
%0 Journal Article
%A Broxton, TJ 
%A Christie, JR 
%A Mannas, SM 
%T Micellar Catalysis of Organic-Reactions. XXI. A Comparison of the Catalytic Activity of Micelles of Cetyltrimethylammonium Bromide and Sulfate on Ester, Amide and Carbamate Hydrolyses
%J Australian Journal of Chemistry
%D 1988/03/01
%V 41
%N 3
%P 325-330
%K 
%R https://doi.org/10.1071/CH9880325
%U https://www.publish.csiro.au/paper/CH9880325 
%X The basic hydrolyses of phenyl acetate, N,4-dimethyl-N-(3&#8242;- nitrophenyl ) benzamide , methyl N-methyl-N-(4&#8242;-nitrophenyl) carbamate and methyl N-(3&#8242;,5&#8242;-dinitrophenyl)-N-methylcarbamate have been studied in cationic micelles of cetyltrimethylammonium bromide (ctab) and sulfate (ctas). Hydrolysis of phenyl acetate and the 4&#8242;-nitro carbamate, which involve rate-determining hydroxide attack, exhibit weak catalysis by both micelles, and the observed rates in each micelle are similar. The hydrolysis of the benzamide and the 3&#8242;,5&#8242;-dinitro carbamate, which involve rate determining C-N bond breaking, show larger catalysis, and, furthermore, micelles of ctab are more effective than micelles of ctas. The observed rates can be explained by the pseudo-phase kinetic model. For reactions involving rate-determining hydroxide attack, the calculated second-order rate constants in micelles of ctab and ctas are similar and much less than those for reaction in water. For reactions involving rate-determining C-N bond breaking the calculated second-order rate constants in micelles of ctab are greater than in micelles of ctas, and similar to those for reaction in water. 
