CD SPECTRA OF DIASTEREOMERIC α-ARYLETHYLAMIDES OF (–)-CAMPHANIC ACID

ABSTRACT

CD spectra of diastereomeric α-arylethylamides 2,3, 4,5 and 6,7 exhibit nearly enantiomorphic CD curves. Interchromophoric charge-transfer interaction between the aromatic and the amide chromophore is observed only in the amide nπ* band region. MM2 calculations suggest that in the lowest-energy conformer of all diastereomeric pairs the aromatic rings as the major chromophores have mirror image positions relative to the plane defined by the amide-lactone chromophoric system.

Keywords:

• CD spectra
• Interchromophoric interaction

ACKNOWLEDGMENTS

The authors are indebted to Dr. A. Lesac for her help with MM2 calculations. M. Hollosi acknowledges the support of OTKA TO22913, and V. Šunjic the support of Ministry of Science of Republic of Croatia, Project 980701. This collaboration was also supported through the co-operation between the Eötvös University of Budapest and University of Zagreb.