THE EFFECT OF AMPHIPHILIC LIQUID CRYSTALLINE SOLVENTS ON THE HYDROLYSIS OF BENZYLIDENE t-BUTYLAMINE N-OXIDE

The rate of hydrolysis of benzylidene t-butylamine N-oxide decreases as the concen- tration of dodecylammonium chloride in water increases until molar concentrations are reached. At these concentrations a maximum inhibition in the rate of hydrolysis is reached which corres- ponds to the formation of the lamellar mesophase. This maximum inhibition, caused by the lamellar structure, appears to be due to long-range electrostatic effects upon the protonated intermediates of the reaction. 1. Introduction. - Anisotropic media orient solute molecules in solution altering rates of reaction, stereochemistry and the ratio of products (l). A major part of the studies investigating the role of anisotropic media on chemical reactions utilize thermotropic liquid crystalline media and only a few investigations are reported with lyotropic liquid crystalline sol- vents (2,3). Furthermore, most of the studies reported include buffer systems within the lyotropic media that may be responsible for altering the texture of the liquid crystalline media.