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2,5-Norbornadiene

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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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
B - John E. Bartmess

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Individual Reactions

Tetracyclo[3.2.0.0(2,7).0(4,6)]heptane = 2,5-Norbornadiene

By formula: C7H8 = C7H8

Quantity Value Units Method Reference Comment
Deltar-90. ± 30.kJ/molAVGN/AAverage of 6 values; Individual data points

C7H7- + Hydrogen cation = 2,5-Norbornadiene

By formula: C7H7- + H+ = C7H8

Quantity Value Units Method Reference Comment
Deltar1672. ± 7.5kJ/molG+TSLee and Squires, 1986gas phase; Between EtNH2, nPrNH2; B
Quantity Value Units Method Reference Comment
Deltar1637. ± 6.3kJ/molIMRBLee and Squires, 1986gas phase; Between EtNH2, nPrNH2; B
Deltar1628. ± 21.kJ/molIMRBWright and Beauchamp, 1981gas phase; B

2,5-Norbornadiene + 2Hydrogen = Norbornane

By formula: C7H8 + 2H2 = C7H12

Quantity Value Units Method Reference Comment
Deltar-296. ± 1.kJ/molChydDoering, Roth, et al., 1988gas phase; ALS
Deltar-291.9 ± 1.5kJ/molChydRogers, Choi, et al., 1980liquid phase; solvent: Hexane; ALS
Deltar-285.0 ± 1.7kJ/molChydTurner, Meador, et al., 1957liquid phase; solvent: Acetic acid; ALS

2,5-Norbornadiene = 1,3-Cyclopentadiene + Acetylene

By formula: C7H8 = C5H6 + C2H2

Quantity Value Units Method Reference Comment
Deltar117.2 ± 2.1kJ/molKinWalsh and Wells, 1975gas phase; Reanalyzed by Pedley, Naylor, et al., 1986, Original value = 118.7 ± 1.3 kJ/mol; ALS

2,5-Norbornadiene = Tetracyclo[3.2.0.0(2,7).0(4,6)]heptane

By formula: C7H8 = C7H8

Quantity Value Units Method Reference Comment
Deltar59. ± 4.kJ/molCisoHarel, Adamson, et al., 1987liquid phase; solvent: Cyclohexane; Photocalorimetry; ALS

1,3-Cyclopentadiene + Acetylene = 2,5-Norbornadiene

By formula: C5H6 + C2H2 = C7H8

Quantity Value Units Method Reference Comment
Deltar-117. ± 2.kJ/molEqkWalsh and Wells, 1975gas phase; ALS

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.

Lee and Squires, 1986
Lee, R.E.; Squires, R.R., Anionic homoaromaticity: A gas phase experimental study, J. Am. Chem. Soc., 1986, 105, 5078. [all data]

Wright and Beauchamp, 1981
Wright, C.A.; Beauchamp, J.L., Infrared spectra of gas phase ions and their use in elucidating reaction mechanisms. Identification of C7H7- structural isomers by multiphoton electron detachment using a low-powered laser, J. Am. Chem. Soc., 1981, 103, 6499. [all data]

Doering, Roth, et al., 1988
Doering, W.E.; Roth, W.R.; Breuckmann, R.; Figge, L.; Lennartz, H.-W.; Fessner, W.-D.; Prinzbach, F.H., Verbotene Reaktionen. - [2 + 2]-Cycloreversion starrer Cyclobutane, Chem. Ber., 1988, 121, 1-9. [all data]

Rogers, Choi, et al., 1980
Rogers, D.W.; Choi, L.S.; Girellini, R.S., Heats of hydrogenation and formation of quadricyclene, norbornadiene, norbornene, and nortricyclene, J. Phys. Chem., 1980, 84, 1810-1814. [all data]

Turner, Meador, et al., 1957
Turner, R.B.; Meador, W.R.; Winkler, R.E., Heats of hydrogenation. I. Apparatus and the heats of hydrogenation of bicyclo[2,2,1]heptene, bicyclo[2,2,1]heptadiene, bicyclo[2,2,2]octene and bicyclo[2,2,2]octadiene, J. Am. Chem. Soc., 1957, 79, 4116-4121. [all data]

Walsh and Wells, 1975
Walsh, R.; Wells, J.M., The enthalpy of formation of bicyclo[2,2,1]hepta-2,5-diene. Thermodynamic functions of bicyclo[2,2,1]heptane and bicyclo[2,2,1]hepta-2,5-diene, J. Chem. Thermodyn., 1975, 7, 149-154. [all data]

Pedley, Naylor, et al., 1986
Pedley, J.B.; Naylor, R.D.; Kirby, S.P., Thermochemical Data of Organic Compounds, Chapman and Hall, New York, 1986, 1-792. [all data]

Harel, Adamson, et al., 1987
Harel, Y.; Adamson, A.W.; Kutal, C.; Grutsch, P.A.; Yasufuku, K., Photocalorimetry. 6. Enthalpies of isomerization of norbornadiene and of substituted norbornadienes to corresponding quadricyclenes, J. Phys. Chem., 1987, 91, 901-904. [all data]


Notes

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