Abstract
DI-IMIDE, HN = NH, as the prototype azo compound and an isoelectronic analogue of C2H4 and O2, is of great interest to the chemist. It is, however, generally considered to be so unstable as to have only a transient existence at ordinary temperatures1–3. Generated in situ in aqueous solution, it has been widely used in recent years as a reducing agent3, but has never been isolated or detected in these systems. It has been detected as a transient in the gas phase in several laboratories. Foner and Hudson4 produced di-imide by an electric discharge through flowing hydrazine vapour, detected it by mass spectrometry, and showed that it could be trapped at − 196° C and regenerated in the gas phase on warming. Trombetti5, in these laboratories, was able to measure the infrared and vacuum-ultraviolet absorption spectrum of the vapour in a similar flow system, and these two studies seemed to indicate a lifetime of at least a second or two. A brief account by Mock6 suggests that the lifetime might be much longer; he observed that when di-imide vapour together with ammonia and hydrazine was admitted to the inlet manifold of a mass spectrometer, a signal at m/e = 30 decayed with a half-life of several minutes and remained detectable for as long as 20 min. Uncertainty and lack of reproducibility of these observations led Mock to conclude only tentatively that di-imide might be as long lived as these data suggest.
Similar content being viewed by others
Article PDF
References
Sidgwick, N. V. S., The Chemical Elements and their Compounds, 711 (Oxford University Press, London, 1950).
Audrieth, L. F., and Ackerson, B., The Chemistry of Hydrazine, 4 (Chapman and Hall, London, 1951).
Hünig, S., Müller, H. R., and Thier, W., Angew. Chem., 77, 368 (1965).
Foner, S., and Hudson, R. L., J. Chem. Phys., 28, 719 (1958).
Trombetti, A., Can. J. Phys., 46, 1005 (1968).
Mock, W. L., thesis, Harvard University (1964).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
WILLIS, C., BACK, R. Stability of Di-imide. Nature 241, 43 (1973). https://doi.org/10.1038/241043a0
Received:
Issue Date:
DOI: https://doi.org/10.1038/241043a0
This article is cited by
-
The preparation, properties and reactions of diimide
Reviews of Chemical Intermediates (1984)
Comments
By submitting a comment you agree to abide by our Terms and Community Guidelines. If you find something abusive or that does not comply with our terms or guidelines please flag it as inappropriate.