cis-Bicyclo[6.1.0]nonane
- Formula: C9H16
- Molecular weight: 124.2233
- IUPAC Standard InChI: InChI=1S/C9H16/c1-2-4-6-9-7-8(9)5-3-1/h8-9H,1-7H2/t8-,9+
- IUPAC Standard InChIKey: FYECUAIUGWFPJF-DTORHVGOSA-N
- CAS Registry Number: 13757-43-2
- 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:
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change 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 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
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | -4.96 ± 0.27 | kcal/mol | Ccb | Wiberg, Lupton, et al., 1984 | Author was aware that data differs from previously reported values; see Lupton, 1970; ALS |
| ΔfH°gas | -5.02 | kcal/mol | N/A | Wiberg, 1980 | Value computed using ΔfHliquid° value of -70.0±1.0 kj/mol from Wiberg, 1980 and ΔvapH° value of 49.0 kj/mol from Chang, McNally, et al., 1970.; DRB |
| ΔfH°gas | -7.46 ± 0.69 | kcal/mol | Ccb | Corbally and Perkins, 1978 | Reanalyzed by Pedley, Naylor, et al., 1986, Original value = -7.29 ± 0.91 kcal/mol; ALS |
| ΔfH°gas | -7.6 ± 1.0 | kcal/mol | Ccb | Chang, McNally, et al., 1970 | ALS |
Constant pressure heat capacity of gas
| Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 38.131 | 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 |
| 52.199 | 400. | ||
| 64.739 | 500. |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, Phase change 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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°liquid | -16.76 ± 0.25 | kcal/mol | Ccb | Wiberg, Lupton, et al., 1984 | Author was aware that data differs from previously reported values; see Lupton, 1970; ALS |
| ΔfH°liquid | -16.73 ± 0.23 | kcal/mol | Ccb | Wiberg, 1980 | Heat of combustion is not reported; ALS |
| ΔfH°liquid | -19.2 ± 0.88 | kcal/mol | Ccb | Corbally and Perkins, 1978 | ALS |
| ΔfH°liquid | -19.4 ± 0.8 | kcal/mol | Ccb | Chang, McNally, et al., 1970 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -1376.25 ± 0.22 | kcal/mol | Ccb | Wiberg, Lupton, et al., 1984 | Author was aware that data differs from previously reported values; see Lupton, 1970; Corresponding ΔfHºliquid = -16.73 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°liquid | -1373.6 ± 0.6 | kcal/mol | Ccb | Chang, McNally, et al., 1970 | Corresponding ΔfHºliquid = -19.4 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Constant pressure heat capacity of liquid
| Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 56.19 | 315. | Chang, McNally, et al., 1970 | DH |
Phase change data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry 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 as indicated in comments:
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 |
|---|---|---|---|---|---|
| ΔvapH° | 11.8 ± 0.1 | kcal/mol | AVG | N/A | Average of 6 values; Individual data points |
Enthalpy of vaporization
| ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 12.0 ± 0.2 | 312. | A | Stephenson and Malanowski, 1987 | Based on data from 297. to 360. K. See also Chang, McNally, et al., 1970.; AC |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Wiberg, Lupton, et al., 1984
Wiberg, K.B.; Lupton, E.C., Jr.; Wasserman, D.J.; de Meijere, A.,
Enthalpies of formation of cis- and trans-1,2-diethylcyclopropane and cis- and trans-bicyclo[6.1.0]nonane. Structural effects on energies of cyclopropane rings,
J. Am. Chem. Soc., 1984, 106, 1740-1744. [all data]
Lupton, 1970
Lupton, E.C., Jr.,
The thermochemistry of some small ring compounds,
Diss. Abs., 1970, 31, 1174-1175. [all data]
Wiberg, 1980
Wiberg, K.B.,
Energies of organic compounds,
Rept. DOE-E(11-1)4060 Prepared for US Dept. of Energy by Yale Univ., New Haven, CT. Avail. NTIS, 1980, 1-24. [all data]
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]
Corbally and Perkins, 1978
Corbally, R.P.; Perkins, M.J.,
Standard enthalpies of formation of cis- and trans- bicyclo[6.1.0]nonanes,
J. Chem. Soc. Chem. Commun., 1978, 778-779. [all data]
Pedley, Naylor, et al., 1986
Pedley, J.B.; Naylor, R.D.; Kirby, S.P.,
Thermochemical Data of Organic Compounds, Chapman and Hall, New York, 1986, 1-792. [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]
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]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, References
- Symbols used in this document:
Cp,gas Constant pressure heat capacity of gas Cp,liquid Constant pressure heat capacity of liquid 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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