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KMID : 1059520080520040369
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Journal of the Korean Chemical Society
2008 Volume.52 No. 4 p.369 ~ p.379
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Synthesis and Spectral Linearity in Substituted Styryl 4-Methyl-1-naphthyl Ketones
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G. Thirunarayanan
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Abstract
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A series of substituted styryl 4-methyl-1-naphthyl ketones [(2E)-1-(4-methyl-1-naphthyl)-3-phenyl-2-propen-1-ones] were synthesized eco-friendly under solvent free conditions using a green catalyst SiO2-H2SO4 in an oven. The catalyst silica is reusable and the yields of chalcones are more than 90%. They are characterized by their physical constants, micro analysis, infrared (KBr, 4000-400 cm-1) and NMR both 1H and 13C and Mass spectral data. From infrared spectra, the s-cis and s-trans vibrations of carbonyl group and deformation modes CH in-plane and out of plane, -CH=CH- out of plane and >C=C< out of plane of vinyl parts, from NMR spectra the ethylenic proton, carbons and carbonyl carbon chemical shifts (ppm) are assigned. These spectral data are correlated with various Hammett substituent constants. From the results of statistical analysis the effect of substituents on CO, α and β proton, carbons and deformation modes are explained.
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KEYWORD
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Solvent Free Synthesis, Silica-sulphuric Acid, Styryl Naphthyl Ketones, IR and NMR Spectra, Substituent Effects, Correlation Analysis
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