Tetracyanoethylene
- Formula: C6N4
- Molecular weight: 128.0910
- IUPAC Standard InChI: InChI=1S/C6N4/c7-1-5(2-8)6(3-9)4-10
- IUPAC Standard InChIKey: NLDYACGHTUPAQU-UHFFFAOYSA-N
- 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
The 3d structure may be viewed using Java or Javascript. - 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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Gas phase ion energetics data
Go To: Top, References, Notes
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
| EA (eV) | Method | Reference | Comment |
|---|---|---|---|
| 3.160 ± 0.020 | LPES | Khuseynov, Fontana, et al., 2012 | B |
| 3.17 ± 0.20 | IMRE | Chowdhury and Kebarle, 1986 | ΔGea(423 K) = -73.0 kcal/mol; ΔSea (estimated) = 0. eu.; B |
| 2.30 ± 0.30 | LPD | Lyons and Palmer, 1976 | B |
| 1.70 ± 0.30 | LPD | Lyons and Palmer, 1975 | B |
| 2.030 ± 0.052 | PD | Lyons and Palmer, 1973 | B |
| 2.884 ± 0.061 | SI | Farragher and Page, 1967 | The Magnetron method, lacking mass analysis, is not considered reliable.; B |
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 11.765 ± 0.008 | PI | Knowles and Nicholson, 1974 | LLK |
| 11.67 ± 0.02 | PI | Kotov and Potapov, 1972 | LLK |
| 11.79 ± 0.05 | PE | Houk and Munchausen, 1976 | Vertical value; LLK |
References
Go To: Top, 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.
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 ion energetics data, References
- Symbols used in this document:
EA Electron affinity - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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