Chiral discrimination of racemic 2,2'-diamino-6-(octanoyloxymethyl)biphenyl and 2,3'-diamino-6-(octanoyloxymethyl)biphenyl in micelles formed either by N-alkyl-NN-dimethyl-N-(S)-(1-phenyl)ethylammonium bromide or sodium N-dodecanoyl-L-prolinate has been investigated by H-1 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. (C) 2004 Elsevier Ltd. All rights reserved.
New biphenylic derivatives: synthesis, characterisation and enantiodiscrimination in chiral aggregates / Romana, Andreani; Cecilia, Bombelli; Stefano, Borocci; Juri, Lah; Giovanna, Mancini; Mencarelli, Paolo; Gorazd, Vesnaver; Villani, Claudio. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 15:6(2004), pp. 987-994. [10.1016/j.tetasy.2004.01.038]
New biphenylic derivatives: synthesis, characterisation and enantiodiscrimination in chiral aggregates
MENCARELLI, Paolo;VILLANI, Claudio
2004
Abstract
Chiral discrimination of racemic 2,2'-diamino-6-(octanoyloxymethyl)biphenyl and 2,3'-diamino-6-(octanoyloxymethyl)biphenyl in micelles formed either by N-alkyl-NN-dimethyl-N-(S)-(1-phenyl)ethylammonium bromide or sodium N-dodecanoyl-L-prolinate has been investigated by H-1 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. (C) 2004 Elsevier Ltd. All rights reserved.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
