Names | |
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Preferred IUPAC name Tetracyclo[2.2.0.02,5.03,6]hexane | |
Identifiers | |
3D model (JSmol) | |
PubChem CID | |
CompTox Dashboard (EPA) | |
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Properties | |
C6H6 | |
Molar mass | 78.114 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Claus' benzene (C6H6) is a hypothetical hydrocarbon and an isomer of benzene. [1] It was proposed by Adolf Karl Ludwig Claus in 1867 [2] as a possible structure for benzene at a time when the structure of benzene was still being debated. The molecule can be described as a hexagon with carbon atoms positioned at the corners, with each carbon connected to its two ortho carbons (the nearest carbons) and the one para carbon connected diametrically. [3] High strain energy makes its synthesis impossible. Although it is often referred to alongside Dewar benzene and prismane, it is not possible to synthesize it, while Dewar benzene and prismane can be. [4]
A fullerene is an allotrope of carbon whose molecules consist of carbon atoms connected by single and double bonds so as to form a closed or partially closed mesh, with fused rings of five to six atoms. The molecules may have hollow sphere- and ellipsoid-like forms, tubes, or other shapes.
Friedrich August Kekulé, later Friedrich August Kekule von Stradonitz, was a German organic chemist. From the 1850s until his death, Kekulé was one of the most prominent chemists in Europe, especially in the field of theoretical chemistry. He was the principal founder of the theory of chemical structure and in particular the Kekulé structure of benzene.
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.
In theoretical chemistry, a conjugated system is a system of connected p-orbitals with delocalized electrons in a molecule, which in general lowers the overall energy of the molecule and increases stability. It is conventionally represented as having alternating single and multiple bonds. Lone pairs, radicals or carbenium ions may be part of the system, which may be cyclic, acyclic, linear or mixed. The term "conjugated" was coined in 1899 by the German chemist Johannes Thiele.
In chemistry, resonance, also called mesomerism, is a way of describing bonding in certain molecules or polyatomic ions by the combination of several contributing structures into a resonance hybrid in valence bond theory. It has particular value for analyzing delocalized electrons where the bonding cannot be expressed by one single Lewis structure. The resonance hybrid is the accurate structure for a molecule or ion; it is an average of the theoretical contributing structures.
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 stereochemistry, a stereocenter of a molecule is an atom (center), axis or plane that is the focus of stereoisomerism; that is, when having at least three different groups bound to the stereocenter, interchanging any two different groups creates a new stereoisomer. Stereocenters are also referred to as stereogenic centers.
Cyclobutadiene is an organic compound with the formula C4H4. It is very reactive owing to its tendency to dimerize. Although the parent compound has not been isolated, some substituted derivatives are robust and a single molecule of cyclobutadiene is quite stable. Since the compound degrades by a bimolecular process, the species can be observed by matrix isolation techniques at temperatures below 35 K. It is thought to adopt a rectangular structure.
In molecular geometry, bond length or bond distance is defined as the average distance between nuclei of two bonded atoms in a molecule. It is a transferable property of a bond between atoms of fixed types, relatively independent of the rest of the molecule.
Prismane or 'Ladenburg benzene' is a polycyclic hydrocarbon with the formula C6H6. It is an isomer of benzene, specifically a valence isomer. Prismane is far less stable than benzene. The carbon (and hydrogen) atoms of the prismane molecule are arranged in the shape of a six-atom triangular prism—this compound is the parent and simplest member of the prismanes class of molecules. Albert Ladenburg proposed this structure for the compound now known as benzene. The compound was not synthesized until 1973.
In organic chemistry, a cyclophane is a hydrocarbon consisting of an aromatic unit and a chain that forms a bridge between two non-adjacent positions of the aromatic ring. More complex derivatives with multiple aromatic units and bridges forming cagelike structures are also known. Cyclophanes are well-studied examples of strained organic compounds.
A cyclic compound is a term for a compound in the field of chemistry in which one or more series of atoms in the compound is connected to form a ring. Rings may vary in size from three to many atoms, and include examples where all the atoms are carbon, none of the atoms are carbon, or where both carbon and non-carbon atoms are present. Depending on the ring size, the bond order of the individual links between ring atoms, and their arrangements within the rings, carbocyclic and heterocyclic compounds may be aromatic or non-aromatic; in the latter case, they may vary from being fully saturated to having varying numbers of multiple bonds between the ring atoms. Because of the tremendous diversity allowed, in combination, by the valences of common atoms and their ability to form rings, the number of possible cyclic structures, even of small size numbers in the many billions.
Dewar benzene (also spelled dewarbenzene) or bicyclo[2.2.0]hexa-2,5-diene is a bicyclic isomer of benzene with the molecular formula C6H6. The compound is named after James Dewar who included this structure in a list of possible C6H6 structures in 1869. However, he did not propose it as the structure of benzene, and in fact he supported the correct structure previously proposed by August Kekulé in 1865.
Picoline refers to any of three isomers of methylpyridine (CH3C5H4N). They are all colorless liquids with a characteristic smell similar to that of pyridine. They are miscible with water and most organic solvents.
In organic chemistry, two molecules are valence isomers when they are constitutional isomers that can interconvert through pericyclic reactions.
In chemistry, an oxocarbon or oxide of carbon is a chemical compound consisting only of carbon and oxygen. The simplest and most common oxocarbons are carbon monoxide (CO) and carbon dioxide. Many other stable or metastable oxides of carbon are known, but they are rarely encountered, such as carbon suboxide and mellitic anhydride.
Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar hexagonal ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms, benzene is classed as a hydrocarbon.
Bicyclopropenyl (bicycloprop-2-enyl, C6H6) is an organic compound and one of several valence isomers of benzene. The molecule can be described as two coupled cyclopropene units. The positions of the alkene groups can vary and therefore two other isomers are known: bicycloprop-1,2-enyl and bicyclopropen-1-yl.
Adolf Karl Ludwig Claus was a German chemist. He is known for his structure of benzene proposed in 1867.
Kekulene is a polycyclic aromatic hydrocarbon which consists of 12 fused benzene rings arranged in a circle. It is therefore classified as a [12]-circulene with the chemical formula C48H24. It was first synthesized in 1978, and was named in honor of August Kekulé, the discoverer of the structure of the benzene molecule.