Octafluorocubane
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Octafluorocubane or perfluorocubane is an
organofluorine compound Organofluorine chemistry describes the chemistry of organofluorine compounds, organic compounds that contain a carbon–fluorine bond. Organofluorine compounds find diverse applications ranging from oil and water repellents to pharmaceuticals, ...
with the formula , consisting of eight
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 ...
atoms joined into a
cube A cube or regular hexahedron is a three-dimensional space, three-dimensional solid object in geometry, which is bounded by six congruent square (geometry), square faces, a type of polyhedron. It has twelve congruent edges and eight vertices. It i ...
, with a
fluorine Fluorine is a chemical element; it has Chemical symbol, symbol F and atomic number 9. It is the lightest halogen and exists at Standard temperature and pressure, standard conditions as pale yellow Diatomic molecule, diatomic gas. Fluorine is extre ...
bonded to each carbon corner. It is a colorless, sublimable solid at room temperature. It has been of longstanding theoretical interest, but was not synthesised until 2022, when it was prepared in several steps from a
cubane Cubane is a synthetic hydrocarbon compound with the Chemical formula, formula . It consists of eight carbon atoms arranged at the corners of a Cube (geometry), cube, with one hydrogen atom attached to each carbon atom. A solid crystalline substanc ...
carboxylic In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an R-group. The general formula of a carboxylic acid is often written as or , sometimes as with R referring to an organyl group (e. ...
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 ...
beginning with its hepta
fluorination In chemistry, halogenation is a chemical reaction which introduces one or more halogens into a chemical compound. Halide-containing compounds are pervasive, making this type of transformation important, e.g. in the production of polymers, drugs. ...
. According to
X-ray crystallography X-ray crystallography is the experimental science of determining the atomic and molecular structure of a crystal, in which the crystalline structure causes a beam of incident X-rays to Diffraction, diffract in specific directions. By measuring th ...
, the C-C distances (1.570 Å) in octafluorocubane are identical in length to those in the parent cubane (1.572 Å). Octafluorocubane has attracted interest from theorists because of its unusual
electronic structure Quantum chemistry, also called molecular quantum mechanics, is a branch of physical chemistry focused on the application of quantum mechanics to chemical systems, particularly towards the quantum-mechanical calculation of electronic contributions ...
, which is indicated by its susceptibility to undergo reduction to a detectable
anion An ion () is an atom or molecule with a net electrical charge. The charge of an electron is considered to be negative by convention and this charge is equal and opposite to the charge of a proton, which is considered to be positive by conven ...
, with the free electron trapped inside of the cube. The compound was voted "favorite molecule of 2022" by readers of ''
Chemical & Engineering News ''Chemical & Engineering News'' (''C&EN'') is a weekly news magazine published by the American Chemical Society (ACS), providing professional and technical news and analysis in the fields of chemistry and chemical engineering.Fluorocarbons Molecular geometry Theoretical chemistry Cyclobutanes Pentacyclic compounds {{molecular-geometry-stub