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
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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:
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 | -45.47 ± 0.13 | kcal/mol | Ccr | Mansson, Nakase, et al., 1968 | ALS |
Constant pressure heat capacity of gas
| Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 8.669 | 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 |
| 10.16 | 100. | ||
| 12.17 | 150. | ||
| 14.66 | 200. | ||
| 18.75 | 273.15 | ||
| 20.17 | 298.15 | ||
| 20.28 | 300. | ||
| 25.657 | 400. | ||
| 30.194 | 500. | ||
| 33.870 | 600. | ||
| 36.857 | 700. | ||
| 39.314 | 800. | ||
| 41.362 | 900. | ||
| 43.086 | 1000. | ||
| 44.55 | 1100. | ||
| 45.79 | 1200. | ||
| 46.85 | 1300. | ||
| 47.78 | 1400. | ||
| 48.57 | 1500. |
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) |
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:
BS - Robert L. Brown and Stephen E. Stein
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Tboil | 400.6 | K | N/A | Weast and Grasselli, 1989 | BS |
| Tboil | 399.2 | K | N/A | Majer and Svoboda, 1985 | |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔvapH° | 10.3 | kcal/mol | N/A | Majer and Svoboda, 1985 | |
| ΔvapH° | 10.25 ± 0.03 | kcal/mol | C | Mansson, Nakase, et al., 1968 | ALS |
| ΔvapH° | 10.3 | kcal/mol | N/A | Mansson, Nakase, et al., 1968 | DRB |
| ΔvapH° | 10.3 ± 0.02 | kcal/mol | C | Mansson, Nakase, et al., 1968 | AC |
Reduced pressure boiling point
| Tboil (K) | Pressure (atm) | Reference | Comment |
|---|---|---|---|
| 342.7 | 0.132 | Aldrich Chemical Company Inc., 1990 | BS |
Enthalpy of vaporization
| ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 8.80 | 399.2 | N/A | Majer and Svoboda, 1985 | |
| 10.3 | 312. | A | Stephenson and Malanowski, 1987 | Based on data from 297. to 388. K.; AC |
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: 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
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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: 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 |
IR Spectrum
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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: Coblentz Society, Inc.
Condensed Phase Spectrum
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Notice: Except where noted, spectra from this collection were measured on dispersive instruments, often in carefully selected solvents, and hence may differ in detail from measurements on FTIR instruments or in other chemical environments. More information on the manner in which spectra in this collection were collected can be found here.
Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.
Additional Data
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| Owner | COBLENTZ SOC. Collection (C) 2018 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
|---|---|
| Origin | DOW CHEMICAL COMPANY |
| Source reference | COBLENTZ NO. 07595 |
| Date | 1965/02/10 |
| Name(s) | 4-methylene-2-oxetanone |
| State | SOLUTION (CS2 FOR 3800-400 CM-1) |
| Instrument | BECKMAN IR-9 (GRATING) |
| Instrument parameters | ORDER CHANGES: 670, 1200, 2000 CM-1 |
| Path length | 0.10 CM SPECTRAL CONTAMINATION DUE TO CS2 AROUND 2800, 2300, 1600-1400, 850, 650 CM-1 |
| Resolution | 2 |
| Sampling procedure | TRANSMISSION |
| Data processing | DIGITIZED BY COBLENTZ SOCIETY (BATCH I) FROM HARD COPY |
Mass spectrum (electron ionization)
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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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
Due to licensing restrictions, this spectrum cannot be downloaded.
| Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
|---|---|
| Origin | NIST Mass Spectrometry Data Center |
| NIST MS number | 334003 |
Gas Chromatography
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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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Van Den Dool and Kratz RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | VF-5MS | 709.2 | Tret'yakov, 2007 | 30. m/0.25 mm/0.25 μm, He; Program: Multi-step temperature program; T(initial)=60C; T(final)=270C |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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]
Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]
Majer and Svoboda, 1985
Majer, V.; Svoboda, V.,
Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [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]
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]
Tret'yakov, 2007
Tret'yakov, K.V.,
Retention Data. NIST Mass Spectrometry Data Center., NIST Mass Spectrometry Data Center, 2007. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, References
- Symbols used in this document:
AE Appearance energy Cp,gas Constant pressure heat capacity of gas Tboil Boiling point 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 ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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