SYNTHESIS, SPECTROSCOPIC PROPERTIES, AND CRYSTAL STRUCTURE OF 1-NAPHTHYL(1-METHYLETHYLIDENE)IMINIUM CHLORIDE

Condensation of 1-naphthylamine with acetone in the presence of Et3N?HCl as a catalyst gave the corresponding 1-naphthyl (1-methylethylidene) iminium chloride (1). The salt was identified and characterized by multinuclear NMR (1H and 13C NMR) and IR spectroscopy. In solution, the two methylenic hydrogens of the N-isopropyl moiety are anisochronous. This result was confirmed by the X-ray investigation of 1 in the solid state. 1 crystallized in the orthorhombic space group Pbca, a = 10.8668(8)?, b = 11.1758(9) ?, c = 18.8726(18)?, ? = ? = ? = 90 ?, Z = 8. The structure was solved by direct methods, and retined by full-matrix least squares techniques to an R factor of 0.0308 for 1874 observed reflections. In the crystal the 1-naphthyl (1-methylethylidene) iminium cation and chloride anion are linked by N?H???Cl hydrogen bond.