Acetylacetone
- Formula: C5H8O2
- Molecular weight: 100.1158
- IUPAC Standard InChI: InChI=1S/C5H8O2/c1-4(6)3-5(2)7/h3H2,1-2H3
- IUPAC Standard InChIKey: YRKCREAYFQTBPV-UHFFFAOYSA-N
- CAS Registry Number: 123-54-6
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript. - Other names: 2,4-Pentanedione; Acetoacetone; Diacetylmethane; Pentane-2,4-dione; 2-Propanone, acetyl-; 2,4-Dioxopentane; 2,4-Pentadione; CH3COCH2COCH3; Acetone, acetyl-; ACAC; Pentanedione; Pentanedione-2,4; Acetyl 2-propanone; UN 2310; 2,4-Pentandione; Pentan-2,4-dione; NSC 5575
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Gas phase thermochemistry data
Go To: Top, Condensed phase 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 | -384.4 ± 1.3 | kJ/mol | Ccb | Hacking and Pilcher, 1979 | Heat of enolization=-11.3±0.4 kJ/mol |
| ΔfH°gas | -420.1 | kJ/mol | Ion | Conrath, Van de Sande, et al., 1974 | Mass spectrometery (enol) |
| ΔfH°gas | -376.1 ± 2.0 | kJ/mol | Cm | Melia and Merrifield, 1969 | Thermochemical cycle |
Condensed phase thermochemistry data
Go To: Top, Gas phase 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°liquid | -427.6 ± 1.1 | kJ/mol | Ccb | Hacking and Pilcher, 1979 | Heat of enolization=-11.3±0.4 kJ/mol |
| ΔfH°liquid | -447.3 ± 8.0 | kJ/mol | Ccb | Vilcu and Perisanu, 1979 | |
| ΔfH°liquid | -414.1 ± 2.0 | kJ/mol | Cm | Melia and Merrifield, 1969 | Thermochemical cycle |
| ΔfH°liquid | -528.94 | kJ/mol | Ccb | Guinchant, 1918 | Author hf288_condensed[kcal/mol]=-131.2 kcal/mol |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -2685.4 ± 0.8 | kJ/mol | Ccb | Hacking and Pilcher, 1979 | Heat of enolization=-11.3±0.4 kJ/mol; Corresponding ΔfHºliquid = -425.5 kJ/mol (simple calculation by NIST; no Washburn corrections) |
| ΔcH°liquid | -2667. ± 12. | kJ/mol | Ccb | Vilcu and Perisanu, 1979 | Corresponding ΔfHºliquid = -443.88 kJ/mol (simple calculation by NIST; no Washburn corrections) |
| ΔcH°liquid | -2687.0 ± 1.5 | kJ/mol | Ccb | Nicholson, 1957 | Corresponding ΔfHºliquid = -423.92 kJ/mol (simple calculation by NIST; no Washburn corrections) |
| ΔcH°liquid | -2581.9 | kJ/mol | Ccb | Guinchant, 1918 | Author hf288_condensed[kcal/mol]=-131.2 kcal/mol; Corresponding ΔfHºliquid = -528.98 kJ/mol (simple calculation by NIST; no Washburn corrections) |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Hacking and Pilcher, 1979
Hacking, J.M.; Pilcher, G.,
Enthalpy of combustion of pentane-2,4-dione,
J. Chem. Thermodyn., 1979, 11, 1015-1017. [all data]
Conrath, Van de Sande, et al., 1974
Conrath, k.; Van de Sande, C.; Vandewalle, M.,
Studies in organic mass spectrometry. XVI. A combined approach to the structures of ions generated from the molecular ions of acyclic β-diketones through loss of small neutral molecules,
Org. Mass Spectrom., 1974, 9, 585-593. [all data]
Melia and Merrifield, 1969
Melia, T.P.; Merrifield, R.,
Thermal properties of acetylacetone,
J. Appl. Chem., 1969, 19, 79-82. [all data]
Vilcu and Perisanu, 1979
Vilcu, R.; Perisanu, S.,
The standard enthalpies of formation of some C, H, O containing compounds,
Rev. Roum. Chim., 1979, 24, 237-243. [all data]
Guinchant, 1918
Guinchant, M.J.,
Etude sur la fonction acide dans les derives metheniques et methiniques,
Ann. Chem., 1918, 10, 30-84. [all data]
Nicholson, 1957
Nicholson, G.R.,
The heat of combustion of acetylacetone,
J. Chem. Soc., 1957, 2431-2432. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, References
- Symbols used in this document:
ΔcH°liquid Enthalpy of combustion 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 - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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