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Dediazoniations of arenediazonium ions part 25 Influence of Substituents on the Exchange of the Diazonio Group for External Molecular Nitrogen and on the N(α), N(β)-Rearrangement in the Diazonio Group
The N(α), N(β)‐rearrangement of the two N‐atoms which can be observed in solutions of [β‐15N]‐labelled p‐substituted benzenediazonium ions follows dual substituent parameter treatments. The reaction yields a negative field and a positive resonance reaction constant (pF =−3.35, pR = 2.47). The magnitude of these constants is, within experimental error, the same as the respective reaction constants for solvolytic dediazoniation. The exchange of the diazonio group of 15N‐labelled p‐substituted benzenediazonium ion yields, however, field and resonance reaction constants which are close to zero. This result is attributed to cancellation of the reaction constants for the forward and reverse steps in the complex mechanism of the exchange reaction.