1,1'-Bicyclopropyl
- Formula: C6H10
- Molecular weight: 82.1436
- IUPAC Standard InChIKey: PGPFRBIKUWKSTJ-UHFFFAOYSA-N
- 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
The 3d structure may be viewed using Java or Javascript. - Other names: Bicyclopropyl; Cyclopropane, cyclopropyl-
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Phase change data
Go To: Top, Gas phase ion energetics data, Gas Chromatography, 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:
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 |
---|---|---|---|---|---|
Tboil | 349.25 | K | N/A | Slabey, 1952 | Uncertainty assigned by TRC = 0.4 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 190.53 | K | N/A | Slabey, 1952 | Uncertainty assigned by TRC = 0.3 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 7.6 ± 0.1 | kcal/mol | C | Pashchenko and Kuznetsova, 2007 | AC |
ΔvapH° | 8.0 ± 0.3 | kcal/mol | E | Beezer, Luttke, et al., 1966 | ALS |
ΔvapH° | 8.13 | kcal/mol | N/A | Beezer, Luttke, et al., 1966 | DRB |
Gas phase ion energetics data
Go To: Top, Phase change data, Gas Chromatography, 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:
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 |
---|---|---|---|
8.9 | PE | Spanget-Larsen, Gleiter, et al., 1982 | LBLHLM |
9.12 ± 0.05 | EI | Wolkoff, Holmes, et al., 1980 | LLK |
9.04 | PE | Bodor, Dewar, et al., 1970 | RDSH |
8.80 ± 0.02 | EI | Winters and Collins, 1969 | RDSH |
9.5 | PE | Spanget-Larsen, Gleiter, et al., 1982 | Vertical value; LBLHLM |
9.6 | PE | Asmus and Klessinger, 1976 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C3H3+ | 11.99 ± 0.18 | ? | EI | Winters and Collins, 1969 | RDSH |
C3H5+ | 10.64 ± 0.14 | ? | EI | Winters and Collins, 1969 | RDSH |
C4H5+ | 11.22 ± 0.14 | ? | EI | Winters and Collins, 1969 | RDSH |
C4H6+ | 9.34 ± 0.06 | ? | EI | Winters and Collins, 1969 | RDSH |
C5H5+ | 12.20 ± 0.13 | ? | EI | Winters and Collins, 1969 | RDSH |
C5H7+ | 9.34 ± 0.05 | CH3 | EI | Wolkoff, Holmes, et al., 1980 | LLK |
C5H7+ | 9.12 ± 0.08 | CH3 | EI | Winters and Collins, 1969 | RDSH |
C6H7+ | 10.97 ± 0.19 | H2+H | EI | Winters and Collins, 1969 | RDSH |
C6H9+ | 9.33 ± 0.15 | H | EI | Winters and Collins, 1969 | RDSH |
Gas Chromatography
Go To: Top, Phase change data, Gas phase ion energetics data, 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
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | Squalane | 120. | 640.2 | Schomburg and Dielmann, 1973 | Column length: 100. m; Column diameter: 0.25 mm |
Capillary | Squalane | 80. | 646.2 | Schomburg and Dielmann, 1973 | Column length: 100. m; Column diameter: 0.25 mm |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Squalane | 640. | Chen, 2008 | Program: not specified |
References
Go To: Top, Phase change data, Gas phase ion energetics data, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
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]
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, Phase change data, Gas phase ion energetics data, Gas Chromatography, References
- Symbols used in this document:
AE Appearance energy Tboil Boiling point Tfus Fusion (melting) point ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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