Acetone
- Formula: C3H6O
- Molecular weight: 58.0791
- IUPAC Standard InChIKey: CSCPPACGZOOCGX-UHFFFAOYSA-N
- CAS Registry Number: 67-64-1
- 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. - Isotopologues:
- Other names: 2-Propanone; β-Ketopropane; Dimethyl ketone; Dimethylformaldehyde; Methyl ketone; Propanone; Pyroacetic ether; (CH3)2CO; Dimethylketal; Ketone propane; Ketone, dimethyl-; Chevron acetone; Rcra waste number U002; UN 1090; Sasetone; Propan-2-one; NSC 135802
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- Other data available:
- Gas phase thermochemistry data
- Condensed phase thermochemistry data
- Phase change data
- Reaction thermochemistry data: reactions 1 to 50
- Henry's Law data
- Gas phase ion energetics data
- Ion clustering data
- IR Spectrum
- Mass spectrum (electron ionization)
- UV/Visible spectrum
- Vibrational and/or electronic energy levels
- Gas Chromatography
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Reaction thermochemistry data
Go To: Top, 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
MS - José A. Martinho Simões
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
B - John E. Bartmess
RCD - Robert C. Dunbar
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.
Reactions 51 to 85
By formula: C3H6O + C2H3ClOS = C5H9ClO2S
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -28. ± 0.4 | kJ/mol | Eqk | Horii, Kawamura, et al., 1972 | liquid phase; solvent: CD3COCD3; NMR; ALS |
By formula: C7H16O2 + H2O = 2C2H6O + C3H6O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 21.2 ± 0.2 | kJ/mol | Cm | Stern and Dorer, 1962 | liquid phase; Heat of hydrolysis; ALS |
By formula: C2H4O2 + C3H6O = C5H8O2 + H2O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 60.2 ± 0.3 | kJ/mol | Cm | Sunner, 1957 | liquid phase; Heat of hydrolysis; ALS |
C12H16CrO5 (solution) + (solution) =
(solution) + C8H6CrO6 (solution)
By formula: C12H16CrO5 (solution) + C3H6O (solution) = C7H16 (solution) + C8H6CrO6 (solution)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -56.5 ± 5.0 | kJ/mol | PAC | Yang, Peters, et al., 1986 | solvent: Heptane; MS |
C14H21MnO2 (solution) + (solution) = C10H11MnO3 (solution) +
(solution)
By formula: C14H21MnO2 (solution) + C3H6O (solution) = C10H11MnO3 (solution) + C7H16 (solution)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -72.8 ± 4.2 | kJ/mol | PAC | Klassen, Selke, et al., 1990 | solvent: Heptane; MS |
(solution) +
(solution) = C8H6O6W (solution) +
(solution)
By formula: C6O6W (solution) + C3H6O (solution) = C8H6O6W (solution) + CO (solution)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 74.9 ± 5.9 | kJ/mol | PC | Nakashima and Adamson, 1982 | solvent: Acetone; MS |
By formula: (K+ • 3C3H6O) + C3H6O = (K+ • 4C3H6O)
Free energy of reaction
ΔrG° (kJ/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
25. | 293. | ES/HPMS | Blades, Klassen, et al., 1995 | gas phase; M |
By formula: C4H8O + H2O = CH4O + C3H6O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -24.04 ± 0.46 | kJ/mol | Eqk | Hine and Arata, 1976 | liquid phase; ALS |
By formula: CH4O + C3H6O = C4H8O + H2O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 24.04 ± 0.46 | kJ/mol | Eqk | Hine and Arata, 1976 | liquid phase; ALS |
By formula: I- + C3H6O = (I- • C3H6O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 50.2 ± 4.2 | kJ/mol | TDAs | Caldwell, Masucci, et al., 1989 | gas phase; B,M |
By formula: C6H12O + C3H6O = C6H10O + C3H8O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 9.9 ± 1.9 | kJ/mol | Eqk | Fedoseenko, Yursha, et al., 1983 | gas phase; At 503 K; ALS |
By formula: C3H6O + I2 = HI + C3H5IO
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 50.6 ± 5.0 | kJ/mol | Eqk | Solly, Golden, et al., 1970 | gas phase; ALS |
C20H17Cl2OPPt (cr) = C17H25ClP2Pt (cr) + (g)
By formula: C20H17Cl2OPPt (cr) = C17H25ClP2Pt (cr) + C3H6O (g)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -33.6 ± 3.2 | kJ/mol | DSC | Brown, Puddephatt, et al., 1974 | Temperature: 394 K; MS |
By formula: C3H6O+ + C3H6O = (C3H6O+ • C3H6O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 51.9 | kJ/mol | PI | Trott, Blais, et al., 1978 | gas phase; ΔrH>; M |
