar reactions.

Ormazabal-Toledo, Rodrigo; Santos, José G; Ríos, Paulina; Castro, Enrique A; Campodónico, Paola R; Contreras, Renato

Ormazabal-Toledo, Rodrigo; Santos, José G; Ríos, Paulina; Castro, Enrique A; Campodónico, Paola R; Contreras, Renato.

Afiliação

Ormazabal-Toledo R; Departamento de Química, Facultad de Ciencias, Universidad de Chile, Casilla 653, Santiago, Chile. rcontrer@uchile.cl

J Phys Chem B ; 117(19): 5908-15, 2013 May 16.

Article em En | MEDLINE | ID: mdl-23597183

RESUMO

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.

Texto completo

Adicionar na Minha BVS

Imprimir

XML

PubMed Links

Buscar no Google

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Revista: J Phys Chem B Assunto da revista: QUIMICA Ano de publicação: 2013 Tipo de documento: Article País de afiliação: Chile País de publicação: Estados Unidos

Texto completo

Adicionar na Minha BVS

Imprimir

XML

PubMed Links

Buscar no Google