The Journal of Organic Chemistry

Determination of oxygen-18 exchange accompanying basic hydrolysis of p-toluamide and N, N-dimethyl-p-toluamide

H Slebocka-Tilk, RS Brown

Index: Slebocka-Tilk, H.; Brown, R. S. Journal of Organic Chemistry, 1988 , vol. 53, # 6 p. 1153 - 1156

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Citation Number: 4

Abstract

The base-catalyzed hydrolysis and'* O-exchange rate constants for p-toluamide (IV) and N, N-dimethyl-ptoluamide (V) have been determined under pseudo-first-order conditions as a function of [OH-] at T= 100 OC, p= 1.0 M. Both sets of rate constants are linearly dependent on [OH-], and therefore the ratio of kex/khyd for IV and V does not change a~ a function of [OH-]. For IV and V the ratios me 3.5 f 0.2 and 0.11 f 0.007 respectively. The fact that V ...