By formula: 2CH4O + C3H6O = H2O + C5H12O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -46. ± 1. | kJ/mol | Cm | Wiberg, Morgan, et al., 1994 | gas phase; ALS |
+
= C13H24O2 +
By formula: C10H20O2 + C3H6O = C13H24O2 + H2O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -4.6 | kJ/mol | Eqk | Anteunis and Rommelaere, 1970 | liquid phase; ALS |
By formula: C4H10O2 + C3H6O = C7H14O2 + H2O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -17. | kJ/mol | Eqk | Anteunis and Rommelaere, 1970 | liquid phase; ALS |
By formula: C4H10O2 + C3H6O = C7H14O2 + H2O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -3. | kJ/mol | Eqk | Anteunis and Rommelaere, 1970 | liquid phase; ALS |
By formula: C2H6O2 + C3H6O = C5H10O2 + H2O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -10. | kJ/mol | Eqk | Anteunis and Rommelaere, 1970 | liquid phase; ALS |
By formula: C5H12O2 + C3H6O = C8H16O2 + H2O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -11. | kJ/mol | Eqk | Anteunis and Rommelaere, 1970 | liquid phase; ALS |
By formula: C3H8O2 + C3H6O = C6H12O2 + H2O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -3. | kJ/mol | Eqk | Anteunis and Rommelaere, 1970 | liquid phase; ALS |
By formula: C3H6O + C3H7ClO2 = C6H11ClO2 + H2O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -12. | kJ/mol | Eqk | Anteunis and Rommelaere, 1970 | liquid phase; ALS |
By formula: C3H8O2 + C3H6O = C6H12O2 + H2O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -23. | kJ/mol | Eqk | Anteunis and Rommelaere, 1970 | liquid phase; ALS |
By formula: C6H10O + C3H8O = C6H12O + C3H6O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -9.9 ± 1.9 | kJ/mol | Eqk | Kabo, Yursha, et al., 1988 | gas phase; ALS |
By formula: C3H5O+ + C3H6O = (C3H5O+ • C3H6O)
Free energy of reaction
ΔrG° (kJ/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
35. | 295. | FA | Mackay, Rakshit, et al., 1982 | gas phase; M |
By formula: (Cu+ • 2C3H6O) + C3H6O = (Cu+ • 3C3H6O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 64. ± 2. | kJ/mol | CIDT | Chu, 2002 | RCD |
By formula: (Cu+ • 3C3H6O) + C3H6O = (Cu+ • 4C3H6O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 61.1 ± 5.0 | kJ/mol | CIDT | Chu, 2002 | RCD |
By formula: C9H12N2 + H2O = C6H8N2 + C3H6O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -43.1 | kJ/mol | Cm | Landrieu, 1905 | solid phase; ALS |
By formula: C2H3O+ + C3H6O = (C2H3O+ • C3H6O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 52.3 | kJ/mol | PI | Trott, Blais, et al., 1978 | gas phase; M |
By formula: C3H6O = C3H6O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -124. | kJ/mol | Eqk | Polkovnikova and Lapiclus, 1974 | gas phase; At 300 K; ALS |
By formula: Cr+ + C3H6O = (Cr+ • C3H6O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 175. ± 14. | kJ/mol | RAK | Lin, Chen, et al., 1997 | RCD |
By formula: Mn+ + C3H6O = (Mn+ • C3H6O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 159. ± 14. | kJ/mol | RAK | Lin, Chen, et al., 1997 | RCD |
By formula: Ag+ + C3H6O = (Ag+ • C3H6O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 160. ± 19. | kJ/mol | RAK | Ho, Yang, et al., 1997 | RCD |
By formula: 2C3H6O = C6H12O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -34.27 | kJ/mol | Eqk | Davis and Burrows, 1936 | liquid phase; ALS |
References
Go To: Top, Reaction thermochemistry data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Horii, Kawamura, et al., 1972
Horii, T.; Kawamura, S.; Tsurugi, J.,
A NMR study of the thioacetic acid-acetone mixture,
Bull. Chem. Soc. Jpn., 1972, 45, 2200-2202. [all data]
Stern and Dorer, 1962
Stern, J.H.; Dorer, F.H.,
Standard heats of formation of 2,2-Dimethoxypropane (1), and 2,2 -Diethoxypropane (1). Group additivity theory and calculated heats of formation and five ketals,
J. Phys. Chem., 1962, 66, 97-99. [all data]
Sunner, 1957
Sunner, S.,
The heat of hydrolysis of i-propenyl acetate and m-cresyl acetate and the heat of formation of acetone,
Acta Chem. Scand., 1957, 11, 1757-1760. [all data]
Yang, Peters, et al., 1986
Yang, G.K.; Peters, K.S.; Vaida, V.,
Chem. Phys. Lett., 1986, 125, 566. [all data]
Klassen, Selke, et al., 1990
Klassen, J.K.; Selke, M.; Sorensen, A.A.; Yang, G.K.,
