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 thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, 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:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | 164.5 | kcal/mol | N/A | Baroody and Carpenter, 1972 | Value computed using ΔfHsolid° value of 607.1 kj/mol from Baroody and Carpenter, 1972 and ΔsubH° value of 81.0 kj/mol from Boyd, 1963.; DRB |
| ΔfH°gas | 170.7 | kcal/mol | N/A | Frankel, Amster, et al., 1966 | Value computed using ΔfHsolid° value of 633.0±2.0 kj/mol from Frankel, Amster, et al., 1966 and ΔsubH° value of 81.0 kj/mol from Boyd, 1963.; DRB |
| ΔfH°gas | 168.5 ± 1.5 | kcal/mol | Ccb | Boyd, 1963 | ALS |
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
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°solid | 145.1 | kcal/mol | Ccb | Baroody and Carpenter, 1972 | |
| ΔfH°solid | 151.4 ± 0.5 | kcal/mol | Ccb | Frankel, Amster, et al., 1966 | |
| ΔfH°solid | 149.1 ± 0.4 | kcal/mol | Ccb | Boyd, 1963 | |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -716.1 ± 0.5 | kcal/mol | Ccb | Frankel, Amster, et al., 1966 | |
| ΔcH°solid | -724.98 | kcal/mol | Ccb | Webster, 1966 | |
| ΔcH°solid | -713.4 ± 0.4 | kcal/mol | Ccb | Boyd, 1963 |
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
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -26.8 | kcal/mol | Kin | Samuilov, Bukharov, et al., 1981 | liquid phase; solvent: Chorobenzene |
| ΔrH° | -25.56 ± 0.70 | kcal/mol | Cm | Rogers, 1972 | liquid phase |
C21H12N4 = +
By formula: C21H12N4 = C6N4 + C15H12
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 14.9 | kcal/mol | Kin | Lotfi and Roberts, 1979 | liquid phase; solvent: CCl4; Spectrophotometrically |
=
+
By formula: C11H8N4 = C6N4 + C5H8
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 37.6 ± 0.8 | kcal/mol | Cm | Rogers, 1971 | solid phase; Heat of formation derived by 77PED/RYL |
+
=
By formula: C6N4 + C5H8 = C11H8N4
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -37.6 ± 0.8 | kcal/mol | Cm | Rogers, 1971 | liquid phase; solvent: Dichloromethane |
+
=
By formula: C9H10O + C6N4 = C15H10N4O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -12.4 | kcal/mol | Cm | Solomonov, Antipin, et al., 1979 | liquid phase; solvent: methylene chloride |
+
= C12H10N4
By formula: C6H10 + C6N4 = C12H10N4
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -39.57 ± 0.44 | kcal/mol | Cm | Rogers, 1972 | liquid phase |
+
=
By formula: C6H8 + C6N4 = C12H8N4
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -28.90 ± 0.77 | kcal/mol | Cm | Rogers, 1972 | liquid phase |
C12H10N4 = +
By formula: C12H10N4 = C6H10 + C6N4
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 39.57 ± 0.44 | kcal/mol | Cm | Rogers, 1972 | solid phase |
=
+
By formula: C12H8N4 = C6H8 + C6N4
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 28.90 ± 0.77 | kcal/mol | Cm | Rogers, 1972 | solid phase |
=
+
By formula: C11H6N4 = C5H6 + C6N4
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 25.56 ± 0.70 | kcal/mol | Cm | Rogers, 1972 | solid phase |
=
+
By formula: C20H10N4 = C14H10 + C6N4
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 9.69 ± 0.50 | kcal/mol | Cm | Rogers, 1972 | solid phase |
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
| 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 thermochemistry data, Condensed phase thermochemistry data, 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.
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]
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, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction 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 ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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