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Dicyanoacetylene
Dicyanoacetylene Structural Formula V2.svg
Carbon-subnitride-3D-balls.png
Carbon-subnitride-3D-vdW.png
Names
Systematic IUPAC name
But-2-ynedinitrile
Identifiers
1071-98-3 YesY
ChemSpider 13449 N
Jmol-3D images Image
PubChem 14068
Properties
C4N2
Molar mass 76.06 g/mol
Density 0.907 g/cm3
Melting point 20.5 °C (68.9 °F; 293.6 K)
Boiling point 76.5 °C (169.7 °F; 349.6 K)
Thermochemistry
+500.4 kJ/mol
Related compounds
Related compounds
Carbon suboxide
Cyanogen
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 N verify (what isYesY/N?)
Infobox references

Dicyanoacetylene, also called carbon subnitride or but-2-ynedinitrile (IUPAC), is a compound of carbon and nitrogen with chemical formula C4N2. It has a linear molecular structure, N≡C−C≡C−C≡N (often abbreviated as NC4N), with alternating triple and single covalent bonds. It can be viewed as acetylene with the two hydrogen atoms replaced by cyanide groups.

At room temperature, dicyanoacetylene is a clear liquid. Because of its high endothermic heat of formation, it can explode to carbon powder and nitrogen gas, and it burns in oxygen with a bright blue-white flame at a temperature of 5260 K (4990 °C, 9010 °F),[1] which is the hottest flame of any chemical reaction.

Synthesis[edit]

Dicyanoacetylene can be prepared by passing nitrogen gas over a sample of graphite heated to temperatures between 2673 to 3000 K.[2]

As a reagent in organic chemistry[edit]

Dicyanoacetylene is a powerful dienophile because the cyanide groups are electron-withdrawing, so it is a useful reagent for Diels-Alder reactions with unreactive dienes. It even adds to the aromatic compound durene (1,2,4,5-tetramethylbenzene) to form a substituted bicyclooctatriene.[3] Only the most reactive of dienophiles can attack such aromatic compounds.

In outer space[edit]

Solid dicyanoacetylene has been detected in Titan's atmosphere by infrared spectroscopy.[4] As the seasons change on Titan, the compound condenses and evaporates in a cycle, which allows scientists on Earth to study Titanian meteorology.

As of 2006, the detection of dicyanoacetylene in the interstellar medium has been impossible, because its symmetry means it has no rotational microwave spectrum. However, similar asymmetric molecules like cyanoacetylene have been observed, and its presence in those environments is therefore suspected.[5]

See also[edit]

References[edit]

  1. ^ Kirshenbaum, A. D.; Grosse, A. V. (1956). "The Combustion of Carbon Subnitride, C4N2, and a Chemical Method for the Production of Continuous Temperatures in the Range of 5000–6000°K". Journal of the American Chemical Society 78 (9): 2020. doi:10.1021/ja01590a075. 
  2. ^ Ciganek, E.; Krespan, C. G. (1968). "Syntheses of Dicyanoacetylene". The Journal of Organic Chemistry 33 (2): 541–544. doi:10.1021/jo01266a014. 
  3. ^ Weis, C. D. (1963). "Reactions of Dicyanoacetylene". Journal of Organic Chemistry 28 (1): 74–78. doi:10.1021/jo01036a015. 
  4. ^ Samuelson, R. E.; Mayo, L. A.; Knuckles, M. A.; Khanna, R. J. (1977). "C4N2 Ice in Titan's North Polar Stratosphere". Planetary and Space Science 45 (8): 941–948. Bibcode:1997P&SS...45..941S. doi:10.1016/S0032-0633(97)00088-3. 
  5. ^ Kołos, R. (2002). "Exotic Isomers of Dicyanoacetylene: A Density Functional Theory and ab initio Study". Journal of Chemical Physics 117 (5): 2063–2067. Bibcode:2002JChPh.117.2063K. doi:10.1063/1.1489992. 

Original courtesy of Wikipedia: http://en.wikipedia.org/wiki/Dicyanoacetylene — Please support Wikipedia.
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2 news items

 
The Daily Galaxy (blog)
Tue, 27 May 2014 08:50:55 -0700

In this experiment, dicyanoacetylene was exposed to laser light at wavelengths as long as 355 nanometers. Light of that wavelength can filter down to Titan's lower atmosphere at a modest intensity, somewhat like the amount of light that comes through ...
 
NASA
Wed, 03 Apr 2013 09:07:30 -0700

In this latest experiment, dicyanoacetylene was exposed to laser light at wavelengths as long as 355 nanometers. Light of that wavelength can filter down to Titan's lower atmosphere at a modest intensity, somewhat like the amount of light that comes ...
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