Hexazine

Hexazine
Systematic name

Hexazine[1]
Other names

Hexaazabenzene
Identifiers
CAS number 7616-35-5 N
PubChem 11966278
ChemSpider 10140271 N
ChEBI CHEBI:36869 N
Gmelin Reference 1819
Jmol-3D images Image 1
Image 2
Properties
Molecular formula N6
Molar mass 84.04 g mol−1
Exact mass 84.018444030 g mol-1
 N (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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).

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 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.[2]

See also

References

  1. ^ "Hexazine - PubChem Public Chemical Database". The PubChem Project. USA: National Center for Biotechnology Information. http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=11966278&loc=ec_rcs. 
  2. ^ 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". Canadian Journal of Chemistry 82 (1): 50–69. doi:10.1139/v03-178. http://pubs.nrc-cnrc.gc.ca/rp/rppdf/v03-178.pdf.