73823-09-3Relevant articles and documents
REACTIONS OF IMIDIC ACID DERIVATIVES WITH NUCLEOPHILIC REAGENTS. MECHANISM OF THE ALKALINE HYDROLISIS OF ARYL N-ARYLARENECARBOXIMIDATES
Prudchenko, A. P.,Drizhd, L. P.,Savelova, V. A.
, p. 1715 - 1719 (2007/10/02)
In the kinetics of the alkaline hydrolysis of aryl-N-phenylbenzimidates PhC(OArX) =NPh(I) in a water-dioxane mixture (1:1 by volume) and with a constant ionic strength in 0.2 M sodium perchlorate first order is observed in each of the reagents.The Hammett ρ and Bronsted β parameters with variation of the substituent in the leaving group are 1.6 and -0.35 respectively.The products from the hydrolysis of compounds (I) (X = 2,4-(NO2)2, 2-NO2-4-COCH3) are benzoic acid and substituted diphenylamines and, in the case of the derivatives of (I) benzanilide and the corresponding phenol.In spite of the different qualitative composition of the hydrolysis products the data for all the substituents (including the ortho substituents) satisfy the Hammett and Bronsted equations.The results are explained in terms of an addition-elimination stage mechanism with the formation of a tetrahedral intermediate product in the rate-determining stage.
