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http://dx.doi.org/10.5012/jkcs.2018.62.4.265

Analysis of the Solvolysis of Anthraquinone-2-Carbonyl Chloride 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)
Publication Information
Journal of the Korean Chemical Society / v.62, no.4, 2018 , pp. 265-268 More about this Journal
Abstract
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 $2.11{\pm}0.11$, the m value of $0.54{\pm}0.06$, and the correlation coefficient of 0.955. The solvolysis reaction of 1 might proceed via an associative $S_N2$ 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).
Keywords
Anthraquinone-2-carbonyl chloride; Extended Grunwald-Winstein equation; Associative $S_N2$ mechanism; Solvent kinetic isotope effect;
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