Tetracyanoethylene

• Formula: C₆N₄
• Molecular weight: 128.0910
• IUPAC Standard InChI: InChI=1S/C6N4/c7-1-5(2-8)6(3-9)4-10 Copy

  
• IUPAC Standard InChIKey: NLDYACGHTUPAQU-UHFFFAOYSA-N Copy
• CAS Registry Number: 670-54-2
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
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• Other names: Ethenetetracarbonitrile; δ2,2'-Bimalononitrile; Ethene, tetracyano-; Ethylenetetracarbonitrile; Tetracyanoethene; TCNE; (NC)2CC(CN)2; Tetrakyanethylen; 1,1,2,2-Tetracyanoethene; 1,1,2,2-Tetracyanoethylene; Ethylene, tetracyano-; 1,1,2,2-Ethenetetracarbonitrile; NSC 24833
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • References
  • Notes
• Other data available:
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
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Gas phase thermochemistry data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Condensed phase thermochemistry data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Phase change data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos

Enthalpy of sublimation

Enthalpy of fusion

Reaction thermochemistry data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

 +  =

By formula: C₅H₆ + C₆N₄ = C₁₁H₆N₄

C₂₁H₁₂N₄ =  + 

By formula: C₂₁H₁₂N₄ = C₆N₄ + C₁₅H₁₂

=  + 

By formula: C₁₁H₈N₄ = C₆N₄ + C₅H₈

 +  =

By formula: C₆N₄ + C₅H₈ = C₁₁H₈N₄

 +  =

By formula: C₉H₁₀O + C₆N₄ = C₁₅H₁₀N₄O

 +  = C₁₂H₁₀N₄

By formula: C₆H₁₀ + C₆N₄ = C₁₂H₁₀N₄

 +  =

By formula: C₆H₈ + C₆N₄ = C₁₂H₈N₄

C₁₂H₁₀N₄ =  + 

By formula: C₁₂H₁₀N₄ = C₆H₁₀ + C₆N₄

=  + 

By formula: C₁₂H₈N₄ = C₆H₈ + C₆N₄

=  + 

By formula: C₁₁H₆N₄ = C₅H₆ + C₆N₄

=  + 

By formula: C₂₀H₁₀N₄ = C₁₄H₁₀ + C₆N₄

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Baroody and Carpenter, 1972
Baroody, E.E.; Carpenter, G.A., Heats of formation of propellant compounds (U), Rpt. Naval Ordnance Systems Command Task No. 331-003/067-1/UR2402-001 for Naval Ordance Station, Indian Head, MD, 1972, 1-9. [all data]

Boyd, 1963
Boyd, R.H., Thermochemistry of cyanocarbons, J. Chem. Phys., 1963, 38, 2529-2535. [all data]

Frankel, Amster, et al., 1966
Frankel, M.B.; Amster, A.B.; Wilson, E.R.; McCormick, M.; McEachern, M., Jr., Synthesis and thermochemistry of tricyanomethyl and other polycyano compounds, Adv. Chem. Ser., 1966, 108-117. [all data]

Webster, 1966
Webster, O.W., Diazotetracyanocyclopentadiene, J. Am. Chem. Soc., 1966, 88, 4055-4060. [all data]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]

Radomska and Radomski, 1991
Radomska, M.; Radomski, R., Phase diagrams in the binary systems of tetracyanoethylene with mesitylene, durene and pentamethylbenzene, Journal of Thermal Analysis, 1991, 37, 4, 693-704, https://doi.org/10.1007/BF01913148 . [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

De Wit, Van Miltenburg, et al., 1983
De Wit, H.G.M.; Van Miltenburg, J.C.; De Kruif, C.G., Thermodynamic properties of molecular organic crystals containing nitrogen, oxygen, and sulphur 1. Vapour pressures and enthalpies of sublimation, The Journal of Chemical Thermodynamics, 1983, 15, 7, 651-663, https://doi.org/10.1016/0021-9614(83)90079-4 . [all data]

Boyd, 1963, 2
Boyd, Richard H., Thermochemistry of Cyanocarbons, J. Chem. Phys., 1963, 38, 10, 2529, https://doi.org/10.1063/1.1733536 . [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press Inc., London, 1970, 643. [all data]

Samuilov, Bukharov, et al., 1981
Samuilov, Ya.D.; Bukharov, S.V.; Konovalov, A.I., Reactivity of tetraphenylcyclopentadiene and tetracyclone in the Diels-Alder reaction with cyanoethylenes, Zh. Org. Khim., 1981, 17, 2389-2393. [all data]

Rogers, 1972
Rogers, F.E., Thermochemistry of the Diels-Alder reactions. II. Heat of addition of several dienes to tetracyanoethylene, J. Phys. Chem., 1972, 76, 106-109. [all data]

Lotfi and Roberts, 1979
Lotfi, M.; Roberts, R.M.G., Kinetics and mechanism of Diels-Alder additions of tetracyanoethylene to anthracene derivatives - I. Substituent effects, Tetrahedron, 1979, 35, 2131-2136. [all data]

Rogers, 1971
Rogers, F.E., Thermochemistry of the Diels-Alder reaction. I. Enthalpy of addition of isoprene to tetracyanoethylene, J. Phys. Chem., 1971, 75, 1734-1737. [all data]

Solomonov, Antipin, et al., 1979
Solomonov, B.N.; Antipin, I.S.; Konovalov, A.I.; Novikov, V.B., Solvation effects in the retro[2 + 2]cycloaddition reaction, Zh. Org. Khim., 1979, 15, 2466-24. [all data]

Notes

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• Symbols used in this document:
  

  Tboil	Boiling point
  Tfus	Fusion (melting) point
  ΔcH°solid	Enthalpy of combustion of solid at standard conditions
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfH°solid	Enthalpy of formation of solid at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔsubH	Enthalpy of sublimation
  ΔsubH°	Enthalpy of sublimation at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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