IR and NMR spectral studies of some 2-hydroxy-1-naphthyl chalcones: Assessment of substituent effects

Abstract

A series of substituted styryl 2-hydroxy-1-naphthyl ketones have been synthesized by crossed-Aldol condensation reaction. These ketones are characterized by their physical constants, IR and NMR data. The IR carbonyl stretching and deformation modes ν (cm−1) of vinyl portion frequencies and 1H and 13C NMR spectral chemical shifts δ (ppm) of ethylenic protons, carbons and carbonyl carbons are correlated with various Hammett sigma constants, field, and resonance and Swain–Lupton parameters by single and multi-regression analysis. From the statistical analysis the effect of substituents on the group frequencies is studied.