Discrimination of the enantiomers of biphenylic derivatives in micellar aggregates formed by chiral amidic surfactants

The chirality of micellar aggregates formed by surfactants derived from l-proline was investigated by using two chiral biphenylic derivatives as probes of chirality. The investigation carried out by 1H NMR, circular dichroism, and HPLC on chiral phase demonstrates that chiral recognition may occur in sites of the aggregates far from the head-group stereogenic centers and it is due to interaction with a whole region of the aggregate rather than with a single monomer in the aggregate. Subtle changes of the structure of the monomer influence the aggregation properties of the surfactants and its expression of chirality.

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(2S)-N-Dodecyl-N,1,1-trimethylpyrrolidinium-2-carboxamide bromideC20H41BrN2O[α]D = −27.3 (c 1.75, MeOH)Absolute configuration: (S)