2-Propanone, 1-fluoro-
- Formula: C3H5FO
- Molecular weight: 76.0696
- IUPAC Standard InChI: InChI=1S/C3H5FO/c1-3(5)2-4/h2H2,1H3
- IUPAC Standard InChIKey: MSWVMWGCNZQPIA-UHFFFAOYSA-N
- CAS Registry Number: 430-51-3
- 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: Fluoroacetone; 1-Fluoro-2-propanone; CH3COCH2F; Mono-fluoroacetone
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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 | 348.2 | K | N/A | 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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
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
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Proton affinity (review) | 190.1 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
| Quantity | Value | Units | Method | Reference | Comment |
| Gas basicity | 182.5 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 9.9 | PE | Young and Cheng, 1976 | LLK |
| 10.20 | PE | Olivato, Guerrero, et al., 1984 | Vertical value; LBLHLM |
| 10.20 ± 0.02 | PE | Young and Cheng, 1976 | Vertical value; LLK |
De-protonation reactions
C3H4FO- + =
By formula: C3H4FO- + H+ = C3H5FO
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 357.6 ± 3.6 | kcal/mol | G+TS | Farid and McMahon, 1980 | gas phase; Between pyrrole, MeNO2; value altered from reference due to change in acidity scale; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 350.2 ± 3.5 | kcal/mol | IMRB | Farid and McMahon, 1980 | gas phase; Between pyrrole, MeNO2; value altered from reference due to change in acidity scale; B |
C3H4FO- + =
By formula: C3H4FO- + H+ = C3H5FO
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 366.1 ± 4.1 | kcal/mol | G+TS | Clair and McMahon, 1980 | gas phase; value altered from reference due to change in acidity scale; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 359.3 ± 4.0 | kcal/mol | IMRB | Clair and McMahon, 1980 | 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.
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]
Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G.,
Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update,
J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018
. [all data]
Young and Cheng, 1976
Young, V.Y.; Cheng, K.L.,
The photoelectron spectra of halogen substituted acetones,
J. Chem. Phys., 1976, 65, 3187. [all data]
Olivato, Guerrero, et al., 1984
Olivato, P.R.; Guerrero, S.A.; Modelli, A.; Granozzi, G.; Jones, D.; Distefano, G.,
Electronic interaction in heterosubstituted acetones studied by means of ultraviolet photoelectron and electron transmission spectroscopy,
J. Chem. Soc. Perkin Trans. 2, 1984, 1505. [all data]
Farid and McMahon, 1980
Farid, R.; McMahon, T.B.,
The gas phase acidities of fluorinated acetones. An ICR investigation of the role of fluorine substituents in the stabilization of planar carbanions,
Can. J. Chem., 1980, 58, 2307. [all data]
Clair and McMahon, 1980
Clair, R.L.; McMahon, T.B.,
An ion cyclotron resonance study of base-induced elimination reactions of fluorinated alcohols and unimolecular loss of HF from chemically activated fluoroalkoxide ions,
Int. J. Mass Spectrom. Ion Phys., 1980, 33, 21. [all data]
Notes
Go To: Top, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
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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