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3-Penten-2-one, 4-hydroxy-


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
Deltafgas-385.3 ± 2.0kJ/molCmMelia and Merrifield, 1969Thermochemical cycle

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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Deltafliquid-426.3 ± 2.0kJ/molCmMelia and Merrifield, 1969Thermochemical cycle; ALS
Quantity Value Units Method Reference Comment
liquid261.4J/mol*KN/AMelia and Merrifield, 1969Extrapolated below 90 K. S(298.15 K) given as 2.611 J/g*K.; DH

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
208.2298.15Melia and Merrifield, 1969T = 80 to 300 K. Csat(liq) = 0.8978 + 3.964x10-3T J/g*K (260 to 300 K); Csat(298.15 K) given as 2.080 J/g*K.; DH

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:
DH - Eugene S. Domalski and Elizabeth D. Hearing
AC - William E. Acree, Jr., James S. Chickos

Enthalpy of fusion

DeltafusH (kJ/mol) Temperature (K) Reference Comment
14.497254.8Melia and Merrifield, 1969DH
14.5254.8Melia and Merrifield, 2007AC

Entropy of fusion

DeltafusS (J/mol*K) Temperature (K) Reference Comment
56.90254.8Melia and Merrifield, 1969DH

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

Acetylacetone = 3-Penten-2-one, 4-hydroxy-

By formula: C5H8O2 = C5H8O2

Quantity Value Units Method Reference Comment
Deltar-7.9 ± 0.4kJ/molKinSchweig, Vermeer, et al., 1974liquid phase; Photoelectron spectroscopy
Deltar-10. ± 0.8kJ/molEqkThompson and Allred, 1971liquid phase; solvent: Cyclohexane; NMR, UV
Deltar-12. ± 0.8kJ/molEqkCalmon, 1969liquid phase

3-Penten-2-one, 4-hydroxy- = Acetylacetone

By formula: C5H8O2 = C5H8O2

Quantity Value Units Method Reference Comment
Deltar16.8kJ/molEqkMines and Thompson, 1975gas phase

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 by: Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard

Ionization energy determinations

IE (eV) Method Reference Comment
9.08 ± 0.01PEHush, Livett, et al., 1987Vertical value

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction 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.

Melia and Merrifield, 1969
Melia, T.P.; Merrifield, R., Thermal properties of acetylacetone, J. Appl. Chem., 1969, 19, 79-82. [all data]

Melia and Merrifield, 2007
Melia, T.P.; Merrifield, R., Thermal properties of acetylacetone, J. Appl. Chem., 2007, 19, 3, 79-82, https://doi.org/10.1002/jctb.5010190305 . [all data]

Schweig, Vermeer, et al., 1974
Schweig, A.; Vermeer, H.; Weidner, U., A photoelectron spectroscopic study of keto-enol tautomerism in acetylacetones - a new application of photoelectron spectroscopy, Chem. Phys. Lett., 1974, 26, 229-233. [all data]

Thompson and Allred, 1971
Thompson, D.W.; Allred, A.L., Keto-enol equilibria in 2,4-Pentanedione and 3,3-dideuterio-2,4-pentanedione, J. Phys. Chem., 1971, 75, 433-435. [all data]

Calmon, 1969
Calmon, J.P., Thermodynamic functions of enolization of aliphatic «beta»-diketones, C. R. Acad. Sci. Paris, 1969, 268, 1435-1438. [all data]

Mines and Thompson, 1975
Mines, G.W.; Thompson, H., Infrared and photoelectron spectra, and keto-enol tautomerism of acetylacetones and acetoacetic esters, Proc. Roy. Soc. London A, 1975, 342, 327-339. [all data]

Hush, Livett, et al., 1987
Hush, N.S.; Livett, M.K.; Peel, J.B.; Willett, G.D., Variable-temperature ultraviolet photoelectron spectroscopy of the keto-enol tautomers of pentane-2,4-dione, Aust. J. Chem., 1987, 40, 599. [all data]


Notes

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