Solubilization and reaction studies of polar substrates in the presence of apolar octahydroxy reverse micelles

Abstract

Octahydroxy tetrameric cyclophane1 containing four cetyl chains was synthesized from resorcinol and cetanal under acidic conditions and was characterized by1HNMR,13CNMR, and elemental analysis. Cyclophane1 forms aggregates with CMC 7.1 × 10−5 M in a nonpolar solvent such as CCl4. The smaller molecule glycine is more solubilized than the bigger lysine, demonstrating size discrimination. The highly polar compounds aspartic acid and glutamic acid, however, required 1.5 mm of1 for solubilization at the detectable limit. Kinetic study of the oxidation of glycine by ninhydrin in the presence of1 revealed that the rate enhancement compares to that in an aqueous environment, whereas the reduction of crystal violet by Hanzchester shows a decrease in the rate over that in aqueous solution.