2-Oxetanone, 4-methylene-
- Formula: C4H4O2
- Molecular weight: 84.0734
- IUPAC Standard InChI: InChI=1S/C4H4O2/c1-3-2-4(5)6-3/h1-2H2
- IUPAC Standard InChIKey: WASQWSOJHCZDFK-UHFFFAOYSA-N
- CAS Registry Number: 674-82-8
- 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: Diketene; Ethenone, dimer; Ketene dimer; 3-Butenoic acid, 3-hydroxy-, β-lactone; 4-Methylene-2-oxetanone; Diketen; Vinylaceto-β-lactone; but-3-en-3-olide
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry 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
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | -190.2 ± 0.54 | kJ/mol | Ccr | Mansson, Nakase, et al., 1968 | ALS |
Constant pressure heat capacity of gas
| Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 36.27 | 50. | Thermodynamics Research Center, 1997 | p=1 bar. Selected entropy and heat capacity at 298.15 K are in close agreement with statistical values calculated by [ Joshi R.M., 1970]. However entropy values at 600 and 1000 K obtained by [ Joshi R.M., 1970] are about 27 J/mol*K lower than selected ones. Estimations by difference method [ Dorofeeva O.V., 1997] give preference for data [ Thermodynamics Research Center, 1997].; GT |
| 42.49 | 100. | ||
| 50.94 | 150. | ||
| 61.35 | 200. | ||
| 78.44 | 273.15 | ||
| 84.41 | 298.15 | ||
| 84.84 | 300. | ||
| 107.35 | 400. | ||
| 126.33 | 500. | ||
| 141.71 | 600. | ||
| 154.21 | 700. | ||
| 164.49 | 800. | ||
| 173.06 | 900. | ||
| 180.27 | 1000. | ||
| 186.4 | 1100. | ||
| 191.6 | 1200. | ||
| 196.0 | 1300. | ||
| 199.9 | 1400. | ||
| 203.2 | 1500. |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry 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°liquid | -233.1 ± 0.46 | kJ/mol | Ccr | Mansson, Nakase, et al., 1968 | |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -1912.5 ± 0.42 | kJ/mol | Ccr | Mansson, Nakase, et al., 1968 | Corresponding ΔfHºliquid = -233.1 kJ/mol (simple calculation by NIST; no Washburn corrections) |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, 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
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: C4H4O2 + H3N = acetoacetamide
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -173.0 | kJ/mol | Kin | Lopatin, Popov, et al., 1992 | liquid phase; solvent: Solution |
+
=
By formula: C4H4O2 + H2O = C4H6O3
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -118.5 | kJ/mol | Kin | Lopatin, Popov, et al., 1992 | liquid phase; solvent: Solution |
+
=
By formula: C2H6O + C4H4O2 = C6H10O3
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -127.0 | kJ/mol | Kin | Lopatin, Popov, et al., 1992 | liquid phase; solvent: Solution |
+
=
By formula: CH4N2O + C4H4O2 = N-(aminocarbonyl)-3-oxobutyramide
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -106.4 | kJ/mol | Kin | Lopatin, Popov, et al., 1992 | liquid phase; solvent: Solution |
2 =
By formula: 2C4H4O2 = C8H8O4
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -91.9 | kJ/mol | Kin | Lopatin, Popov, et al., 1992 | liquid phase; solvent: Solution |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry 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.
Mansson, Nakase, et al., 1968
Mansson, M.; Nakase, Y.; Sunner, S.,
The enthalpies of combustion and formation of diketene,
Acta Chem. Scand., 1968, 22, 171-174. [all data]
Thermodynamics Research Center, 1997
Thermodynamics Research Center,
Selected Values of Properties of Chemical Compounds., Thermodynamics Research Center, Texas A&M University, College Station, Texas, 1997. [all data]
Joshi R.M., 1970
Joshi R.M.,
Thermodynamic properties of some monomeric compounds in the standard ideal gas state,
J. Polym. Sci., Part A-2, 1970, 8, 679-687. [all data]
Dorofeeva O.V., 1997
Dorofeeva O.V.,
Unpublished results. Thermocenter of Russian Academy of Science, Moscow, 1997. [all data]
Lopatin, Popov, et al., 1992
Lopatin, E.B.; Popov, V.V.; Epshtein, N.A.; Mikhaleva, L.M.; Makarov, Yu.N.,
Kinetic and thermochemical characteristics of diketene-based reactions,
Khim.-Farm. Zh., 1992, 26, 76-78. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, References
- Symbols used in this document:
Cp,gas Constant pressure heat capacity of gas 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 ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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