Ethanol, 2-fluoro-
- Formula: C2H5FO
- Molecular weight: 64.0589
- IUPAC Standard InChIKey: GGDYAKVUZMZKRV-UHFFFAOYSA-N
- CAS Registry Number: 371-62-0
- 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: Ethylene fluorohydrin; 2-Fluoro-1-ethanol; 2-Fluoroethanol; CH2FCH2OH; β-Fluoroethanol; TL 741
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Phase change data
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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:
BS - Robert L. Brown and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
Reduced pressure boiling point
Tboil (K) | Pressure (atm) | Reference | Comment |
---|---|---|---|
376.2 | 0.996 | Aldrich Chemical Company Inc., 1990 | BS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
10.5 | 288. | GS | Stephenson and Malanowski, 1987 | Based on data from 273. to 333. K. See also Redemann, Chaikin, et al., 1948 and Dykyj, 1970.; AC |
Reaction thermochemistry 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 as indicated in comments:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
RCD - Robert C. Dunbar
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
By formula: F- + C2H5FO = (F- • C2H5FO)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 34.8 ± 2.0 | kcal/mol | IMRE | 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,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 26.3 | cal/mol*K | N/A | Larson and McMahon, 1983 | gas phase; switching reaction(F-)H2O, Entropy change calculated or estimated; Arshadi, Yamdagni, et al., 1970; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 27.0 ± 2.0 | kcal/mol | IMRE | 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,M |
C2H4FO- + =
By formula: C2H4FO- + H+ = C2H5FO
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 371.2 ± 2.9 | kcal/mol | G+TS | Graul, Schnute, et al., 1990 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 364.6 ± 2.8 | kcal/mol | CIDC | Graul, Schnute, et al., 1990 | gas phase; B |
ΔrG° | 363.5 ± 3.5 | kcal/mol | IMRB | Clair and McMahon, 1980 | gas phase; Between HF and acetone; value altered from reference due to change in acidity scale; B |
ΔrG° | 364.9 ± 3.4 | kcal/mol | IMRB | Dawson and Jennings, 1977 | gas phase; Between HF and acetone; value altered from reference due to change in acidity scale; B |
By formula: CN- + C2H5FO = (CN- • C2H5FO)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 20.4 ± 3.5 | kcal/mol | IMRE | Larson and McMahon, 1987 | gas phase; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 25.3 | cal/mol*K | N/A | Larson and McMahon, 1987 | gas phase; switching reaction,Thermochemical ladder(CN-)H2O, Entropy change calculated or estimated; Payzant, Yamdagni, et al., 1971; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 12.9 ± 2.3 | kcal/mol | IMRE | Larson and McMahon, 1987 | gas phase; B,M |
By formula: Cl- + C2H5FO = (Cl- • C2H5FO)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 20.5 ± 2.0 | kcal/mol | IMRE | Larson and McMahon, 1984 | gas phase; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 25.0 | cal/mol*K | N/A | Larson and McMahon, 1984, 2 | gas phase; switching reaction(Cl-)t-C4H9OH, Entropy change calculated or estimated; French, Ikuta, et al., 1982; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 13.0 ± 2.0 | kcal/mol | IMRE | Larson and McMahon, 1984 | gas phase; B,M |
+ = C2H4D5F2O-
By formula: F- + C2H5FO = C2H4D5F2O-
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrG° | 26.5 ± 2.0 | kcal/mol | IMRE | Wilkinson, Szulejko, et al., 1992 | gas phase; Reported relative to ROH..F-, 0.5 kcal/mol weaker.; B |
By formula: Na+ + C2H5FO = (Na+ • C2H5FO)
Free energy of reaction
ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
23.6 | 298. | IMRE | McMahon and Ohanessian, 2000 | Anchor alanine=39.89; RCD |
Gas phase ion energetics data
Go To: Top, Phase change data, Reaction thermochemistry data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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) | 171.0 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 163.8 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
10.66 | PE | Koppel, Molder, et al., 1983 | LBLHLM |
11.05 | PE | Baker, Betteridge, et al., 1971 | LLK |
11.05 | PE | Baker, Betteridge, et al., 1971 | LLK |
10.98 | PE | Hoppilliard and Solgadi, 1980 | Vertical value; LLK |
De-protonation reactions
C2H4FO- + =
By formula: C2H4FO- + H+ = C2H5FO
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 371.2 ± 2.9 | kcal/mol | G+TS | Graul, Schnute, et al., 1990 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 364.6 ± 2.8 | kcal/mol | CIDC | Graul, Schnute, et al., 1990 | gas phase; B |
ΔrG° | 363.5 ± 3.5 | kcal/mol | IMRB | Clair and McMahon, 1980 | gas phase; Between HF and acetone; value altered from reference due to change in acidity scale; B |
ΔrG° | 364.9 ± 3.4 | kcal/mol | IMRB | Dawson and Jennings, 1977 | gas phase; Between HF and acetone; value altered from reference due to change in acidity scale; B |
Ion clustering data
Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
RCD - Robert C. Dunbar
Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.
