acetyl fluoride
- Formula: C2H3FO
- Molecular weight: 62.0430
- IUPAC Standard InChI: InChI=1S/C2H3FO/c1-2(3)4/h1H3
- IUPAC Standard InChIKey: JUCMRTZQCZRJDC-UHFFFAOYSA-N
- CAS Registry Number: 557-99-3
- Chemical structure:
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Condensed phase thermochemistry data
Go To: Top, 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 | -111.47 ± 0.02 | kcal/mol | Cm | Pritchard and Skinner, 1950 | Corrected for CODATA value of ΔfH; HF(100) |
| ΔfH°liquid | -112.4 ± 0.1 | kcal/mol | Cm | Pritchard and Skinner, 1950, 2 | Heat of formation derived by Cox and Pilcher, 1970, see Carson and Skinner, 1949 and Pritchard and Skinner, 1950 |
| ΔfH°liquid | -110.6 ± 0.7 | kcal/mol | Cm | Carson and Skinner, 1949 |
Reaction thermochemistry data
Go To: Top, 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 as indicated in comments:
B - John E. Bartmess
ALS - 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
C2H2FO- + =
By formula: C2H2FO- + H+ = C2H3FO
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 355.9 ± 3.8 | kcal/mol | G+TS | Farid and McMahon, 1980 | gas phase; Between MeCOCH2F, cyclopentadiene; value altered from reference due to change in acidity scale; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 349.0 ± 3.7 | kcal/mol | IMRB | Farid and McMahon, 1980 | gas phase; Between MeCOCH2F, cyclopentadiene; value altered from reference due to change in acidity scale; B |
2 +
=
+
+
By formula: 2HNaO + C2H3FO = C2H3NaO2 + FNa + H2O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -13.42 ± 0.02 | kcal/mol | Cm | Pritchard and Skinner, 1950 | liquid phase; Corrected for CODATA value of ΔfH; HF(100); ALS |
| ΔrH° | -42.4 | kcal/mol | Cm | Carson and Skinner, 1949 | liquid phase; ALS |
References
Go To: Top, 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.
Pritchard and Skinner, 1950
Pritchard, H.O.; Skinner, H.A.,
The heat of hydrolysis of acetyl fluoride,
J. Chem. Soc., 1950, 1099. [all data]
Pritchard and Skinner, 1950, 2
Pritchard, H.O.; Skinner, H.A.,
The heats of hydrolysis of the chloro-substituted acetyl chlorides,
J. Chem. Soc., 1950, 272-276. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]
Carson and Skinner, 1949
Carson, A.S.; Skinner, H.A.,
201. Carbon-halogen bond energies in the acetyl halides,
J. Chem. Soc., 1949, 936-939. [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]
Notes
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, References
- Symbols used in this document:
ΔfH°liquid Enthalpy of formation of liquid at standard conditions 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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