1,1'-Bicyclopropyl

• Formula: C₆H₁₀
• Molecular weight: 82.1436
• IUPAC Standard InChI: InChI=1S/C6H10/c1-2-5(1)6-3-4-6/h5-6H,1-4H2 Copy

  
• IUPAC Standard InChIKey: PGPFRBIKUWKSTJ-UHFFFAOYSA-N Copy
• CAS Registry Number: 5685-46-1
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
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• Other names: Bicyclopropyl; Cyclopropane, cyclopropyl-
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• 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
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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
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Constant pressure heat capacity of gas

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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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.

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 compiled as indicated in comments:
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
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 C₆H₁₀⁺ (ion structure unspecified)

Ionization energy determinations

Appearance energy determinations

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

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References

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

Beezer, Luttke, et al., 1966
Beezer, A.E.; Luttke, W.; Meijere, A.; Mortimer, C.T., Heat of formation of bicyclopropyl, J. Chem. Soc. B, 1966, 648-649. [all data]

Godunov I.A., 1991
Godunov I.A., Bicyclopropyl: molecular internal rotation potential functions and thermodynamic properties, Zh. Fiz. Khim., 1991, 65, 3254-3259. [all data]

Slabey, 1952
Slabey, V.A., Reaction of Cyclopropyl Chloride with Lithium. Isolation of Dicyclopropyl, J. Am. Chem. Soc., 1952, 74, 4928-30. [all data]

Pashchenko and Kuznetsova, 2007
Pashchenko, L.L.; Kuznetsova, T.S., The enthalpies of vaporization of some hydrocarbons with three-membered rings, Russ. J. Phys. Chem., 2007, 81, 11, 1738-1742, https://doi.org/10.1134/S0036024407110040 . [all data]

Spanget-Larsen, Gleiter, et al., 1982
Spanget-Larsen, J.; Gleiter, R.; Gubernator, K.; Ternansky, R.J.; Paquette, L.A., Electronic and molecular structure of simple bicyclopropyls. Photoelectron spectroscopy and model calculations, J. Org. Chem., 1982, 47, 3082. [all data]

Wolkoff, Holmes, et al., 1980
Wolkoff, P.; Holmes, J.L.; Lossing, F.P., On the formation of cyclopentenium cations from all C₆H₁₀⁺ molecular ion structures, Can. J. Chem., 1980, 58, 251. [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, 1969
Winters, R.E.; Collins, J.H., Mass spectrometric studies of structural isomers. II.Mono- and bicyclic C₆H₁₀ molecules, Org. Mass Spectrom., 1969, 2, 299. [all data]

Asmus and Klessinger, 1976
Asmus, P.; Klessinger, M., Wechselwirkung der Walsh-Orbitale in Bicyclopropyl, Angew. Chem., 1976, 88, 343. [all data]

Schomburg and Dielmann, 1973
Schomburg, G.; Dielmann, G., Use of retention increments for identification and correlation of saturated and unsaturated cyclopropane hydrocarbons by means of Kovats indices, Anal. Chem., 1973, 45, 9, 1647-1658, https://doi.org/10.1021/ac60331a021 . [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

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• Symbols used in this document:
  

  AE	Appearance energy
  Cp,gas	Constant pressure heat capacity of gas
  Tboil	Boiling point
  Tfus	Fusion (melting) 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 at standard conditions

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