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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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Reaction 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
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | 90. ± 30. | kJ/mol | AVG | N/A | Average of 8 values; Individual data points |
Constant pressure heat capacity of gas
| Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 112.7 | 298.15 | Walsh R., 1975 | Two 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 |
| 113.6 | 300. | ||
| 157.1 | 400. | ||
| 193.9 | 500. | ||
| 223.7 | 600. | ||
| 248.1 | 700. | ||
| 268.2 | 800. | ||
| 285.2 | 900. | ||
| 299.5 | 1000. |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, Reaction 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
DH - Eugene S. Domalski and Elizabeth D. Hearing
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°liquid | 29.7 ± 1.7 | kJ/mol | Ccb | Hall, Smith, et al., 1973 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -4213. ± 2. | kJ/mol | Ccb | Hall, Smith, et al., 1973 | Corresponding ΔfHºliquid = 29.7 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔfH°solid | 44.4 ± 2.0 | kJ/mol | Ccr | Steele, Chirico, et al., 1996 | Hfusion=3.2±0.2 kJ/mol; ALS |
| ΔfH°solid | 53.5 ± 3.2 | kJ/mol | Ccb | Steele, 1978 | ALS |
| ΔfH°solid | 41.4 ± 1.4 | kJ/mol | Ccb | Kozina, Bychikhina, et al., 1976 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -4228.2 ± 2.0 | kJ/mol | Ccr | Steele, Chirico, et al., 1996 | Hfusion=3.2±0.2 kJ/mol; Corresponding ΔfHºsolid = 44.44 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°solid | -4237.2 ± 3.2 | kJ/mol | Ccb | Steele, 1978 | Corresponding ΔfHºsolid = 53.5 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°solid | -4225.1 ± 1.3 | kJ/mol | Ccb | Kozina, Bychikhina, et al., 1976 | Corresponding ΔfHºsolid = 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 |
|---|---|---|---|
| 129.9 | 298.15 | Steele, 1978 | DH |
| 129.9 | 297. | Hall, Smith, et al., 1973 | DH |
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:
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
+
=
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, 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
- Symbols used in this document:
Cp,gas Constant pressure heat capacity of gas Cp,solid Constant pressure heat capacity of solid ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions 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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