Nitrite ion as a nitrosating reagent. Nitrosation of morpholine and diethylamine in the presence of formaldehyde

The kinetics of the nitrosation of morpholine and diethylamine in the presence of formaldehyde has been studied at pH values between 6.5–8.2 and 6.9–8.7, respectively. The results are interpreted through a mechanism that implies the reaction between both the nitrite NO2– and iminium R2[graphic omitted]CH2 ions. The latter ion results from the dehydration of the conjugated acid of the carbinolamine, R2[graphic omitted]HCH2OH, the initial product of the amine–formaldehyde reaction. The results allow the calculation of the equilibrium constants of formation of carbinolamine, R2NCH2OH, and methanediamine, R2NCH2NR2(only for the morpholine–formaldehyde system), and their conjugate acids.