Synthesis and spectroscopic study of some new N-natphthyl substituted 2-phenylacetamides

Abstract

In a continuation of our previous works the conformations of new N-(1,2,3,4-tetrahydro-1-napthyl and 1,2,3,4-tetrahydro-2-napthyl) substituted 2-phenylacetamides, PhCH2CONHR, were investigated by vibrational, 1H n.m.r. and mass spectra. N-monosubstituted 2-phenylacetamides were obtained by using the known Schotten-Baumann reaction of acylation of synthetized amides with phenylacetic chloride. On the basis of IR-data for diluted solutions(concentration below 10-3 mol. dm-3) of N-monosubstituted 2-phenylacetamides in carbontetrachloride the exact position of N-H stretching band were established. The informations concerning the fragmentation routes, the effect of overall and partial structures as well as the influence of the amide group substituents on the fragmentation pattern, were obtained by the study of the metastable ions. The investigation of the mass spectra of the deuterium labelled and the comparison with the corresponding unlabelled compound, gave the fragmentation pattern of the various conformers. From IR, NMR and mass data it can be concluded that our synthetized N-naphthyl substituted 2-phenylacetamides exist in cis and trans form.