Publications [#233387] of Andrew T. McPhail

Journal Articles

  1. Porter, NA; Ok, D; Huff, JB; Adams, CM; McPhail, AT; Kim, K, "Equilibration of Diastereomeric Two-Chain Surfactants. Hydrophobic Control of Organic Stereochemistry", Journal of the American Chemical SocietyMarch,, 1988, 110(6), 1896-1901, American Chemical Society (ACS) [Gateway.cgi], [doi].
    (last updated on 2025/07/05)

    Abstract:
    Four two-chain dicarboxylic acid surfactants linked with a carbonyl group were synthesized and studied. The compounds exist as meso and (±) diastereomers, and they form aggregates, presumably micelles, at concentrations >10−5 M. Equilibration of the diacids in benzene at 60 °C (p-toluenesulfonic acid catalyst) gives a 50/50 mixture of meso and (±) diastereomers. Equilibration of the diacids in aqueous base with or without added cosurfactants (CTAB, DDAB) gives mixtures favoring the meso diastereomer by as much as 90/10. This perturbation of diastereomeric equilibria is discussed in terms of hydrophobic enforcement of organic stereochemistry. © 1988, American Chemical Society. All rights reserved.