Home Symbol which looks like a small house Up Solid circle with an upward pointer in it

Ethanol, 2,2,2-trifluoro-

Data at NIST subscription sites:

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.


Ion clustering 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 compiled as indicated in comments:
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
B - John E. Bartmess

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

CH6N+ + Ethanol, 2,2,2-trifluoro- = (CH6N+ bullet Ethanol, 2,2,2-trifluoro-)

By formula: CH6N+ + C2H3F3O = (CH6N+ bullet C2H3F3O)

Bond type: Hydrogen bonds of the type NH+-O between organics

Quantity Value Units Method Reference Comment
Deltar19.1kcal/molPHPMSMeot-Ner, 1984gas phase; M
Quantity Value Units Method Reference Comment
Deltar28.5cal/mol*KPHPMSMeot-Ner, 1984gas phase; M

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

By formula: CN- + C2H3F3O = (CN- bullet C2H3F3O)

Quantity Value Units Method Reference Comment
Deltar24.00 ± 0.80kcal/molTDAsLarson, Szulejko, et al., 1988gas phase; B,M
Deltar24.6 ± 3.5kcal/molIMRELarson and McMahon, 1987gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar30.cal/mol*KPHPMSLarson, Szulejko, et al., 1988gas phase; M
Deltar26.1cal/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
Deltar15.10 ± 0.20kcal/molTDAsLarson, Szulejko, et al., 1988gas phase; B
Deltar16.4 ± 2.3kcal/molIMRELarson and McMahon, 1987gas phase; B,M

C2H4F3O+ + Ethanol, 2,2,2-trifluoro- = (C2H4F3O+ bullet Ethanol, 2,2,2-trifluoro-)

By formula: C2H4F3O+ + C2H3F3O = (C2H4F3O+ bullet C2H3F3O)

Bond type: Hydrogen bonds of the type OH-O between organics

Quantity Value Units Method Reference Comment
Deltar31.8kcal/molICRLarson and McMahon, 1982gas phase; switching reaction(H2O)2H+, Entropy change calculated or estimated; Cunningham, Payzant, et al., 1972, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986; M
Quantity Value Units Method Reference Comment
Deltar28.9cal/mol*KN/ALarson and McMahon, 1982gas phase; switching reaction(H2O)2H+, Entropy change calculated or estimated; Cunningham, Payzant, et al., 1972, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986; M
Quantity Value Units Method Reference Comment
Deltar23.2kcal/molICRLarson and McMahon, 1982gas phase; switching reaction(H2O)2H+, Entropy change calculated or estimated; Cunningham, Payzant, et al., 1972, Lias, Liebman, et al., 1984, Keesee and Castleman, 1986; M

cyclopentadienide anion + Ethanol, 2,2,2-trifluoro- = (cyclopentadienide anion bullet Ethanol, 2,2,2-trifluoro-)

By formula: C5H5- + C2H3F3O = (C5H5- bullet C2H3F3O)

Quantity Value Units Method Reference Comment
Deltar20.6 ± 1.0kcal/molTDAsMeot-ner, 1988gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar24.3cal/mol*KPHPMSMeot-ner, 1988gas phase; M
Quantity Value Units Method Reference Comment
Deltar13.3 ± 1.0kcal/molTDAsMeot-ner, 1988gas phase; B

thiophenoxide anion + Ethanol, 2,2,2-trifluoro- = (thiophenoxide anion bullet Ethanol, 2,2,2-trifluoro-)

By formula: C6H5S- + C2H3F3O = (C6H5S- bullet C2H3F3O)

Quantity Value Units Method Reference Comment
Deltar21.0kcal/molPHPMSSieck and Meot-ner, 1989gas phase; M
Quantity Value Units Method Reference Comment
Deltar25.1cal/mol*KPHPMSSieck and Meot-ner, 1989gas phase; M

thiophenoxide anion + Ethanol, 2,2,2-trifluoro- = C8H8F3OS-

By formula: C6H5S- + C2H3F3O = C8H8F3OS-

Quantity Value Units Method Reference Comment
Deltar21.00 ± 0.20kcal/molTDAsSieck and Meot-ner, 1989gas phase; B
Quantity Value Units Method Reference Comment
Deltar13.50 ± 0.60kcal/molTDAsSieck and Meot-ner, 1989gas phase; B

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

By formula: Cl- + C2H3F3O = (Cl- bullet C2H3F3O)

Quantity Value Units Method Reference Comment
Deltar24.0 ± 2.0kcal/molIMRELarson and McMahon, 1984gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar25.0cal/mol*KN/ALarson and McMahon, 1984gas phase; switching reaction(Cl-)CH3COOH, Entropy change calculated or estimated; Larson and McMahon, 1984, 2; M
Quantity Value Units Method Reference Comment
Deltar16.5 ± 2.0kcal/molIMRELarson and McMahon, 1984gas phase; B,M

