New biphenylic derivatives: synthesis, characterisation and enantiodiscrimination in chiral aggregates

Chiral discrimination of racemic 2,2?-diamino-6-(octanoyloxymethyl)biphenyl and 2,3?-diamino-6-(octanoyloxymethyl)biphenyl in micelles formed either by N-alkyl-N,N-dimethyl-N-(S)-(1-phenyl)ethylammonium bromide or sodium N-dodecanoyl-l-prolinate has been investigated by 1H NMR spectroscopy. The rotational barrier of 2,3?-diamino-6-(octanoyloxymethyl)biphenyl has been evaluated by HPLC and by dynamic NMR. The rotational barrier of 2,3?-diamino-6-(acetoxymethyl)biphenyl was evaluated by theoretical calculations and compared with the experimental data relative to its analogue.