Hydrogen bond contribution to preferential solvation in SNAr reactions
Date
2013
Type:
Artículo
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8
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Publisher
ACS Publications
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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.
Description
Centro de Química Médica
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Citation
J. Phys. Chem. B, 2013, 117 (19), pp 5908–5915
Keywords
SNAr Reactions, Hydrogen, kinetic study