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
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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 | 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) |
Phase change 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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔsubH° | 119.7 ± 8.0 | kJ/mol | V | Steele, Gammon, et al., 1985 | ALS |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
120. ± 8. | 365. | HSA | Steele, Gammon, et al., 1985 | Based on data from 353. to 378. K.; AC |
141. ± 4.2 | 323. | V | Hopkins, Bostwick, et al., 1976 | ALS |
141. ± 4. | 333. | ME | Hopkins, Bostwick, et al., 1976 | Based on data from 323. to 343. K. See also Stephenson and Malanowski, 1987.; AC |
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: 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 |
Mass spectrum (electron ionization)
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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
Spectrum
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Additional Data
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Due to licensing restrictions, this spectrum cannot be downloaded.
Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | Japan AIST/NIMC Database- Spectrum MS-NW-7225 |
NIST MS number | 235961 |
UV/Visible spectrum
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Spectrum
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Additional Data
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Source | Blackburn, 1966 |
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Owner | INEP CP RAS, NIST OSRD Collection (C) 2007 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
Origin | INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS |
Source reference | RAS UV No. 19828 |
Instrument | Unicam SP 700 |
Melting point | 119-120 |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Mass spectrum (electron ionization), UV/Visible spectrum, 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]
Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw,
Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2
. [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]
Blackburn, 1966
Blackburn, E.V.,
UV atlas of organic compounds, 1966, 2, D10/74. [all data]
Notes
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- 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 ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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