2-Cyclopropen-1-one, 2,3-diphenyl-
- Formula: C15H10O
- Molecular weight: 206.2393
- IUPAC Standard InChIKey: HCIBTBXNLVOFER-UHFFFAOYSA-N
- CAS Registry Number: 886-38-4
- Chemical structure:
This structure is also available as a 2d Mol file - Other names: Cyclopropenone, diphenyl-; Cyclopropenone, 2,3-diphenyl-; Diphenylcyclopropenone; 2,3-Diphenylcyclopropenone; 2,3-Diphenyl-2-cyclopropen-1-one; Diphencyprone; DPC; 2,3-diphenylcycloprop-2-en-1-one
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Gas phase thermochemistry data
Go To: Top, Condensed 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | 317.7 ± 8.2 | kJ/mol | Ccr | Steele, Gammon, et al., 1985 | |
ΔfH°gas | 360. ± 20. | kJ/mol | Cpha | Grabowski, Simon, et al., 1984 | |
ΔfH°gas | 552.3 | kJ/mol | Ccb | Hopkins, Bostwick, et al., 1976 |
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 |
---|---|---|---|---|---|
ΔcH°liquid | -7562. ± 20. | kJ/mol | Ccb | Greenberg, Tomkins, et al., 1983 | Corresponding ΔfHºliquid = 230.2 kJ/mol (simple calculation by NIST; no Washburn corrections) |
Quantity | Value | Units | Method | Reference | Comment |
ΔfH°solid | 198.0 ± 2.0 | kJ/mol | Ccr | Steele, Gammon, et al., 1985 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -7529.8 ± 1.8 | kJ/mol | Ccr | Steele, Gammon, et al., 1985 | Corresponding ΔfHºsolid = 198.03 kJ/mol (simple calculation by NIST; no Washburn corrections) |
ΔcH°solid | -7742.9 | kJ/mol | Ccb | Hopkins, Bostwick, et al., 1976 | Corresponding ΔfHºsolid = 411. kJ/mol (simple calculation by NIST; no Washburn corrections) |
Reaction thermochemistry 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 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: C15H10O = C14H10 + CO
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -28. ± 5.0 | kJ/mol | Cpha | Hung and Grabowski, 1992 | liquid phase; solvent: Alkane |
ΔrH° | 18. ± 10. | kJ/mol | Cpha | Herman and Goodman, 1989 | solid phase; solvent: Acetonitrile/water |
ΔrH° | -41. ± 12. | kJ/mol | Cpha | Grabowski, Simon, et al., 1984 | liquid phase; solvent: Benzene |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry 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.
Steele, Gammon, et al., 1985
Steele, W.V.; Gammon, B.E.; Smith, N.K.; Chickos, J.S.; Greenberg, A.; Liebman, J.F.,
The standard molar enthalpy of formation of 2,3-diphenylcycloprop-2-en-1-one,
J. Chem. Thermodyn., 1985, 17, 505-511. [all data]
Grabowski, Simon, et al., 1984
Grabowski, J.J.; Simon, J.D.; Peters, K.S.,
Heat of formation of diphenylcyclopropenone by photoacoustic calorimetry,
J. Am. Chem. Soc., 1984, 106, 4615-4616. [all data]
Hopkins, Bostwick, et al., 1976
Hopkins, H.P., Jr.; Bostwick, D.; Alexander, C.J.,
The thermochemistry of diphenylcyclopropenone. Strain vs. delocalization energy,
J. Am. Chem. Soc., 1976, 98, 1355-1357. [all data]
Greenberg, Tomkins, et al., 1983
Greenberg, A.; Tomkins, R.P.T.; Dobrovolny, M.; Liebman, J.F.,
The strain energy of diphenylcyclopropenone: A reexamination,
J. Am. Chem. Soc., 1983, 105, 6855-6858. [all data]
Hung and Grabowski, 1992
Hung, R.R.; Grabowski, J.J.,
Enthalpy measurements in organic solvents by photoacoustic calorimetry: a solution to the reaction volume problem,
J. Am. Chem. Soc., 1992, 114, 351-353. [all data]
Herman and Goodman, 1989
Herman, M.S.; Goodman, J.L.,
Determination of the enthalpy and reaction volume changes of organic photoreactions using photoacoustic calorimetry,
J. Am. Chem. Soc., 1989, 111, 1849-1854. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, References
- Symbols used in this document:
ΔcH°liquid Enthalpy of combustion of liquid at standard conditions 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 ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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