2-Cyclopropen-1-one, 2,3-diphenyl-

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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
Δfgas317.7 ± 8.2kJ/molCcrSteele, Gammon, et al., 1985 
Δfgas360. ± 20.kJ/molCphaGrabowski, Simon, et al., 1984 
Δfgas552.3kJ/molCcbHopkins, 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
Δcliquid-7562. ± 20.kJ/molCcbGreenberg, Tomkins, et al., 1983Corresponding Δfliquid = 230.2 kJ/mol (simple calculation by NIST; no Washburn corrections)
Quantity Value Units Method Reference Comment
Δfsolid198.0 ± 2.0kJ/molCcrSteele, Gammon, et al., 1985 
Quantity Value Units Method Reference Comment
Δcsolid-7529.8 ± 1.8kJ/molCcrSteele, Gammon, et al., 1985Corresponding Δfsolid = 198.03 kJ/mol (simple calculation by NIST; no Washburn corrections)
Δcsolid-7742.9kJ/molCcbHopkins, Bostwick, et al., 1976Corresponding Δfsolid = 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
Δsub119.7 ± 8.0kJ/molVSteele, Gammon, et al., 1985ALS

Enthalpy of sublimation

ΔsubH (kJ/mol) Temperature (K) Method Reference Comment
120. ± 8.365.HSASteele, Gammon, et al., 1985Based on data from 353. - 378. K.; AC
141. ± 4.2323.VHopkins, Bostwick, et al., 1976ALS
141. ± 4.333.MEHopkins, Bostwick, et al., 1976Based on data from 323. - 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

2-Cyclopropen-1-one, 2,3-diphenyl- = Diphenylacetylene + Carbon monoxide

By formula: C15H10O = C14H10 + CO

Quantity Value Units Method Reference Comment
Δr-28. ± 5.0kJ/molCphaHung and Grabowski, 1992liquid phase; solvent: Alkane
Δr18. ± 10.kJ/molCphaHerman and Goodman, 1989solid phase; solvent: Acetonitrile/water
Δr-41. ± 12.kJ/molCphaGrabowski, Simon, et al., 1984liquid phase; solvent: Benzene

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:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

Ionization energy determinations

IE (eV) Method Reference Comment
10.56PEMuller, Schweig, et al., 1978Vertical value; LLK
8.47PEDehmlow, Dehmlow, et al., 1977Vertical value; LLK

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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Mass spectrum
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Additional Data

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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

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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.

Data compiled by: Victor Talrose, Alexander N. Yermakov, Alexy A. Usov, Antonina A. Goncharova, Axlexander N. Leskin, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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UVVis spectrum
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Additional Data

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Source Blackburn, 1966
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, Gas phase ion energetics 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]

Muller, Schweig, et al., 1978
Muller, C.; Schweig, A.; Vermeer, H., Photoelectron spectra of 1,2-diphenylcyclopropene, 2,3-diphenylcyclopropenone, 2,3-diphenylcyclopropenethione, 2,3-diphenylthiirene and 1-oxide; cis-stilbene, An experimental verification of conjugative inductive interactions, J. Am. Chem. Soc., 1978, 100, 8056. [all data]

Dehmlow, Dehmlow, et al., 1977
Dehmlow, E.V.; Dehmlow, S.S.; Marschner, F., Chemische und photoelektronenspektroskopische Eigenschaften von cyclopropylsubstituierten Cyclopropenonen, Chem. Ber., 1977, 110, 154. [all data]

Blackburn, 1966
Blackburn, E.V., UV atlas of organic compounds, 1966, 2, D10/74. [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, References