Clustering reactions
By formula: CN- + C2H5FO = (CN- • C2H5FO)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 20.4 ± 3.5 | kcal/mol | IMRE | Larson and McMahon, 1987 | gas phase; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 25.3 | cal/mol*K | N/A | Larson and McMahon, 1987 | gas phase; switching reaction,Thermochemical ladder(CN-)H2O, Entropy change calculated or estimated; Payzant, Yamdagni, et al., 1971; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 12.9 ± 2.3 | kcal/mol | IMRE | Larson and McMahon, 1987 | gas phase; B,M |
By formula: Cl- + C2H5FO = (Cl- • C2H5FO)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 20.5 ± 2.0 | kcal/mol | IMRE | Larson and McMahon, 1984 | gas phase; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 25.0 | cal/mol*K | N/A | Larson and McMahon, 1984, 2 | gas phase; switching reaction(Cl-)t-C4H9OH, Entropy change calculated or estimated; French, Ikuta, et al., 1982; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 13.0 ± 2.0 | kcal/mol | IMRE | Larson and McMahon, 1984 | gas phase; B,M |
+ = C2H4D5F2O-
By formula: F- + C2H5FO = C2H4D5F2O-
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrG° | 26.5 ± 2.0 | kcal/mol | IMRE | Wilkinson, Szulejko, et al., 1992 | gas phase; Reported relative to ROH..F-, 0.5 kcal/mol weaker.; B |
By formula: F- + C2H5FO = (F- • C2H5FO)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 34.8 ± 2.0 | kcal/mol | IMRE | 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,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 26.3 | cal/mol*K | N/A | Larson and McMahon, 1983 | gas phase; switching reaction(F-)H2O, Entropy change calculated or estimated; Arshadi, Yamdagni, et al., 1970; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 27.0 ± 2.0 | kcal/mol | IMRE | 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,M |
By formula: Na+ + C2H5FO = (Na+ • C2H5FO)
Free energy of reaction
ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
23.6 | 298. | IMRE | McMahon and Ohanessian, 2000 | Anchor alanine=39.89; RCD |
IR Spectrum
Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, Mass spectrum (electron ionization), Gas Chromatography, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Condensed Phase Spectrum
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Additional Data
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Detailed documentation for this spectrum is available.
Owner | Public domain |
---|---|
Origin | Pacific Northwest National Laboratory Under IARPA Contract |
Date | March 2017 |
State | liquid |
Instrument | Bruker Tensor 27 FTIR |
Instrument resolution | 2.0 cm-1 |
IR source | Silicon carbide glow bar |
Aperture | 3 mm |
Beam splitter | Broadband potassium bromide (KBr) |
Detector | DLTGS at room temperature |
Scanner velocity | 10 kHz |
Phase correction | Mertz |
Interferogram zero fill | 4x |
Spectral interval after zero fill | 0.4823 cm-1 |
Spectral range | 7800 to 400 cm-1 (1.282 to 25 microns) |
Resolution | 0.48212986 |
Apodization | Norton-Beer, Medium |
Folding limits | 15802 to 0 cm-1 |
Number of interferograms averaged per single channel spectrum | 128 |
Mass spectrum (electron ionization)
Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Gas Chromatography, 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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
Due to licensing restrictions, this spectrum cannot be downloaded.
Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
NIST MS number | 185 |
Gas Chromatography
Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), 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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | OV-101 | 494. | Zenkevich, 2005 | 25. m/0.20 mm/0.10 μm, N2/He, 6. K/min; Tstart: 50. C; Tend: 250. C |
References
Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]
Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw,
Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2
. [all data]
Redemann, Chaikin, et al., 1948
Redemann, C. Ernst; Chaikin, Saul W.; Fearing, Ralph B.; Rotariu, George J.; Savit, Joseph; Hoesen, Drusilla van,
The Vapor Pressures of Forty-one Fluorine-containing Organic Compounds 1,
J. Am. Chem. Soc., 1948, 70, 11, 3604-3606, https://doi.org/10.1021/ja01191a017
. [all data]
Dykyj, 1970
Dykyj, J.,
Petrochemica, 1970, 10, 2, 51. [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]
Arshadi, Yamdagni, et al., 1970
Arshadi, M.; Yamdagni, R.; Kebarle, P.,
Hydration of Halide Negative Ions in the Gas Phase. II. Comparison of Hydration Energies for the Alkali Positive and Halide Negative Ions,
J. Phys. Chem., 1970, 74, 7, 1475, https://doi.org/10.1021/j100702a014
. [all data]
Graul, Schnute, et al., 1990
Graul, S.T.; Schnute, M.E.; Squires, R.R.,
Gas-Phase Acidities of Carboxylic Acids and Alcohols from Collision-Induced Dissociation of Dimer Cluster Ions,
Int. J. Mass Spectrom. Ion Proc., 1990, 96, 2, 181, https://doi.org/10.1016/0168-1176(90)87028-F
. [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]
Dawson and Jennings, 1977
Dawson, J.H.J.; Jennings, K.R.,
Relative gas phase acidities of some fluoroalcohols,
Int. J. Mass Spectrom. Ion Phys., 1977, 25, 47. [all data]
Larson and McMahon, 1987
Larson, J.W.; McMahon, T.B.,
Hydrogen bonding in gas phase anions. The energetics of interaction between cyanide ion and bronsted acids,
J. Am. Chem. Soc., 1987, 109, 6230. [all data]
Payzant, Yamdagni, et al., 1971
Payzant, J.D.; Yamdagni, R.; Kebarle, P.,
Hydration of CN-, NO2-, NO3-, and HO- in the gas phase,
Can. J. Chem., 1971, 49, 3308. [all data]
Larson and McMahon, 1984
Larson, J.W.; McMahon, T.B.,
Hydrogen bonding in gas phase anions. An experimental investigation of the interaction between chloride ion and bronsted acids from ICR chloride exchange equilibria,
J. Am. Chem. Soc., 1984, 106, 517. [all data]
Larson and McMahon, 1984, 2
Larson, J.W.; McMahon, T.B.,
Gas phase negative ion chemistry of alkylchloroformates,
Can. J. Chem., 1984, 62, 675. [all data]
French, Ikuta, et al., 1982
French, M.A.; Ikuta, S.; Kebarle, P.,
Hydrogen bonding of O-H and C-H hydrogen donors to Cl-. Results from mass spectrometric measurement of the ion-molecule equilibria RH + Cl- = RHCl-,
Can. J. Chem., 1982, 60, 1907. [all data]
Wilkinson, Szulejko, et al., 1992
Wilkinson, F.E.; Szulejko, J.E.; Allison, C.E.; Mcmahon, T.B.,
Fourier Transform Ion Cyclotron Resonance Investigation of the Deuterium Isotope Effect on Gas Phase Ion/Molecule Hydrogen Bonding Interactions in Alcohol-Fluoride Adduct Ions,
Int. J. Mass Spectrom., 1992, 117, 487-505, https://doi.org/10.1016/0168-1176(92)80110-M
. [all data]
McMahon and Ohanessian, 2000
McMahon, T.B.; Ohanessian, G.,
An Experimental and Ab Initio Study of the Nature of the Binding in Gas-Phase Complexes of Sodium Ions,
Chem. Eur. J., 2000, 6, 16, 2931, https://doi.org/10.1002/1521-3765(20000818)6:16<2931::AID-CHEM2931>3.0.CO;2-7
. [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]
Koppel, Molder, et al., 1983
Koppel, I.A.; Molder, U.H.; Pikver, R.J.,
Photoelectron spectra of molecules. I. Alcohols,
Org. React. Tartu, 1983, 20, 45. [all data]
Baker, Betteridge, et al., 1971
Baker, A.D.; Betteridge, D.; Kemp, N.R.; Kirby, R.E.,
Application of photoelectron spectrometry to pesticide analysis. II.Photoelectron spectra of hydroxy-, and halo-alkanes and halohydrins,
Anal. Chem., 1971, 43, 375. [all data]
Hoppilliard and Solgadi, 1980
Hoppilliard, Y.; Solgadi, D.,
Conformational analysis of 2-haloethanols and 2-methoxyethylhalides in a photoelectron spectrometer,
Tetrahedron, 1980, 36, 377. [all data]
Zenkevich, 2005
Zenkevich, I.G.,
Experimentally measured retention indices., 2005. [all data]
Notes
Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, References
- Symbols used in this document:
T Temperature Tboil Boiling point ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy of reaction at standard conditions ΔvapH Enthalpy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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