Benzotriyne or cyclo arbon is a

hypothetical compound A hypothetical chemical compound is a chemical compound that has been conceived of, but is not known to have been synthesized, observed, or isolated (identified or shown to exist). Some hypothetical compounds cannot form at all. Others might tur ...

, an

allotrope of carbon Carbon is capable of forming many allotropy, allotropes (structurally different forms of the same element) due to its Valence (chemistry), valency. Well-known forms of carbon include diamond and graphite. In recent decades, many more allotrope ...

with

molecular formula In chemistry, a chemical formula is a way of presenting information about the chemical proportions of atoms that constitute a particular chemical compound or molecule, using chemical element symbols, numbers, and sometimes also other symbols, ...

. The molecule is a

ring Ring may refer to: * Ring (jewellery), a round band, usually made of metal, worn as ornamental jewelry * To make a sound with a bell, and the sound made by a bell :(hence) to initiate a telephone connection Arts, entertainment and media Film and ...

of six

carbon Carbon () is a chemical element with the symbol C and atomic number 6. It is nonmetallic and tetravalent In chemistry, the valence (US spelling) or valency (British spelling) of an element is the measure of its combining capacity with o ...

atoms, connected by alternating

triple Triple is used in several contexts to mean "threefold" or a " treble": Sports * Triple (baseball), a three-base hit * A basketball three-point field goal * A figure skating jump with three rotations * In bowling terms, three strikes in a row * ...

and

single bond In chemistry, a single bond is a chemical bond between two atoms involving two valence electrons. That is, the atoms share one pair of electrons where the bond forms. Therefore, a single bond is a type of covalent bond. When shared, each of th ...

s. It is, therefore, a potential member of the cyclo 'n''arbon family. There have been a few attempts to synthesize benzotriyne, e.g. by

pyrolysis The pyrolysis (or devolatilization) process is the thermal decomposition of materials at elevated temperatures, often in an inert atmosphere. It involves a change of chemical composition. The word is coined from the Greek-derived elements ''py ...

mellitic anhydride Mellitic anhydride, the anhydride of mellitic acid, is an organic compound with the formula C12O9. Containing no other elements (e.g., hydrogen) besides carbon and oxygen, mellitic anhydride is an oxide of carbon (oxocarbon), and, along with CO2 ...

, but without success . Recent investigations have concluded that benzotriyne is unlikely to exist due to the large

angle strain In organic chemistry, ring strain is a type of instability that exists when bonds in a molecule form angles that are abnormal. Strain is most commonly discussed for small rings such as cyclopropanes and cyclobutanes, whose internal angles are su ...

. A likely alternative

isomer In chemistry, isomers are molecules or polyatomic ions with identical molecular formulae – that is, same number of atoms of each element – but distinct arrangements of atoms in space. Isomerism is existence or possibility of isomers. Iso ...

would be a

cyclic Cycle, cycles, or cyclic may refer to: Anthropology and social sciences * Cyclic history, a theory of history * Cyclical theory, a theory of American political history associated with Arthur Schlesinger, Sr. * Social cycle, various cycles in soc ...

cumulene In organic chemistry, a cumulene is a compound having three or more ''cumulative'' (consecutive) double bonds. They are analogous to allenes, only having a more extensive chain. The simplest molecule in this class is butatriene (), which is also ...

called cyclohexahexaene, which should itself be a metastable species. The name ''cracatene'' was suggested for this compound (after

Karel Čapek Karel Čapek (; 9 January 1890 – 25 December 1938) was a Czech writer, playwright and critic. He has become best known for his science fiction, including his novel ''War with the Newts'' (1936) and play ''R.U.R.'' (''Rossum's Universal Ro ...

Krakatit ''Krakatit'' is a 1948 Czechoslovak science fiction mystery film directed by Otakar Vávra, starring Karel Höger as a chemist who suffers from delirium and regret after inventing a powerful explosive. The film is based on Karel Čapek's novel wit ...

, a hypothetical explosive).

References

Cyclocarbons Hypothetical chemical compounds Polyynes Six-membered rings {{theoretical-chem-stub