Journal
ORGANIC LETTERS
Volume 2, Issue 2, Pages 127-130Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol991215k
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[GRAPHICS] We have analyzed the different catalytic effects of surfactant aggregates upon the rate-determining hydroxide ion induced deprotonation reaction of 1. Vesicles are more effective catalysts than micelles, most likely providing a more apolar microenvironment at the substrate binding sites. We suggest that this leads to a catalytic reaction involving less strongly hydrated hydroxide ions. In the case of DODAB and DODAC vesicles, binding of cholesterol to the bilayer further increases the catalytic efficiency.
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