Hexazine

 ( Azines ) 

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, hexazine would be the final member of the azabenzene (azine) series, in which all of the 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, , and ).

While a neutrally charged hexazine species has not yet been synthesized, two negatively charged variants, N₆^2- and N₆^4-, have been produced in potassium-nitrogen compounds under very high pressures (> 40 GPa) and temperatures (> 2000 K). In particular, N₆^4- is Aromaticity, respecting Hückel's rule, while N₆^2- is Antiaromaticity. The synthesis of the structural isomer, the linear hexanitrogen, C_2h-N₆, was published in 2025.

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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. Additionally, it has been predicted computationally that the hexazine molecule is highly unstable, possibly due to the on the nitrogen atoms, which may repel each other electrostatically and/or cause electron-donation to sigma antibonding orbitals. A figure-8-shaped isomer is predicted to be metastable.

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See also

• 6-membered rings with other numbers of nitrogen atoms: , , , , and (like hexazine, theoretical)
• Azide
• Pentazole (HN₅)
• Other molecular of nitrogen: tetranitrogen (N₄), hexanitrogen (N₆), octaazacubane (N₈)
• Other inorganic benzene analogues: borazine, hexaphosphabenzene

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Further reading

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External links

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