Hexazine

Chembox new
ImageFile = Hexazine_by_Kryptid.jpg
Formula = N₆
MolarMass = 84.0402 g/mol

Hexazine (also known as hexaazabenzene) is a hypothetical allotrope of nitrogen composed of 6 nitrogen atoms arranged in a ring-like structure analogous to that of benzene. It would be the final member of the azabenzene (azine) series, having all of the methylidyne groups of the benzene molecule replaced with nitrogen atoms. The two last members of this series, hexazine and pentazine, have not been observed, although all other members of the azine series have (such as pyridine, pyrimidine, pyridazine, pyrazine, 1,3,5-triazine and tetrazine).

tability

The hexazine molecule bears a structural similarity to the very stable benzene molecule. Like benzene, it has been calculated that hexazine is likely an aromatic molecule. Despite this, it has yet to be synthesized. In fact, it has been predicted computationally that the hexazine molecule is highly unstable. It has been suggested that this predicted instability is caused by the lone pairs on the nitrogen atoms, which may repel each other electrostatically and/or cause electron-donation to sigma antibonding orbitals. [ [http://pubs.nrc-cnrc.gc.ca/rp/rppdf/v03-178.pdf Azabenzenes (azines) - The nitrogen derivatives of benzene with one to six N atoms] ]

ee also

*Azide
*Nitrogen
*Pentazole

References

*cite journal
title = Azabenzenes (azines) — The nitrogen derivatives of benzene with one to six N atoms: Stability, homodesmotic stabilization energy, electron distribution, and magnetic ring current; a computational study
author = Jürgen Fabian and E. Lewars
journal = Can. J. Chem.
volume = 82
issue = 1
pages = 50–69
year = 2004
url =
doi = 10.1139/v03-178
*cite journal
title = Cyclic D_6h Hexaazabenzene-A Relative Minimum on the N₆ Potential Energy Hypersurface?
author = Paul Saxe and Henry F. Schaefer III
journal = J. Am. Chem. Soc.
volume = 105
issue =
pages = 1760–1764
year = 1983
url =
doi =
*cite journal
title = Is Hexazine Stable?
author = Hanspeter Huber
journal = Angewandte Chemie International Edition in English
volume = 21
issue = 1
pages = 64–65
year = 1982
url =
doi = 10.1002/anie.198200641
* cite journal
title = Structures, bonding and energies of N [6] isomers
author = M. N. Glukhovtsev ; Paul von Ragué Schleyer
journal = Chemical Physics Letters
volume = 198
issue = 6
pages = 547–554
year = 1992
url =
doi =
*cite journal
title = Can hexazine (N6) be stable?
author = Ha, Tae-Kyu; Cimiraglia, R.; Nguyen, Minh Tho
journal = Chemical Physics Lette
volume = 83
issue = 2
pages = 317–319
year = 1981
url =
doi =