1,3-Butanedione, 1-phenyl-
- Formula: C10H10O2
- Molecular weight: 162.1852
- IUPAC Standard InChIKey: CVBUKMMMRLOKQR-UHFFFAOYSA-N
- CAS Registry Number: 93-91-4
- 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: α-Acetylacetophenone; Acetoacetophenone; Acetylbenzoylmethane; Benzoylacetone; 1-Benzoyl-2-propanone; 1-Phenyl-1,3-butanedione; 2-Acetylacetophenone; 2-Propanone, benzoyl-; 1-Benzoylacetone; Benzoyl-aceton; NSC 4015; 1-phenylbutane-1,3-dione
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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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -58.34 ± 0.69 | kcal/mol | Cm | Ribeiro da Silva and Monte, 1992 | ALS |
ΔfH°gas | -60.06 ± 0.69 | kcal/mol | Ccb | Ferrao and Ribeiro Da Silva, 1981 | ALS |
ΔfH°gas | -67.97 | kcal/mol | N/A | Farrar and Jones, 1964 | Value computed using ΔfHliquid° value of -340±4.6 kj/mol from Farrar and Jones, 1964 and ΔvapH° value of 55.6 kj/mol from missing citation.; DRB |
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 |
---|---|---|---|---|---|
ΔfH°liquid | -81.2 ± 1.1 | kcal/mol | Ccb | Farrar and Jones, 1964 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -1200.9 ± 1.3 | kcal/mol | Ccb | Farrar and Jones, 1964 | Corresponding ΔfHºliquid = -81.20 kcal/mol (simple calculation by NIST; no Washburn corrections) |
Quantity | Value | Units | Method | Reference | Comment |
ΔfH°solid | -80.09 ± 0.67 | kcal/mol | Ccb | Ferrao and Ribeiro Da Silva, 1981 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -1202.0 ± 0.60 | kcal/mol | Ccb | Ferrao and Ribeiro Da Silva, 1981 | Corresponding ΔfHºsolid = -80.11 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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
DRB - Donald R. Burgess, Jr.
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 533.15 | K | N/A | Sabatier and Mailhe, 1909 | Uncertainty assigned by TRC = 3. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 331. | K | N/A | Wolfrom and Bobbitt, 1956 | Uncertainty assigned by TRC = 3. K; TRC |
Tfus | 333.15 | K | N/A | Sabatier and Mailhe, 1909 | Uncertainty assigned by TRC = 1. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 13.3 | kcal/mol | E | Farrar and Jones, 1964 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 21.75 ± 0.15 | kcal/mol | V | Ribeiro da Silva and Monte, 1992 | crystal phase; ALS |
ΔsubH° | 21.7 ± 0.1 | kcal/mol | ME | Ribeiro da Silva and Monte, 1992 | AC |
ΔsubH° | 20.0 | kcal/mol | N/A | Ferrao and Ribeiro Da Silva, 1981 | DRB |
Enthalpy of sublimation
ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
20.0 | 289. | V | Stephenson and Malanowski, 1987 | Based on data from 278. to 300. K. See also Aihara, 1959.; AC |
20.02 ± 0.10 | 331.3 | V | Aihara, 1959, 2 | crystal phase; ALS |
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: John E. Bartmess
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
C10H9O2- + =
By formula: C10H9O2- + H+ = C10H10O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 339.9 ± 2.3 | kcal/mol | G+TS | Cumming and Kebarle, 1978 | gas phase |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 333.0 ± 2.0 | kcal/mol | IMRE | Cumming and Kebarle, 1978 | 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.
Ribeiro da Silva and Monte, 1992
Ribeiro da Silva, M.A.V.; Monte, M.J.S.,
Vapour pressures and standard molar enthalpies of sublimation of four crystalline B-diketones,
J. Chem. Thermodyn., 1992, 24, 1219-1228. [all data]
Ferrao and Ribeiro Da Silva, 1981
Ferrao, M.L.C.C.H.; Ribeiro Da Silva, M.A.V.,
Enthalpies of combustion of four methyl-substituted heptane-3,5-diones and benzoylacetone,
J. Chem. Thermodyn., 1981, 13, 567-571. [all data]
Farrar and Jones, 1964
Farrar, D.T.; Jones, M.M.,
Heats of combustion and bond energies in some octahedral iron(III) complexes with β-diketones,
J. Phys. Chem., 1964, 68, 1717-1721. [all data]
Sabatier and Mailhe, 1909
Sabatier, P.; Mailhe, A.,
New Applications of the General Method of Hydrogenation with Various Metals,
Ann. Chim. Phys., 1909, 16, 70. [all data]
Wolfrom and Bobbitt, 1956
Wolfrom, M.L.; Bobbitt, J.M.,
Periodate Oxidation of Cyclic 1,3-Diketones,
J. Am. Chem. Soc., 1956, 78, 2489-93. [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]
Aihara, 1959
Aihara, Ariyuki,
Estimation of the Energy of Hydrogen Bonds Formed in Crystals. I. Sublimation Pressures of Some Organic Molecular Crystals and the Additivity of Lattice Energy,
Bull. Chem. Soc. Jpn., 1959, 32, 11, 1242-1248, https://doi.org/10.1246/bcsj.32.1242
. [all data]
Aihara, 1959, 2
Aihara, A.,
Estimation of the energy of hydrogen bonds formed in crystals. I. Sublimation pressures of some organic molecular crystals and the additivity of lattice energy,
Bull. Chem. Soc. Jpn., 1959, 32, 1242. [all data]
Cumming and Kebarle, 1978
Cumming, J.B.; Kebarle, P.,
Summary of gas phase measurements involving acids AH. Entropy changes in proton transfer reactions involving negative ions. Bond dissociation energies D(A-H) and electron affinities EA(A),
Can. J. Chem., 1978, 56, 1. [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:
Tboil Boiling point Tfus Fusion (melting) point ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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