[NMR spectroscopy of selegiline and related compounds]

In the course of the 1H NMR investigation of Selegiline and compounds related to it, the 3J coupling constants of the protons of the alpha and the beta carbon of the beta-phenyl-ethylamine moiety were determined. The rotameric population around the single bond of the alpha and beta carbons were calculated from these values. It is discussed how substituents at the alpha-carbon atom, at the nitrogen atom and on the phenyl ring as well as the solvent influence the conformational equilibria. The optical purity of the samples were determined using chiral europium shift reagents, however different reagents have to be used for primary, secondary and tertiary amine derivatives. The coordination process between p-F-amphetamine and Eu(tcf)3 was studied in detail, the formation constant of the complex and the bound shifts were determined.