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2,5-Norbornadiene

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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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Quantity Value Units Method Reference Comment
Deltafgas240. ± 20.kJ/molAVGN/AAverage of 6 values; Individual data points

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
105.60298.15Walsh R., 1975Selected value of S(298.15 K) is in excellent agreement with that calculated by force field method [ Lenz T.G., 1989].; GT
106.36300.
144.47400.
176.36500.
202.00600.
222.80700.
239.95800.
254.35900.
266.481000.

Condensed 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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Deltafliquid213.8 ± 3.0kJ/molCcbSteele, 1978ALS
Deltafliquid178.7 ± 1.0kJ/molCcbHall, Smith, et al., 1973ALS
Quantity Value Units Method Reference Comment
Deltacliquid-4111.7 ± 3.0kJ/molCcbSteele, 1978Corresponding «DELTA»fliquid = 213.8 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Deltacliquid-4076.7 ± 1.0kJ/molCcbHall, Smith, et al., 1973Corresponding «DELTA»fliquid = 178.8 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Deltacliquid-4099.kJ/molCcbSkuratov, Kozina, et al., 1958Corresponding «DELTA»fliquid = 201. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
161.2298.15Steele, 1978DH
116.1297.Hall, Smith, et al., 1973DH

Reaction thermochemistry data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, References, Notes

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

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

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, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Notes

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

Walsh R., 1975
Walsh R., 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]

Lenz T.G., 1989
Lenz T.G., Force-field calculations giving accurate conformation, Hf(T), S(T), and Cp(T) for unsaturated acyclic and cyclic hydrocarbons, J. Phys. Chem., 1989, 93, 1588-1592. [all data]

Steele, 1978
Steele, W.V., The standard enthalpies of formation of a series of C7, bridged-ring hydrocarbons: norbornane, norbornene, nortricyclene, norbornadiene, and quadricyclane, J. Chem. Thermodyn., 1978, 10, 919-927. [all data]

Hall, Smith, et al., 1973
Hall, H.K., Jr.; Smith, C.D.; Baldt, J.H., Enthalpies of formation of norticyclene, norbornene, norbornadiene, and quadricyclane, J. Am. Chem. Soc., 1973, 95, 3197-3201. [all data]

Skuratov, Kozina, et al., 1958
Skuratov, S.M.; Kozina, M.P.; Shtocher, S.M.; Prevalova, N.M.; Kamkina, L.S.; Zuko, V.D., Heats of combustion of cyclic compounds, Bull. Chem. Thermodyn., 1958, 1, 21. [all data]

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

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, References