Dicyanoacetylene

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.

Dicyanoacetylene

Names
Preferred IUPAC name But-2-ynedinitrile
Identifiers
CAS Number	1071-98-3 N
3D model (JSmol)	Interactive image
ChemSpider	13449 N
PubChem CID	14068
CompTox Dashboard (EPA)	DTXSID50147919
InChI InChI=1S/C4N2/c5-3-1-2-4-6 N Key: ZEHZNAXXOOYTJM-UHFFFAOYSA-N N InChI=1/C4N2/c5-3-1-2-4-6 Key: ZEHZNAXXOOYTJM-UHFFFAOYAR
SMILES N#CC#CC#N
Properties
Chemical formula	C4N2
Molar mass	76.058 g·mol−1
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
Std enthalpy of formation (ΔfH⦵298)	+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 is YN ?) Infobox references

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 5,260 K (4,990 °C; 9,010 °F), the hottest flame in oxygen; burned in ozone at high pressure the flame temperature exceeds 6,000 K (5,730 °C; 10,340 °F).^[1]

Synthesis

Dicyanoacetylene can be prepared by passing nitrogen gas over a sample of graphite heated to temperatures between 2,673 and 3,000 K (2,400 and 2,727 °C; 4,352 and 4,940 °F).^[2] It may also be synthesized via a reaction between a dihaloacetylene and a cyanide salt:^{[citation needed]}

${\displaystyle {\ce {C2X2 + 2 R-CN -> C4N2 + 2 RX}}}$

As a reagent in organic chemistry

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

Solid dicyanoacetylene has been detected in the atmosphere of Titan 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^[update], 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

• Cyanogen, N≡C−C≡N
• Diacetylene, H−C≡C−C≡C−H
• Cyanopolyynes

References

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 5000–6000K". 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. (1997). "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.