2,4,6-Cycloheptatrien-1-one, 2-hydroxy-
- Formula: C7H6O2
- Molecular weight: 122.1213
- IUPAC Standard InChI: InChI=1S/C7H6O2/c8-6-4-2-1-3-5-7(6)9/h1-5H,(H,8,9)
- IUPAC Standard InChIKey: MDYOLVRUBBJPFM-UHFFFAOYSA-N
- CAS Registry Number: 533-75-5
- 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: Tropolone; Purpurocatechol; 2-Hydroxy-2,4,6-cycloheptatriene-1-one; 2-Hydroxy-2,4,6-cycloheptatrien-1-one; 2-hydroxycyclohepta-2,4,6-trienone
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Gas phase ion energetics 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
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | -156. ± 1. | kJ/mol | Ccb | Hubbard, Katz, et al., 1952 | |
| ΔfH°gas | -155. | kJ/mol | Ccb | Cook, Gibb, et al., 1951 |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics 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
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°solid | -239.7 ± 2.6 | kJ/mol | Ccb | Tanaka and Watase, 1956 | Reanalyzed by Cox and Pilcher, 1970, Original value = -240. kJ/mol |
| ΔfH°solid | -239.5 ± 0.8 | kJ/mol | Ccb | Hubbard, Katz, et al., 1952 | |
| ΔfH°solid | -239. | kJ/mol | Ccb | Cook, Gibb, et al., 1951 | |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -3382. ± 2. | kJ/mol | Ccb | Jackson, Hung, et al., 1971 | Corresponding ΔfHºsolid = -230. kJ/mol (simple calculation by NIST; no Washburn corrections) |
| ΔcH°solid | -3370. | kJ/mol | Ccb | Tanaka and Watase, 1956 | Corresponding ΔfHºsolid = -240. kJ/mol (simple calculation by NIST; no Washburn corrections) |
| ΔcH°solid | -3372.6 | kJ/mol | Ccb | Hubbard, Katz, et al., 1952 | Corresponding ΔfHºsolid = -239.4 kJ/mol (simple calculation by NIST; no Washburn corrections) |
| ΔcH°solid | -3373. ± 4. | kJ/mol | Ccb | Cook, Gibb, et al., 1951 | Corresponding ΔfHºsolid = -239. kJ/mol (simple calculation by NIST; no Washburn corrections) |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Condensed phase 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:
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 9.86 ± 0.02 | EI | Higasi, Nozoe, et al., 1957 | RDSH |
Appearance energy determinations
| Ion | AE (eV) | Other Products | Method | Reference | Comment |
|---|---|---|---|---|---|
| C6H6O+ | 10.8 | CO | EI | Williams, Cooks, et al., 1968 | RDSH |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase 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.
Hubbard, Katz, et al., 1952
Hubbard, W.N.; Katz, C.; Guthrie, G.B., Jr.; Waddington, G.,
The heat of combustion and resonance energy of tropolone,
J. Am. Chem. Soc., 1952, 74, 4456-44. [all data]
Cook, Gibb, et al., 1951
Cook, J.W.; Gibb, A.R.; Raphael, R.A.; Somerville, A.R.,
Tropolones. Part I. The preparation and general characteristics of tropolone,
J. Chem. Soc., 1951, 503-511. [all data]
Tanaka and Watase, 1956
Tanaka, T.; Watase, T.,
Resonance energies of tropolone and hinokitiol,
Tech. Rpt., Osaka Univ., 1956, 6, 367-371. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]
Jackson, Hung, et al., 1971
Jackson, W.; Hung, T.S.; Hopkins, H.P., Jr.,
Delocalization energies of troponoids from bomb calorimetric and vapour pressure measurements,
J. Chem. Thermodyn., 1971, 3, 347-353. [all data]
Higasi, Nozoe, et al., 1957
Higasi, K.; Nozoe, T.; Omura, I.,
Ionization potentials of some organic molecules. IV. Troponoid compounds,
Bull. Chem. Soc. Japan, 1957, 30, 408. [all data]
Williams, Cooks, et al., 1968
Williams, D.H.; Cooks, R.G.; Howe, I.,
Studies in mass spectrometry. XXXI. A comparison of reaction rates in common ions generated via fragmentation and direct ionization,
J. Am. Chem. Soc., 1968, 90, 6759. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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