Analysis of the Solvolysis of Anthraquinone-2-Carbonyl Chloride in Various Mixed Solvents
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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).
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 ± 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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