3-Butyn-2-one
- Formula: C4H4O
- Molecular weight: 68.0740
- IUPAC Standard InChI: InChI=1S/C4H4O/c1-3-4(2)5/h1H,2H3
- IUPAC Standard InChIKey: XRGPFNGLRSIPSA-UHFFFAOYSA-N
- CAS Registry Number: 1423-60-5
- 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: Methyl ethynyl ketone; 1-Butyn-3-one; Ketone, ethynyl methyl; Ethynyl methyl ketone; Acetylacetylene; Acetylethyne; But-3-yn-2-one; 3-Butyne-2-one
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Phase change data
Go To: Top, 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: Robert L. Brown and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Tboil | 358. | K | N/A | Farchan Laboratories, 1990 |
Reduced pressure boiling point
| Tboil (K) | Pressure (atm) | Reference |
|---|---|---|
| 357.2 | 0.989 | Weast and Grasselli, 1989 |
Gas phase ion energetics data
Go To: Top, Phase change 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:
B - John E. Bartmess
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
View reactions leading to C4H4O+ (ion structure unspecified)
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 10.25 | EI | Burgers, Holmes, et al., 1982 | LBLHLM |
| 10.19 | PE | Willett and Baer, 1980 | LLK |
| 10.28 | PE | Terlouw, Burgers, et al., 1979 | LLK |
| 10.25 ± 0.05 | EI | Holmes and Terlouw, 1979 | LLK |
| 10.17 | PE | Carlier and Mouvier, 1979 | Vertical value; LLK |
Appearance energy determinations
| Ion | AE (eV) | Other Products | Method | Reference | Comment |
|---|---|---|---|---|---|
| C2H+ | 17.95 | CH3+CO? | EI | Majer, Patrick, et al., 1961 | RDSH |
| C2H3O+ | 12.10 ± 0.10 | C2H | PE | Willett and Baer, 1980 | LLK |
| C2H3O+ | 11.85 | C2H | EI | Majer, Patrick, et al., 1961 | RDSH |
| C3HO+ | 11.00 ± 0.10 | CH3 | PE | Willett and Baer, 1980 | LLK |
| C3HO+ | 11.0 | CH3 | EI | Majer, Patrick, et al., 1961 | RDSH |
| C3H3+ | 11.55 ± 0.10 | CHO | PE | Willett and Baer, 1980 | LLK |
| C3H4+ | 11.0 ± 0.2 | CO | EI | Mommers, Burgers, et al., 1984 | LBLHLM |
| C3H4+ | 10.68 ± 0.05 | CO | PE | Willett and Baer, 1980 | LLK |
De-protonation reactions
C4H3O- + =
By formula: C4H3O- + H+ = C4H4O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 360.0 ± 2.3 | kcal/mol | G+TS | Taft and Topsom, 1987 | gas phase; value altered from reference due to change in acidity scale; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 352.3 ± 2.2 | kcal/mol | IMRE | Taft and Topsom, 1987 | gas phase; value altered from reference due to change in acidity scale; B |
References
Go To: Top, Phase change 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.
Farchan Laboratories, 1990
Farchan Laboratories,
Research Chemicals Catalog, Farchan Laboratories, Gainesville, FL, 1990, 91. [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]
Burgers, Holmes, et al., 1982
Burgers, P.C.; Holmes, J.L.; Lossing, F.P.; Mommers, A.A.; Povel, F.R.; Terlouw, J.K.,
Isomeric and tautomeric [C4H4O]+ ions. Their thermochemistry and collisionally induced fragmentation characteristics,
Can. J. Chem., 1982, 60, 2246. [all data]
Willett and Baer, 1980
Willett, G.D.; Baer, T.,
Thermochemistry and dissociation dynamics of state-selected C4H4X ions. 2. Furan 3-butyn-2-one,
J. Am. Chem. Soc., 1980, 102, 6769. [all data]
Terlouw, Burgers, et al., 1979
Terlouw, J.K.; Burgers, P.C.; Holmes, J.L.,
Thermochemistry and generation of vinylketene,
J. Am. Chem. Soc., 1979, 101, 225. [all data]
Holmes and Terlouw, 1979
Holmes, J.L.; Terlouw, J.K.,
Structures of [C4H4O]+ ions produced from 2- and 4-pyrone,
J. Am. Chem. Soc., 1979, 101, 4973. [all data]
Carlier and Mouvier, 1979
Carlier, P.; Mouvier, G.,
Etude par spectrometrie de photoelectrons de la structure electronique des ynals et des ynones conjugues,
J. Electron Spectrosc. Relat. Phenom., 1979, 17, 169. [all data]
Majer, Patrick, et al., 1961
Majer, J.R.; Patrick, C.R.; Robb, J.C.,
Appearance potentials of the acetyl radical-ion,
J. Chem. Soc. Faraday Trans., 1961, 57, 14. [all data]
Mommers, Burgers, et al., 1984
Mommers, A.A.; Burgers, P.C.; Holmes, J.L.; Terlouw, J.K.,
Isomeric [C3H4]+ ions: Their identification and generation in dissociative ionizations,
Org. Mass Spectrom., 1984, 19, 7. [all data]
Taft and Topsom, 1987
Taft, R.W.; Topsom, R.D.,
The Nature and Analysis of Substituent Effects,
Prog. Phys. Org. Chem., 1987, 16, 1. [all data]
Notes
Go To: Top, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy Tboil Boiling point 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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