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Issue 3, 1996
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Kinetics and mechanism of the reaction of nitrous acid with 2,4-dinitrophenylhydrazine

Pierre Bernheim,  Agnes Dobos,  Anne M. M. Doherty,  Neil Haine  and  Geoffrey Stedman 

Abstract

Arylhydrazines react with excess nitrous acid to form mixtures of the diazonium ion and aryl azide. By use of the weakly basic 2,4-dinitrophenylhydrazine (DNP), pKa= 1.55, information about the mechanism of the diazotisation reaction has been obtained. Three successive stages can be observed. The initial reaction consists of parallel nitrosations by N2O3 and NO+ of the free base DNP at the terminal nitrogen. This is followed by a stage with the rate independent of [HNO2], almost certainly a tautomerisation, probably to form ArN[double bond, length half m-dash]NNHOH and ArNHN[double bond, length half m-dash]NOH. The former is converted to ArN3 while the latter undergoes a further electrophilic nitrosation by NO+ of a conjugate base species to yield a di-N,N′-nitrosoarylhydrazine, a precursor to the diazonium ion.

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Article type: Paper
DOI: 10.1039/P29960000275
Citation: J. Chem. Soc., Perkin Trans. 2, 1996,0, 275-280
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    Kinetics and mechanism of the reaction of nitrous acid with 2,4-dinitrophenylhydrazine

    P. Bernheim, A. Dobos, A. M. M. Doherty, N. Haine and G. Stedman, J. Chem. Soc., Perkin Trans. 2, 1996, 0, 275
    DOI: 10.1039/P29960000275

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