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2-Norbornene

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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
Deltafgas90. ± 30.kJ/molAVGN/AAverage of 8 values; Individual data points

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
112.7298.15Walsh R., 1975Two sets of calculated functions are given by [ Walsh R., 1976] for two vibrational assignments. The difference between the two sets is about 8 J/mol*K for S(T) values. S(298.15 K) recommended here is in good agreement with value obtained from detail force field calculation [ Lenz T.G., 1989].; GT
113.6300.
157.1400.
193.9500.
223.7600.
248.1700.
268.2800.
285.2900.
299.51000.

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
Deltafliquid29.7 ± 1.7kJ/molCcbHall, Smith, et al., 1973ALS
Quantity Value Units Method Reference Comment
Deltacliquid-4213. ± 2.kJ/molCcbHall, Smith, et al., 1973Corresponding «DELTA»fliquid = 29.7 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
Deltafsolid44.4 ± 2.0kJ/molCcrSteele, Chirico, et al., 1996Hfusion=3.2±0.2 kJ/mol; ALS
Deltafsolid53.5 ± 3.2kJ/molCcbSteele, 1978ALS
Deltafsolid41.4 ± 1.4kJ/molCcbKozina, Bychikhina, et al., 1976ALS
Quantity Value Units Method Reference Comment
Deltacsolid-4228.2 ± 2.0kJ/molCcrSteele, Chirico, et al., 1996Hfusion=3.2±0.2 kJ/mol; Corresponding «DELTA»fsolid = 44.44 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Deltacsolid-4237.2 ± 3.2kJ/molCcbSteele, 1978Corresponding «DELTA»fsolid = 53.5 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS
Deltacsolid-4225.1 ± 1.3kJ/molCcbKozina, Bychikhina, et al., 1976Corresponding «DELTA»fsolid = 41.4 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS

Constant pressure heat capacity of solid

Cp,solid (J/mol*K) Temperature (K) Reference Comment
129.9298.15Steele, 1978DH
129.9297.Hall, Smith, et al., 1973DH

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:
B - John E. Bartmess
ALS - 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

norbornenide anion + Hydrogen cation = 2-Norbornene

By formula: C7H9- + H+ = C7H10

Quantity Value Units Method Reference Comment
Deltar1682. ± 13.kJ/molG+TSLee and Squires, 1986gas phase; Between NH3, EtNH2. Assigned as vinylic site by authors.; B
Quantity Value Units Method Reference Comment
Deltar1648. ± 13.kJ/molIMRBLee and Squires, 1986gas phase; Between NH3, EtNH2. Assigned as vinylic site by authors.; B

Hydrogen + 2-Norbornene = Norbornane

By formula: H2 + C7H10 = C7H12

Quantity Value Units Method Reference Comment
Deltar-137. ± 0.4kJ/molChydDoering, Roth, et al., 1988gas phase; ALS
Deltar-141.5 ± 1.2kJ/molChydRogers, Choi, et al., 1980liquid phase; solvent: Hexane; Author was aware that data differs from previously reported values; ALS
Deltar-138.6 ± 0.88kJ/molChydTurner, Meador, et al., 1957liquid phase; solvent: Acetic acid; ALS

2-Norbornene + Trifluoroacetic acid = exo-Norborneol, trifluoroacetate

By formula: C7H10 + C2HF3O2 = C9H11F3O2

Quantity Value Units Method Reference Comment
Deltar-64.15 ± 0.23kJ/molCacWiberg, Wasserman, et al., 1985liquid phase; solvent: Trifluoroacetic acid; Trifluoroacetolysis; ALS

2-Norbornene + Hydrogen chloride = Bicyclo[2.2.1]heptane, 2-chloro-, exo-

By formula: C7H10 + HCl = C7H11Cl

Quantity Value Units Method Reference Comment
Deltar-70.9 ± 1.5kJ/molCmArnett and Pienta, 1980liquid phase; solvent: Methylene chloride; Hydrochlorination; ALS

2-Norbornene = 1,3-Cyclopentadiene + Ethylene

By formula: C7H10 = C5H6 + C2H4

Quantity Value Units Method Reference Comment
Deltar97.2 ± 2.5kJ/molEqkWalsh and Wells, 1976gas 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]

Walsh R., 1976
Walsh R., The enthalpy of formation and thermodynamic functions of bicyclo[2.2.1]hept-2-ene, J. Chem. Thermodyn., 1976, 8, 55-60. [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]

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]

Steele, Chirico, et al., 1996
Steele, W.V.; Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A.; Smith, N.K., Thermodynamic properties and ideal-gas enthalpies of formation for butyl vinyl ether, 1,2-dimethoxyethane, methyl glycolate, bicyclo[2.2.1]hept-2-ene, 5-vinylbicyclo[2.2.1]hept-2-ene, trans-azobenzene, butyl acrylate, di-tert-butyl ether, and hexane-1,6-diol, J. Chem. Eng. Data, 1996, 41, 1285-1302. [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]

Kozina, Bychikhina, et al., 1976
Kozina, M.P.; Bychikhina, L.V.; Gal'chenko, G.L.; Mil'vitskaya, E.M.; Ordubadi, M.; Plate, A.F., Enthalpies of nortricyclene and norbornene formation, Dokl. Akad. Nauk SSSR, 1976, 226, 1105-1108. [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]

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]

Wiberg, Wasserman, et al., 1985
Wiberg, K.B.; Wasserman, D.J.; Martin, E.J.; Murcko, M.A., Enthalpies of hydration of alkenes. 3. Cycloalkenes, J. Am. Chem. Soc., 1985, 107, 6019-6022. [all data]

Arnett and Pienta, 1980
Arnett, E.M.; Pienta, N.J., Stabilities of carbonium ions in solution. 12. Heats of formation of alkyl chlorides as an entree to heats of solvation of aliphatic carbonium ions, J. Am. Chem. Soc., 1980, 102, 3329-3334. [all data]

Walsh and Wells, 1976
Walsh, R.; Wells, J.M., The enthalpy of formation and thermodynamic functions of bicyclo[2,2,1]hept-2-ene, J. Chem. Thermodyn., 1976, 8, 55-60. [all data]


Notes

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