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
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• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Phase change data
  • Reaction thermochemistry data
  • IR Spectrum
  • Mass spectrum (electron ionization)
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• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

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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

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, Gas phase thermochemistry data, Condensed phase 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.

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]

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, Gas phase thermochemistry data, Condensed phase thermochemistry data, Gas phase ion energetics data, References

• Symbols used in this document:
  

  EA	Electron affinity
  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

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