J. Am. Chem. Soc., 1990, 112, 1267. [all data]
Nakashima and Adamson, 1982
Nakashima, M.; Adamson, A.W.,
J. Phys. Chem., 1982, 86, 2905. [all data]
Blades, Klassen, et al., 1995
Blades, A.T.; Klassen, J.S.; Kebarle, P.,
Free Energies of Hydration in the Gas Phase on the Anions of Some Oxo Acids of C, N, S, P, Cl and I,
J. Am. Chem. Soc., 1995, 117, 42, 10563, https://doi.org/10.1021/ja00147a019
. [all data]
Hine and Arata, 1976
Hine, J.; Arata, K.,
Keto-Enol tautomerism. II. The calorimetrical determination of the equilibrium constants for keto-enol tautomerism for cyclohexanone,
Bull. Chem. Soc. Jpn., 1976, 49, 3089-3092. [all data]
Caldwell, Masucci, et al., 1989
Caldwell, G.W.; Masucci, J.A.; Ikonomou, M.G.,
Negative Ion Chemical Ionization Mass Spectrometry - Binding of Molecules to Bromide and Iodide Anions,
Org. Mass Spectrom., 1989, 24, 1, 8, https://doi.org/10.1002/oms.1210240103
. [all data]
Fedoseenko, Yursha, et al., 1983
Fedoseenko, V.I.; Yursha, I.A.; Kabo, G.Ya.,
Equilibrium and thermodynamics of cyclohexanol dehydrogenation reactions,
Dokl. Akad. Nauk BSSR, 1983, 27, 926-929. [all data]
Solly, Golden, et al., 1970
Solly, R.K.; Golden, D.M.; Benson, S.W.,
Thermochemical properties of iodoacetone. Intramolecular electrostatic interactions in polar molecules,
J. Am. Chem. Soc., 1970, 92, 4653-4656. [all data]
Brown, Puddephatt, et al., 1974
Brown, M.P.; Puddephatt, R.J.; Upton, C.E.E.; Lavington, S.W.,
J. Chem. Soc., Dalton Trans., 1974, 1613.. [all data]
Trott, Blais, et al., 1978
Trott, W.M.; Blais, N.C.; Walters, E.A.,
Molecular beam photoionization study of acetone and acetone-d6,
J. Chem. Phys., 1978, 69, 3150. [all data]
Wiberg, Morgan, et al., 1994
Wiberg, K.B.; Morgan, K.M.; Maltz, H.,
Thermochemistry of carbonyl reactions. 6. A study of hydration equilibria,
J. Am. Chem. Soc., 1994, 116, 11067-11077. [all data]
Anteunis and Rommelaere, 1970
Anteunis, M.; Rommelaere, Y.,
NMR experiments on acetals. XXIX. The ease of acetonide formation of some glycols,
Bull. Soc. Chim. Belg., 1970, 79, 523-530. [all data]
Kabo, Yursha, et al., 1988
Kabo, G.J.; Yursha, I.A.; Frenkel, M.L.; Poleshchuk, P.A.; Fedoseenko, V.I.; Ladutko, A.I.,
Thermodynamic properties of cyclohexanol and cyclohexanone,
J. Chem. Thermodyn., 1988, 20, 429-437. [all data]
Mackay, Rakshit, et al., 1982
Mackay, G.I.; Rakshit, A.B.; Bohme, D.K.,
An Experimental Study of the Reactivity and Relative Basicity of the Methoxide Anion in the Gas Phase at Room Temperature, and their Perturbation by Methanol Solvent,
Can. J. Chem., 1982, 60, 20, 2594, https://doi.org/10.1139/v82-373
. [all data]
Chu, 2002
Chu, Y.,
Solvation of Copper Ions by Acetone. Structures and Sequential Binding Energies of Cu+(acetone)x, x=1-4 From Collision-Induced Dissociation and Theoretical Studies,
J. Am. Soc. Mass Spectrom., 2002, 13, 5, 453, https://doi.org/10.1016/S1044-0305(02)00355-0
. [all data]
Landrieu, 1905
Landrieu, M.Ph.,
Thermochimie. - Thermochimie des hydrazones,
Compt. Rend., 1905, 141, 358-361. [all data]
Polkovnikova and Lapiclus, 1974
Polkovnikova, A.G.; Lapiclus, V.L.,
Calculation of the equilibrium and heat of isomerization of propylene oxide on a lithium phosphate catalyst,
Neftekhimiya, 1974, 14, 113-115. [all data]
Lin, Chen, et al., 1997
Lin, C.-Y.; Chen, Q.; Chen, H.; Freiser, B.S.,
Bond Dissociation Energy Determinations for MOC(CH3)2+ and MOC(CD3)2+ (M=Cr, Mn) Using Continuous Ejection and Radiative Association Methods,
Int. J. Mass Spectrom. Ion Proc., 1997, 167/168, 713, https://doi.org/10.1016/S0168-1176(97)00131-6
. [all data]
Ho, Yang, et al., 1997
Ho, Y.-P.; Yang, Y.-C.; Klippenstein, S.J.; Dunbar, R.C.,
Binding Energies of Ag+ and Cd+ Complexes from Analysis of Radiative Association Kinetics,
J. Phys. Chem. A, 1997, 101, 18, 3338, https://doi.org/10.1021/jp9637284
. [all data]
Davis and Burrows, 1936
Davis, G.L.; Burrows, G.H.,
Equilibrium and free energy relationships in the system acetone-diacetone alcohol,
J. Am. Chem. Soc., 1936, 58, 311-312. [all data]
Notes
Go To: Top, Reaction thermochemistry data, References
- Symbols used in this document:
T Temperature ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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