Bicyclo[4.1.0]heptane

• Formula: C₇H₁₂
• Molecular weight: 96.1702
• IUPAC Standard InChI: InChI=1S/C7H12/c1-2-4-7-5-6(7)3-1/h6-7H,1-5H2 Copy

  
• IUPAC Standard InChIKey: WPHGSKGZRAQSGP-UHFFFAOYSA-N Copy
• CAS Registry Number: 286-08-8
• 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: Norcarane; cis-Bicyclo[4.1.0]heptane
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Gas phase ion energetics data
  • Mass spectrum (electron ionization)
  • Gas Chromatography
  • References
  • Notes
• Options:
  • Switch to calorie-based units

Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, NIST Subscription Links, 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
DRB - Donald R. Burgess, Jr.
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Constant pressure heat capacity of gas

Condensed phase thermochemistry data

Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, NIST Subscription Links, 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

Phase change data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, NIST Subscription Links, 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:
BS - Robert L. Brown and Stephen E. Stein
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.

Enthalpy of vaporization

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, NIST Subscription Links, 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:
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

Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Gas Chromatography, NIST Free Links, NIST Subscription Links, 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.

For Zoom

1.) Enter the desired X axis range (e.g., 100, 200)

2.) Check here for automatic Y scaling

3.) Press here to zoom

Additional Data

Gas Chromatography

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), NIST Free Links, NIST Subscription Links, 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

Kovats' RI, non-polar column, isothermal

View large format table.

Normal alkane RI, non-polar column, custom temperature program

View large format table.

References

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

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Chang, McNally, et al., 1970
Chang, Sho-ju.; McNally, D.; Shary-Tehrany, S.; Hickey, S.M.J.; Boyd, R.H., The heats of combustion and strain energies of bicylo[n.m.O]alkanes, J. Am. Chem. Soc., 1970, 92, 3109-3118. [all data]

Timofeeva, Kozina, et al., 1970
Timofeeva, L.P.; Kozina, M.P.; Skuratov, S.M.; Nefedov, O.M.; Novitskaya, N.N., Heats of combustion of norcarane and 1-cyclohexylnorcarane, Moscow Univ. Chem. Bull. (Engl. Transl.), 1970, 25, 19-21. [all data]

Chang S., 1970
Chang S., The heats of combustion and strain energies of bicyclo[n.m.0]alkanes, J. Am. Chem. Soc., 1970, 92, 3109-3118. [all data]

Buckingham and Donaghy, 1982
Buckingham, J.; Donaghy, S.M., Dictionary of Organic Compounds: Fifth Edition, Chapman and Hall, New York, 1982, 1. [all data]

Doering and Hoffman, 1964
Doering, W. vonE.; Hoffman, A.K., The Addition of Dichlorocarbene to Olefins, J. Am. Chem. Soc., 1964, 76, 6162-5. [all data]

Simmons and Smith, 1959
Simmons, H.E.; Smith, R.D., A New Synthesis of Cyclopropanes, J. Am. Chem. Soc., 1959, 81, 4256. [all data]

Doering and Hoffman, 1954
Doering, W. vonE.; Hoffman, A.K., J. Am. Chem. Soc., 1954, 76, 6162. [all data]

Osmont, Catoire, et al., 2008
Osmont, Antoine; Catoire, Laurent; Gokalp, Iskender, Physicochemical Properties and Thermochemistry of Propellanes, Energy Fuels, 2008, 22, 4, 2241-2257, https://doi.org/10.1021/ef8000423 . [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [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, Gleiter, et al., 1973
Heilbronner, E.; Gleiter, R.; Hoshi, T.; Meijere, A., The interaction of Walsh-orbitals in diademane and related hydrocarbons, Helv. Chim. Acta, 1973, 56, 1594. [all data]

Engewald, Epsch, et al., 1976
Engewald, W.; Epsch, K.; Welsch, Th.; Graefe, J., Molekülstruktur und Retentionsverhalten. VI. Retentionsverhalten von bicycle[n.m.0]alkanen bei der gas-adsorptions- und gas-verteilungs-chromatographie, J. Chromatogr., 1976, 119, 119-128, https://doi.org/10.1016/S0021-9673(00)86776-X . [all data]

Schomburg, 1966
Schomburg, G., Gaschromatographische Retentionsdaten und struktur chemischer verbindungen. III. Alkylverzweigte und ungesättigte cyclische Kohlenwasserstoffe, J. Chromatogr., 1966, 23, 18-41, https://doi.org/10.1016/S0021-9673(01)98653-4 . [all data]

Chen, 2008
Chen, H.-F., Quantitative prediction of gas chromatography retention indices with support vector machines, radial basis neutral networks and multiple linear regression, Anal. Chim. Acta, 2008, 609, 1, 24-36, https://doi.org/10.1016/j.aca.2008.01.003 . [all data]

Notes

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

• Symbols used in this document:
  

  AE	Appearance energy
  Cp,gas	Constant pressure heat capacity of gas
  Tboil	Boiling point
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfH°liquid	Enthalpy of formation of liquid at standard conditions
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization 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.