Dicyanoacetylene, also called carbon subnitride or but-2-ynedinitrile (

IUPAC The International Union of Pure and Applied Chemistry (IUPAC ) is an international federation of National Adhering Organizations working for the advancement of the chemical sciences, especially by developing nomenclature and terminology. It is ...

), is a compound of

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 ...

and

nitrogen Nitrogen is the chemical element with the symbol N and atomic number 7. Nitrogen is a nonmetal and the lightest member of group 15 of the periodic table, often called the pnictogens. It is a common element in the universe, estimated at se ...

with

chemical 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, ...

. It has a linear molecular structure, (often abbreviated as ), with alternating triple and single

covalent bond A covalent bond is a chemical bond that involves the sharing of electrons to form electron pairs between atoms. These electron pairs are known as shared pairs or bonding pairs. The stable balance of attractive and repulsive forces between atoms ...

s. It can be viewed as

acetylene Acetylene (systematic name: ethyne) is the chemical compound with the formula and structure . It is a hydrocarbon and the simplest alkyne. This colorless gas is widely used as a fuel and a chemical building block. It is unstable in its pure ...

with the two hydrogen atoms replaced by

cyanide Cyanide is a naturally occurring, rapidly acting, toxic chemical that can exist in many different forms. In chemistry, a cyanide () is a chemical compound that contains a functional group. This group, known as the cyano group, consists of ...

groups. At room temperature, dicyanoacetylene is a clear liquid. Because of its high

endothermic In thermochemistry, an endothermic process () is any thermodynamic process with an increase in the enthalpy (or internal energy ) of the system.Oxtoby, D. W; Gillis, H.P., Butler, L. J. (2015).''Principle of Modern Chemistry'', Brooks Cole. p. ...

heat of formation In chemistry and thermodynamics, the standard enthalpy of formation or standard heat of formation of a compound is the change of enthalpy during the formation of 1 mole of the substance from its constituent elements in their reference state, wit ...

, it can explode to carbon powder and nitrogen gas, and it burns in

oxygen Oxygen is the chemical element with the symbol O and atomic number 8. It is a member of the chalcogen group in the periodic table, a highly reactive nonmetal, and an oxidizing agent that readily forms oxides with most elements as wel ...

with a bright blue-white flame at a temperature of 5260 K (4990 °C, 9010 °F), the hottest flame in oxygen; burnt in

ozone Ozone (), or trioxygen, is an inorganic molecule with the chemical formula . It is a pale blue gas with a distinctively pungent smell. It is an allotrope of oxygen that is much less stable than the diatomic allotrope , breaking down in the lo ...

at high pressure the flame temperature exceeds 6000 K (5730 °C, 10340 °F).

Synthesis

Dicyanoacetylene can be prepared by passing

nitrogen gas Nitrogen is the chemical element with the symbol N and atomic number 7. Nitrogen is a nonmetal and the lightest member of group 15 of the periodic table, often called the pnictogens. It is a common element in the universe, estimated at seventh ...

over a sample of

graphite Graphite () is a crystalline form of the element carbon. It consists of stacked layers of graphene. Graphite occurs naturally and is the most stable form of carbon under standard conditions. Synthetic and natural graphite are consumed on large ...

heated to temperatures between 2673 and 3000 K.

As a reagent in organic chemistry

Dicyanoacetylene is a powerful dienophile because the cyanide groups are

electron-withdrawing In chemistry, an electron-withdrawing group (EWG) is a substituent that has some of the following kinetic and thermodynamic implications: *with regards to electron transfer, electron-withdrawing groups enhance the oxidizing power tendency of th ...

, so it is a useful reagent for Diels-Alder reactions with unreactive dienes. It even adds to the

aromatic In chemistry, aromaticity is a chemical property of cyclic ( ring-shaped), ''typically'' planar (flat) molecular structures with pi bonds in resonance (those containing delocalized electrons) that gives increased stability compared to satur ...

compound

durene Durene, or 1,2,4,5-tetramethylbenzene, is an organic compound with the formula C6H2(CH3)4. It is a colourless solid with a sweet odor. The compound is classified as an alkylbenzene. It is one of three isomers of tetramethylbenzene, the other t ...

(1,2,4,5-tetramethylbenzene) to form a substituted bicyclooctatriene. Only the most reactive of dienophiles can attack such aromatic compounds.

In outer space

Solid dicyanoacetylene has been detected in the

atmosphere of Titan The atmosphere of Titan is the dense layer of gases surrounding Titan, the largest moon of Saturn. It is the only thick atmosphere of a natural satellite in the Solar System. Titan's lower atmosphere is primarily composed of nitrogen (94.2%), ...

infrared spectroscopy Infrared spectroscopy (IR spectroscopy or vibrational spectroscopy) is the measurement of the interaction of infrared radiation with matter by absorption, emission, or reflection. It is used to study and identify chemical substances or function ...

. As the seasons change on Titan, the compound condenses and evaporates in a cycle, which allows scientists on Earth to study Titanian meteorology. , the detection of dicyanoacetylene in the

interstellar medium In astronomy, the interstellar medium is the matter and radiation that exist in the space between the star systems in a galaxy. This matter includes gas in ionic, atomic, and molecular form, as well as dust and cosmic rays. It fills interstella ...

has been impossible, because its symmetry means it has no rotational microwave spectrum. However, similar asymmetric molecules like

cyanoacetylene Cyanoacetylene is an organic compound with formula or . It is the simplest cyanopolyyne. Cyanoacetylene has been detected by spectroscopic methods in interstellar clouds, in the coma of comet Hale–Bopp and in the atmosphere of Saturn's m ...

have been observed, and its presence in those environments is therefore suspected.

References

{{reflist Conjugated nitriles Alkyne derivatives

Synthesis

As a reagent in organic chemistry

In outer space

See also

References