• Journal of the Korean Chemical Society
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• v.60 no.1
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• pp.16-20
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• 2016

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 N_T solvent nucleophilicity scale, Y_Cl 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 S_N2 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.