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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 41, Number 3
JKCSEZ 41(3)
June 20, 1997 

Acid-Catalyzed Hydrolysis Mechanism of 3,3-Bis(methylthio)-2-propen-1-phenyl-1-one Derivatives

3,3-Bis(methylthio)-2-propen-1-phenyl-1-one 유도체들의 산-촉매 가수분해 반응 메카니즘
Ki-Sung Kwon, Chan-Hun Park, Nack-Do Sung

30℃의 센(-Ho < 2.23) 과염소산 수용액 속에서 3,3-bis(methylthio)-2-propen-1-phenyl-1-one 유도체들의 산-촉매 가수분해 반응을 속도론적으로 연구하였다. 치환기 효과, 가수분해 생성물의 분석, Bunnett식 및 Bunnett-Olsen식의 hydration 파라미터(ω 및 ø)로부터 3.8M 이하의 묽은 산 용액에서는 A-1형 반응(3.3 > ω, 0.58 > ø 및 ρ < 0)이 그리고 3.8M 이상의 진한 산 용액에서는 A-2형 반응(0 < ω, 0 < ø 및 ρ > 0)메카니즘으로 산-촉매 가수분해 반응이 일어난다.

Acid-catalyzed hydrolysis of 3,3-bis(methylthio)-2-propen-1-phenyl-1-one derivatives were studied kinetically in concentrated aqueous hydroperchloric acid(-Ho < 2.23) at 30℃. The substituent effect, analysis of hydrolysis product, hydration parameter(ω & ø) from the Bunnett equation and the Bunnett-Olsen equation on the rate indicate that the acid-catalyzed hydrolysis of the substrates below 3.8 M hydroperchloric acid media occurs through A-1 type reaction(3.3 > ω, 0.58 > ø & ρ < 0) mechanism and above 3.8 M hydroperchloric acid, the reaction proceeds A-2 type reaction(0 < ω, 0 < ø & ρ > 0) mechanism.

138 - 143
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