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 Copy

  
• IUPAC Standard InChIKey: UMRZSTCPUPJPOJ-UHFFFAOYSA-N Copy
• 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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• Information on this page:
  • Gas phase thermochemistry data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Phase change data
• Data at other public NIST sites:
  • Microwave spectra (on physics lab web site)
  • Gas Phase Kinetics Database
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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

Constant pressure heat capacity of gas

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

 +  =

By formula: H₂ + C₇H₁₀ = C₇H₁₂

 + 2 =

By formula: C₇H₈ + 2H₂ = C₇H₁₂

 +  =

By formula: H₂ + C₇H₁₀ = C₇H₁₂

2 +  =

By formula: 2H₂ + C₇H₈ = C₇H₁₂

 +  =

By formula: H₂ + C₇H₁₀ = C₇H₁₂

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)

Ionization energy determinations

Appearance energy determinations

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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Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.

Additional Data

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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Additional Data

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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Kovats' RI, polar column, isothermal

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

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References

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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]

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]

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, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, References

• Symbols used in this document:
  

  AE	Appearance energy
  Cp,gas	Constant pressure heat capacity of gas
  IE (evaluated)	Recommended ionization energy
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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