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Norbornane

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Gas phase thermochemistry data

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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
Deltafgas-13.13 ± 0.25kcal/molCcbAn, Zhu, et al., 1987ALS
Deltafgas-13.1 ± 1.1kcal/molCcbSteele, 1978Reanalyzed by Pedley, Naylor, et al., 1986, Original value = -14.7 ± 0.81 kcal/mol; ALS
Deltafgas-12.4kcal/molN/ABoyd, Sanwal, et al., 1971Value computed using «DELTA»fHsolid° value of -92.1±2.2 kj/mol from Boyd, Sanwal, et al., 1971 and «DELTA»subH° value of 40.1 kj/mol from An, Zhu, et al., 1987.; DRB
Deltafgas-12.4kcal/molN/ABedford, Beezer, et al., 1963Value computed using «DELTA»fHsolid° value of -92.1±2.7 kj/mol from Bedford, Beezer, et al., 1963 and «DELTA»subH° value of 40.1 kj/mol from An, Zhu, et al., 1987.; DRB

Constant pressure heat capacity of gas

Cp,gas (cal/mol*K) Temperature (K) Reference Comment
28.700298.15Walsh R., 1975Selected 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
28.920300.
40.540400.
50.480500.
58.590600.
65.229700.
70.760800.
75.421900.
79.3911000.

Condensed phase thermochemistry data

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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
Deltafsolid-22.70 ± 0.25kcal/molCcbAn, Zhu, et al., 1987ALS
Deltafsolid-24.38 ± 0.79kcal/molCcbSteele, 1978ALS
Deltafsolid-22.01 ± 0.52kcal/molCcbBoyd, Sanwal, et al., 1971ALS
Deltafsolid-22.01 ± 0.65kcal/molCcbBedford, Beezer, et al., 1963see also Boyd, Sanwal, et al., 1971; ALS
Quantity Value Units Method Reference Comment
Deltacsolid-1045.55 ± 0.23kcal/molCcbAn, Zhu, et al., 1987Corresponding «DELTA»fsolid = -22.70 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Deltacsolid-1043.9 ± 0.79kcal/molCcbSteele, 1978Corresponding «DELTA»fsolid = -24.40 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Deltacsolid-1046.24 ± 0.52kcal/molCcbBedford, Beezer, et al., 1963see also Boyd, Sanwal, et al., 1971; Corresponding «DELTA»fsolid = -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
36.09298.15Steele, 1978DH

Phase change data

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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
Tboil381.KN/ADesty and Whyman, 1957Uncertainty assigned by TRC = 3. K; TRC
Quantity Value Units Method Reference Comment
Tfus360.KN/ABurwell, Shim, et al., 1957Uncertainty assigned by TRC = 2. K; TRC
Tfus360.9KN/ABirch and Dean, 1954Uncertainty assigned by TRC = 1.5 K; TRC
Quantity Value Units Method Reference Comment
Deltasub10. ± 1.kcal/molAVGN/AAverage of 8 values; Individual data points

Enthalpy of sublimation

DeltasubH (kcal/mol) Temperature (K) Method Reference Comment
9.63 ± 0.1293.GSVerevkin and Emel'yanenko, 2004Based on data from 278. - 308. K.; AC
9.6 ± 0.2305.TSGCClark, Knox, et al., 1975Based on data from 284. - 326. K.; AC
9.59 ± 0.20284.VBoyd, Sanwal, et al., 1971ALS

Enthalpy of fusion

DeltafusH (kcal/mol) Temperature (K) Method Reference Comment
1.06360.8DSCVerevkin and Emel'yanenko, 2004AC

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


Reaction thermochemistry data

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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

Hydrogen + 2-Norbornene = Norbornane

By formula: H2 + C7H10 = C7H12

Quantity Value Units Method Reference Comment
Deltar-32.8 ± 0.1kcal/molChydDoering, Roth, et al., 1988gas phase
Deltar-33.82 ± 0.28kcal/molChydRogers, Choi, et al., 1980liquid phase; solvent: Hexane; Author was aware that data differs from previously reported values
Deltar-33.13 ± 0.21kcal/molChydTurner, Meador, et al., 1957liquid phase; solvent: Acetic acid

2,5-Norbornadiene + 2Hydrogen = Norbornane

By formula: C7H8 + 2H2 = C7H12

Quantity Value Units Method Reference Comment
Deltar-70.8 ± 0.3kcal/molChydDoering, Roth, et al., 1988gas phase
Deltar-69.77 ± 0.36kcal/molChydRogers, Choi, et al., 1980liquid phase; solvent: Hexane
Deltar-68.11 ± 0.41kcal/molChydTurner, Meador, et al., 1957liquid phase; solvent: Acetic acid

Hydrogen + Tricyclo[2.2.1.0(2,6)]heptane = Norbornane

By formula: H2 + C7H10 = C7H12

Quantity Value Units Method Reference Comment
Deltar-31.1 ± 0.2kcal/molChydFlury, Grob, et al., 1988liquid phase; solvent: Isooctane
Deltar-32.58 ± 0.52kcal/molChydRogers, Choi, et al., 1980liquid phase; solvent: Hexane; Author was aware that data differs from previously reported values

2Hydrogen + Tetracyclo[3.2.0.0(2,7).0(4,6)]heptane = Norbornane

By formula: 2H2 + C7H8 = C7H12

Quantity Value Units Method Reference Comment
Deltar-91.95 ± 0.43kcal/molChydRogers, Choi, et al., 1980liquid phase; solvent: Hexane
Deltar-92.03 ± 0.49kcal/molChydTurner, Goebel, et al., 1968liquid phase; solvent: Acetic acid

