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http://dx.doi.org/10.5012/jkcs.2016.60.1.16

Studies of Solvolyses of Biphenyl-4-carbonyl Chloride by Extended Grunwald-Winstein Equation  

Choi, Hojune (Department of Chemistry Education and Research Instituted of Natural Science, Gyeongsang National University)
Koh, HanJoong (Department of Science Education, Jeonju National University of Education)
Yang, Kiyull (Department of Chemistry Education and Research Instituted of Natural Science, Gyeongsang National University)
Koo, InSun (Department of Chemistry Education and Research Instituted of Natural Science, Gyeongsang National University)
Publication Information
Journal of the Korean Chemical Society / v.60, no.1, 2016 , pp. 16-20 More about this Journal
Abstract
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.
Keywords
Biphenyl-4-carbonyl chloride; Extended Grunwald-Winstein equation; Dissociative SN2 mechanism;
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