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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 21, Number 4
JKCSEZ 21(4)
August 20, 1977 

Nucleophilic Displacement at Sulfur Center (Ⅸ). Solvolysis of Naphthalene Sulfonyl Chlorides in Acetone Water Mixtures

황의 친핵성 치환반응 (제9보). 물-아세톤 혼합용매 속에서 1-염화 및 2-염화나프탈렌 술포닐의 가용매 분해반응
Tae Seop Uhm, Ikchoon Lee, Euk Suk Lee

엄태섭, 이익춘, 이억석
1-염화 및 2-염화나프탈렌술포닐의 가용매 분해반응을 아세톤-물혼합용매속에서 전기전도도법으로 실시하여 여러가지 용매 파라미터 및 활성화파라미터와 관련지워 용매효과와 반응 메카니즘을 논의하였다. 반응은 Sn2 메카니즘으로 진행되나 물함량이 크면 bond-breaking이 약간 증가한다. 또한 바닥상태 안정화효과와 천이상태에서의 peri-hydrogen효과 때문에 2-나프탈렌 화합물의 반응속도가 1-나프탈렌 화합물의 반응속도보다 빨랐으며 이 효과는 에탄올-물 혼합용매속에서와 비슷하였다.

The solvolysis of 1-naphthalene-and 2-naphthalenesulfonyl chlorides in acetone-water mixtures have been studied by means of conductometry. The solvent effect and mechanism have been discussed in terms of variation in solvent composition and activation parameters. The reaction was predominantly SN2 type, but bond breaking increased with the increase of water content. The rate constant for 1-naphthyl compound was smaller than that of 2-naphthyl compound due to the ground state stabilization effect and peri-hydrogen effect, and the latter effect was similar to that in ethanol-water mixtures.

262 - 269
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