Effects of alkyl chain lengths of gallates upon their distribution and reactivity towards diphenylpicryl hydracil radicals in Triton X‐100 micellar solutions

Abstract

AbstractThe reactivity of ethyl‐, propyl‐ and octylgallate towards diphenylpicryl hydracil radicals has been measured in homogeneous solution (ethanol) and in Triton X‐100 micellar solutions. Similar reactivities were measured in homogeneous solutions, indicating that the length of the alkyl chain does not influence the reactivity of the phenolic groups. On the other hand, different reactivities were measured in micellar solutions, particularly at low (5 mM) surfactant concentrations. Data obtained at different surfactant concentrations allow estimation of partitioning of the gallates and their intramicellar bimolecular rate constant. The values obtained indicate that all the observed differences in reactivity are attributable to differences in substrate partitioning between the micellar and aqueous pseudophases. In fact, similar values of the intramicellar rate constants were obtained, suggesting that the average location of the reactive groups inside the micelles is independent of the solute alkyl chain length. Copyright © 2009 John Wiley & Sons, Ltd.