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Ethanol, 2-fluoro-

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Phase change 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:
BS - Robert L. Brown and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos

Reduced pressure boiling point

Tboil (K) Pressure (bar) Reference Comment
376.21.01Aldrich Chemical Company Inc., 1990BS

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
44.1288.GSStephenson and Malanowski, 1987Based on data from 273. - 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

Fluorine anion + Ethanol, 2-fluoro- = (Fluorine anion bullet Ethanol, 2-fluoro-)

By formula: F- + C2H5FO = (F- bullet C2H5FO)

Quantity Value Units Method Reference Comment
Deltar146. ± 8.4kJ/molIMRELarson and McMahon, 1983gas 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
Deltar110.J/mol*KN/ALarson and McMahon, 1983gas phase; switching reaction(F-)H2O, Entropy change calculated or estimated; Arshadi, Yamdagni, et al., 1970; M
Quantity Value Units Method Reference Comment
Deltar113. ± 8.4kJ/molIMRELarson and McMahon, 1983gas 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- + Hydrogen cation = Ethanol, 2-fluoro-

By formula: C2H4FO- + H+ = C2H5FO

Quantity Value Units Method Reference Comment
Deltar1553. ± 12.kJ/molG+TSGraul, Schnute, et al., 1990gas phase; B
Quantity Value Units Method Reference Comment
Deltar1525. ± 12.kJ/molCIDCGraul, Schnute, et al., 1990gas phase; B
Deltar1521. ± 15.kJ/molIMRBClair and McMahon, 1980gas phase; Between HF and acetone; value altered from reference due to change in acidity scale; B
Deltar1527. ± 14.kJ/molIMRBDawson and Jennings, 1977gas phase; Between HF and acetone; value altered from reference due to change in acidity scale; B

CN- + Ethanol, 2-fluoro- = (CN- bullet Ethanol, 2-fluoro-)

By formula: CN- + C2H5FO = (CN- bullet C2H5FO)

Quantity Value Units Method Reference Comment
Deltar85. ± 15.kJ/molIMRELarson and McMahon, 1987gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar106.J/mol*KN/ALarson and McMahon, 1987gas phase; switching reaction,Thermochemical ladder(CN-)H2O, Entropy change calculated or estimated; Payzant, Yamdagni, et al., 1971; M
Quantity Value Units Method Reference Comment
Deltar54.0 ± 9.6kJ/molIMRELarson and McMahon, 1987gas phase; B,M

Chlorine anion + Ethanol, 2-fluoro- = (Chlorine anion bullet Ethanol, 2-fluoro-)

By formula: Cl- + C2H5FO = (Cl- bullet C2H5FO)

Quantity Value Units Method Reference Comment
Deltar85.8 ± 8.4kJ/molIMRELarson and McMahon, 1984gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar105.J/mol*KN/ALarson and McMahon, 1984, 2gas phase; switching reaction(Cl-)t-C4H9OH, Entropy change calculated or estimated; French, Ikuta, et al., 1982; M
Quantity Value Units Method Reference Comment
Deltar54.4 ± 8.4kJ/molIMRELarson and McMahon, 1984gas phase; B,M

Fluorine anion + Ethanol, 2-fluoro- = C2H4D5F2O-

By formula: F- + C2H5FO = C2H4D5F2O-

Quantity Value Units Method Reference Comment
Deltar111. ± 8.4kJ/molIMREWilkinson, Szulejko, et al., 1992gas phase; Reported relative to ROH..F-, 0.5 kcal/mol weaker.; B

Sodium ion (1+) + Ethanol, 2-fluoro- = (Sodium ion (1+) bullet Ethanol, 2-fluoro-)

By formula: Na+ + C2H5FO = (Na+ bullet C2H5FO)

Free energy of reaction

DeltarG° (kJ/mol) T (K) Method Reference Comment
98.7298.IMREMcMahon and Ohanessian, 2000Anchor alanine=39.89; RCD

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 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)715.6kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity685.2kJ/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
10.66PEKoppel, Molder, et al., 1983LBLHLM
11.05PEBaker, Betteridge, et al., 1971LLK
11.05PEBaker, Betteridge, et al., 1971LLK
10.98PEHoppilliard and Solgadi, 1980Vertical value; LLK

