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KMID : 1059519900340030221
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Journal of the Korean Chemical Society
1990 Volume.34 No. 3 p.221 ~ p.226
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Solvolysis of Substituted Phenacyl Tosylates
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Park Byung-Soo
Kim Sung-Hong
Yoh Soo-Dong
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Abstract
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The solvolysis of substitued phenacyl tosylates was studied in binary solvent mixtures of methanol-acetonitrile and methanol-acetone at 55℃. Except for m-nitrophenacyl tosylate, the rate constants were increased with both of electron-donating substituents and electron-withdrawing ones and its rate constants were the largest in the binary solvent mixtures of 90% MeOH-10% MeCN. The results show that the reactions were changed with dissociative SN2 mechanism judging from the magnitude of 1/m values going from the electron-withdrawing group to the electron-donating one of the substrate. And above results were consisted with the account for the PES model and QM approach.
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KEYWORD
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