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{{Chembox
{{Chembox
| Verifiedfields = changed
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| verifiedrevid = 398940665
| Watchedfields = changed
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| ImageFile = Trinitrotriazine.png
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| verifiedrevid = 470616140
| ImageSize = 150px
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| ImageFileL1 = Trinitrotriazine.svg
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| IUPACName = 2,4,6-Trinitro-1,3,5-triazine
| ImageSizeL1 = 130
| ImageAltL1 = Skeletal formula of trinitrotriazine
| ImageFileR1 = Trinitrotriazine-3D-spacefill.png
| ImageSizeR1 = 130
| ImageAltR1 = Space-filling model of the trinitrotriazine molecule
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| PIN = 2,4,6-Trinitro-1,3,5-triazine
| OtherNames =
| OtherNames =
| Section1 = {{Chembox Identifiers
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 15188373
| ChemSpiderID = 15188373
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = QHHATGLDAJAQBL-UHFFFAOYSA-N
| StdInChIKey = QHHATGLDAJAQBL-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|changed|??}}
| SMILES1 = O=N(=O)c1nnnc(c1N(=O)=O)N(=O)=O
| CASNo = 140218-59-3
| CASNo = 140218-59-3
| PubChem =
| PubChem = 21997109
| SMILES = O=[N+]([O-])C1=NC([N+]([O-])=O)=NC([N+]([O-])=O)=N1
| SMILES = O=[N+]([O-])C1=NC([N+]([O-])=O)=NC([N+]([O-])=O)=N1
}}
}}
| Section2 = {{Chembox Properties
|Section2={{Chembox Properties
| C=3 | N=6 | O=6
| Formula = C<sub>3</sub>N<sub>6</sub>O<sub>6</sub>
| MolarMass = 216.07
| Appearance =
| Appearance =
| Density =
| Density =
| MeltingPt =
| MeltingPt =
| BoilingPt =
| BoilingPt =
| Solubility =
| Solubility =
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| Section3 = {{Chembox Hazards
|Section3={{Chembox Hazards
| MainHazards =
| MainHazards =
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| FlashPt =
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| Section6 = {{Chembox Explosive
|Section6={{Chembox Explosive
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'''Trinitrotriazine''', or '''2,4,6-trinitro-1,3,5-triazine''', is a theoretical [[explosive]] compound. Synthesis of this compound has been elusive despite its simple structure,<ref>G. D. Hartman, R. D. Hartman and J. E. Schwering. ''Tetrahedron Letters''. 1983; 24: 1011.</ref><ref>M. D. Coburn, C. L. Coon, H. H. Hayden and A. R. Mitchell. ''Synthesis''. 1986: 490.</ref> as conventional [[nitration]] of [[triazine]] becomes increasingly more difficult as more nitro groups are added. A successful route would more likely proceed by trimerisation of nitryl cyanide, but this precursor also has not yet been synthesised.<ref>Korkin AA. Bartlett RJ. Theoretical Prediction of 2,4,6-Trinitro-1,3,5-triazine (TNTA). A New, Powerful, High-Energy Density Material? ''Journal of the American Chemical Society''. 1996; 118: 12244-12245.</ref>
'''Trinitrotriazine''', or '''2,4,6-trinitro-1,3,5-triazine''', is a theoretical [[explosive]] compound. Synthesis of this compound has been elusive despite its simple structure,<ref>G. D. Hartman, R. D. Hartman and J. E. Schwering. ''Tetrahedron Letters''. 1983; 24: 1011.</ref><ref>M. D. Coburn, C. L. Coon, H. H. Hayden and A. R. Mitchell. ''Synthesis''. 1986: 490.</ref> as conventional [[nitration]] of [[triazine]] becomes increasingly more difficult as more nitro groups are added. A successful route would more likely proceed by [[trimerisation]] of [[nitryl cyanide]].<ref>Korkin AA. Bartlett RJ. Theoretical Prediction of 2,4,6-Trinitro-1,3,5-triazine (TNTA). A New, Powerful, High-Energy Density Material? ''Journal of the American Chemical Society''. 1996; 118: 12244-12245.</ref> The precursor nitryl cyanide was first synthesized by Rahm et al. in 2014.<ref>Rahm, M., Bélanger-Chabot, G., Haiges, R. and Christe, K. O. (2014), Nitryl Cyanide, NCNO<sub>2</sub>. Angew. Chem. Int. Ed., 53: 6893–6897</ref>


