Bicyclo[3.1.0]hexane
- Formula: C6H10
- Molecular weight: 82.1436
- IUPAC Standard InChIKey: JAPMJSVZDUYFKL-UHFFFAOYSA-N
- CAS Registry Number: 285-58-5
- 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. - Stereoisomers:
- Other names: Norsabinane; Northujane
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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 |
---|---|---|---|---|---|
ΔfH°gas | 39. ± 3. | kJ/mol | Ccb | Chang, McNally, et al., 1970 | ALS |
Constant pressure heat capacity of gas
Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
100.50 | 298.15 | Chang S., 1970 | These values were calculated by a method of force field; their uncertainties may exceed 5-10 J/mol*K.; GT |
137.99 | 400. | ||
171.21 | 500. |
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 |
---|---|---|---|---|---|
ΔfH°liquid | 5. ± 3. | kJ/mol | Ccb | Chang, McNally, et al., 1970 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -3795. ± 2. | kJ/mol | Ccb | Chang, McNally, et al., 1970 | Corresponding ΔfHºliquid = 5.0 kJ/mol (simple calculation by NIST; no Washburn corrections) |
ΔcH°liquid | -3818. | kJ/mol | Ccb | Konovalon, 1926 | Heat of combustion at 15°C; Corresponding ΔfHºliquid = 28. 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, Chris Muzny director
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 355. | K | N/A | Simmons and Smith, 1959 | Uncertainty assigned by TRC = 2. K; TRC |
Tboil | 353.77 | K | N/A | Anonymous, 1949 | Uncertainty assigned by TRC = 0.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 195.49 | K | N/A | Anonymous, 1949 | Uncertainty assigned by TRC = 0.3 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 33.5 ± 0.4 | kJ/mol | V | Chang, McNally, et al., 1970 | ALS |
ΔvapH° | 34.0 | kJ/mol | N/A | Chang, McNally, et al., 1970 | DRB |
ΔvapH° | 33.5 ± 0.4 | kJ/mol | N/A | Chang, McNally, et al., 1970 | AC |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
33.7 | 286. | A | Stephenson and Malanowski, 1987 | Based on data from 273. to 300. K.; AC |
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:
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 |
---|---|---|---|
9.28 ± 0.05 | EI | Wolkoff and Holmes, 1979 | LLK |
9.16 ± 0.02 | EI | Winters and Collins, 1969 | RDSH |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C3H3+ | 12.98 ± 0.19 | ? | EI | Winters and Collins, 1969 | RDSH |
C3H5+ | 11.65 ± 0.14 | ? | EI | Winters and Collins, 1969 | RDSH |
C4H5+ | 12.62 ± 0.11 | ? | EI | Winters and Collins, 1969 | RDSH |
C4H6+ | 10.28 ± 0.05 | ? | EI | Winters and Collins, 1969 | RDSH |
C5H5+ | 13.20 ± 0.12 | ? | EI | Winters and Collins, 1969 | RDSH |
C5H7+ | 9.88 ± 0.05 | CH3 | EI | Wolkoff and Holmes, 1979 | LLK |
C5H7+ | 9.68 ± 0.07 | CH3 | EI | Winters and Collins, 1969 | RDSH |
C6H7+ | 11.60 ± 0.15 | H2+H | EI | Winters and Collins, 1969 | RDSH |
C6H9+ | 10.20 ± 0.10 | H | EI | Winters and Collins, 1969 | RDSH |
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
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | Squalane | 50. | 670. | Schomburg, 1966 |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Squalane | 678. | Chen, 2008 | Program: not specified |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, 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.
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]
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]
Konovalon, 1926
Konovalon, D.-P.,
Sur Les Chaleurs de Combustion de Quelques hydrocarbures cycliques,
J. Chim. Phys., 1926, 23, 359-362. [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]
Anonymous, 1949
Anonymous, R.,
, Am. Pet. Inst. Res. Proj. 45, Ohio State Univ., 1949. [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]
Wolkoff and Holmes, 1979
Wolkoff, P.; Holmes, J.L.,
Isomeric cyclic [C6H10]+ ions. The energy barrier to ring opening,
Can. J. Chem., 1979, 57, 348. [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]
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, Gas Chromatography, References
- 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 ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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