Synthesis, characterization and spectral correlations in substituted styryl 6-methyl-2-naphthyl ketones

Abstract

Thirteen substituted styryl 6-methyl-2-naphthyl ketones [(2E)-1-(6-methyl-2-naphthyl)-3-phenyl-2-propen-1-ones] are synthesized using eco-friendly benign stereo selective crossed - aldol condensation reaction assisted by silica-sulphuric acid reagent under solvent-free conditions. The yield of chalcones is more than 90%. No decrease in the yield is observed during synthesis and demonstrating that silica-sulphuric acid can be reused in crossed-aldol condensation reaction without environmental discharge. They have been characterized by their physical constants, micro analysis, infrared, NMR and mass spectral data. These spectral data are subjected to correlate various Hammett substituent constants with single and multiparameter correlation equations. From the results of statistical analysis, the influence of electronic effects of substituents on the spectral data of carbonyl group, vinyl proton and carbons of the ketones are explained.