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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 41, Number 6
JKCSEZ 41(6)
December 20, 1997 

Kinetics and Mechanism of the Hydrolysis of Diazidophenylmethane Derivatives

Diazidophenylmethane 유도체들의 가수분해반응 메카니즘에 대한 반응속도론적 연구
Ki-Sung Kwon, Jee-Hyung Seo, Yong-Gu Lee

Diazidophenylmethane 유도체들(X:p-H, p-OCH3, p-F, p-CH3)을 합성하여 25℃의 50:50(v/v) MeOH/H2O 혼합용매(μ=0.1:KCl)에서의 pH 변화에 따른 가수분해 반응 속도상수를 측정하여 유도된 반응속도식과 치환기효과, 용매효과, 염효과, 열역학적 활성화 파라미터, 그리고 생성물분석의 결과로부터 낮은 pH(0 ≤ pH < 2)에서는 Sn2CA, 중간 pH (2 < pH < 12)에서는 Sn1, 그리고 높은 pH(12 < pH ≤ 14)에서는 Sn2 반응메카니즘을 각각 제안하였다.

Diazidophenylmethane derivatives(X : p-H, p-OCH3, p-F, p-CH3) were synthesized and the rate constants of hydrolysis of diazidophenylmethane derivatives were determined by UV spectrophotometry in 50:50(v/v) aqueous methanol at 25 ℃. On the basis of rate equation, substituent effect, activation parameters, solvent effect, salt effect, and product analysis, it may be concluded that the hydrolysis of diazidophenylmethane derivatives proceed through SN2CA mechanism below pH 2.0, while above pH 12.0 through SN2 mechanism, and in the range of pH from 2 to 12 through SN1 mechanism respectively.

313 - 319
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