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
Δfgas75.9 ± 2.0kcal/molCcrSteele, Gammon, et al., 1985 
Δfgas86. ± 4.kcal/molCphaGrabowski, Simon, et al., 1984 
Δfgas132.0kcal/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-1807.4 ± 4.8kcal/molCcbGreenberg, Tomkins, et al., 1983Corresponding Δfliquid = 55.03 kcal/mol (simple calculation by NIST; no Washburn corrections)
Quantity Value Units Method Reference Comment
Δfsolid47.33 ± 0.47kcal/molCcrSteele, Gammon, et al., 1985 
Quantity Value Units Method Reference Comment
Δcsolid-1799.67 ± 0.43kcal/molCcrSteele, Gammon, et al., 1985Corresponding Δfsolid = 47.330 kcal/mol (simple calculation by NIST; no Washburn corrections)
Δcsolid-1850.6kcal/molCcbHopkins, Bostwick, et al., 1976Corresponding Δfsolid = 98.3 kcal/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
Δsub28.6 ± 1.9kcal/molVSteele, Gammon, et al., 1985ALS

Enthalpy of sublimation

ΔsubH (kcal/mol) Temperature (K) Method Reference Comment
29. ± 2.365.HSASteele, Gammon, et al., 1985Based on data from 353. to 378. K.; AC
33.8 ± 1.0323.VHopkins, Bostwick, et al., 1976ALS
33.7 ± 1.333.MEHopkins, Bostwick, et al., 1976Based on data from 323. to 343. K. See also Stephenson and Malanowski, 1987.; AC

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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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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References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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]

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]


Notes

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