
TY  - JOUR
A1  - Broxton, TJ 
A1  - Christie, JR 
A1  - Mannas, SM 
T1  - 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
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1988
VL  - 41
IS  - 3
SP  - 325
EP  - 330
KW  - 
UR  - https://doi.org/10.1071/CH9880325 
N2  - 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. 
ER  -

