Synthesis, spectral studies, antimicrobial and insect antifeedant activities of some substituted styryl 4′-fluorophenyl ketones

Abstract

Good yield of some substituted styryl 4′-fluorophenyl ketones were synthesized by solvent free fly-ash:water catalyzed eco-friendly environmentally benign Aldol reaction. These chalcones were characterized by physical constants, micro analysis and spectral data. Antimicrobial and insect antifeedant activities were measured in all chalcones. The group frequencies of all chalcones like carbonyl stretches νCO, C–F and the deformation modes of vinyl part of CH– out of plane, in-plane, CHCH out of plane and >CC< out of plane (cm−1), the vinyl hydrogen and carbons δ(ppm) of Hα, Hβ, Cα, Cβ and CO were assigned and these frequencies were correlated with various kinds of substituent constants. 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 have been explained.

Keywords

• Environmentally benign reaction
• 4′-Fluorophenyl chalcones
• IR and NMR spectra
• Antimicrobial and insect antifeedant activities
• Hammett correlation