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Tetracyanoethylene

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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

1,3-Cyclopentadiene + Tetracyanoethylene = Bicyclo[2.2.1]hept-5-ene-2,2,3,3-tetracarbonitrile

By formula: C5H6 + C6N4 = C11H6N4

Quantity Value Units Method Reference Comment
Deltar-112.kJ/molKinSamuilov, Bukharov, et al., 1981liquid phase; solvent: Chorobenzene
Deltar-106.9 ± 2.9kJ/molCmRogers, 1972liquid phase

C21H12N4 = Tetracyanoethylene + Anthracene, 9-methyl-

By formula: C21H12N4 = C6N4 + C15H12

Quantity Value Units Method Reference Comment
Deltar62.3kJ/molKinLotfi and Roberts, 1979liquid phase; solvent: CCl4; Spectrophotometrically

3-Methyl-4-cyclohexene-1,1,2,2-tetracarbonitrile = Tetracyanoethylene + Isoprene

By formula: C11H8N4 = C6N4 + C5H8

Quantity Value Units Method Reference Comment
Deltar157. ± 3.kJ/molCmRogers, 1971solid phase; Heat of formation derived by 77PED/RYL

Tetracyanoethylene + Isoprene = 3-Methyl-4-cyclohexene-1,1,2,2-tetracarbonitrile

By formula: C6N4 + C5H8 = C11H8N4

Quantity Value Units Method Reference Comment
Deltar-157. ± 3.kJ/molCmRogers, 1971liquid phase; solvent: Dichloromethane

Benzene, (1-methoxyethenyl)- + Tetracyanoethylene = 1,1,2,2-Cyclobutanetetracarbonitrile, 3-methoxy-3-phenyl-

By formula: C9H10O + C6N4 = C15H10N4O

Quantity Value Units Method Reference Comment
Deltar-51.8kJ/molCmSolomonov, Antipin, et al., 1979liquid phase; solvent: methylene chloride

1,3-Butadiene, 2,3-dimethyl- + Tetracyanoethylene = C12H10N4

By formula: C6H10 + C6N4 = C12H10N4

Quantity Value Units Method Reference Comment
Deltar-165.6 ± 1.8kJ/molCmRogers, 1972liquid phase

1,3-Cyclohexadiene + Tetracyanoethylene = Bicyclo[2.2.2]oct-5-ene-2,2,3,3-tetracarbonitrile

By formula: C6H8 + C6N4 = C12H8N4

Quantity Value Units Method Reference Comment
Deltar-120.9 ± 3.2kJ/molCmRogers, 1972liquid phase

C12H10N4 = 1,3-Butadiene, 2,3-dimethyl- + Tetracyanoethylene

By formula: C12H10N4 = C6H10 + C6N4

Quantity Value Units Method Reference Comment
Deltar165.6 ± 1.8kJ/molCmRogers, 1972solid phase

Bicyclo[2.2.2]oct-5-ene-2,2,3,3-tetracarbonitrile = 1,3-Cyclohexadiene + Tetracyanoethylene

By formula: C12H8N4 = C6H8 + C6N4

Quantity Value Units Method Reference Comment
Deltar120.9 ± 3.2kJ/molCmRogers, 1972solid phase

Bicyclo[2.2.1]hept-5-ene-2,2,3,3-tetracarbonitrile = 1,3-Cyclopentadiene + Tetracyanoethylene

By formula: C11H6N4 = C5H6 + C6N4

Quantity Value Units Method Reference Comment
Deltar106.9 ± 2.9kJ/molCmRogers, 1972solid phase

9,10-Dihydro-9,10-ethanoanthracene-11,11,12,12-tetracarbonitrile = Anthracene + Tetracyanoethylene

By formula: C20H10N4 = C14H10 + C6N4

Quantity Value Units Method Reference Comment
Deltar40.5 ± 2.1kJ/molCmRogers, 1972solid 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

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