Journal of the Korean Chemical Society (대한화학회지)

Korean Chemical Society (대한화학회)
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Solvolysis of (1S)-(+)-Menthyl Chloroformate in Various Mixed Solvents

  • Koh, Han Joong (Department of Science Education, Jeonju National University of Education) ;
  • Kang, Suk Jin (Department of Science Education, Jeonju National University of Education)
  • Received : 2021.06.28
  • Accepted : 2021.07.21
  • Published : 2021.10.20
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Abstract

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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References

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