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2-Norbornene

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

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Individual Reactions

norbornenide anion + Hydrogen cation = 2-Norbornene

By formula: C7H9- + H+ = C7H10

Quantity Value Units Method Reference Comment
Deltar402.1 ± 3.1kcal/molG+TSLee and Squires, 1986gas phase; Between NH3, EtNH2. Assigned as vinylic site by authors.; B
Quantity Value Units Method Reference Comment
Deltar393.9 ± 3.0kcal/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-32.8 ± 0.1kcal/molChydDoering, Roth, et al., 1988gas phase; ALS
Deltar-33.82 ± 0.28kcal/molChydRogers, Choi, et al., 1980liquid phase; solvent: Hexane; Author was aware that data differs from previously reported values; ALS
Deltar-33.13 ± 0.21kcal/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-15.333 ± 0.055kcal/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-16.94 ± 0.37kcal/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
Deltar23.2 ± 0.60kcal/molEqkWalsh and Wells, 1976gas phase; ALS

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.

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

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