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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 50, Number 3
JKCSEZ 50(3)
June 20, 2006 

 
Title
Synthesis and Substituent Effects in Substituted Styryl 4-Methoxy-1-Naphthyl Ketones

다양한 치환기가 붙은 Styryl 4-Methoxy-1-Naphthyl Ketone의 합성과 치환기 효과에 관한 연구
Author
G. Thirunarayanan*, P. Ananthakrishna Nadar

G. Thirunarayanan*, P. Ananthakrishna Nadar
Keywords
합성, 치환기 효과, 적외선 분광법, 핵자기공명 분광법, 나프틸 칼콘 , Synthesis, Substituent Effects, Infrared Spectroscopy, NMR Spectroscopy, Naphthyl Chalcones
Abstract
초음파를 이용한 응축 반응을 이용하여 다양한 치환기가 붙은 4-methoxy-1-naphthyl ketone화합물들을 90% 이상의 높은 수율로 합성하였으며, 생성된 화합물물들을 미세 분석법, IR, 1H, 13C NMR 분석법 등을 이용하여 확인하였다. IR 스펙트럼에서 s-ciss-trans C=O stretching 모드를 확인하였으며, NMR 데이터로부터 에틸렌의 탄소와 수소에 대한 chemical shift를 확인하였다. 이러한 분광데이터를 이용하여 여러 분자들에 대한 Hammet 치환기 상수값 들을 얻을 수 있었으며, 이들로부터 가용매 분해반응에 미치는 치환기 효과를 해석할 수 있었다.

A series of substituted styryl 4-methoxy-1-naphthyl ketones [(2E)-1-(4-methoxy-1-naphthyl)-3-phenyl-2-propen-1-ones] were synthesized using facile method of microwave assisted condensation reaction. The yield of chalcones is more than 90%. They are characterized by their physical constants, micro analysis, infrared (KBr, 4000-400 cm-1) and NMR both 1H and 13C spectral data. From infrared spectra, the s-cis and s-trans stretching vibrations of carbonyl group, from NMR spectra the ethylenic proton and 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 and carbons are explained.

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