Nature 409, 977 (22 February 2001) | doi:10.1038/35059310

Oxide formation: reaction details studied, reported in brief

Howard Maskill1

  1. Institute for Fundamental Research in Organic Chemistry (IFOC), Kyushu University, Higashi-ku, Fukuoka, 812-8581, Japan


Nineteen years ago, I published a sonnet in Nature1 reporting new chemistry carried out at the University of Stirling. Although this application of the sonnet form was well received by critics, it has not subsequently been widely followed.

My present sojourn in Japan has caused me to consider the haiku. It is, with only 17 syllables in its English language form, of legendary brevity. The form is not extensively known outside Japan and the following is illustrative (although not original in content).

"War-time Deprivation and Hope"
Yes! We have no bananas,
We have no bananas today.
But soon?

On the positive side, this brevity provides little scope for waffle in the discussion section of a scientific publication but, on the down side, experimental details must be kept to a minimum (I rule out, of course, the option of stringing together haiku as not within the best traditions). The 17 syllables are normally 5, 7, 5 but some latitude is allowed, as with the usual allusions to nature, the seasons, and other conventions of form and content2 (although purists might quibble).

Since the relatively recent discovery of the wide-ranging biological effects of nitric oxide (NO), considerable effort has been applied to the discovery of compounds which will liberate it under physiological conditions. Some N-nitrosohydroxylamines are such compounds3. However, we have discovered that closely related N-nitrosohydroxylamines undergo an alternative decomposition under very similar reaction conditions to liberate nitrous oxide, N2O (refs 4,5). Moreover, this alternative reaction involves highly electrophilic intermediates analogous to ones involved in reactions of nitrosamines, for example, which are known to be seriously hazardous to human health. Investigation of the molecular basis of these alternative reactions of N-nitrosohydroxylamines was, therefore, of some importance.

As a further attempt to encourage the scientific community to explore alternative forms of scientific reporting, and to draw to the attention of a wider readership our recent work at Newcastle on the mechanisms of decomposition of N-nitrosohydroxylamines in which we identify the molecular basis of the alternative reaction channels referred to above6, I submit for consideration for publication in Nature the following.

"Decomposition of
N-nitrosohydroxylamines"4, 5, 6
Nitric or nitrous?
The leaving groups determine
Which oxide will form.





1. Maskill, H. Nature 294, 606 (1981). | ISI |
2. Henderson, H. G. Haiku in English (C. E. Tuttle, Rutland, 1967).
3. Saavedra, J.& Keefer, L. Chem. Brit. 36(7), 30 (July 2000).
4. Maskill, H., Menneer, I. D.& Smith, D. I. J. Chem. Soc., Chem. Commun. 1855 (1995) | ISI |
5. Haider, J., Hill, M. N. S., Menneer, I. D., Maskill, H.& Smith, J. G. J. Chem. Soc., Chem. Commun. 1571 (1997).
6. Bhat, J. I. et al. J. Chem. Soc., Perkin Trans. 2, 1435 (2000).