2-Norbornene
- Formula: C7H10
- Molecular weight: 94.1543
- IUPAC Standard InChI: InChI=1S/C7H10/c1-2-7-4-3-6(1)5-7/h1-2,6-7H,3-5H2
- IUPAC Standard InChIKey: JFNLZVQOOSMTJK-UHFFFAOYSA-N
- CAS Registry Number: 498-66-8
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript. - Other names: Bicyclo[2.2.1]hept-2-ene; Bicyclo[2.2.1]heptene; Norbornene; Norbornylene; Norcamphene; Norfenchene; 2-Norbornylene; 3,6-Endomethylenecyclohexene; Bicyclo[2.2.1]-2-heptene; NSC 120425; 8,9,10-trinorborn-2-ene
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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
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Individual Reactions
+
=
By formula: C7H9- + H+ = C7H10
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1682. ± 13. | kJ/mol | G+TS | Lee and Squires, 1986 | gas phase; Between NH3, EtNH2. Assigned as vinylic site by authors.; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1648. ± 13. | kJ/mol | IMRB | Lee and Squires, 1986 | gas phase; Between NH3, EtNH2. Assigned as vinylic site by authors.; B |
+
=
By formula: H2 + C7H10 = C7H12
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -137. ± 0.4 | kJ/mol | Chyd | Doering, Roth, et al., 1988 | gas phase; ALS |
| ΔrH° | -141.5 ± 1.2 | kJ/mol | Chyd | Rogers, Choi, et al., 1980 | liquid phase; solvent: Hexane; Author was aware that data differs from previously reported values; ALS |
| ΔrH° | -138.6 ± 0.88 | kJ/mol | Chyd | Turner, Meador, et al., 1957 | liquid phase; solvent: Acetic acid; ALS |
+
=
By formula: C7H10 + C2HF3O2 = C9H11F3O2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -64.15 ± 0.23 | kJ/mol | Cac | Wiberg, Wasserman, et al., 1985 | liquid phase; solvent: Trifluoroacetic acid; Trifluoroacetolysis; ALS |
+
=
By formula: C7H10 + HCl = C7H11Cl
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -70.9 ± 1.5 | kJ/mol | Cm | Arnett and Pienta, 1980 | liquid phase; solvent: Methylene chloride; Hydrochlorination; ALS |
=
+
By formula: C7H10 = C5H6 + C2H4
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 97.2 ± 2.5 | kJ/mol | Eqk | Walsh and Wells, 1976 | gas 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
- Symbols used in this document:
ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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