STEREOCHEMISTRY AND CURVATURE EFFECTS IN SUPRAMOLECULAR ORGANIZATION AND SEPARATION PROCESSES OF MICELLAR N-ALKYLALDONAMIDE MIXTURES

D- or L-configured glucon-, mannon-, and galactonamides bearing N-octyl or N-dodecyl substituents were mixed pairwise in a 1:1 molar ratio in aqueous solution and then converted to micellar fibers. By electron microscopy we observed chain length induced racemate resolution, formation of simple or complex hybrid structures or quantitative separation of individual fibers, as well as ideal mixing of the components within one fiber. Separations were traced back to stereochemical dissimilarities between the outer hydroxymethine groups of both components. Different lengths of the hydrophobic chains slowed fiber formation down and allowed the detection of intermediate micellar clusters. © 1990, American Chemical Society. All rights reserved.