“Hexazine”的意思、由来-开放百科全书

词条

Hexazine

释义

Stability
See also
References

{{Chembox
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| ImageFile = Hexazine.svg
| ImageFile_Ref = {{chemboximage|correct|??}}
| ImageSize = 244
| ImageName = Kekulé and aromatic, skeletal formulae of hexazine
| ImageFile2 = Hexazine3.png
| ImageFile2_Ref = {{chemboximage|correct|??}}
| ImageSize2 = 244
| ImageName2 = Ball and stick, and spacefill models of hexazine
| SystematicName = Hexazine^[1]
| OtherNames = Hexaazabenzene
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|changed|??}}
| CASNo = 7616-35-5
| PubChem = 11966278 {{PubChem|correct|pubchem}}
| ChemSpiderID = 10140271
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 36869
| Gmelin = 1819
| SMILES = n1nnnnn1
| SMILES1 = N1=NN=NN=N1
| StdInChI = 1S/N6/c1-2-4-6-5-3-1
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = YRBKSJIXFZPPGF-UHFFFAOYSA-N
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
}}
|Section2={{Chembox Properties
| N=6
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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. 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).

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 lone pairs on the nitrogen atoms, which may repel each other electrostatically and/or cause electron-donation to sigma antibonding orbitals.^[2]

References

1. ^{{Cite web|url = https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=11966278&loc=ec_rcs|title = Hexazine - PubChem Public Chemical Database|work = The PubChem Project|location = USA|publisher = National Center for Biotechnology Information}}
2. ^{{cite journal |author = J. Fabian and E. Lewars |year = 2004 |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 |url = http://pubs.nrc-cnrc.gc.ca/rp/rppdf/v03-178.pdf |journal = Canadian Journal of Chemistry |volume = 82 |issue = 1 |pages = 50–69 |doi = 10.1139/v03-178 |deadurl = yes |archiveurl = https://web.archive.org/web/20050329185413/http://pubs.nrc-cnrc.gc.ca/rp/rppdf/v03-178.pdf |archivedate = 2005-03-29 |df = }}

*{{cite journal

| author = P. Saxe and H. F. Schaefer III
| year = 1983
| title = Cyclic D_6h Hexaazabenzene-A Relative Minimum on the N₆ Potential Energy Hypersurface?
| journal = Journal of the American Chemical Society
| volume = 105 | issue = 7| pages = 1760–1764
| doi =10.1021/ja00345a010
}}

{{cite journal

| author = H. Huber
| year = 1982
| title = Is Hexazine Stable?
| journal = Angewandte Chemie International Edition
| volume = 21 | issue = 1 | pages = 64–65
| doi = 10.1002/anie.198200641
}}

{{cite journal

| author = M. N. Glukhovtsev and P. von Ragué Schleyer
| year = 1992
| title = Structures, bonding and energies of N[6] isomers
| journal = Chemical Physics Letters
| volume = 198 | issue = 6 | pages = 547–554
| doi =10.1016/0009-2614(92)85029-A
}}

{{cite journal

| author = T.-K. Ha, R. Cimiraglia and M.T. Nguyen
| year = 1981
| title = Can hexazine (N6) be stable?
| journal = Chemical Physics Letters
| volume = 83 | issue = 2 | pages = 317–319
| doi =10.1016/0009-2614(81)85471-1
}}

5 : Nitrogen heterocycles|Aromatic compounds|Hypothetical chemical compounds|Allotropes of nitrogen|Six-membered rings

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Stability

See also

References