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KMID : 1059520210650050309
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Journal of the Korean Chemical Society
2021 Volume.65 No. 5 p.309 ~ p.312
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Solvolysis of (1S)-(+)-Menthyl Chloroformate in Various Mixed Solvents
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Koh Han-Joong
Kang Suk-Jin
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Abstract
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The solvolysis of (1s)-(+)-menthyl chloroformate (1) were studied kinetically in 28 pure and various mixed solvents. The analysis using the extended Grunwald-Winstein equation in the solvolysis of 1 obtained the l value of 2.46 ± 0.18, the m value of 0.91 ± 0.07, and the correlation coefficient of 0.950. The solvolysis of 1 might proceed via an associative SN2 mechanism enhancing bond making than bond breaking in the transition state (TS). The value of l/m is 2.7 within the ranges of value found in associative SN2 reaction. This interpretation is further supported by a relatively large solvent kinetic isotope effect (SKIE, 2.16).
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KEYWORD
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(1s)-(+)-Menthyl chloroformate, Extended Grunwald-Winstein equation, Associative SN2 mechanism, Solvent kinetic isotope effect
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