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Denitrosation of Nitrosamines - a Quantitative Study. Reactions of N-Methyl-N-nitrosoaniline, N-Nitrosoproline, Dimethylnitrosamine and Nitrososarcosine

DOI: 10.1039/P29910001099

Source and publish data:

Journal of the Chemical Society. Perkin transactions II p. 1099 - 1104 (1991)

Update date:2022-08-16

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Authors:

Dix, Leslie R.Dix, Leslie R.

Oh, Shirlene M. N. Y. F.Oh, Shirlene M. N. Y. F.

Williams, D. Lyn H.Williams, D. Lyn H.

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Article abstract of DOI:10.1039/P29910001099

Rate measurements are reported for the denitrosation of N-methyl-N-nitrosoaniline (NMNA), N-nitrosoproline (NPr), dimethylnitrosamine (DMN), N-nitrososarcosine (NS) and N-nitrosopyrrolidine (NPy), in acid solution in the presence of nucleophilic catalysts in the following solvent systems: water, ethanol, various aqueous acetic acid solutions (up to 80percent acetic acid) and acetonitrile.The most reactive solvent system is 80percent acetic acid-water containing bromide ion (or thiourea) as a nucleophilic catalyst.The results, together with some earlier work in water, are discussed (a) in terms of the changing relative reactivities of the nucleophiles as the polarity of the solvent is changed, and (b) in terms of electron-withdrawing properties of any substituents which can effect both the protonation equilibria and also the rate constant for nucleophilic attack of the protonated form of the nitrosamine.

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