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 semitrivi ...

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 that are held together by Force, attractive forces known as chemical bonds; depending on context, the term may or may not include ions that satisfy this criterion. In quantum physics, organic chemi ...

that was proposed by Clara Lazen, a fifth-grader in

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, who conceived of its structure and built a model in 2012. She is credited as co-author of a

scientific paper Scientific literature encompasses a vast body of academic papers that spans various disciplines within the natural and social sciences. It primarily consists of academic papers that present original empirical research and theoretical ...

on the molecule, which uses

computational chemistry Computational chemistry is a branch of chemistry that uses computer simulations to assist in solving chemical problems. It uses methods of theoretical chemistry incorporated into computer programs to calculate the structures and properties of mol ...

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 Molecular geometry, three-dimensional position of the atoms and the chemical bond, bonds between them. The atoms are typically represente ...

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

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. Zoellner checked the molecule against the

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

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 a chemical element; it has chemical symbol, symbol O and atomic number 8. It is a member of the chalcogen group (periodic table), group in the periodic table, a highly reactivity (chemistry), reactive nonmetal (chemistry), non ...

nitrogen Nitrogen is a chemical element; it has Symbol (chemistry), symbol N and atomic number 7. Nitrogen is a Nonmetal (chemistry), nonmetal and the lightest member of pnictogen, group 15 of the periodic table, often called the Pnictogen, pnictogens. ...

, and

carbon Carbon () is a chemical element; it has chemical symbol, symbol C and atomic number 6. It is nonmetallic and tetravalence, tetravalent—meaning that its atoms are able to form up to four covalent bonds due to its valence shell exhibiting 4 ...

, 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, to determine whether the molecules of explosive substance or mixture contains enough oxygen to fully oxidize the other atom ...

, 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 ''electron donor''). In ot ...

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 Computational chemistry is a branch of chemistry that uses computer simulations to assist in solving chemical problems. It uses methods of theoretical chemistry incorporated into computer programs to calculate the structures and properties of mol ...

studies indicate that it is only

metastable In chemistry and physics, metastability is 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 is onl ...

, with other

structural isomer In chemistry, a structural isomer (or constitutional isomer in the IUPAC nomenclature) of a compound is a compound that contains the same number and type of atoms, but with a different connectivity (i.e. arrangement of bonds) between them. The ...

s 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. As such, various nitroso groups can be categorized as ''C''-nitroso compounds (e.g., nitrosoalkanes; ), ''S''-nitros ...

ester In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...

(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. Compounds containing the general connective motif of two atoms connected by three one-atom linkers have been synthesized, including the all-carbon bicyclo .1.1entane and derivatives thereof, and several other elemental analogs have been mentioned in patents.

Prediction

Properties

References

Further reading