Chiral Recognition and Molecular Interaction in Cellulose Derivatives

Article abstract of DOI:10.1021/j100193a020

Nineteen 1,3-bis(aryl)propane derivatives and six model compounds with a single chromophore were used to explore the chiral discrimination ability of cellulose derivatives, in particular cellulose triphenylcarbamate (CTC), in connection with the mode of interaction of these probe molecules with adsorbents.The interaction was evaluated by conformational analysis of the probe molecules and circular dichroism.The 1,3-bis(aryl)propanes with 9-anthryl moieties possessed a highly limited conformation owing to the bulky substituent and hardly changed their shape on CTCas evidenced by CD spectra; thus, they may be regarded as "rigid" substrates.However, these "rigid" substrates were resolved quite effectively.On the other hand, those with 2-naphthyl moieties possessed a number of stable conformations and could change their shape in diastereomeric complexes on CTC; thus, they may be assumed as "soft" substrates, against which the chiral discrimination was inefficient.The present study revealed that the optical resolution may be interpreted at least partly in terms of the "rigid" and "soft" concept.