Cubane
- Formula: C8H8
- Molecular weight: 104.1491
- IUPAC Standard InChI: InChI=1S/C8H8/c1-2-5-3(1)7-4(1)6(2)8(5)7/h1-8H
- IUPAC Standard InChIKey: TXWRERCHRDBNLG-UHFFFAOYSA-N
- CAS Registry Number: 277-10-1
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
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Gas phase thermochemistry data
Go To: Top, Phase change data, Reaction 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
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | Ccb | Kybett, Carroll, et al., 1966 | uncertain value: 622.2 ± 4.2 kJ/mol; ALS | ||
| ΔfH°gas | 597.1 ± 5.0 | kJ/mol | Ccb | Kybett, Carroll, et al., 1966, 2 | Value recomputed with updated enthalpy of sublimation from Bashir-Hashemi, Chickos, et al., 2004. The value used in the original paper is now deemed unreliable. |
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:
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis
DH - Eugene S. Domalski and Elizabeth D. Hearing
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔvapH° | 44.6 ± 0.8 | kJ/mol | CGC | Bashir-Hashemi, Chickos, et al., 2004 | AC |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔsubH° | 55.2 ± 2.0 | kJ/mol | AC+CGC | Bashir-Hashemi, Chickos, et al., 2004 | AC |
| ΔsubH° | ME | Kybett, Carroll, et al., 1966, 2 | uncertain value: 80.3 ± 1.6 kJ/mol; in Ref. Diky, Frenkel, et al., 2003 the authors state that the value of 80.3 kJ/mole from Kybett, Carroll, et al., 1966, 2 pertains to the average temperature and not to 298 K. The authors give a value of 79.1±1.7 for the 298 K value; AC |
Enthalpy of sublimation
| ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 80. ± 2. | 239. | V | Kybett, Carroll, et al., 1966 | ALS |
Enthalpy of fusion
| ΔfusH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 8.7 | 404.9 | AC | White, Wasylishen, et al., 1992 | AC |
Entropy of fusion
| ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 15.08 | 394. | White, Wasylishen, et al., 1992, 2 | CAL |
| 21.49 | 404.9 |
Enthalpy of phase transition
| ΔHtrs (kJ/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
|---|---|---|---|---|---|
| 5.940 | 395.04 | crystaline, II | crystaline, I | White, Wasylishen, et al., 1992 | DH |
| 8.700 | 404.9 | crystaline, I | liquid | White, Wasylishen, et al., 1992 | DH |
Entropy of phase transition
| ΔStrs (J/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
|---|---|---|---|---|---|
| 15.37 | 395.04 | crystaline, II | crystaline, I | White, Wasylishen, et al., 1992 | DH |
| 22.7 | 404.9 | crystaline, I | liquid | White, Wasylishen, et al., 1992 | DH |
Reaction 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: John E. Bartmess
Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.
Individual Reactions
C8H7- + =
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1688. ± 13. | kJ/mol | G+TS | Hare, Emrick, et al., 1997 | gas phase; Comparable to ammonia; D exchange with ND3 |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1659. ± 13. | kJ/mol | IMRB | Hare, Emrick, et al., 1997 | gas phase; Comparable to ammonia; D exchange with ND3 |
References
Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Kybett, Carroll, et al., 1966
Kybett, B.D.; Carroll, S.; Natalis, P.; Bonnell, D.W.; Margrave, J.L.; Franklin, J.L.,
Thermodynamic properties of cubane,
J. Am. Chem. Soc., 1966, 88, 626. [all data]
Kybett, Carroll, et al., 1966, 2
Kybett, B.D.; Carroll, S.; Natalis, P.; Bonnell, D.W.; Margrave, J.L.; Franklin, J.L.,
Thermodynamic Properties of Cubane,
J. Am. Chem. Soc., 1966, 88, 3, 626-626, https://doi.org/10.1021/ja00955a056
. [all data]
Bashir-Hashemi, Chickos, et al., 2004
Bashir-Hashemi, A.; Chickos, James S.; Hanshaw, William; Zhao, Hui; Farivar, Behzad S.; Liebman, Joel F.,
The enthalpy of sublimation of cubane,
Thermochimica Acta, 2004, 424, 1-2, 91-97, https://doi.org/10.1016/j.tca.2004.05.022
. [all data]
Diky, Frenkel, et al., 2003
Diky, Vladimir V.; Frenkel, Michael; Karpushenkava, Larisa S.,
Thermodynamics of sublimation of cubane: natural anomaly or experimental error?,
Thermochimica Acta, 2003, 408, 1-2, 115-121, https://doi.org/10.1016/S0040-6031(03)00318-6
. [all data]
White, Wasylishen, et al., 1992
White, M.A.; Wasylishen, R.E.; Eaton, P.E.; Xiong, Y.; Pramod, K.; Nodari, N.,
Orientational disorder in solid cubane: a thermodynamic and 13C NMR study,
J. Phys. Chem., 1992, 96(1), 421-425. [all data]
White, Wasylishen, et al., 1992, 2
White, M.A.; Wasylishen, R.E.; Eaton, P.E.; Xiong, Y.; Pramod, K.; Nodari, N.,
Orientational disorder in solid cubane: a thermodynamic and carbon-13 NMR study,
J. Phys. Chem., 1992, 96, 1, 421, https://doi.org/10.1021/j100180a078
. [all data]
Hare, Emrick, et al., 1997
Hare, M.; Emrick, T.; Eaton, P.E.; Kass, S.R.,
Cubyl Anion Formation and an Experimental Determination of the Acidity and C-H Bond Dissociation Energy of Cubane,
J. Am. Chem. Soc., 1997, 119, 1, 237, https://doi.org/10.1021/ja9627858
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, References
- Symbols used in this document:
ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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