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Bicyclo[2.2.1]hept-5-ene-2,2,3,3-tetracarbonitrile

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Gas 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
Deltafgas738.9kJ/molCmRogers, 1972 

Phase change 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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos

Quantity Value Units Method Reference Comment
Deltasub117.2 ± 5.4kJ/molVRogers, 1972ALS

Enthalpy of sublimation

DeltasubH (kJ/mol) Temperature (K) Method Reference Comment
117.2 ± 5.4408.MGRogers, 1972See also Pedley and Rylance, 1977.; AC

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

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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

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

References

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

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]

Pedley and Rylance, 1977
Pedley, J.B.; Rylance, J., , Computer Analysed Thermochemical Data: Organic and Organometallic Compounds, University of Sussex, Brighton, 1977. [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]


Notes

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