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 (pKa1≈3.2) of the diprotonated form and of the dissociation of the monoprotonated form of carbinolamine (pKa2≈4.7) were estimated. The equilibrium constants of formation (K1) and dehydration (K2) of the carbinolamine intermediate were determined.