CF3O anion
- Formula: CF3O-
- Molecular weight: 85.0059
- CAS Registry Number: 57178-38-8
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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: John E. Bartmess
Electron affinity of neutral species
| EAneutral (eV) | Method | Reference | Comment |
|---|---|---|---|
| 4.39 ± 0.12 | D-EA | Huey, Dunlea, et al., 1996 | Agrees with G2 calculation: Segovia and Ventura, 1997, Burk, Koppel, et al., 2000, Chyall and Squires, 1996 |
| 3.62 ± 0.11 | D-EA | Taft, Koppel, et al., 1990 | In conflict with Huey, Dunlea, et al., 1996. Bracketing here may be for CF3O- + AH -> CF2=O + HF + A-. |
| >3.86808 | IMRB | Huey, Dunlea, et al., 1996 | EA > NO3 |
| 3.70 ± 0.50 | EIAE | Spyrou, Hunter, et al., 1984 | From CF3OCF2H |
| 4.1313 | D-EA | Larson and McMahon, 1983 | These relative affinities are ca. 10 kcal/mol weaker than threshold values (see Wenthold and Squires, 1995) for donors greater than ca. 27 kcal/mol in free energy. This discrepancy has not yet been resolved, though the stronger value appears preferable. |
| >1.90 ± 0.20 | EIAE | MacNeil and Thynne, 1972 | From CF3OOCF3 |
| 1.90 ± 0.10 | EIAE | Thynne and MacNeil, 1970 | From CF3OF |
| 1.34862 | SI | Page and Goode, 1969 | The Magnetron method, lacking mass analysis, is not considered reliable. |
Protonation reactions
CF3O- + =
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1380. ± 8.4 | kJ/mol | G+TS | Huey, Dunlea, et al., 1996 | gas phase; Agrees with G2 calculation: Segovia and Ventura, 1997, Burk, Koppel, et al., 2000, Chyall and Squires, 1996 |
| ΔrH° | 1454. ± 7.9 | kJ/mol | G+TS | Taft, Koppel, et al., 1990 | gas phase; In conflict with Huey, Dunlea, et al., 1996. Bracketing here may be for CF3O- + AH -> CF2=O + HF + A-. |
| ΔrH° | <1431. ± 7.5 | kJ/mol | D-EA | Huey, Dunlea, et al., 1996 | gas phase; EA > NO3 |
| ΔrH° | 1405.1 | kJ/mol | Acid | Larson and McMahon, 1983 | gas phase; These relative affinities are ca. 10 kcal/mol weaker than threshold values (see Wenthold and Squires, 1995) for donors greater than ca. 27 kcal/mol in free energy. This discrepancy has not yet been resolved, though the stronger value appears preferable. |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1351. ± 6.7 | kJ/mol | IMRB | Huey, Dunlea, et al., 1996 | gas phase; Agrees with G2 calculation: Segovia and Ventura, 1997, Burk, Koppel, et al., 2000, Chyall and Squires, 1996 |
| ΔrG° | 1425. ± 6.3 | kJ/mol | IMRB | Taft, Koppel, et al., 1990 | gas phase; In conflict with Huey, Dunlea, et al., 1996. Bracketing here may be for CF3O- + AH -> CF2=O + HF + A-. |
| ΔrG° | 1377. ± 5.0 | kJ/mol | H-TS | Larson and McMahon, 1983 | gas phase; These relative affinities are ca. 10 kcal/mol weaker than threshold values (see Wenthold and Squires, 1995) for donors greater than ca. 27 kcal/mol in free energy. This discrepancy has not yet been resolved, though the stronger value appears preferable. |
References
Go To: Top, 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.
Huey, Dunlea, et al., 1996
Huey, L.G.; Dunlea, E.J.; Howard, C.J.,
Gas-Phase Acidity of CF3OH,
J. Phys. Chem., 1996, 100, 16, 6504, https://doi.org/10.1021/jp953058m
. [all data]
Segovia and Ventura, 1997
Segovia, M.; Ventura, O.N.,
Density functional and G2 study of the strength of the OH bond in CF3OH,
Chem. Phys. Lett., 1997, 277, 5-6, 490-496, https://doi.org/10.1016/S0009-2614(97)00860-9
. [all data]
Burk, Koppel, et al., 2000
Burk, P.; Koppel, I.A.; Rummel, A.; Trummal, A.,
Can O-H acid be more acidic than its S-H analog? A G2 study of fluoromethanols and fluoromethanethiols,
J. Phys. Chem. A, 2000, 104, 7, 1602-1607, https://doi.org/10.1021/jp993487a
. [all data]
Chyall and Squires, 1996
Chyall, L.J.; Squires, R.R.,
The Proton Affinity and Absolute Heat of Formation of Trifluoromethanpl,
J. Phys. Chem., 1996, 100, 16435. [all data]
Taft, Koppel, et al., 1990
Taft, R.W.; Koppel, I.J.; Topsom, R.D.; Anvia, F.,
Acidities of OH Compounds, including Alcohols, Phenols, Carboxylic Acids, and Mineral Acids,
J. Am. Chem. Soc., 1990, 112, 6, 2047, https://doi.org/10.1021/ja00162a001
. [all data]
Spyrou, Hunter, et al., 1984
Spyrou, S.M.; Hunter, S.R.; Christophorou, L.G.,
Studies of Negative Ion Formation in Fluoroethers and Fluorosulphides using Low-Energy (10 eV) Electron Beam and Electron Swarm Techniques.,
J. Chem. Phys., 1984, 81, 10, 4481, https://doi.org/10.1063/1.447417
. [all data]
Larson and McMahon, 1983
Larson, J.W.; McMahon, T.B.,
Strong hydrogen bonding in gas-phase anions. An ion cyclotron resonance determination of fluoride binding energetics to bronsted acids from gas-phase fluoride exchange equilibria measurements,
J. Am. Chem. Soc., 1983, 105, 2944. [all data]
Wenthold and Squires, 1995
Wenthold, P.G.; Squires, R.R.,
Bond dissociation energies of F2(-) and HF2(-). A gas-phase experimental and G2 theoretical study,
J. Phys. Chem., 1995, 99, 7, 2002, https://doi.org/10.1021/j100007a034
. [all data]
MacNeil and Thynne, 1972
MacNeil, K.A.G.; Thynne, J.C.J.,
Negative ion formation at low electron energies by hexafluorodimethyl peroxide,
Int. J. Mass Spectrom. Ion Phys., 1972, 9, 135. [all data]
Thynne and MacNeil, 1970
Thynne, J.C.J.; MacNeil, K.A.G.,
Ionisation and dissociation of carbonyl fluoride and trifluoromethyl hypofluorite by electron impact,
Intern. J. Mass Spectrom. Ion Phys., 1970, 5, 95. [all data]
Page and Goode, 1969
Page, F.M.; Goode, G.C.,
Negative Ions and the Magnetron., Wiley, NY, 1969. [all data]
Notes
Go To: Top, Gas phase ion energetics data, References
- Symbols used in this document:
EAneutral Electron affinity of neutral species 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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