Tetranitratoxycarbon,

systematic name A systematic name is a name given in a systematic way to one unique group, organism, object or chemical substance, out of a specific population or collection. Systematic names are usually part of a nomenclature. A semisystematic name or semitrivial ...

tetra(nitrato-''O'',''O'',''O''-methyl)methane (often shortened to tetrakis(nitratoxycarbon)methane), is a hypothetical

molecule A molecule is a group of two or more atoms held together by attractive forces known as chemical bonds; depending on context, the term may or may not include ions which satisfy this criterion. In quantum physics, organic chemistry, and bioche ...

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 : ''For a broader class of literature, see Academic publishing.'' Scientific literature comprises scholarly publications that report original empirical and theoretical work in the natural and social sciences. Within an academic field, scienti ...

on the molecule, which uses computational chemistry to predict that the molecule could actually exist.

Prediction

Science teacher Kenneth Boehr was using

ball-and-stick model In chemistry, the ball-and-stick model is a molecular model of a chemical substance which displays both the three-dimensional position of the atoms and the bonds between them. The atoms are typically represented by spheres, connected by rods ...

s to represent simple molecules during a fifth-grade class, when ten-year-old Clara Lazen assembled a complex model and asked whether it was a real molecule. It is unclear if Lazen randomly or deliberately assembled this particular molecule. Unsure if the molecule existed, Boehr sent a picture of the model to a chemist friend, Robert Zoellner at

Humboldt State University California State Polytechnic University, Humboldt also known as Cal Poly Humboldt, Humboldt or Cal Poly"Cal Poly" may also refer to California Polytechnic State University in San Luis Obispo, California or California State Polytechnic Universi ...

. Zoellner checked the molecule against the

Chemical Abstracts CAS (formerly Chemical Abstracts Service) is a division of the American Chemical Society. It is a source of chemical information. CAS is located in Columbus, Ohio, United States. Print periodicals ''Chemical Abstracts'' is a periodical index tha ...

database and confirmed that Lazen's model was of a structural type that had not been reported before. Zoellner wrote a paper on the molecule, published in ''

Computational and Theoretical Chemistry ''Computational and Theoretical Chemistry'' is a peer-reviewed scientific journal published by Elsevier. It was established in 1985 as ''Journal of Molecular Structure: THEOCHEM'', a spin-off of the '' Journal of Molecular Structure''. It obtained ...

'', crediting Lazen and Boehr as co-authors.

Properties

Tetranitratoxycarbon consists of

oxygen Oxygen is the chemical element with the symbol O and atomic number 8. It is a member of the chalcogen group in the periodic table, a highly reactive nonmetal, and an oxidizing agent that readily forms oxides with most elements as ...

nitrogen Nitrogen is the chemical element with the symbol N and atomic number 7. Nitrogen is a nonmetal and the lightest member of group 15 of the periodic table, often called the pnictogens. It is a common element in the universe, estimated at se ...

, and

carbon Carbon () is a chemical element with the symbol C and atomic number 6. It is nonmetallic and tetravalent—its atom making four electrons available to form covalent chemical bonds. It belongs to group 14 of the periodic table. Carbon mak ...

, with molecular structure . Its oxygen-rich formula, in particular, a positive

oxygen balance Oxygen balance (OB, OB%, or Ω) is an expression that is used to indicate the degree to which an explosive can be oxidized. If an explosive molecule contains just enough oxygen to fully oxidize the other atoms in the explosive. For example, fully ...

, means it does not require any external

oxidizer An oxidizing agent (also known as an oxidant, oxidizer, electron recipient, or electron acceptor) is a substance in a redox chemical reaction that gains or " accepts"/"receives" an electron from a (called the , , or ). In other words, an oxid ...

to undergo complete oxidation, and may thus have explosive or other high-energy properties. However, it is expected to be too thermally unstable for practical use. 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 In chemistry and physics, metastability denotes an intermediate energetic state within a dynamical system other than the system's state of least energy. A ball resting in a hollow on a slope is a simple example of metastability. If the ball i ...

, with other structural isomers such as the carboxylic

nitroso In organic chemistry, nitroso refers to a functional group in which the nitric oxide () group is attached to an organic moiety (chemistry), moiety. As such, various nitroso groups can be categorized as ''C''-nitroso compounds (e.g., nitrosoalkane ...

ester In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides a ...

(C(=O)ONO) being more stable. 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, including the all-carbon analog ( bicyclo .1.1entane).

Possible reactions

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.

Prediction

Properties

Possible reactions

References

Further reading