• Journal of the Korean Chemical Society
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• v.65 no.5
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• pp.309-312
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• 2021

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 S_N2 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 S_N2 reaction. This interpretation is further supported by a relatively large solvent kinetic isotope effect (SKIE, 2.16).