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Nonlinear structure–reactivity correlations. The hydrolysis of 2,4,6-trinitrophenyl acetate catalyzed by general bases

✍ Scribed by Rita H. De Rossi; Alberto Nuñez

Book ID: 102927870
Publisher: John Wiley and Sons
Year: 1983
Tongue: English
Weight: 505 KB
Volume: 15
Category: Article
ISSN: 0538-8066
DOI: 10.1002/kin.550151013

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✦ Synopsis

The hydrolysis of 2,4,6-trinitrophenyl acetate was studied in the presence of several carboxylic bases and tertiary amines. Carboxylic bases pyridine and imidazole react as nucleophilic catalysts, while 2,4-dimethyl and 2,4,6-trimethyl pyridine react as general-base catalysts. The nonlinear structure-reactivity correlations (log h,,t versus log k o ~ and log h,,, versus pK of the leaving group) for the series of aryl acetates are discussed, and it is suggested that there is a change in transition-state structure along the series.

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