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KMID : 1059520160600010016
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Journal of the Korean Chemical Society
2016 Volume.60 No. 1 p.16 ~ p.20
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Studies of Solvolyses of Biphenyl-4-carbonyl Chloride by Extended Grunwald-Winstein Equation
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Choi Ho-Jun
Koh Han-Joong
Yang Ki-Yull
Koo In-Sun
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Abstract
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The solvolysis rate constants of biphenyl-4-carbonyl chloride (C6H5C6H5COCl, 1) in 19 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 0.31±0.10, 0.46±0.05, and 0.96±0.20 for l, m, and h, respectively. These l, m, and h values can be considered to support a dissciative SN2 reaction pathway. This interpretation is further supported by the activation parameters, i.e., relatively small positive ΔH‡ (15.3~16.1 kcal/mol) values and large negative ΔS‡ (-17.2~-20.0 cal/mol·K) values.
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KEYWORD
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Biphenyl-4-carbonyl chloride, Extended Grunwald-Winstein equation, Dissociative SN2 mechanism
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