Bicyclo[4.2.0]octa-1,3,5-triene
- Formula: C8H8
- Molecular weight: 104.1491
- IUPAC Standard InChI: InChI=1S/C8H8/c1-2-4-8-6-5-7(8)3-1/h1-4H,5-6H2
- IUPAC Standard InChIKey: UMIVXZPTRXBADB-UHFFFAOYSA-N
- CAS Registry Number: 694-87-1
- 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: Benzocyclobutene; Benzocyclobutane; Benzocyclobutene, 1,2-dihydro-; Cardene; 1,2-Dihydrobenzocyclobutene
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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 | 155.7 ± 0.9 | kJ/mol | Ccb | Roth, Biermann, et al., 1978 | |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -4447.0 ± 0.9 | kJ/mol | Ccb | Roth, Biermann, et al., 1978 | Corresponding ΔfHºliquid = 155.6 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:
BS - Robert L. Brown and Stephen E. Stein
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔvapH° | 43.7 ± 0.1 | kJ/mol | V | Roth, Biermann, et al., 1978 | ALS |
| ΔvapH° | 43.7 | kJ/mol | N/A | Roth, Biermann, et al., 1978 | DRB |
Reduced pressure boiling point
| Tboil (K) | Pressure (bar) | Reference | Comment |
|---|---|---|---|
| 323.6 to 324. | 0.027 | Buckingham and Donaghy, 1982 | BS |
Reaction 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
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
=
By formula: C8H8 = C8H8
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -54.8 | kJ/mol | Kin | Roth and Scholz, 1981 | gas phase |
| ΔrH° | -44.2 ± 1.9 | kJ/mol | Cm | Roth, Biermann, et al., 1978 | liquid phase |
C8H8N2O = +
By formula: C8H8N2O = N2O + C8H8
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -41.2 ± 0.54 | kJ/mol | Kin | Oth, Olsen, et al., 1977 | liquid phase; solvent: THF; At 413 K |
3 +
=
By formula: 3H2 + C8H8 = C8H14
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -210.5 ± 0.1 | kJ/mol | Chyd | Turner, Goebel, et al., 1968 | liquid phase; solvent: Acetic acid |
=
By formula: C8H8 = C8H8
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 46.4 ± 0.8 | kJ/mol | Eqk | Roth, Ebbrecht, et al., 1988 | gas phase |
References
Go To: Top, Condensed 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.
Roth, Biermann, et al., 1978
Roth, W.R.; Biermann, M.; Dekker, H.; Jochems, R.; Mosselman, C.; Hermann, H.,
Energy profile of the o-quinodimethane-benzocyclobutene equilibrium,
Chem. Ber., 1978, 111, 3892-3903. [all data]
Buckingham and Donaghy, 1982
Buckingham, J.; Donaghy, S.M.,
Dictionary of Organic Compounds: Fifth Edition, Chapman and Hall, New York, 1982, 1. [all data]
Roth and Scholz, 1981
Roth, W.R.; Scholz, B.P.,
Energy profile of the o-quinodimethane = benzocyclobutene equilibrium. Part 2.,
Chem. Ber., 1981, 114, 3741-3750. [all data]
Oth, Olsen, et al., 1977
Oth, J.F.M.; Olsen, H.; Synder, J.P.,
Energetics of heteroextrusion reactions. N2 vs. N2O,
J. Am. Chem. Soc., 1977, 99, 8505-8507. [all data]
Turner, Goebel, et al., 1968
Turner, R.B.; Goebel, P.; Mallon, B.J.; Doering, W.E.; Coburn, J.F., Jr.; Pomerantz, M.,
Heats of hydrogenation. VIII. Compounds with three- and four-membered rings,
J. Am. Chem. Soc., 1968, 90, 4315-4322. [all data]
Roth, Ebbrecht, et al., 1988
Roth, W.R.; Ebbrecht, T.; Beitat, A.,
o-Quinodimethane-benzocyclobutene equilibrium: oxygen trapping technique,
Chem. Ber., 1988, 121, 1357-1358. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, References
- Symbols used in this document:
Tboil Boiling point ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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