Equilibria of formation and dehydration of the carbinolamine intermediate in the reaction of benzaldehyde with hydrazine

Measurement of polarographic limiting currents at equilibria made it possible at pH 3-7 to simultaneously determine concentrations of benzaldehyde, of its hydrazone and of the carbinolamine derivative. The dependence of concentration of carbinolamine at equilibrium on pH indicated presence of its di-, mono-, and unprotonated forms. Acid dissociation constants of the formation (pK(a)(2)approximate to 3.2)of the diprotonated form and of the dissociation of the monoprotonated form of carbinolamine (pK(a)(2)approximate to 4.7) were estimated. The equilibrium constants of formation (K-1) and dehydration (K-2) of the carbinolamine intermediate were determined. (c) 2007 Published by Elsevier Ltd.