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1,1'-Bicyclopropyl

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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

Quantity Value Units Method Reference Comment
Deltafgas130. ± 5.0kJ/molCcbBeezer, Luttke, et al., 1966ALS

Constant pressure heat capacity of gas

Cp,gas (J/mol*K) Temperature (K) Reference Comment
71.99200.Godunov I.A., 1991GT
108.05298.15
108.80300.
148.45400.
182.36500.
209.56600.
231.50700.
249.58800.
264.78900.
277.741000.

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

Quantity Value Units Method Reference Comment
Deltafliquid96.0 ± 3.8kJ/molCcbBeezer, Luttke, et al., 1966 
Quantity Value Units Method Reference Comment
Deltacliquid-3886.1 ± 3.3kJ/molCcbBeezer, Luttke, et al., 1966Corresponding «DELTA»fliquid = 95.90 kJ/mol (simple calculation by NIST; no Washburn corrections)

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, Kenneth Kroenlein 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
Tboil349.25KN/ASlabey, 1952Uncertainty assigned by TRC = 0.4 K; TRC
Quantity Value Units Method Reference Comment
Tfus190.53KN/ASlabey, 1952Uncertainty assigned by TRC = 0.3 K; TRC
Quantity Value Units Method Reference Comment
Deltavap31.7 ± 0.5kJ/molCPashchenko and Kuznetsova, 2007AC
Deltavap33. ± 1.kJ/molEBeezer, Luttke, et al., 1966ALS
Deltavap34.0kJ/molN/ABeezer, Luttke, et al., 1966DRB

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:


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

IE (eV) Method Reference Comment
8.9PESpanget-Larsen, Gleiter, et al., 1982LBLHLM
9.12 ± 0.05EIWolkoff, Holmes, et al., 1980LLK
9.04PEBodor, Dewar, et al., 1970RDSH
8.80 ± 0.02EIWinters and Collins, 1969RDSH
9.5PESpanget-Larsen, Gleiter, et al., 1982Vertical value; LBLHLM
9.6PEAsmus and Klessinger, 1976Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C3H3+11.99 ± 0.18?EIWinters and Collins, 1969RDSH
C3H5+10.64 ± 0.14?EIWinters and Collins, 1969RDSH
C4H5+11.22 ± 0.14?EIWinters and Collins, 1969RDSH
C4H6+9.34 ± 0.06?EIWinters and Collins, 1969RDSH
C5H5+12.20 ± 0.13?EIWinters and Collins, 1969RDSH
C5H7+9.34 ± 0.05CH3EIWolkoff, Holmes, et al., 1980LLK
C5H7+9.12 ± 0.08CH3EIWinters and Collins, 1969RDSH
C6H7+10.97 ± 0.19H2+HEIWinters and Collins, 1969RDSH
C6H9+9.33 ± 0.15HEIWinters and Collins, 1969RDSH

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

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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.
NIST MS number 456

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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

View large format table.

Column type Active phase Temperature (C) I Reference Comment
CapillarySqualane120.640.2Schomburg and Dielmann, 1973Column length: 100. m; Column diameter: 0.25 mm
CapillarySqualane80.646.2Schomburg and Dielmann, 1973Column length: 100. m; Column diameter: 0.25 mm

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

View large format table.

Column type Active phase I Reference Comment
CapillarySqualane640.Chen, 2008Program: not specified

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, Notes

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

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, References