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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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 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° | -32.8 ± 0.1 | kcal/mol | Chyd | Doering, Roth, et al., 1988 | gas phase |
| ΔrH° | -33.82 ± 0.28 | kcal/mol | Chyd | Rogers, Choi, et al., 1980 | liquid phase; solvent: Hexane; Author was aware that data differs from previously reported values |
| ΔrH° | -33.13 ± 0.21 | kcal/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° | -70.8 ± 0.3 | kcal/mol | Chyd | Doering, Roth, et al., 1988 | gas phase |
| ΔrH° | -69.77 ± 0.36 | kcal/mol | Chyd | Rogers, Choi, et al., 1980 | liquid phase; solvent: Hexane |
| ΔrH° | -68.11 ± 0.41 | kcal/mol | Chyd | Turner, Meador, et al., 1957 | liquid phase; solvent: Acetic acid |
+
=
By formula: H2 + C7H10 = C7H12
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -31.1 ± 0.2 | kcal/mol | Chyd | Flury, Grob, et al., 1988 | liquid phase; solvent: Isooctane |
| ΔrH° | -32.58 ± 0.52 | kcal/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° | -91.95 ± 0.43 | kcal/mol | Chyd | Rogers, Choi, et al., 1980 | liquid phase; solvent: Hexane |
| ΔrH° | -92.03 ± 0.49 | kcal/mol | Chyd | Turner, Goebel, et al., 1968 | liquid phase; solvent: Acetic acid |
+
=
By formula: H2 + C7H10 = C7H12
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -52.6 ± 0.2 | kcal/mol | Chyd | Flury, Grob, et al., 1988 | liquid phase; solvent: Isooctane |
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.
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, Reaction thermochemistry data, References
- Symbols used in this document:
ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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