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Chemists have long sought to identify stable all-nitrogen chemical species. N2, of course, is ubiquitous; and N3鈥�, the azide anion, is well characterized. But what about N4聽and higher?
Several studies, mostly theoretical, have been done in search of N4. In 1996, Mikhail N. Glukhovtsev at the University of Sydney and Sergei Laiter at the University of North Carolina (Chapel Hill) calculated that the聽聽increase in the order open-chain N4聽triplet diradical < tetrazetetetrahedrane < planar tetrazete. The researchers attributed the higher energies of tetrahedral and planar N4聽to ring strain and antiaromaticity, respectively. Note the reversal in the energies of the cyclic N4s versus those of the isoelectronic carbon systems tetrahedrane and cyclobutadiene.
In 2000, J. George Radziszewski and coauthors at the Colorado School of Mines and the National Renewable Energy Laboratory (both in Golden, CO),聽聽and assigned its structure to tetrazetetetrahedrane.
In another 1996 theoretical study, Glukhovtsev, Haijun Jiao, and Paul von Ragu茅 Schleyer at the University of Erlangen-Nuremberg (Germany) and Rostov University (Rostov on Don, Russia) found that聽. An example is N8, azidopentazole. They attributed the stability to the aromaticity of the N5听谤颈苍驳蝉.
This past year,聽聽Yehuda Haas and colleagues at the Hebrew University of Jerusalem prepared the cyclopentazole anion, N5鈥�, by reducing phenylpentazole with sodium metal. The sodium salt of the anion in tetrahydrofuran solution is indefinitely stable below 鈥�40 潞C and has a half-life of minutes at ambient temperature.
MOTW Update:
February 6, 2017
The聽cyclopentazole anion's sodium salt was the first stable N5compound ever synthesized. But this salt is stable only in aqueous solution. More recently, Chong Zhang, Chengguo Sun, and coauthors in China prepared聽: (N5)6(H3O)3(NH4)4Cl.

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