Free-radical reductions of arenediazonium ions in aqueous solution. Part III. Kinetics of reactions of toluene-p-diazonium ions with ethanol, propan-2-ol, and acetaldehyde
- 1 January 1975
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 7,p. 751-755
- https://doi.org/10.1039/p29750000751
Abstract
The kinetics of the radiation induced chain reaction between toluene-p-diazonium ions (ArN2 +) and the reducing agents ethanol, propan-2-ol, and acetaldehyde (RH2) is consistent with a mechanism involving both α- and β-hydrogen abstraction from RH2 by the p-tolyl radical. The ratio kα/kβ for these reactions has been determined for each of the reducing agents above. α-ṘH Radicals reduce diazonium ions and propagate the chain. β-ṘH Radicals react either with RH2 to give α-ṘH radicals [reaction (11)] or with ArN2 + in a chain-terminating step [reaction (12)]. The rate constant ratios k11/k12 have been determined and the ratio is larger for acetaldehyde than for the alcohols. The reasons for this and the nature of reaction (12) are discussed, and it is postulated that the β-ṘH radicals add to the terminal nitrogen of the diazonium ions.Keywords
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