It has a perfect [[oxygen balance]], potentially making it a very powerful explosive, though calculations predict it would be fairly unstable and inferior to the related compound 3,6-dinitro-1,2,4,5-tetrazine.<ref>Jinshan Li. An Ab Initio Theoretical Study of 2,4,6-Trinitro-1,3,5-Triazine, 3,6-Dinitro-1,2,4,5-Tetrazine, and 2,5,8-Trinitro-Tri-s-Triazine. ''Propellants, Explosives, Pyrotechnics.'' December 2008; 33(6):443-447.</ref>
Trinitrotriazine has a neutral [[oxygen balance]], potentially making it a very powerful explosive, though calculations predict it would be fairly unstable and inferior to the related compound 3,6-dinitro-1,2,4,5-tetrazine.<ref>Jinshan Li. An Ab Initio Theoretical Study of 2,4,6-Trinitro-1,3,5-Triazine, 3,6-Dinitro-1,2,4,5-Tetrazine, and 2,5,8-Trinitro-Tri-s-Triazine, more commonly known as RDX. ''Propellants, Explosives, Pyrotechnics.'' December 2008; 33(6):443-447.</ref>


==See also==
==See also==
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[[Category:Triazines]]
[[Category:Triazines]]
[[Category:Nitro compounds]]
[[Category:Nitro compounds]]
[[Category:Hypothetical chemical compounds]]




{{Explosive-stub}}
{{theoretical-chem-stub}}

Latest revision as of 10:37, 11 March 2023

Trinitrotriazine
Skeletal formula of trinitrotriazine
Space-filling model of the trinitrotriazine molecule
Names
Preferred IUPAC name
2,4,6-Trinitro-1,3,5-triazine
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C3N6O6/c10-7(11)1-2(8(12)13)4-6-5-3(1)9(14)15 checkY
    Key: QHHATGLDAJAQBL-UHFFFAOYSA-N checkY
  • O=[N+]([O-])C1=NC([N+]([O-])=O)=NC([N+]([O-])=O)=N1
Properties
C3N6O6
Molar mass 216.069 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Trinitrotriazine, or 2,4,6-trinitro-1,3,5-triazine, is a theoretical explosive compound. Synthesis of this compound has been elusive despite its simple structure,[1][2] as conventional nitration of triazine becomes increasingly more difficult as more nitro groups are added. A successful route would more likely proceed by trimerisation of nitryl cyanide.[3] The precursor nitryl cyanide was first synthesized by Rahm et al. in 2014.[4]

Trinitrotriazine has a neutral oxygen balance, potentially making it a very powerful explosive, though calculations predict it would be fairly unstable and inferior to the related compound 3,6-dinitro-1,2,4,5-tetrazine.[5]

See also

[edit]
  • RDX (hexahydro-1,3,5-trinitro-1,3,5-triazine)

References

[edit]
  1. ^ G. D. Hartman, R. D. Hartman and J. E. Schwering. Tetrahedron Letters. 1983; 24: 1011.
  2. ^ M. D. Coburn, C. L. Coon, H. H. Hayden and A. R. Mitchell. Synthesis. 1986: 490.
  3. ^ Korkin AA. Bartlett RJ. Theoretical Prediction of 2,4,6-Trinitro-1,3,5-triazine (TNTA). A New, Powerful, High-Energy Density Material? Journal of the American Chemical Society. 1996; 118: 12244-12245.
  4. ^ Rahm, M., Bélanger-Chabot, G., Haiges, R. and Christe, K. O. (2014), Nitryl Cyanide, NCNO2. Angew. Chem. Int. Ed., 53: 6893–6897
  5. ^ Jinshan Li. An Ab Initio Theoretical Study of 2,4,6-Trinitro-1,3,5-Triazine, 3,6-Dinitro-1,2,4,5-Tetrazine, and 2,5,8-Trinitro-Tri-s-Triazine, more commonly known as RDX. Propellants, Explosives, Pyrotechnics. December 2008; 33(6):443-447.


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