De-protonation reactions

C2H4FO- + Hydrogen cation = Ethanol, 2-fluoro-

By formula: C2H4FO- + H+ = C2H5FO

Quantity Value Units Method Reference Comment
Deltar1553. ± 12.kJ/molG+TSGraul, Schnute, et al., 1990gas phase; B
Quantity Value Units Method Reference Comment
Deltar1525. ± 12.kJ/molCIDCGraul, Schnute, et al., 1990gas phase; B
Deltar1521. ± 15.kJ/molIMRBClair and McMahon, 1980gas phase; Between HF and acetone; value altered from reference due to change in acidity scale; B
Deltar1527. ± 14.kJ/molIMRBDawson and Jennings, 1977gas phase; Between HF and acetone; value altered from reference due to change in acidity scale; B

Ion clustering 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. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

Clustering reactions

CN- + Ethanol, 2-fluoro- = (CN- bullet Ethanol, 2-fluoro-)

By formula: CN- + C2H5FO = (CN- bullet C2H5FO)

Quantity Value Units Method Reference Comment
Deltar85. ± 15.kJ/molIMRELarson and McMahon, 1987gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar106.J/mol*KN/ALarson and McMahon, 1987gas phase; switching reaction,Thermochemical ladder(CN-)H2O, Entropy change calculated or estimated; Payzant, Yamdagni, et al., 1971; M
Quantity Value Units Method Reference Comment
Deltar54.0 ± 9.6kJ/molIMRELarson and McMahon, 1987gas phase; B,M

Chlorine anion + Ethanol, 2-fluoro- = (Chlorine anion bullet Ethanol, 2-fluoro-)

By formula: Cl- + C2H5FO = (Cl- bullet C2H5FO)

Quantity Value Units Method Reference Comment
Deltar85.8 ± 8.4kJ/molIMRELarson and McMahon, 1984gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar105.J/mol*KN/ALarson and McMahon, 1984, 2gas phase; switching reaction(Cl-)t-C4H9OH, Entropy change calculated or estimated; French, Ikuta, et al., 1982; M
Quantity Value Units Method Reference Comment
Deltar54.4 ± 8.4kJ/molIMRELarson and McMahon, 1984gas phase; B,M

Fluorine anion + Ethanol, 2-fluoro- = C2H4D5F2O-

By formula: F- + C2H5FO = C2H4D5F2O-

Quantity Value Units Method Reference Comment
Deltar111. ± 8.4kJ/molIMREWilkinson, Szulejko, et al., 1992gas phase; Reported relative to ROH..F-, 0.5 kcal/mol weaker.; B

Fluorine anion + Ethanol, 2-fluoro- = (Fluorine anion bullet Ethanol, 2-fluoro-)

By formula: F- + C2H5FO = (F- bullet C2H5FO)

Quantity Value Units Method Reference Comment
Deltar146. ± 8.4kJ/molIMRELarson and McMahon, 1983gas 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
Deltar110.J/mol*KN/ALarson and McMahon, 1983gas phase; switching reaction(F-)H2O, Entropy change calculated or estimated; Arshadi, Yamdagni, et al., 1970; M
Quantity Value Units Method Reference Comment
Deltar113. ± 8.4kJ/molIMRELarson and McMahon, 1983gas 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

Sodium ion (1+) + Ethanol, 2-fluoro- = (Sodium ion (1+) bullet Ethanol, 2-fluoro-)

By formula: Na+ + C2H5FO = (Na+ bullet C2H5FO)

Free energy of reaction

DeltarG° (kJ/mol) T (K) Method Reference Comment
98.7298.IMREMcMahon and Ohanessian, 2000Anchor 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.

Data compiled by: Tanya L. Myers, Russell G. Tonkyn, Ashley M. Oeck, Tyler O. Danby, John S. Loring, Matthew S. Taubman, Stephen W. Sharpe, Jerome C. Birnbaum, and Timothy J. Johnson

Condensed Phase Spectrum

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IR 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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Mass spectrum
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Additional Data

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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

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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

View large format table.

Column type Active phase I Reference Comment
CapillaryOV-101494.Zenkevich, 200525. m/0.20 mm/0.10 «mu»m, 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