2-Norbornene

Data at NIST subscription sites:

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.


Reaction thermochemistry data

Go To: Top, 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:
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
Δr1682. ± 13.kJ/molG+TSLee and Squires, 1986gas phase; Between NH3, EtNH2. Assigned as vinylic site by authors.; B
Quantity Value Units Method Reference Comment
Δr1648. ± 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
Δr-137. ± 0.4kJ/molChydDoering, Roth, et al., 1988gas phase; ALS
Δr-141.5 ± 1.2kJ/molChydRogers, Choi, et al., 1980liquid phase; solvent: Hexane; Author was aware that data differs from previously reported values; ALS
Δr-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
Δr-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
Δr-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
Δr97.2 ± 2.5kJ/molEqkWalsh and Wells, 1976gas 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]

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, Reaction thermochemistry data, References