Chiral derivatives of 2-(1-naphthyl)-2-phenylacetic acid.

The spectral properties of diastereomeric esters and amides (1b-20b), derived from optically pure 2-(1-naphthyl)-2-phenylacetic acids (1-NPA), were systematically investigated. It was found that all compounds prepared exhibit the NMR spectral nonequivalence (Deltadelta) with regular sign distribution of particular groups according to the predicted model. Further, the analysis of data revealed that the phenyl ring is responsible for a shielding effect (upfield shift) instead of a naphthyl one. This conclusion is supported by the crystallographic analysis showing the almost ap-arrangement of the acid methine hydrogen atom and carbonyl group. In this arrangement, the phenyl ring faces toward the ester part of the molecule while the naphthyl one is orthogonal to the phenyl plane. Therefore, the mutual position of phenyl and alkyl groups with respect to the central molecule co-planarity thus determines the chemical shifts of the alcohol/amine substituents. The relative magnitude of the Deltadelta corresponds to those of Mosher's derivatives. (c) 2004 Wiley-Liss, Inc.