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:
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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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Gas phase thermochemistry data

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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
Δ_fH°_gas	164.5	kcal/mol	N/A	Baroody and Carpenter, 1972	Value computed using Δ_fH_solid° value of 607.1 kj/mol from Baroody and Carpenter, 1972 and Δ_subH° value of 81.0 kj/mol from Boyd, 1963.; DRB
Δ_fH°_gas	170.7	kcal/mol	N/A	Frankel, Amster, et al., 1966	Value computed using Δ_fH_solid° value of 633.0±2.0 kj/mol from Frankel, Amster, et al., 1966 and Δ_subH° value of 81.0 kj/mol from Boyd, 1963.; DRB
Δ_fH°_gas	168.5 ± 1.5	kcal/mol	Ccb	Boyd, 1963	ALS

Condensed phase thermochemistry data

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

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_solid	145.1	kcal/mol	Ccb	Baroody and Carpenter, 1972
Δ_fH°_solid	151.4 ± 0.5	kcal/mol	Ccb	Frankel, Amster, et al., 1966
Δ_fH°_solid	149.1 ± 0.4	kcal/mol	Ccb	Boyd, 1963
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_solid	-716.1 ± 0.5	kcal/mol	Ccb	Frankel, Amster, et al., 1966
Δ_cH°_solid	-724.98	kcal/mol	Ccb	Webster, 1966
Δ_cH°_solid	-713.4 ± 0.4	kcal/mol	Ccb	Boyd, 1963

Reaction thermochemistry data

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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

+ Tetracyanoethylene =

By formula: C₅H₆ + C₆N₄ = C₁₁H₆N₄

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-26.8	kcal/mol	Kin	Samuilov, Bukharov, et al., 1981	liquid phase; solvent: Chorobenzene
Δ_rH°	-25.56 ± 0.70	kcal/mol	Cm	Rogers, 1972	liquid phase

C₂₁H₁₂N₄ = Tetracyanoethylene +

By formula: C₂₁H₁₂N₄ = C₆N₄ + C₁₅H₁₂

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	14.9	kcal/mol	Kin	Lotfi and Roberts, 1979	liquid phase; solvent: CCl4; Spectrophotometrically

= Tetracyanoethylene +

By formula: C₁₁H₈N₄ = C₆N₄ + C₅H₈

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	37.6 ± 0.8	kcal/mol	Cm	Rogers, 1971	solid phase; Heat of formation derived by 77PED/RYL

Tetracyanoethylene + =

By formula: C₆N₄ + C₅H₈ = C₁₁H₈N₄

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-37.6 ± 0.8	kcal/mol	Cm	Rogers, 1971	liquid phase; solvent: Dichloromethane

+ Tetracyanoethylene =

By formula: C₉H₁₀O + C₆N₄ = C₁₅H₁₀N₄O

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-12.4	kcal/mol	Cm	Solomonov, Antipin, et al., 1979	liquid phase; solvent: methylene chloride

+ Tetracyanoethylene = C₁₂H₁₀N₄

By formula: C₆H₁₀ + C₆N₄ = C₁₂H₁₀N₄

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-39.57 ± 0.44	kcal/mol	Cm	Rogers, 1972	liquid phase

+ Tetracyanoethylene =

By formula: C₆H₈ + C₆N₄ = C₁₂H₈N₄

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-28.90 ± 0.77	kcal/mol	Cm	Rogers, 1972	liquid phase

C₁₂H₁₀N₄ = + Tetracyanoethylene

By formula: C₁₂H₁₀N₄ = C₆H₁₀ + C₆N₄

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	39.57 ± 0.44	kcal/mol	Cm	Rogers, 1972	solid phase

= + Tetracyanoethylene

By formula: C₁₂H₈N₄ = C₆H₈ + C₆N₄

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	28.90 ± 0.77	kcal/mol	Cm	Rogers, 1972	solid phase

= + Tetracyanoethylene

By formula: C₁₁H₆N₄ = C₅H₆ + C₆N₄

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	25.56 ± 0.70	kcal/mol	Cm	Rogers, 1972	solid phase

= + Tetracyanoethylene

By formula: C₂₀H₁₀N₄ = C₁₄H₁₀ + C₆N₄

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	9.69 ± 0.50	kcal/mol	Cm	Rogers, 1972	solid phase

References

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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]

Notes

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Symbols used in this document:

Δ_cH°_solid	Enthalpy of combustion of solid at standard conditions
Δ_fH°_gas	Enthalpy of formation of gas at standard conditions
Δ_fH°_solid	Enthalpy of formation of solid at standard conditions
Δ_rH°	Enthalpy of reaction at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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