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Nonlinear structure–reactivity correlations. The hydrolysis of 2,4,6‐trinitrophenyl acetate catalyzed by general bases
Author(s) -
De Rossi Rita H.,
Nuñez Alberto
Publication year - 1983
Publication title -
international journal of chemical kinetics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.341
H-Index - 68
eISSN - 1097-4601
pISSN - 0538-8066
DOI - 10.1002/kin.550151013
Subject(s) - chemistry , reactivity (psychology) , pyridine , nucleophile , hydrolysis , imidazole , catalysis , aryl , medicinal chemistry , base (topology) , organic chemistry , medicine , mathematical analysis , alkyl , alternative medicine , mathematics , pathology
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 k cat versus log k OH and log k cat versus p K 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.