Bicyclo[3.2.1]octa-2,6-diene
- Formula: C8H10
- Molecular weight: 106.1650
- IUPAC Standard InChI: InChI=1S/C8H10/c1-2-7-4-5-8(3-1)6-7/h1-2,4-5,7-8H,3,6H2
- IUPAC Standard InChIKey: VTYQQMGYHHVPMX-UHFFFAOYSA-N
- CAS Registry Number: 4096-95-1
- Chemical structure:
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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 | 37.7 ± 0.2 | kcal/mol | Chyd | Roth, Adamczak, et al., 1991 | |
| ΔfH°gas | 38.0 ± 1.5 | kcal/mol | Ccb | Hassenruck, Martin, et al., 1987 |
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 as indicated in comments:
B - John E. Bartmess
ALS - 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
C8H9- + =
By formula: C8H9- + H+ = C8H10
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 379.5 ± 2.1 | kcal/mol | G+TS | Lee and Squires, 1986 | gas phase; 1.4 kcal > MeOH; value altered from reference due to change in acidity scale; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 372.6 ± 2.0 | kcal/mol | IMRE | Lee and Squires, 1986 | gas phase; 1.4 kcal > MeOH; value altered from reference due to change in acidity scale; B |
2 +
=
By formula: 2H2 + C8H10 = C8H14
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -60.8 ± 0.2 | kcal/mol | Chyd | Roth, Adamczak, et al., 1991 | liquid phase; ALS |
| ΔrH° | -57.86 ± 0.27 | kcal/mol | Chyd | Turner, Jarrett, et al., 1973 | liquid phase; solvent: Acetic acid; ALS |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry 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:
B - John E. Bartmess
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
View reactions leading to C8H10+ (ion structure unspecified)
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 8.44 ± 0.01 | PI | Demeo and El-Sayed, 1970 | RDSH |
De-protonation reactions
C8H9- + =
By formula: C8H9- + H+ = C8H10
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 379.5 ± 2.1 | kcal/mol | G+TS | Lee and Squires, 1986 | gas phase; 1.4 kcal > MeOH; value altered from reference due to change in acidity scale; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 372.6 ± 2.0 | kcal/mol | IMRE | Lee and Squires, 1986 | gas phase; 1.4 kcal > MeOH; value altered from reference due to change in acidity scale; B |
References
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Roth, Adamczak, et al., 1991
Roth, W.R.; Adamczak, O.; Breuckmann, R.; Lennartz, H.-W.; Boese, R.,
Die Berechnung von Resonanzenergien; das MM2ERW-Kraftfeld,
Chem. Ber., 1991, 124, 2499-2521. [all data]
Hassenruck, Martin, et al., 1987
Hassenruck, K.; Martin, H.-D.; Mayer, B.; Urbanek, T.; Zirwes, T.; Walsh, R.; Beckhaus, H.-D.,
An Experimental Approach to the C8H10 Hypersurface. Kinetic and Thermochemical Investigations on a Formally Forbidden Ground-state [2σ + 2π] Cycloaddition,
Chem. Ber., 1987, 120, 177-186. [all data]
Lee and Squires, 1986
Lee, R.E.; Squires, R.R.,
Anionic homoaromaticity: A gas phase experimental study,
J. Am. Chem. Soc., 1986, 105, 5078. [all data]
Turner, Jarrett, et al., 1973
Turner, R.B.; Jarrett, A.D.; Goebel, P.; Mallon, B.J.,
Heats of hydrogenation. 9. Cyclic acetylenes and some miscellaneous olefins,
J. Am. Chem. Soc., 1973, 95, 790-792. [all data]
Demeo and El-Sayed, 1970
Demeo, D.A.; El-Sayed, M.A.,
Ionization potential and structure of olefins,
J. Chem. Phys., 1970, 52, 2622. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
ΔfH°gas Enthalpy of formation of gas at standard conditions ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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