32745-07-6Relevant articles and documents
Nitrogen Protonation of N-Nitrosodimethylamine
Keefer, Larry K.,Hrabie, Joseph A.,Hilton, Bruce D.,Wilbur, David
, p. 7459 - 7462 (1988)
Evidence for the presence of the Me2N(H)NO+ ion at kinetically significant concentrations in aqueous solutions of N-nitrosodimethylamine (NDMA) at pH =/ E equilibration in the resulting NDMA-d3 was measured by nuclear magnetic resonance spectroscopy as a function of pD.The reaction was first order in +>, with the plot of observed first-order rate constants versus +> having a slope of k/+> =1E-2 M-1 s-1 at 3 deg C and an ionic strength of 0.2 M.The observed rate date were used to estimate Ka for N-protonated NDMA as 1E12-1E13 M by assuming that the rates of rotation about the N-N bond in Me2N(H)NO+ and of its deprotonation are similar to those for the isoelectronic N-protonated carboxamide function.The trisubstituted nitrogen of the nitrosamine thus appears to be several orders of magnitude less basic than that of the carboxamides.