Hypercubane is a hypothetical polycyclic hydrocarbon with the chemical formula C₄₀H₂₄. It is a molecular analog of the four-dimensional

hypercube In geometry, a hypercube is an ''n''-dimensional analogue of a square ( ) and a cube ( ); the special case for is known as a ''tesseract''. It is a closed, compact, convex figure whose 1- skeleton consists of groups of opposite parallel l ...

tesseract In geometry, a tesseract or 4-cube is a four-dimensional hypercube, analogous to a two-dimensional square and a three-dimensional cube. Just as the perimeter of the square consists of four edges and the surface of the cube consists of six ...

. Hypercubane possesses an unconventional geometry of the carbon framework. It has ''O_h'' symmetry like classic

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 ...

C₈H₈. The structure is that of octamethyl cubane—a carbon attached to each corner of cubane itself—having each of those carbon substituents joined to each of its neighbors by an

ethylene Ethylene (IUPAC name: ethene) is a hydrocarbon which has the formula or . It is a colourless, flammable gas with a faint "sweet and musky" odour when pure. It is the simplest alkene (a hydrocarbon with carbon–carbon bond, carbon–carbon doub ...

-1,2-diyl linker to form an outer cage. The edge of each inner core and its outer linker form a

cyclohexene Cyclohexene is a hydrocarbon with the formula . It is a cycloalkene. At room temperature, cyclohexene is a colorless liquid with a sharp odor. Among its uses, it is an chemical intermediate, intermediate in the commercial synthesis of nylon. Prod ...

History

Hypercubane was first proposed in 2014 by Pichierri and studied computationally by

density functional theory Density functional theory (DFT) is a computational quantum mechanical modelling method used in physics, chemistry and materials science to investigate the electronic structure (or nuclear structure) (principally the ground state) of many-body ...

. The initial model of hypercubane was constructed from octamethylcubane by removing unnecessary hydrogen atoms and adding the ethylene bridges as well as intercarbon bonds between the sp² and sp³ atoms. To facilitate the future hypercubane spectroscopic identification chemical shifts for both ¹³C and ¹H NMR-active nuclei have been calculated by Pichierri. Two years later, in 2016, studying the pyrolysis of hypercubane by means of tight-binding

molecular dynamics Molecular dynamics (MD) is a computer simulation method for analyzing the Motion (physics), physical movements of atoms and molecules. The atoms and molecules are allowed to interact for a fixed period of time, giving a view of the dynamics ( ...

simulations, Maslov and Katin demonstrated that hypercubane possessed high thermal stability comparable with the classic cubane C₈H₈. It was shown that hypercubane lifetime at room temperature tended to infinity. Therefore, it can be assumed that hypercubane is a kinetically stable molecular system. Among the possible hypercubane decomposition products at high temperatures (more than 1000 K) one can observe polycyclic airscrew-like hydrocarbon C₃₄H₁₈ based on three combined graphene fragments passivated by hydrogen atoms and three isolated acetylene molecules.

Synthesis

As of July 2025, there has been no method describing the synthesis of hypercubane.

References

{{theoretical-chem-stub Hypothetical chemical compounds Molecular geometry Polycyclic nonaromatic hydrocarbons

History

Synthesis

See also

References