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


Vol. 52,  No. 4, pp. 369-379, Aug.  2008
10.5012/jkcs.2008.52.4.369


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  Abstract

치환된 styryl 4-methyl-1-naphthyl ketones [(2E)-1-(4-methyl-1-naphthyl)-3-phenyl-2-propen-1-ones]의 계열은 오븐에서 친환경 촉매 Si2-2S4를 사용하여 solvent free하에서 환경친화적으로 합성되었다. 촉매 실리카는 재사용이 가 능하고 chalcones의 수율이 거의 90%이상이다. 이물질을 물리적인 상수, micro분석, 적외선 스펙트럼과1H와 13C NMR 스 펙트럼, mass 스펙트럼 데이터를 통해 구조분석 하였다. 카르보닐기의 s-시스와 s-트란스의 진동, CH의 평면내와 평면외의 진동, -CH=CH-의 평면외, >C=C< 평면외, vinyl부분의 평면외 진동 피크를 적외선 스펙트럼으로 분석하였고, NMR을 이 용하여 에틸렌의 수소/탄소 및 카르보닐 탄소의 피크를 확인하였다. 이 스펙트럼 데이터는 다양한 Hammett 치환상수와 연 관이 있다. 카르보닐기에서 치환기 효과의 통계적인 분석의 결과로부터 α, β 수소/탄소 및 그들의 변형모드가 설명되어진다. 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 Si2-2S4 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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  Cite this article

[IEEE Style]

G. Thirunarayanan, "Synthesis and Spectral Linearity in Substituted Styryl 4-Methyl-1-naphthyl Ketones," Journal of the Korean Chemical Society, vol. 52, no. 4, pp. 369-379, 2008. DOI: 10.5012/jkcs.2008.52.4.369.

[ACM Style]

G. Thirunarayanan. 2008. Synthesis and Spectral Linearity in Substituted Styryl 4-Methyl-1-naphthyl Ketones. Journal of the Korean Chemical Society, 52, 4, (2008), 369-379. DOI: 10.5012/jkcs.2008.52.4.369.

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ISSN(Print) 1017-2548
ISSN(Online) 2234-8530