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Hexanitrobenzene

From Wikipedia, the free encyclopedia
Hexanitrobenzene
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name
Hexanitrobenzene
Other names
1,2,3,4,5,6-Hexanitrobenzene
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C6N6O12/c13-7(14)1-2(8(15)16)4(10(19)20)6(12(23)24)5(11(21)22)3(1)9(17)18 checkY
    Key: BVKZIAODKDJPLW-UHFFFAOYSA-N checkY
  • InChI=1/C6N6O12/c13-7(14)1-2(8(15)16)4(10(19)20)6(12(23)24)5(11(21)22)3(1)9(17)18
    Key: BVKZIAODKDJPLW-UHFFFAOYAP
  • c1(c(c(c(c(c1[N+](=O)[O-])[N+](=O)[O-])[N+](=O)[O-])[N+](=O)[O-])[N+](=O)[O-])[N+](=O)[O-]
Properties
C6N6O12
Molar mass348.10 g/mol
AppearanceYellow or brown powdered crystals
Density1.985g/cm3
Melting point256 to 264 °C (493 to 507 °F; 529 to 537 K)
Explosive data
Shock sensitivityNone
Friction sensitivityNone
Detonation velocity9,340m/s[1]
RE factor1.8
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Hexanitrobenzene, also known asHNB, is anitrobenzene compound in which sixnitro groups are bonded to all six positions of a centralbenzene ring. It is a high-densityexplosivecompound withchemical formulaC6N6O12, obtained byoxidizing theamine group ofpentanitroaniline withhydrogen peroxide insulfuric acid.

Properties

[edit]
Perspective view of the crystal structure of hexanitrobenzene, showing the rotation of the nitro groups.[2]
Left: Ball-and-stick structure.
Right: van der Waals space-filling structure.

The stableconformation of this molecule has the nitro groups rotated out of the plane of the central benzene ring. The molecule adopts a propeller-like conformation in which the nitro groups are rotated about 53° from planar.[2]

HNB has the undesirable property of being moderately sensitive to light and, therefore, hard to utilize safely. As of 2021, it is not used in any production explosives applications, though it is used as a precursor chemical in one method of production ofTATB, another explosive.

HNB was experimentally used as a gas source for explosively pumpedgas dynamic laser.[3] In this application, HNB andtetranitromethane are preferred to more conventional explosives because the explosion productsCO2 andN2 are a simple enough mixture to simulate gas dynamic processes and quite similar to conventional gas dynamic laser medium. The water and hydrogen products of many other explosives could interfere with vibrational states ofCO2 in this type of laser.

Preparation

[edit]

During World War II, a method of synthesis of hexanitrobenzene was suggested in Germany, and the product was supposed to be manufactured on a semi-industrial scale according to the following scheme:

C6H3(NO2)3 → C6H3(NHOH)3 (partial reduction)
C6H3(NHOH)3 → C6(NO2)3(NHOH)3 (nitration)
C6(NO2)3(NHOH)3 → C6(NO2)6 (oxidation)

Complete nitration of benzene is practically impossible because the nitro groups aredeactivating groups for further nitration.

Additional properties

[edit]
  • Chapman-Jouget detonation pressure: 43 GPa
  • Crystal Density: 2.01

See also

[edit]

Notes

[edit]
  1. ^Accurate determination of pair potentials for a CwHxNyOz system of molecules: A semiempirical method, Thiel et al., 1995
  2. ^abBart, J. C. J. (1968). "The crystal structure of a modification of hexaphenylbenzene".Acta Crystallographica Section B.24 (10):1277–1287.Bibcode:1968AcCrB..24.1277B.doi:10.1107/S0567740868004176.
  3. ^Condensed explosive gas dynamic laser, United States Patent 4099142

References

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