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
- Permanent link for this species. Use this link for bookmarking this species for future reference.
- Information on this page:
- Other data available:
- Data at other public NIST sites:
- Options:
Data at NIST subscription sites:
NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.
Condensed phase thermochemistry data
Go To: Top, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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 | -22.70 ± 0.25 | kcal/mol | Ccb | An, Zhu, et al., 1987 | ALS |
ΔfH°solid | -24.38 ± 0.79 | kcal/mol | Ccb | Steele, 1978 | ALS |
ΔfH°solid | -22.01 ± 0.52 | kcal/mol | Ccb | Boyd, Sanwal, et al., 1971 | ALS |
ΔfH°solid | -22.01 ± 0.65 | kcal/mol | Ccb | Bedford, Beezer, et al., 1963 | see also Boyd, Sanwal, et al., 1971; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -1045.55 ± 0.23 | kcal/mol | Ccb | An, Zhu, et al., 1987 | Corresponding ΔfHºsolid = -22.70 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°solid | -1043.9 ± 0.79 | kcal/mol | Ccb | Steele, 1978 | Corresponding ΔfHºsolid = -24.40 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°solid | -1046.24 ± 0.52 | kcal/mol | Ccb | Bedford, Beezer, et al., 1963 | see also Boyd, Sanwal, et al., 1971; Corresponding ΔfHºsolid = -22.01 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Constant pressure heat capacity of solid
Cp,solid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
36.09 | 298.15 | Steele, 1978 | DH |
Phase change data
Go To: Top, Condensed phase thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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° | 10. ± 1. | kcal/mol | AVG | N/A | Average of 8 values; Individual data points |
Enthalpy of sublimation
ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
9.63 ± 0.1 | 293. | GS | Verevkin and Emel'yanenko, 2004 | Based on data from 278. to 308. K.; AC |
9.6 ± 0.2 | 305. | TSGC | Clark, Knox, et al., 1975 | Based on data from 284. to 326. K.; AC |
9.59 ± 0.20 | 284. | V | Boyd, Sanwal, et al., 1971 | ALS |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
1.06 | 360.8 | DSC | Verevkin and Emel'yanenko, 2004 | AC |
Gas phase ion energetics data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Mass spectrum (electron ionization), 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 |
Mass spectrum (electron ionization)
Go To: Top, Condensed phase thermochemistry data, Phase change data, 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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.
Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
Due to licensing restrictions, this spectrum cannot be downloaded.
Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | Japan AIST/NIMC Database- Spectrum MS-NW-9198 |
NIST MS number | 235491 |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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]
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]
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]
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, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), References
- Symbols used in this document:
AE Appearance energy Cp,solid Constant pressure heat capacity of solid IE (evaluated) Recommended ionization energy Tboil Boiling point Tfus Fusion (melting) point ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions 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
- The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
- Customer support for NIST Standard Reference Data products.