Pronounced Self-Induced Diastereomeric Anisochronism in Anisidine Amino Acid Diamides.

ABSTRACT

The emergent properties resulting from selective supramolecular interactions are of significant importance for materials and chemical systems. For the directed use of such properties, a fundamental understanding of the interaction mechanism and the resulting mode of function is necessary for a tailored design. The self-induced diastereomeric anisochronism effect (SIDA), which occurs in the intermolecular interaction of chiral molecules, generates unique properties such as chiral self-recognition and nonlinear effects. Here we show that anisidine amino acid diamides lead to extraordinary signal splitting in NMR spectra through supramolecular interaction and homochiral self-recognition. By systematic experiments we have investigated the underlying SIDA effect, explored its limits and finally successfully utilized it in the determination of enantiomeric ratios by NMR spectroscopy of chiral 'SIDA-inactive' compounds such as thalidomide.