Recognition in organized aggregates formed by a chiral amidic surfactant

Chiral discrimination of racemic 2-carboxy-2'-dodecyloxy-6-nitrobiphenyl by aqueous micelles of sodium N-dodecanoyl-L-prolinate was observed by IH NMR. 2D ROESY experiments show that the biphenylic system interacts preferentially with one of the two domains respectively formed by the E and Z isomers of sodium N-dodecanoyl-L-prolinate and that the biphenylic solute induces larger and more rigid aggregates. An estimate of the rotational barrier of the biphenylic system both in aggregating and in nonaggregating conditions has been carried out by dynamic NMR, and results are in good agreement with reported data obtained by racemization rates.