Hexazine
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| Names | |
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| Preferred IUPAC name
Hexazine (preselected name) | |
| Systematic IUPAC name
Hexaazabenzene | |
| Other names | |
| Identifiers | |
3D model (
JSmol ) |
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| ChEBI | |
| ChemSpider | |
| 1819 | |
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| N6 | |
| Molar mass | 84.042 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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. As a neutrally charged species, it would be the final member of the azabenzene (azine) series, in which all of the methine groups of the benzene molecule have been 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, triazines, and tetrazines
).
While a neutrally charged hexazine species has not yet been synthesized, two negatively charged variants, [N6]2-[2] and [N6]4-,[3] have been produced in potassium-nitrogen compounds under very high pressures (> 40 GPa) and temperatures (> 2000 K). In particular, [N6]4- is aromatic, respecting Hückel's rule, while [N6]2- is anti-aromatic.
Stability
The hexazine molecule bears a structural similarity to the very stable benzene molecule. Like benzene, it has been calculated that hexazine is likely an
See also
- 6-membered rings with other numbers of nitrogen atoms: pyridines, diazines, triazines, tetrazines, and (like hexazine, theoretical) pentazines
- Azide
- Pentazole (HN5)
- Other molecular allotropes of nitrogen: tetranitrogen (N4), octaazacubane(N8)
- Other inorganic benzene analogues: borazine, hexaphosphabenzene
References
- ^ "Hexazine - PubChem Public Chemical Database". The PubChem Project. USA: National Center for Biotechnology Information.
- S2CID 226222305.
- S2CID 257377020.
- ^
J. Fabian and E. Lewars (2004). "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" (PDF). doi:10.1139/v03-178. Archived from the original(PDF) on 2005-03-29.
Further reading
- P. Saxe and H. F. Schaefer III (1983). "Cyclic D6h Hexaazabenzene-A Relative Minimum on the N6 Potential Energy Hypersurface?". .
- H. Huber (1982). "Is Hexazine Stable?". .
- M. N. Glukhovtsev and P. von Ragué Schleyer (1992). "Structures, bonding and energies of N[6] isomers". .
- T.-K. Ha, R. Cimiraglia and M.T. Nguyen (1981). "Can hexazine (N6) be stable?". .
External links
Media related to Hexazine at Wikimedia Commons
