Carbonic difluoride
- Formula: CF2O
- Molecular weight: 66.0069
- IUPAC Standard InChIKey: IYRWEQXVUNLMAY-UHFFFAOYSA-N
- CAS Registry Number: 353-50-4
- 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: Carbonyl fluoride; Carbon difluoride oxide; Carbon fluoride oxide (COF2); Carbon oxyfluoride; Carbonyl difluoride; Difluoroformaldehyde; Fluoroformyl fluoride; Fluorophosgene; COF2; Fluophosgene; Difluorooxomethane; Difluorophosgene; Carbon fluoride oxide; Rcra waste number U033; UN 2417; Carbon oxyfluoride (COF2)
- Permanent link for this species. Use this link for bookmarking this species for future reference.
- Information on this page:
- Other data available:
- Data at other public NIST sites:
- Options:
Gas phase ion energetics data
Go To: Top, 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
L - Sharon G. Lias
Data compiled as indicated in comments:
B - John E. Bartmess
LL - Sharon G. Lias and Joel F. Liebman
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 CF2O+ (ion structure unspecified)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 13.04 ± 0.03 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 159.3 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 152.2 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
ΔfH°(+) ion | 155. | kcal/mol | N/A | N/A | |
Quantity | Value | Units | Method | Reference | Comment |
ΔfH(+) ion,0K | 156. | kcal/mol | N/A | N/A |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
13.035 ± 0.030 | PI | Buckley, Johnson, et al., 1995 | LL |
13.04 | PE | Thomas and Thompson, 1972 | LLK |
13.02 | PE | Brundle, Robin, et al., 1972 | LLK |
13.2 ± 0.1 | EI | Workman and Duncan, 1970 | RDSH |
14.6 ± 0.1 | EI | Thynne and MacNeil, 1970 | RDSH |
13.6 | PE | Johnson, Powis, et al., 1979 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C+ | 36. ± 1. | 2F+O? | EI | Thynne and MacNeil, 1970 | RDSH |
CF+ | 27.0 ± 0.3 | ? | EI | Thynne and MacNeil, 1970 | RDSH |
CFO+ | 14.736 ± 0.012 | F | PI | Buckley, Johnson, et al., 1995 | LL |
CFO+ | 14.9 ± 0.2 | F | PI | Johnson, Powis, et al., 1979 | LLK |
COF+ | 16.0 ± 0.1 | F | EI | Thynne and MacNeil, 1970 | RDSH |
CF2+ | 25.6 ± 0.3 | O | EI | Thynne and MacNeil, 1970 | RDSH |
F+ | 38. ± 1. | ? | EI | Thynne and MacNeil, 1970 | RDSH |
O+ | 35. ± 1. | ? | EI | Thynne and MacNeil, 1970 | RDSH |
De-protonation reactions
CF3O- + =
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 329.8 ± 2.0 | kcal/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; B |
ΔrH° | 347.5 ± 1.9 | kcal/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-.; B |
ΔrH° | <341.9 ± 1.8 | kcal/mol | D-EA | Huey, Dunlea, et al., 1996 | gas phase; EA > NO3; B |
ΔrH° | 335.83 | kcal/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.; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 323.0 ± 1.6 | kcal/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; B |
ΔrG° | 340.7 ± 1.5 | kcal/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-.; B |
ΔrG° | 329.0 ± 1.2 | kcal/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.; B |
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.
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]
Buckley, Johnson, et al., 1995
Buckley, T.J.; Johnson, R.D.; Huie, R.E.; Zhang, Z.; Kuo, S.C.; Klemm, R.B.,
Ionization energies, appearance energies, and thermochemistry of CF2O and FCO,
J. Phys. Chem., 1995, 99, 4879. [all data]
Thomas and Thompson, 1972
Thomas, R.K.; Thompson, H.,
Photoelectron spectra of carbonyl halides and related compounds,
Proc. R. Soc. London A:, 1972, 327, 13. [all data]
Brundle, Robin, et al., 1972
Brundle, C.R.; Robin, M.B.; Kuebler, N.A.; Basch, H.,
Perfluoro effect in photoelectron spectroscopy. I. Nonaromatic molecules,
J. Am. Chem. Soc., 1972, 94, 1451. [all data]
Workman and Duncan, 1970
Workman, G.L.; Duncan, A.B.F.,
Electronic spectrum of carbonyl fluoride,
J. Chem. Phys., 1970, 52, 3204. [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]
Johnson, Powis, et al., 1979
Johnson, K.M.; Powis, I.; Danby, C.J.,
The fragmentation of COCl2+ and COF2+ ions studied by the photoelectron-photoion coincidence technique,
Int. J. Mass Spectrom. Ion Phys., 1979, 32, 1. [all data]
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]
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]
Notes
Go To: Top, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy IE (evaluated) Recommended ionization energy ΔfH(+) ion,0K Enthalpy of formation of positive ion at 0K 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
- The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
- Customer support for NIST Standard Reference Data products.