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Tetranitratoxycarbon 3D stick.png
Preferred IUPAC name
Other names
  • Tetra(nitrato-O,O,O-methyl)methane
  • Tetrakis(nitratoxycarbon)methane
  • 3,3',3'',3'''-Methanetrayltetrayltetrakis-2,4,5-trioxa-1-azabicyclo[1.1.1]pentane[1]
3D model (JSmol)
  • InChI=1S/C5N4O12/c10-2(11-6(10)12-2)1(3-13-7(14-3)15-3,4-16-8(17-4)18-4)5-19-9(20-5)21-5
  • N(O1)(O2)OC12C(C(O1)(O2)ON12)(C(O1)(O2)ON12)C(O1)(O2)ON12
Molar mass 308.071 g·mol−1
Density 1.87 g/cm3 (predicted)[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Tetranitratoxycarbon, systematic name tetra(nitrato-O,O,O-methyl)methane (often shortened to tetrakis(nitratoxycarbon)methane),[3] is a hypothetical molecule that was proposed by Clara Lazen, a fifth-grader in Kansas City, Missouri, who conceived of its structure and built a model in 2012. She is credited as co-author of a scientific paper on the molecule, which uses computational chemistry to predict that the molecule could actually exist.


Science teacher Kenneth Boehr was using ball-and-stick models to represent simple molecules during a fifth-grade class, when ten-year-old Clara Lazen[4] assembled a complex model and asked whether it was a real molecule.[5] It is unclear if Lazen randomly or deliberately assembled this particular molecule.[6]

Unsure if the molecule existed, Boehr sent a picture of the model to a chemist friend, Robert Zoellner at Humboldt State University.[4][5] Zoellner checked the molecule against the Chemical Abstracts database[4] and confirmed that Lazen's model was of a structural type that had not been reported before.[5]

Zoellner wrote a paper on the molecule, published in Computational and Theoretical Chemistry, crediting Lazen and Boehr as co-authors.[3]


Tetranitratoxycarbon consists of oxygen, nitrogen, and carbon, with molecular structure C(CO
. Its oxygen-rich formula, in particular, a positive oxygen balance, means it does not require any external oxidizer to undergo complete oxidation, and thus may have explosive other high-energy properties.[3] However, it is expected to be too thermally unstable for practical use.[7]

The nitratoxycarbon functional group itself—a carbon atom and a nitrogen atom linked by three oxygen-atom bridges—has yet to be observed in any chemical compound. Computational chemistry studies indicate that it is only metastable, with other structural isomers such as the carboxylic nitroso-ester (C(=O)ONO) being more stable.[3] As such this functional group is likely to remain purely hypothetical and no method for its synthesis has yet been proposed. However, several other elemental variations have been synthesized[citation needed], including the all-carbon analog (bicyclo[1.1.1]pentane).

Possible reactions[edit]

Several reactions of tetranitratoxycarbon have been investigated computationally. For example, one possible equation for its decomposition is:

C(CO3N)4 → 5 CO2 + O2 + 2 N2

that is predicted to have a standard enthalpy change of −1326 kJ/mol based on bond-energy calculation methods. Another potential reaction is its combustion in the presence of oxygen:

C(CO3N)4 + O2 → 5 CO2 + 2 NO2 + N2

that is predicted to have a standard enthalpy change of −1144 kJ/mol.


  1. ^ CAS
  2. ^ Buszek, Robert J.; Lindsay, C. Michael; Boatz, Jerry A. (February 2013). "Tetrakis(nitratoxycarbon)methane (Née CLL-1) as a Potential Explosive Ingredient: a Theoretical Study". Propellants, Explosives, Pyrotechnics. 38 (1): 9–13. doi:10.1002/prep.201200156.
  3. ^ a b c d Zoellner, Robert W.; Lazen, Clara L.; Boehr, Kenneth M. (2012). "A computational study of novel nitratoxycarbon, nitritocarbonyl, and nitrate compounds and their potential as high energy materials". Computational and Theoretical Chemistry. 979: 33–37. doi:10.1016/j.comptc.2011.10.011.
  4. ^ a b c "Professor Confirms, Publishes 10-year-old's New Molecule". Humboldt State Now. Humboldt University. Retrieved 3 February 2012.
  5. ^ a b c "10-Year-Old Accidentally Creates New Molecule in Science Class". Popular Science. Retrieved 3 February 2012.
  6. ^ "Clara Lazen, Ten-Year-Old Fifth Grader, Discovers New Molecule (VIDEO)". Huffington Post. 3 February 2012. Retrieved 28 February 2018.
  7. ^ "Ten Year Old "discovers" explosive". Explosci.com Now. Explosci. Retrieved 20 March 2012.[dead link]

Further reading[edit]

G, Calvo, Luis; Rodolfo, Pumachagua (2015). "Evaluación teórica de nuevos derivados nitratoxicarbono de tetraedrano" [Theoretical evaluation of new derivatives of the tetrahedrane nitratoxycarbon]. Revista de la Sociedad Química del Perú (in Spanish). 81 (1). doi:10.37761/rsqp.v81i1.6. ISSN 1810-634X. open access