Norbornane
- Formula: C7H12
- Molecular weight: 96.1702
- 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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Phase change data
Go To: Top, Gas phase ion energetics 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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 381. | K | N/A | Desty and Whyman, 1957 | Uncertainty assigned by TRC = 3. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 360. | K | N/A | Burwell, Shim, et al., 1957 | Uncertainty assigned by TRC = 2. K; TRC |
Tfus | 360.9 | K | N/A | Birch and Dean, 1954 | Uncertainty assigned by TRC = 1.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 41. ± 5. | kJ/mol | AVG | N/A | Average of 8 values; Individual data points |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
40.3 ± 0.4 | 293. | GS | Verevkin and Emel'yanenko, 2004 | Based on data from 278. to 308. K.; AC |
40.0 ± 0.8 | 305. | TSGC | Clark, Knox, et al., 1975 | Based on data from 284. to 326. K.; AC |
40.1 ± 0.84 | 284. | V | Boyd, Sanwal, et al., 1971 | ALS |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
4.45 | 360.8 | DSC | Verevkin and Emel'yanenko, 2004 | AC |
Gas phase ion energetics data
Go To: Top, Phase change data, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data evaluated as indicated in comments:
L - Sharon G. Lias
Data compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
View reactions leading to C7H12+ (ion structure unspecified)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 9.77 ± 0.03 | eV | N/A | N/A | L |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.74 | PE | Demeo and Yencha, 1970 | RDSH |
9.80 | PE | Bodor, Dewar, et al., 1970 | RDSH |
9.93 ± 0.02 | EI | Winters and Collins, 1968 | RDSH |
10.2 | PE | Heilbronner and Martin, 1972 | Vertical value; LLK |
10.15 | PE | Bischof, Heilbronner, et al., 1971 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C3H3+ | 14.03 ± 0.09 | ? | EI | Winters and Collins, 1968 | RDSH |
C3H5+ | 13.22 ± 0.12 | ? | EI | Winters and Collins, 1968 | RDSH |
C4H5+ | 13.44 ± 0.11 | ? | EI | Winters and Collins, 1968 | RDSH |
C4H6+ | 11.12 ± 0.03 | ? | EI | Winters and Collins, 1968 | RDSH |
C4H7+ | 10.60 ± 0.10 | ? | EI | Winters and Collins, 1968 | RDSH |
C5H7+ | 10.60 ± 0.10 | C2H5 | EI | Winters and Collins, 1968 | RDSH |
C5H8+ | 10.30 ± 0.07 | C2H4 | EI | Winters and Collins, 1968 | RDSH |
C6H9+ | 10.17 ± 0.06 | CH3 | EI | Winters and Collins, 1968 | RDSH |
References
Go To: Top, Phase change data, Gas phase ion energetics data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Desty and Whyman, 1957
Desty, D.H.; Whyman, B.H.F.,
Anal. Chem., 1957, 29, 320. [all data]
Burwell, Shim, et al., 1957
Burwell, R.L.; Shim, B.K.C.; Rowlinson, H.C.,
The Exchange between Hydrocarbons and Deuterium on Plladium Catalysts,
J. Am. Chem. Soc., 1957, 79, 5142. [all data]
Birch and Dean, 1954
Birch, S.F.; Dean, R.A.,
A Ring Clousre Reaction by Desulfurization with Raney Nickel,
Justus Liebigs Ann. Chem., 1954, 585, 234. [all data]
Verevkin and Emel'yanenko, 2004
Verevkin, Sergey P.; Emel'yanenko, Vladimir N.,
Enthalpy of Formation and Strain of Norbornane from Thermochemical Measurements and from ab Initio Calculations,
J. Phys. Chem. A, 2004, 108, 31, 6575-6580, https://doi.org/10.1021/jp0490554
. [all data]
Clark, Knox, et al., 1975
Clark, Timothy; Knox, Trevor; Mackle, Henry; McKervey, M. Anthony; Rooney, John J.,
Heats of sublimation of some cage hydrocarbons by a temperature scanning technique,
J. Chem. Soc., Faraday Trans. 1, 1975, 71, 0, 2107, https://doi.org/10.1039/f19757102107
. [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]
Demeo and Yencha, 1970
Demeo, D.A.; Yencha, A.J.,
Photoelectron spectra of bicyclic and exocyclic olefins,
J. Chem. Phys., 1970, 53, 4536. [all data]
Bodor, Dewar, et al., 1970
Bodor, N.; Dewar, M.J.S.; Worley, S.D.,
Photoelectron spectra of molecules. III. Ionization potentials of some cyclic hydrocarbons and their derivatives, and heats of formation and ionization potentials calculated by the MINDO SCF MO method,
J. Am. Chem. Soc., 1970, 92, 19. [all data]
Winters and Collins, 1968
Winters, R.E.; Collins, J.H.,
Mass spectrometric studies of structural isomers. I. Mono- and bicyclic C7H12 molecules,
J. Am. Chem. Soc., 1968, 90, 1235. [all data]
Heilbronner and Martin, 1972
Heilbronner, E.; Martin, H.D.,
The π-orbital sequence in norbornadiene and related hydrocarbons,
Helv. Chim. Acta, 1972, 55, 1490. [all data]
Bischof, Heilbronner, et al., 1971
Bischof, P.; Heilbronner, E.; Prinzbach, H.; Martin, H.D.,
A photoelectron-spectroscopic investigation of the homoconjugative interaction between π- and Walsh-orbitals in endo- and exo- cyclopropano-norbornene,
Helv. Chim. Acta, 1971, 54, 1072. [all data]
Notes
Go To: Top, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy IE (evaluated) Recommended ionization energy Tboil Boiling point Tfus Fusion (melting) point ΔfusH Enthalpy of fusion ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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