Hydrogen + Tricyclo-[3.2.0.0(2,7)]heptane = Norbornane

By formula: H2 + C7H10 = C7H12

Quantity Value Units Method Reference Comment
Deltar-52.6 ± 0.2kcal/molChydFlury, Grob, et al., 1988liquid phase; solvent: Isooctane

Gas phase ion energetics data

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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 ± 0.03eVN/AN/AL

Ionization energy determinations

IE (eV) Method Reference Comment
9.74PEDemeo and Yencha, 1970RDSH
9.80PEBodor, Dewar, et al., 1970RDSH
9.93 ± 0.02EIWinters and Collins, 1968RDSH
10.2PEHeilbronner and Martin, 1972Vertical value; LLK
10.15PEBischof, Heilbronner, et al., 1971Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C3H3+14.03 ± 0.09?EIWinters and Collins, 1968RDSH
C3H5+13.22 ± 0.12?EIWinters and Collins, 1968RDSH
C4H5+13.44 ± 0.11?EIWinters and Collins, 1968RDSH
C4H6+11.12 ± 0.03?EIWinters and Collins, 1968RDSH
C4H7+10.60 ± 0.10?EIWinters and Collins, 1968RDSH
C5H7+10.60 ± 0.10C2H5EIWinters and Collins, 1968RDSH
C5H8+10.30 ± 0.07C2H4EIWinters and Collins, 1968RDSH
C6H9+10.17 ± 0.06CH3EIWinters and Collins, 1968RDSH

IR Spectrum

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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

Gas Phase Spectrum

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IR spectrum
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Additional Data

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Owner NIST Standard Reference Data Program
Collection (C) 2018 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin NIST Mass Spectrometry Data Center
State gas
Instrument HP-GC/MS/IRD

This IR spectrum is from the NIST/EPA Gas-Phase Infrared Database .


Mass spectrum (electron ionization)

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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

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Mass spectrum
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Additional Data

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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

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


Gas Chromatography

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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

Kovats' RI, non-polar column, isothermal

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Column type Active phase Temperature (C) I Reference Comment
CapillarySqualane50.748.7Bajus, Veselý, et al., 1979Column length: 100. m; Column diameter: 0.25 mm
CapillarySqualane70.752.9Bajus, Veselý, et al., 1979Column length: 100. m; Column diameter: 0.25 mm
CapillarySqualane40.745.2Stopp, Engewald, et al., 1978Column length: 70. m; Column diameter: 0.23 mm
PackedSE-30140.748.Heintz, Gruselle, et al., 1976Chromosorb W (60-80 mesh); Column length: 2. m
PackedSqualane27.742.Hively and Hinton, 1968He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
PackedSqualane49.747.Hively and Hinton, 1968He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
PackedSqualane67.754.Hively and Hinton, 1968He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
PackedSqualane86.759.Hively and Hinton, 1968He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
PackedSqualane150.777.Schomburg, 1964 

Kovats' RI, polar column, isothermal

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Column type Active phase Temperature (C) I Reference Comment
PackedCarbowax 20M140.860.Heintz, Gruselle, et al., 1976Chromosorb W (60-80 mesh); Column length: 2. m

Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Column type Active phase I Reference Comment
CapillaryDB-5756.3Xu, van Stee, et al., 200330. m/0.25 mm/1. «mu»m, He, 2.5 K/min; Tstart: 50. C; Tend: 200. C

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, 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]

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]

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]

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 «pi»-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 «pi»- and Walsh-orbitals in endo- and exo- cyclopropano-norbornene, Helv. Chim. Acta, 1971, 54, 1072. [all data]

Bajus, Veselý, et al., 1979
Bajus, M.; Veselý, V.; Leclercq, P.A.; Rijks, J.A., Steam cracking of hydrocarbons. 2. Pyrolysis of methylcyclohexane, Ind. Eng. Chem. Prod. Res. Dev., 1979, 18, 2, 135-142, https://doi.org/10.1021/i360070a012 . [all data]

Stopp, Engewald, et al., 1978
Stopp, I.; Engewald, W.; Kühn, H.; Welsch, Th., Molekülstruktur und retentionsverhalten. VIII. Zum gaschromatographischen retentionsverhalten von dicyclopentadienderivaten, J. Chromatogr., 1978, 147, 21-30, https://doi.org/10.1016/S0021-9673(00)85113-4 . [all data]

Heintz, Gruselle, et al., 1976
Heintz, M.; Gruselle, M.; Druilhe, A.; Lefort, D., Relations entre structure chimique et données de rétention en chromatographie en phase gaseuse. VI. Alcools et esters méthyliques de structures cycliques, Chromatographia, 1976, 9, 8, 367-372, https://doi.org/10.1007/BF02330385 . [all data]

Hively and Hinton, 1968
Hively, R.A.; Hinton, R.E., Variation of the retention index with temperature on squalane substrates, J. Gas Chromatogr., 1968, 6, 4, 203-217, https://doi.org/10.1093/chromsci/6.4.203 . [all data]

Schomburg, 1964
Schomburg, G., Gas-Chromatographische Retentionsdaten und Struktur Chemischer Verbindungen. I. Verzweigte Aliphatische und Alicyclische Carbonsäure-Methylester, J. Chromatogr., 1964, 14, 157-177, https://doi.org/10.1016/S0021-9673(00)86608-X . [all data]

Xu, van Stee, et al., 2003
Xu, X.; van Stee, L.L.P.; Williams, J.; Beens, J.; Adahchour, M.; Vreuls, R.J.J.; Brinkman, U.A.Th.; Lelieveld, J., Comprehensive two-dimensional gas chromatography (GC×GC) measurements of volatile organic compounds in the atmosphere, Atmos. Chem. Phys., 2003, 3, 3, 665-682, https://doi.org/10.5194/acp-3-665-2003 . [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, References