Conclusions
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1.
In the N-nitration of N-(nitroso)nitroalkylamines by concentrated deuteronitric acid, a significant kinetic isotope effect is observed for bis(2,2-dinitropropyl)-N-nitrosoamine and bis(2,2-dinitrobutyl)-N-nitrosoamine. In the case of bis(2-fluoro-2,2-dinitroethyl)-N-nitrosoamine, the value of kH/kD is quite small.
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2.
The observed difference in the kinetic H/D isotope effects is explained by the mechanisms of conversion of the N-nitrosoamines, and it is related to the influence of the nitroalkyl substituants.
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E. M. Sogomonyan, R. G. Gafurov, B. L. Korsunskii, and L. T. Eremenko, Izv. Akad. Nauk SSSR, Ser. Khim., 1508 (1981).
R. G. Gafurov, E. M. Sogomonyan, and L. T. Eremenko, Izv. Akad. Nauk SSSR, Ser. Khim., 2606 (1971).
R. G. Gafurov, E. M. Sogomonyan, A. F. Zholudev, and L. T. Eremenko, Izv. Akad. Nauk SSSR, Ser. Khim., 1648 (1978).
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 7, pp. 1488–1490, July, 1982.
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Sogomonyan, E.M., Gafurov, R.G., Korsunskii, B.L. et al. Kinetics of N-nitration of N-(nitroso)-nitroalkylamines by concentrated DNO3 . Russ Chem Bull 31, 1327–1329 (1982). https://doi.org/10.1007/BF00954147
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DOI: https://doi.org/10.1007/BF00954147