![]() | |
![]() | |
Identifiers | |
---|---|
3D model (JSmol) | |
CompTox Dashboard (EPA) | |
| |
| |
Properties | |
C40H24 | |
Molar mass | 504.632 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Hypercubane is a hypothetical polycyclic hydrocarbon with the chemical formula C40H24. It is a molecular analog of the four-dimensional hypercube or tesseract. Hypercubane possesses an unconventional geometry of the carbon framework. It has Oh symmetry like classic cubane 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-1,2-diyl linker to form an outer cage. The edge of each inner core and its outer linker form a cyclohexene.
Hypercubane was first proposed in 2014 by Pichierri and studied computationally by density functional theory. [1] 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. [1] Two years later, in 2016, studying the pyrolysis of hypercubane by means of tight-binding molecular dynamics simulations, Maslov and Katin demonstrated that hypercubane possessed high thermal stability comparable with the classic cubane C8H8. [2] 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. [2]
To date[ when? ], there has been no method describing the synthesis of hypercubane.
Aromatic compounds or arenes are organic compounds "with a chemistry typified by benzene" and "cyclically conjugated." The word "aromatic" originates from the past grouping of molecules based on odor, before their general chemical properties were understood. The current definition of aromatic compounds does not have any relation to their odor. Aromatic compounds are now defined as cyclic compounds satisfying Hückel's Rule. Aromatic compounds have the following general properties:
In organic chemistry, an alkene, or olefin, is a hydrocarbon containing a carbon–carbon double bond. The double bond may be internal or in the terminal position. Terminal alkenes are also known as α-olefins.
Ethylene is a hydrocarbon which has the formula C2H4 or H2C=CH2. It is a colourless, flammable gas with a faint "sweet and musky" odour when pure. It is the simplest alkene.
In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons are examples of group 14 hydrides. Hydrocarbons are generally colourless and hydrophobic; their odor is usually faint, and may be similar to that of gasoline or lighter fluid. They occur in a diverse range of molecular structures and phases: they can be gases, liquids, low melting solids or polymers.
In chemistry, a structural isomer of a compound is another compound whose molecule has the same number of atoms of each element, but with logically distinct bonds between them. The term metamer was formerly used for the same concept.
Molecular dynamics (MD) is a computer simulation method for analyzing the 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 dynamic "evolution" of the system. In the most common version, the trajectories of atoms and molecules are determined by numerically solving Newton's equations of motion for a system of interacting particles, where forces between the particles and their potential energies are often calculated using interatomic potentials or molecular mechanical force fields. The method is applied mostly in chemical physics, materials science, and biophysics.
In organic chemistry, the cycloalkanes are the monocyclic saturated hydrocarbons. In other words, a cycloalkane consists only of hydrogen and carbon atoms arranged in a structure containing a single ring, and all of the carbon-carbon bonds are single. The larger cycloalkanes, with more than 20 carbon atoms are typically called cycloparaffins. All cycloalkanes are isomers of alkanes.
Cubane is a synthetic hydrocarbon compound with the formula C8H8. It consists of eight carbon atoms arranged at the corners of a cube, with one hydrogen atom attached to each carbon atom. A solid crystalline substance, cubane is one of the Platonic hydrocarbons and a member of the prismanes. It was first synthesized in 1964 by Philip Eaton and Thomas Cole. Before this work, Eaton believed that cubane would be impossible to synthesize due to the "required 90 degree bond angles". The cubic shape requires the carbon atoms to adopt an unusually sharp 90° bonding angle, which would be highly strained as compared to the 109.45° angle of a tetrahedral carbon. Once formed, cubane is quite kinetically stable, due to a lack of readily available decomposition paths. It is the simplest hydrocarbon with octahedral symmetry.
In organic chemistry, a propyl group is a three-carbon alkyl substituent with chemical formula −CH2CH2CH3 for the linear form. This substituent form is obtained by removing one hydrogen atom attached to the terminal carbon of propane. A propyl substituent is often represented in organic chemistry with the symbol Pr.
A polycyclic aromatic hydrocarbon (PAH) is a class of organic compounds that is composed of multiple aromatic rings. The simplest representative is naphthalene, having two aromatic rings, and the three-ring compounds anthracene and phenanthrene. PAHs are uncharged, non-polar and planar. Many are colorless. Many of them are found in coal and in oil deposits, and are also produced by the incomplete combustion of organic matter—for example, in engines and incinerators or when biomass burns in forest fires.
In organic chemistry, a Platonic hydrocarbon is a hydrocarbon whose structure matches one of the five Platonic solids, with carbon atoms replacing its vertices, carbon–carbon bonds replacing its edges, and hydrogen atoms as needed.
In chemistry, the carbon–hydrogen bond is a chemical bond between carbon and hydrogen atoms that can be found in many organic compounds. This bond is a covalent, single bond, meaning that carbon shares its outer valence electrons with up to four hydrogens. This completes both of their outer shells, making them stable.
Heptanitrocubane is an experimental high explosive based on the cubic eight-carbon cubane molecule and closely related to octanitrocubane. Seven of the eight hydrogen atoms at the corners of the cubane molecule are replaced by nitro groups, giving the final molecular formula C8H(NO2)7.
In chemistry, methanium is a complex positive ion with formula [CH5]+ or [CH3(H2)]+, bearing a +1 electric charge. It is a superacid and one of the onium ions, indeed the simplest carbonium ion.
Cuneane is a saturated hydrocarbon with the formula C8H8 and a 3D structure resembling a wedge, hence the name. Cuneane may be produced from cubane by metal-ion-catalyzed σ-bond rearrangement. Similar reactions are known for homocubane and bishomocubane.
Carbon pentaoxide, carbon pentoxide or tetraoxolan-5-one is an unstable molecular oxide of carbon. The molecule has been produced and studied at cryogenic temperatures. The molecule is important in atmospheric chemistry and in the study of cold ices in the outer solar system and interstellar space. The substance could form and be present on Ganymede or Triton, moons in the outer solar system.
A carbon nanothread is a sp3-bonded, one-dimensional carbon crystalline nanomaterial. The tetrahedral sp3-bonding of its carbon is similar to that of diamond. Nanothreads are only a few atoms across, more than 300,000 times thinner than a human hair. They consist of a stiff, strong carbon core surrounded by hydrogen atoms. Carbon nanotubes, although also one-dimensional nanomaterials, in contrast have sp2-carbon bonding as is found in graphite. The smallest carbon nanothread has a diameter of only 0.2 nanometers, much smaller than the diameter of a single-wall carbon nanotube.
Thermal rearrangements of aromatic hydrocarbons are considered to be unimolecular reactions that directly involve the atoms of an aromatic ring structure and require no other reagent than heat. These reactions can be categorized in two major types: one that involves a complete and permanent skeletal reorganization (isomerization), and one in which the atoms are scrambled but no net change in the aromatic ring occurs (automerization). The general reaction schemes of the two types are illustrated in Figure 1.
A cubane-type cluster is an arrangement of atoms in a molecular structure that forms a cube. In the idealized case, the eight vertices are symmetry equivalent and the species has Oh symmetry. Such a structure is illustrated by the hydrocarbon cubane. With chemical formula C8H8, cubane has carbon atoms at the corners of a cube and covalent bonds forming the edges. Most cubanes have more complicated structures, usually with nonequivalent vertices. They may be simple covalent compounds or macromolecular or supramolecular cluster compounds.
Group 14 hydrides are chemical compounds composed of hydrogen atoms and group 14 atoms.