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
- Permanent link for this species. Use this link for bookmarking this species for future reference.
- Information on this page:
- Other data available:
- Options:
Data at NIST subscription sites:
NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.
Reaction thermochemistry 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 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° | -112. | kJ/mol | Kin | Samuilov, Bukharov, et al., 1981 | liquid phase; solvent: Chorobenzene |
| ΔrH° | -106.9 ± 2.9 | kJ/mol | Cm | Rogers, 1972 | liquid phase |
C21H12N4 = +
By formula: C21H12N4 = C6N4 + C15H12
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 62.3 | kJ/mol | Kin | Lotfi and Roberts, 1979 | liquid phase; solvent: CCl4; Spectrophotometrically |
=
+
By formula: C11H8N4 = C6N4 + C5H8
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 157. ± 3. | kJ/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° | -157. ± 3. | kJ/mol | Cm | Rogers, 1971 | liquid phase; solvent: Dichloromethane |
+
=
By formula: C9H10O + C6N4 = C15H10N4O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -51.8 | kJ/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° | -165.6 ± 1.8 | kJ/mol | Cm | Rogers, 1972 | liquid phase |
+
=
By formula: C6H8 + C6N4 = C12H8N4
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -120.9 ± 3.2 | kJ/mol | Cm | Rogers, 1972 | liquid phase |
C12H10N4 = +
By formula: C12H10N4 = C6H10 + C6N4
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 165.6 ± 1.8 | kJ/mol | Cm | Rogers, 1972 | solid phase |
=
+
By formula: C12H8N4 = C6H8 + C6N4
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 120.9 ± 3.2 | kJ/mol | Cm | Rogers, 1972 | solid phase |
=
+
By formula: C11H6N4 = C5H6 + C6N4
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 106.9 ± 2.9 | kJ/mol | Cm | Rogers, 1972 | solid phase |
=
+
By formula: C20H10N4 = C14H10 + C6N4
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 40.5 ± 2.1 | kJ/mol | Cm | Rogers, 1972 | solid phase |
References
Go To: Top, Reaction thermochemistry 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]
Notes
Go To: Top, Reaction thermochemistry data, References
- Symbols used in this document:
ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
- The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
- Customer support for NIST Standard Reference Data products.