Abstract
Hammett σm and σp values have been determined for the phenyl-ONN-azoxy and phenyl-NNO-azoxy groups by measuring the pKa values of the phenylazoxybenzoic acids in 50% ethanol. The σp+ value for phenyl-ONN-azoxy has been evaluated both from the rate of solvolysis of 4-phenyl-ONN-azoxyphenyldimethylcarbinyl chloride in aqueous acetone, and from the rate of bromination by acidified hypobromous acid. The two values obtained differ markedly, and the variations are interpreted in terms of differences in the geometry of the transition states for the two reactions.
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Schedule a callMore From: Journal of the Chemical Society, Perkin Transactions 2
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