Norbornane
- Formula: C7H12
- Molecular weight: 96.1702
- IUPAC Standard InChI: InChI=1S/C7H12/c1-2-7-4-3-6(1)5-7/h6-7H,1-5H2
- IUPAC Standard InChIKey: UMRZSTCPUPJPOJ-UHFFFAOYSA-N
- CAS Registry Number: 279-23-2
- 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]heptane; Cyclohexane, 1,4-endo-methylene-; Norbornylane; Norcamphane; Norfenchane; Norsantane; 1,4-Endomethylenecyclohexane
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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
DRB - Donald R. Burgess, Jr.
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | -54.9 ± 1.1 | kJ/mol | Ccb | An, Zhu, et al., 1987 | ALS |
| ΔfH°gas | -54.7 ± 4.7 | kJ/mol | Ccb | Steele, 1978 | Reanalyzed by Pedley, Naylor, et al., 1986, Original value = -61.6 ± 3.4 kJ/mol; ALS |
| ΔfH°gas | -52.0 | kJ/mol | N/A | Boyd, Sanwal, et al., 1971 | Value computed using ΔfHsolid° value of -92.1±2.2 kj/mol from Boyd, Sanwal, et al., 1971 and ΔsubH° value of 40.1 kj/mol from An, Zhu, et al., 1987.; DRB |
| ΔfH°gas | -52.0 | kJ/mol | N/A | Bedford, Beezer, et al., 1963 | Value computed using ΔfHsolid° value of -92.1±2.7 kj/mol from Bedford, Beezer, et al., 1963 and ΔsubH° value of 40.1 kj/mol from An, Zhu, et al., 1987.; DRB |
Constant pressure heat capacity of gas
| Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 120.08 | 298.15 | Walsh R., 1975 | Selected value of S(298.15 K) is in good agreement with that calculated by force field method [ Boyd R.H., 1971, Lenz T.G., 1989]. Discrepancy with S(500 K) [ Boyd R.H., 1971] amounts to 8.9 J/mol*K. Discrepancies between Cp(T) values calculated by [ Boyd R.H., 1971] and given here amount to 10.7-12.7 J/mol*K in the temperature range 298.15-500 K.; GT |
| 121.00 | 300. | ||
| 169.62 | 400. | ||
| 211.21 | 500. | ||
| 245.14 | 600. | ||
| 272.92 | 700. | ||
| 296.06 | 800. | ||
| 315.56 | 900. | ||
| 332.17 | 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°solid | -95.0 ± 1.1 | kJ/mol | Ccb | An, Zhu, et al., 1987 | ALS |
| ΔfH°solid | -102.0 ± 3.3 | kJ/mol | Ccb | Steele, 1978 | ALS |
| ΔfH°solid | -92.1 ± 2.2 | kJ/mol | Ccb | Boyd, Sanwal, et al., 1971 | ALS |
| ΔfH°solid | -92.1 ± 2.7 | kJ/mol | Ccb | Bedford, Beezer, et al., 1963 | see also Boyd, Sanwal, et al., 1971; ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -4374.59 ± 0.97 | kJ/mol | Ccb | An, Zhu, et al., 1987 | Corresponding ΔfHºsolid = -94.96 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°solid | -4367.5 ± 3.3 | kJ/mol | Ccb | Steele, 1978 | Corresponding ΔfHºsolid = -102.1 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°solid | -4377.5 ± 2.2 | kJ/mol | Ccb | Bedford, Beezer, et al., 1963 | see also Boyd, Sanwal, et al., 1971; Corresponding ΔfHºsolid = -92.09 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 |
|---|---|---|---|
| 151.0 | 298.15 | Steele, 1978 | 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 by: 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: H2 + C7H10 = C7H12
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -137. ± 0.4 | kJ/mol | Chyd | Doering, Roth, et al., 1988 | gas phase |
| 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 |
| ΔrH° | -138.6 ± 0.88 | kJ/mol | Chyd | Turner, Meador, et al., 1957 | liquid phase; solvent: Acetic acid |
+ 2
=
By formula: C7H8 + 2H2 = C7H12
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -296. ± 1. | kJ/mol | Chyd | Doering, Roth, et al., 1988 | gas phase |
| ΔrH° | -291.9 ± 1.5 | kJ/mol | Chyd | Rogers, Choi, et al., 1980 | liquid phase; solvent: Hexane |
| ΔrH° | -285.0 ± 1.7 | kJ/mol | Chyd | Turner, Meador, et al., 1957 | liquid phase; solvent: Acetic acid |
+
=
By formula: H2 + C7H10 = C7H12
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -130. ± 0.8 | kJ/mol | Chyd | Flury, Grob, et al., 1988 | liquid phase; solvent: Isooctane |
| ΔrH° | -136.3 ± 2.2 | kJ/mol | Chyd | Rogers, Choi, et al., 1980 | liquid phase; solvent: Hexane; Author was aware that data differs from previously reported values |
2 +
=
By formula: 2H2 + C7H8 = C7H12
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -384.7 ± 1.8 | kJ/mol | Chyd | Rogers, Choi, et al., 1980 | liquid phase; solvent: Hexane |
| ΔrH° | -385.1 ± 2.1 | kJ/mol | Chyd | Turner, Goebel, et al., 1968 | liquid phase; solvent: Acetic acid |
+
=
By formula: H2 + C7H10 = C7H12
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -220. ± 0.8 | kJ/mol | Chyd | Flury, Grob, et al., 1988 | liquid phase; solvent: Isooctane |
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.
An, Zhu, et al., 1987
An, X-W.; Zhu, H-P.; Hu, R-H.,
Heats of combustion and formation of norbornane,
Thermochim. Acta, 1987, 121, 473-477. [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]
Pedley, Naylor, et al., 1986
Pedley, J.B.; Naylor, R.D.; Kirby, S.P.,
Thermochemical Data of Organic Compounds, Chapman and Hall, New York, 1986, 1-792. [all data]
Boyd, Sanwal, et al., 1971
Boyd, R.H.; Sanwal, S.N.; Shary-Tehrany, S.; McNally, D.,
The thermochemistry, thermodynamic functions, and molecular structures of some cyclic hydrocarbons,
J. Phys. Chem., 1971, 75, 1264-1271. [all data]
Bedford, Beezer, et al., 1963
Bedford, A.F.; Beezer, A.E.; Mortimer, C.T.; Springall, H.D.,
Heats of combustion and molecular structure. Part IX. Bicylo[2,2,1]heptane, 7-oxabicyclo[2,2,1]heptane, and exo- and endo-2-methyl-7-oxabicyclo[2,2,1]heptane,
J. Chem. Soc., 1963, 3823-3828. [all data]
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]
Boyd R.H., 1971
Boyd R.H.,
The thermochemistry, thermodynamic functions, and molecular structures of some cyclic hydrocarbons,
J. Phys. Chem., 1971, 75, 1264-1271. [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]
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]
Flury, Grob, et al., 1988
Flury, P.; Grob, C.A.; Wang, G.Y.; Lennatz, H.-W.; Roth, W.R.,
113. Norbornanes. Bridging strain in norbornyl and oxanorbornyl cations,
Helv. Chim. Acta, 1988, 71, 1017-1024. [all data]
Turner, Goebel, et al., 1968
Turner, R.B.; Goebel, P.; Mallon, B.J.; Doering, W.E.; Coburn, J.F., Jr.; Pomerantz, M.,
Heats of hydrogenation. VIII. Compounds with three- and four-membered rings,
J. Am. Chem. Soc., 1968, 90, 4315-4322. [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°solid Enthalpy of combustion of solid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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