3-Penten-2-one, 4-hydroxy-
- Formula: C5H8O2
- Molecular weight: 100.1158
- IUPAC Standard InChI: InChI=1S/C5H8O2/c1-4(6)3-5(2)7/h3,6H,1-2H3/b4-3-
- IUPAC Standard InChIKey: POILWHVDKZOXJZ-ARJAWSKDSA-N
- CAS Registry Number: 1522-20-9
- Chemical structure:
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change 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 | -92.10 ± 0.48 | kcal/mol | Cm | Melia and Merrifield, 1969 | Thermochemical 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 |
|---|---|---|---|---|---|
| ΔfH°liquid | -101.89 ± 0.48 | kcal/mol | Cm | Melia and Merrifield, 1969 | Thermochemical cycle; ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| S°liquid | 62.48 | cal/mol*K | N/A | Melia and Merrifield, 1969 | Extrapolated below 90 K. S(298.15 K) given as 2.611 J/g*K.; DH |
Constant pressure heat capacity of liquid
| Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 49.76 | 298.15 | Melia and Merrifield, 1969 | T = 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
| ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 3.4649 | 254.8 | Melia and Merrifield, 1969 | DH |
| 3.47 | 254.8 | Melia and Merrifield, 2007 | AC |
Entropy of fusion
| ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 13.60 | 254.8 | Melia and Merrifield, 1969 | DH |
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: C5H8O2 = C5H8O2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -1.9 ± 0.1 | kcal/mol | Kin | Schweig, Vermeer, et al., 1974 | liquid phase; Photoelectron spectroscopy |
| ΔrH° | -2.4 ± 0.2 | kcal/mol | Eqk | Thompson and Allred, 1971 | liquid phase; solvent: Cyclohexane; NMR, UV |
| ΔrH° | -2.8 ± 0.2 | kcal/mol | Eqk | Calmon, 1969 | liquid phase |
=
By formula: C5H8O2 = C5H8O2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 4.02 | kcal/mol | Eqk | Mines and Thompson, 1975 | gas phase |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change 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.
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 β-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]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid S°liquid Entropy of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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