Kinetic Studies on the Formation of N-Nitroso Compounds, X. The Nitrosation of N-Methylacetamide and Its Differences with Respect to the Nitrosation of Amines

Article abstract of DOI:10.1007/BF00798771

The kinetics of the nitrosation of N-methylacetamide have been studied using specrophotometry.Significant differences with respect to the mechanism of nitrosation of amines were observed: the absence of catalysis by halides, the existence of general basic catalysis by acetate and its chlorated derivatives obeying Broensted's law (with β = 0.49), and the primary isotopic effect (with a ratio of 7.9 between the rate constants for the elementary process in H2O and D2O).All this indicates that the slow step of the mechanism must be the transfer of a proton from the protonated nitrosamide to the reaction medium. - Keywords: Kinetics of nitrosation; N-Nitrosation of N-methylacetamide; Proton transfer