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:
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • IR Spectrum
  • Mass spectrum (electron ionization)
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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

Gas phase ion energetics 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:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
B - John E. Bartmess

Electron affinity determinations

Ionization energy determinations

References

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Notes

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

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]

Khuseynov, Fontana, et al., 2012
Khuseynov, D.; Fontana, M.T.; Sanov, A., Photoelectron spectroscopy and photochemistry of tetracyanoethylene radical anion in the gas phase, Chem. Phys. Lett., 2012, 550, 15-18, https://doi.org/10.1016/j.cplett.2012.08.035 . [all data]

Chowdhury and Kebarle, 1986
Chowdhury, S.; Kebarle, P., Electron affinities of di- and tetracyanoethylene and cyanobenzenes based on measurements of gas-phase electron transfer equilibria, J. Am. Chem. Soc., 1986, 108, 5453. [all data]

Lyons and Palmer, 1976
Lyons, L.E.; Palmer, L.D., The electron affinity of tetracyanoethylene and other organic electron acceptors, Aust. J. Chem., 1976, 29, 1919. [all data]

Lyons and Palmer, 1975
Lyons, L.E.; Palmer, L.D., A Surface ionization source and quadrupole mass filter for photodetachment studies, Int. J. Mass Spectrom. Ion Phys., 1975, 16, 431. [all data]

Lyons and Palmer, 1973
Lyons, L.E.; Palmer, L.D., Photodetachment of electrons from tetracyanoethylene nNegative ions, Chem. Phys. Lett., 1973, 21, 442. [all data]

Farragher and Page, 1967
Farragher, A.L.; Page, F.M., Experimental Determination of Electron Affinities. Part 11. - Electron Capture by Some Cyanocarbons and Related Compounds, Trans. Farad. Soc., 1967, 63, 2369, https://doi.org/10.1039/tf9676302369 . [all data]

Knowles and Nicholson, 1974
Knowles, D.J.; Nicholson, A.J.C., Ionization energies of formic and acetic acid monomers, J. Chem. Phys., 1974, 60, 1180. [all data]

Kotov and Potapov, 1972
Kotov, B.V.; Potapov, V.K., Ionization potentials of strong organic electron acceptors, Khim. Vys. Energ., 1972, 6, 375. [all data]

Houk and Munchausen, 1976
Houk, K.N.; Munchausen, L.L., Ionization potentials, electron affinities, reactivities of cyanoalkenes related electron-deficient alkenes. A frontier molecular orbital treatment of cyanoalkene reactivities in cycloaddition, electrophilic, nucleophilic, and radical reactions., J. Am. Chem. Soc., 1976, 98, 937. [all data]

Notes

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, References

• Symbols used in this document:
  

  EA	Electron affinity
  ΔrH°	Enthalpy of reaction at standard conditions

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