摘要：

The isomer distribution in the non-catalytic chlorination of toluene in acetic acid at 25° has been determined to be 59.78% ortho, 0.48% meta and 39.74% para. The relative rate of chlorination of benzene and toluene under these conditions is 1.00/344. These data establish the partial rate factors for the non-catalytic chlorination of toluene to be of = 617, mf = 4.95 and pf = 820. Excellent agreement is observed between the observed rates of chlorination of the isomeric xylenes and the rates calculated using these partial rate factors. Chlorination of m-xylene yields 23.0% 2- and 77.0% 4-chloro-1,3-dimethylbenzene. The small discrepancy with the calculated values, 27.3% 2- and 72.7% 4-, is attributed to the "double ortho effect" accompanying substitution in the 2- position.

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