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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 18, Number 6
JKCSEZ 18(6)
December 20, 1974 

The Kinetics and Mechanism of Nucleophilic Addition of Hydrogen Cyanide to α-Cyano-β-piperonylacrylic Acid

α-Cyano-β-Piperonylacrylic Acid에 대한 Hydrogen Cyanide의 친핵성 첨가반응에 관한 연구
Ki-Sung Kwon, Tae-Rin Kim

권기성, 김태린
α-Cyano-β-piperonylacrylic acid(CPA)에 대한 hydorogen cyanide의 진핵성 첨가 반응속도 상수를 측정하여 넓은 pH범위에서 잘 맞는 반응 속도식을 구하였다. 이 식에 의하면 pH3이하에서는 CPA에 대해 hydrogen cyanide분자의 첨가 반응이 일어나지만 pH6에서 8사이는 hydrogen cyanide가 α-cyano-β-piperonyl acrylate ion에 첨가함을 알수 있고, 또 pH 3과 6사이에서는 이들 두 반응이 경쟁적으로 일어난다. 그리고 pH9이상에서는 α-cyano-β-piperonyl acrylate ion에 cyanide ion이 첨가하는 반응이 일어나며 pH3에서 9까지의 모든 복잡한 반응 메카니즘도 이식으로 충분히 설명할 수 있음을 알았다.

The rate constant of the addition of hydrogen cyanide to α-cyano-β-piperonylacrylic acid (CPA) were determined by UV spectrophotometry at various pH and a rate equation which can be applied over wide pH range was obtained. From this equation, one may conclude that below pH 3 the reaction is started by the addition of hydrogen cyanide molecule to CPA, however, at pH 6~8, hydrogen cyanide is added to α-cyano-β-piperonyl acrylate anion. From pH 3 to 6, these two reaction are competitive. Above pH 9, the reaction is proceeded by the addition of cyanide ion to α-cyano-β-piperonyl acrylate ion. From pH 3 to 9, the complex reaction mechanism can also be fully explained by the rate equation obtained.

423 - 429
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