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Synthesis and Spectral Linearity in Substituted Styryl 4-Methyl-1-naphthyl Ketones

G. Thirunarayanan
대한화학회|2008.08|대한화학회지 (Journal of the Korean Chemical Society)|제52권 제4호|pp. 369-379

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참고문헌

키워드

Correlation Analysis연관 분석치환기 효과Substituent EffectsSolvent Free SynthesisSilica-sulphuric AcidStyryl Naphthyl KetonesIR and NMR SpectraSolvent free 합성황산실리카Styryl naphthyl ketonesIR and NMR 스펙트럼
주제분류화학

초록

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.

Abstract

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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