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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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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | 47.7 ± 0.2 | kcal/mol | Ccb | Roth, Biermann, et al., 1978 |
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: 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° | -13.1 | kcal/mol | Kin | Roth and Scholz, 1981 | gas phase |
| ΔrH° | -10.6 ± 0.45 | kcal/mol | Cm | Roth, Biermann, et al., 1978 | liquid phase |
C8H8N2O = +
By formula: C8H8N2O = N2O + C8H8
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -9.85 ± 0.13 | kcal/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° | -50.32 ± 0.03 | kcal/mol | Chyd | Turner, Goebel, et al., 1968 | liquid phase; solvent: Acetic acid |
=
By formula: C8H8 = C8H8
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 11.1 ± 0.2 | kcal/mol | Eqk | Roth, Ebbrecht, et al., 1988 | gas phase |
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 C8H8+ (ion structure unspecified)
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 8.74 ± 0.05 | EI | Franklin and Carroll, 1969 | RDSH |
| 8.66 ± 0.03 | PE | Heilbronner, Hoshi, et al., 1976 | Vertical value; LLK |
| 8.66 | PE | Brogli, Giovannini, et al., 1973 | Vertical value; LLK |
Appearance energy determinations
| Ion | AE (eV) | Other Products | Method | Reference | Comment |
|---|---|---|---|---|---|
| C3H3+ | 14.16 ± 0.15 | ? | EI | Franklin and Carroll, 1969 | RDSH |
| C4H2+ | 17.69 ± 0.30 | 2C2H2+H2 | EI | Franklin and Carroll, 1969 | RDSH |
| C4H3+ | 18.68 ± 0.10 | 2C2H2+H | EI | Franklin and Carroll, 1969 | RDSH |
| C4H4+ | 16.01 ± 0.15 | 2C2H2 | EI | Franklin and Carroll, 1969 | RDSH |
| C5H3+ | 17.34 ± 0.10 | C2H2+CH3? | EI | Franklin and Carroll, 1969 | RDSH |
| C6H5+ | 15.58 ± 0.10 | C2H2+H | EI | Franklin and Carroll, 1969 | RDSH |
| C6H6+ | 11.55 ± 0.10 | C2H2 | EI | Franklin and Carroll, 1969 | RDSH |
| C8H6+ | 11.84 ± 0.10 | H2 | EI | Franklin and Carroll, 1969 | RDSH |
| C8H7+ | 11.94 ± 0.10 | H | EI | Franklin and Carroll, 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
Van Den Dool and Kratz RI, polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | DB-Wax | 1263. | Shimoda, Peralta, et al., 1996 | 60. m/0.25 mm/0.25 μm, He, 3. K/min; Tstart: 50. C; Tend: 230. C |
| Capillary | DB-Wax | 1269. | Shimoda, Shigematsu, et al., 1995 | 60. m/0.25 mm/0.25 μm, 2. K/min; Tstart: 50. C; Tend: 230. C |
| Capillary | DB-Wax | 1258. | Sumitani, Suekane, et al., 1994 | He, 40. C @ 5. min, 3. K/min; Column length: 60. m; Column diameter: 0.25 mm; Tend: 200. C |
Normal alkane RI, polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | SOLGel-Wax | 1272. | Johanningsmeier and McFeeters, 2011 | 30. m/0.25 mm/0.25 μm, Helium; Program: 40 0C (2 min) 5 0C/min -> 140 0C 10 0C/min -> 250 0C (3 min) |
| Capillary | SOLGel-Wax | 1269. | Johanningsmeier and McFeeters, 2011 | 30. m/0.25 mm/0.25 μm, Helium; Program: not specified |
References
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry 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.
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]
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]
Franklin and Carroll, 1969
Franklin, J.L.; Carroll, S.R.,
The effect of molecular structure on ionic decomposition. I. An electron impact study of seven C8H8 isomers,
J. Am. Chem. Soc., 1969, 91, 5940. [all data]
Heilbronner, Hoshi, et al., 1976
Heilbronner, E.; Hoshi, T.; von Rosenberg, J.L.; Hafner, K.,
Alkyl-induced, natural hypsochromic shifts of the 2A←2X and 2B←2X transitions of azulene and naphthalene radical cations,
Nouv. J. Chim., 1976, 1, 105. [all data]
Brogli, Giovannini, et al., 1973
Brogli, F.; Giovannini, E.; Heilbronner, E.; Schurter, R.,
Die photoelektronen spektren der benzocycloalkene,
Chem. Ber., 1973, 106, 961. [all data]
Shimoda, Peralta, et al., 1996
Shimoda, M.; Peralta, R.R.; Osajima, Y.,
Headspace gas analysis of fish sauce,
J. Agric. Food Chem., 1996, 44, 11, 3601-3605, https://doi.org/10.1021/jf960345u
. [all data]
Shimoda, Shigematsu, et al., 1995
Shimoda, M.; Shigematsu, H.; Shiratsuchi, H.; Osajima, Y.,
Comparison of the odor concentrates by SDE and adsorptive column method from green tea infusion,
J. Agric. Food Chem., 1995, 43, 6, 1616-1620, https://doi.org/10.1021/jf00054a037
. [all data]
Sumitani, Suekane, et al., 1994
Sumitani, H.; Suekane, S.; Nakatani, A.; Tatsuka, K.,
Changes in composition of volatile compounds in high pressure treated peach,
J. Agric. Food Chem., 1994, 42, 3, 785-790, https://doi.org/10.1021/jf00039a037
. [all data]
Johanningsmeier and McFeeters, 2011
Johanningsmeier, S.D.; McFeeters, R.F.,
Detection of volatile spoilage metabolites in fermented cucumbers using nontargeted, comprehensive 2-dimensional gas chromatography-time-of-flight mass spectrometry (GCxGCxTOFMS),
J. Food Sci., 2011, 76, 1, c168-c177, https://doi.org/10.1111/j.1750-3841.2010.01918.x
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Gas Chromatography, References
- Symbols used in this document:
AE Appearance energy ΔfH°gas Enthalpy of formation of gas at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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