FTIR AND H-1-NMR SPECTRAL STUDY OF 3-(SUBSTITUTED BENZAMIDO)-5,6,7,8-TETRAHYDRO-5,8-METHANOISOQUINOLINES AND RELATED-COMPOUNDS

The title benzamide derivatives were synthesized. FTIR spectra of the benzamides having substituents p-NH2, p-OCH3, p-CH3 3, p-F, H 5, p-Cl, p-CF3, p-CN, p-NO2 9 and m-Cl 10 and their related compounds were measured in dilute n-heptane, CCl4, CHCl3 and CH2Cl2 solutions. H-1 NMR spectra of the benzamides were also measured in CDCl3 solution. Substituent effects on these spectra were investigated. The results were theoretically considered together with CNDO/2 calculation ones. Conformational analysis of 5 was carried out by the AMI method, and the results were compared with the X-ray structural data of 3, 5, 9 and 10. The intermolecular hydrogen bondings in crystals of the benzamides were examined based on the frequency shifts of their C = O stretching vibration bands.