Diazomethane acid-base equilibria

The reactivity sequence stated by Staudinger and Gaule was the very early qualitative precursor for the quantitative determination of the acid-base equilibrium constant of diazomethane by McGarrity and Smyth (1980). The major difficulty of... 

It would appear today, however, that the acid-base equilibrium of diazomethane with its anion is better known in the gas-phase than in solution The same group (DePuy et al., 1989) investigated reactions of the diazomethyl anion with CS2, COS, CO2, SO2, and with a series of a,)ff-unsaturated aldehydes and ketones — all in the gas phase using a flowing afterglow apparatus (DePuy and Bierbaum, 1981) and selected ion flow tube techniques (Van Doren et al., 1987). 

What evidence is there for the individual reaction steps The acid-base reaction (Eq. 2) has the characteristics of a Broensted equilibrium, as has been shown in the case of diazomethane-benzoic acid (in toluene).4 Further evidence for this is provided by the reactions of diazoacetic ester and diazo ketones.6 7 The occurrence of free, mobile diazonium cations is also supported by the fact that solutions of diazomethane in methanol show greater conductivity than solutions of pure solvent.8... 

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