
%0 Journal Article
%A O'Conner, CJ 
%A Ramage, RE 
%T Reactions of N-Aryl-4-chlorobenzamides in sulphuric acid
%J Australian Journal of Chemistry
%D 1977/03/01
%V 30
%N 3
%P 527-534
%K 
%R https://doi.org/10.1071/CH9770527
%U https://www.publish.csiro.au/paper/CH9770527 
%X Rate constants of reaction of 4-chloro-N-phenylbenzamide at 353 and 373 K, and of N-benzyl-4-chlorobenzamide at 373 K have been studied in aqueous sulphuric acid. The rate acidity profiles in <40% w/w H2SO4 show the typical bell shape normally observed for the A2 hydrolysis of amides. However, with increasing acidity there is competition from sulphonation on the N-aryl substituent and subsequent A 2 hydrolysis of the sulphonated intermediates. At >75% w/w H2SO4, sulphonated 4-chloro- N-phenylbenzamide is charred. At >52% w/w H2SO4, sulphonation of N- benzyl-4-chlorobenzamide ceases and is replaced by A 1 hydrolysis of the substrate. 
