Benzocyclobuten-1(2H)-one
- Formula: C8H6O
- Molecular weight: 118.1326
- IUPAC Standard InChI: InChI=1S/C8H6O/c9-8-5-6-3-1-2-4-7(6)8/h1-4H,5H2
- IUPAC Standard InChIKey: XOGFXHMYHKGOGP-UHFFFAOYSA-N
- CAS Registry Number: 3469-06-5
- 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: Benzocyclobutenone; Bicyclo(4.2.0)octa-1,3,5-trien-7-one
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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:
B - John E. Bartmess
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
View reactions leading to C8H6O+ (ion structure unspecified)
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 8.99 | EI | Mamer, Lossing, et al., 1970 | RDSH |
De-protonation reactions
C8H5O- + =
By formula: C8H5O- + H+ = C8H6O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 359.8 ± 2.2 | kcal/mol | G+TS | Broadus and Kass, 1999 | gas phase; Correction to direction of ΔGacid reported in literature: Kass, private communication; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 352.1 ± 2.1 | kcal/mol | IMRE | Broadus and Kass, 1999 | gas phase; Correction to direction of ΔGacid reported in literature: Kass, private communication; B |
References
Go To: Top, 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.
Mamer, Lossing, et al., 1970
Mamer, A.; Lossing, F.P.; Hedaya, E.; Kent, M.E.,
Pyrolysis of bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylic anhydride,
Can. J. Chem., 1970, 48, 3606. [all data]
Broadus and Kass, 1999
Broadus, K.M.; Kass, S.R.,
Benzocyclobutenone enolate: an anion with an antiaromatic resonance structure,
J. Chem. Soc. Perkin Trans., 1999, 2, 11, 2389-2396, https://doi.org/10.1039/a905868k
. [all data]
Notes
Go To: Top, Gas phase ion energetics data, References
- Symbols used in this document:
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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