The reactions of methylbenzenes with 2,3-dichloro-5,6-dicyano-p-benzoquinone

Abstract

The rates of decay of the charge-transfer complexes formed between 2,3-dichloro-5,6-dicyano-p-benzoquinone and various methylated benzenes have been measured. The results are interpreted in terms of a monomolecular decomposition of the charge-transfer complex and/or a bimolecular reaction of free dichlorodicyanobenzoquinone with free hydrocarbon. The association constants for initial complex formation have been evaluated from the kinetic data. These agree with direct determinations from optical density measurements of initial absorption of solutions equimolar with respect to dichlorodicyanobenzoquinone and hydrocarbon, but there is disagreement with direct evaluations of association constant from optical measurements on solutions where the hydrocarbon is in large excess (Benesi Hildebrand method). The final products are 2,3-dichloro-5,6-dicyanoquinol mono- and di-ethers.