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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 34, Number 9
BKCSDE 34(9)
September 20, 2013 

Correlation of the Rates of Solvolysis of Electron-Rich Benzoyl Chloride Using the Extended Grunwald-Wistein Equation
Hyunjung Oh, Hojune Choi, Jong Keun Park, Kiyull Yang, In Sun Koo*
Piperonyloyl chloride, Extended Grunwald-Winstein equation, SN1 mechanism, Solvent kinetic isotope effect, Product selectivity
The solvolysis rate constants of piperonyloyl chloride (1) in 27 different solvents are well correlated with the extended Grunwald-Winstein equation, using the NT solvent nucleophilicity scale, YCl solvent ionizing scale, and I aromatic ring parameter with sensitivity values of 0.30 ± 0.05, 0.71 ± 0.02, and 0.60 ± 0.04 for l, m, and h, respectively. The solvent kinetic isotope effect values (SKIE, kMeOH/kMeOD and k50%MeOD-50%D2O) of 1.16 and 1.12 were also in accord with the values for the SN1 mechanism and/or the dissociative SN2 mechanism. The product selectivity values (S) for solvolysis of 1 in alcohol/water mixtures were in the range of 0.5 to 1.9, which is also consistent with the proposed unimolecular ionization mechanism.
2697 - 2701
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