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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 62, Number 4
JKCSEZ 62(4)
August 20, 2018 

Analysis of the Solvolysis of Anthraquinone-2-Carbonyl Chloride in Various Mixed Solvents
Han Joong Koh*, Suk Jin Kang
Anthraquinone-2-carbonyl chloride, Extended Grunwald-Winstein equation, Associative SN2 mechanism, Solvent kinetic isotope effect
The solvolyses of anthraquinone-2-carbonyl chloride (1) were studied kinetically in 27 pure and various mixed solvents. The analysis using the extended Grunwald-Winstein equation in the solvolyses of anthraquinone-2-carbonyl chloride (1) obtained the l value of 2.11 ± 0.11, the m value of 0.54 ± 0.06, and the correlation coefficient of 0.955. The solvolysis reaction of 1 might proceed via an associative SN2 mechanism enhancing bond making than bond breaking in the transition state (TS). This interpretation is further supported by a relatively large solvent kinetic isotope effect (SKIE, 2.27).
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