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Hexazine

Hexazine
Kekulé and aromatic, skeletal formulae of hexazine
Ball and stick, and spacefill models of hexazine
Names
Preferred IUPAC name
Hexazine (preselected name)
Systematic IUPAC name
Hexaazabenzene
Other names
Hexazabenzene[1]
Hexaazabenzene
Azabenzene
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
1819
  • InChI=1S/N6/c1-2-4-6-5-3-1 ☒N
    Key: YRBKSJIXFZPPGF-UHFFFAOYSA-N ☒N
  • n1nnnnn1
  • N1=NN=NN=N1
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.

  1. ^ "Hexazine - PubChem Public Chemical Database". The PubChem Project. USA: National Center for Biotechnology Information.
  2. ^ Wang, Yu; Bykov, Maxim; Chepkasov, Ilya; Samtsevich, Artem; Bykova, Elena; Zhang, Xiao; Jiang, Shu-qing; Greenberg, Eran; Chariton, Stella; Prakapenka, Vitali B.; Oganov, Artem R.; Goncharov, Alexander F. (July 2022). "Stabilization of hexazine rings in potassium polynitride at high pressure". Nature Chemistry. 14 (7): 794–800. arXiv:2010.15995. Bibcode:2022NatCh..14..794W. doi:10.1038/s41557-022-00925-0. ISSN 1755-4330. PMID 35449217. S2CID 226222305.
  3. ^ Laniel, Dominique; Trybel, Florian; Yin, Yuqing; Fedotenko, Timofey; Khandarkhaeva, Saiana; Aslandukov, Andrey; Aprilis, Georgios; Abrikosov, Alexei I.; Bin Masood, Talha; Giacobbe, Carlotta; Bright, Eleanor Lawrence; Glazyrin, Konstantin; Hanfland, Michael; Wright, Jonathan; Hotz, Ingrid (2023-03-06). "Aromatic hexazine [N6]4− anion featured in the complex structure of the high-pressure potassium nitrogen compound K9N56". Nature Chemistry. 15 (5): 641–646. Bibcode:2023NatCh..15..641L. doi:10.1038/s41557-023-01148-7. ISSN 1755-4349. PMID 36879075. S2CID 257377020.

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