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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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 | -55.72 ± 0.11 | kcal/mol | Ccr | Mansson, Nakase, et al., 1968 | |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -457.11 ± 0.10 | kcal/mol | Ccr | Mansson, Nakase, et al., 1968 | Corresponding ΔfHºliquid = -55.72 kcal/mol (simple calculation by NIST; no Washburn corrections) |
Reaction thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Gas phase ion energetics 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° | -41.35 | kcal/mol | Kin | Lopatin, Popov, et al., 1992 | liquid phase; solvent: Solution |
+
=
By formula: C4H4O2 + H2O = C4H6O3
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -28.32 | kcal/mol | Kin | Lopatin, Popov, et al., 1992 | liquid phase; solvent: Solution |
+
=
By formula: C2H6O + C4H4O2 = C6H10O3
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -30.35 | kcal/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° | -25.43 | kcal/mol | Kin | Lopatin, Popov, et al., 1992 | liquid phase; solvent: Solution |
2 =
By formula: 2C4H4O2 = C8H8O4
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -22.0 | kcal/mol | Kin | Lopatin, Popov, et al., 1992 | liquid phase; solvent: Solution |
Gas phase ion energetics 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 by: Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
Ionization energy determinations
| IE (eV) | Method | Reference |
|---|---|---|
| 9.6 ± 0.02 | EI | Olivares, Flesch, et al., 1984 |
Appearance energy determinations
| Ion | AE (eV) | Other Products | Method | Reference | Comment |
|---|---|---|---|---|---|
| C3H4O+ | 10.0 ± 0.04 | CO | EI | Olivares, Flesch, et al., 1984 |
References
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics 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]
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]
Olivares, Flesch, et al., 1984
Olivares, J.A.; Flesch, G.D.; Svec, H.J.,
Mass spectrometry of five ketene dimers,
Int. J. Mass Spectrom. Ion Processes, 1984, 56, 293. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy ΔcH°liquid Enthalpy of combustion of liquid 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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