萘醌類化合物之合成及其酮基振動頻率之檢討

Synthesis of Naphthoquinone Derivatives and Study on its C=O Stretching Frequency

劉英玫(Ying-Mei Liu) ； 許順吉(Shuenn-Jyi Sheu)

《化學》 46卷4期 (1988/12) Pp. 266-272

https://doi.org/10.6623/chem.1988040

摘要

本文由1,4-萘醌的加成和消去反應合成化合物1~7，由2-甲基-1,4-萘醌的加成和消去反應合成化合物8∼10，而由1,5-二硝基苯的氧化和取代反應順利合成化合物11~14等共計十四個醌類化合物，其中化合物12和13為新化合物。這類化合物在1765~1640 cm^(-1)間之C＝O伸縮振動吸收頻率明顯地受取代基的體積效應和電子效應所支配，其中以與羥基形成分子內氫鍵時有最大的頻率變動，取代基能與醌基產生良好共振形式時，其頻率之減少次之。

並列摘要

Fourteen naphthoquinone derivatives had been synthesized via three routes: through a series of addition and elimination reactions, compounds 1-7 were synthesized from 1,4-naphthoquinone, and compound 8-10 were synthesized from 2-methyl- 1,4-naphthoquinone; and undergoing a oxidation and substitution reactions, compounds 11-14 were made from 1,5-dinitro- benzene. The C=O stretching vibration of these compounds were found in the region of 1765-1640 cm^(-1), and the detailed differences were discussed.