At room temperature, dicyanoacetylene is a clear liquid. Because of its high endothermicheat 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), the hottest flame in oxygen; burnt in ozone at high pressure the flame temperature exceeds 6000 K (5730 °C, 10340 °F).[1]
Dicyanoacetylene can be prepared by passing nitrogen gas over a sample of graphite heated to temperatures between 2673 and 3000 K.[2]
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]
^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.
^Ciganek, E.; Krespan, C. G. (1968). "Syntheses of Dicyanoacetylene". The Journal of Organic Chemistry. 33 (2): 541–544. doi:10.1021/jo01266a014.
^Weis, C. D. (1963). "Reactions of Dicyanoacetylene". Journal of Organic Chemistry. 28 (1): 74–78. doi:10.1021/jo01036a015.
^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.
^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.
February 25, 2023
dicyanoacetylene, also, called, carbon, subnitride, ynedinitrile, iupac, compound, carbon, nitrogen, with, chemical, formula, c4n2, linear, molecular, structure, often, abbreviated, nc4n, with, alternating, triple, single, covalent, bonds, viewed, acetylene, w. 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 NamesPreferred IUPAC name But 2 ynedinitrileIdentifiersCAS Number 1071 98 3 N3D model JSmol Interactive imageChemSpider 13449 NPubChem CID 14068CompTox Dashboard EPA DTXSID50147919InChI InChI 1S C4N2 c5 3 1 2 4 6 NKey ZEHZNAXXOOYTJM UHFFFAOYSA N NInChI 1 C4N2 c5 3 1 2 4 6Key ZEHZNAXXOOYTJM UHFFFAOYARSMILES N CC CC NPropertiesChemical formula C 4N 2Molar mass 76 058 g mol 1Density 0 907 g cm3Melting point 20 5 C 68 9 F 293 6 K Boiling point 76 5 C 169 7 F 349 6 K ThermochemistryStd enthalpy offormation DfH 298 500 4 kJ molRelated compoundsRelated compounds Carbon suboxide CyanogenExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N 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 5260 K 4990 C 9010 F the hottest flame in oxygen burnt in ozone at high pressure the flame temperature exceeds 6000 K 5730 C 10340 F 1 Contents 1 Synthesis 2 As a reagent in organic chemistry 3 In outer space 4 See also 5 ReferencesSynthesis EditDicyanoacetylene can be prepared by passing nitrogen gas over a sample of graphite heated to temperatures between 2673 and 3000 K 2 As a reagent in organic chemistry EditDicyanoacetylene 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 EditSolid 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 EditCyanogen N C C N Diacetylene H C C C C H CyanopolyynesReferences Edit 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 Ciganek E Krespan C G 1968 Syntheses of Dicyanoacetylene The Journal of Organic Chemistry 33 2 541 544 doi 10 1021 jo01266a014 Weis C D 1963 Reactions of Dicyanoacetylene Journal of Organic Chemistry 28 1 74 78 doi 10 1021 jo01036a015 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 amp SS 45 941S doi 10 1016 S0032 0633 97 00088 3 Kolos 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 Retrieved from https en wikipedia org w index php title Dicyanoacetylene amp oldid 1114087497, wikipedia, wiki, book, books, library,