Fluorine anion + Ethanol, 2,2,2-trifluoro- = C2H2D3F4O-

By formula: F- + C2H3F3O = C2H2D3F4O-

Quantity Value Units Method Reference Comment
Deltar30.5 ± 2.0kcal/molIMREWilkinson, Szulejko, et al., 1992gas phase; Reported relative to ROH..F-, 0.5 kcal/mol weaker.; B

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

By formula: F- + C2H3F3O = (F- bullet C2H3F3O)

Quantity Value Units Method Reference Comment
Deltar39.1 ± 2.0kcal/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
Deltar26.8cal/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
Deltar31.1 ± 2.0kcal/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

HS- + Ethanol, 2,2,2-trifluoro- = (HS- bullet Ethanol, 2,2,2-trifluoro-)

By formula: HS- + C2H3F3O = (HS- bullet C2H3F3O)

Quantity Value Units Method Reference Comment
Deltar26.80 ± 0.50kcal/molTDAsSieck and Meot-ner, 1989gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar22.6cal/mol*KPHPMSSieck and Meot-ner, 1989gas phase; M
Quantity Value Units Method Reference Comment
Deltar20.1 ± 1.5kcal/molTDAsSieck and Meot-ner, 1989gas phase; B

Iodide + Ethanol, 2,2,2-trifluoro- = (Iodide bullet Ethanol, 2,2,2-trifluoro-)

By formula: I- + C2H3F3O = (I- bullet C2H3F3O)

Quantity Value Units Method Reference Comment
Deltar20.1 ± 1.0kcal/molTDAsCaldwell, Masucci, et al., 1989gas phase; B,M

References

Go To: Top, Ion clustering data, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Meot-Ner, 1984
Meot-Ner, (Mautner)M., The Ionic Hydrogen Bond and Ion Solvation. 1. -NH+ O-, -NH+ N- and -OH+ O- Bonds. Correlations with Proton Affinity. Deviations Due to Structural Effects, J. Am. Chem. Soc., 1984, 106, 5, 1257, https://doi.org/10.1021/ja00317a015 . [all data]

Larson, Szulejko, et al., 1988
Larson, J.W.; Szulejko, J.E.; McMahon, T.B., Gas Phase Lewis Acid-Base Interactions. An Experimental Determination of Cyanide Binding Energies From Ion Cyclotron Resonance and High-Pressure Mass Spectrometric Equilibrium Measurements., J. Am. Chem. Soc., 1988, 110, 23, 7604, https://doi.org/10.1021/ja00231a004 . [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, 1982
Larson, J.W.; McMahon, T.B., Formation, Thermochemistry, and Relative Stabilities of Proton - Bound dimers of Oxygen n - Donor Bases from Ion Cyclotron Resonance Solvent - Exchange Equilibria Measurements, J. Am. Chem. Soc., 1982, 104, 23, 6255, https://doi.org/10.1021/ja00387a016 . [all data]

Cunningham, Payzant, et al., 1972
Cunningham, A.J.; Payzant, J.D.; Kebarle, P., A Kinetic Study of the Proton Hydrate H+(H2O)n Equilibria in the Gas Phase, J. Am. Chem. Soc., 1972, 94, 22, 7627, https://doi.org/10.1021/ja00777a003 . [all data]

Lias, Liebman, et al., 1984
Lias, S.G.; Liebman, J.F.; Levin, R.D., Evaluated gas phase basicities and proton affinities of molecules heats of formation of protonated molecules, J. Phys. Chem. Ref. Data, 1984, 13, 695. [all data]

Keesee and Castleman, 1986
Keesee, R.G.; Castleman, A.W., Jr., Thermochemical data on Ggs-phase ion-molecule association and clustering reactions, J. Phys. Chem. Ref. Data, 1986, 15, 1011. [all data]

Meot-ner, 1988
Meot-ner, M., The Ionic Hydrogen Bond and Solvation. 7. Interaction Energies of Carbanions with Solvent Molecules, J. Am. Chem. Soc., 1988, 110, 12, 3858, https://doi.org/10.1021/ja00220a022 . [all data]

Sieck and Meot-ner, 1989
Sieck, L.W.; Meot-ner, M., Ionic Hydrogen Bond and Ion Solvation. 8. RS-..HOR Bond Strengths. Correlation with Acidities., J. Phys. Chem., 1989, 93, 4, 1586, https://doi.org/10.1021/j100341a079 . [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]

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]

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]

Caldwell, Masucci, et al., 1989
Caldwell, G.W.; Masucci, J.A.; Ikonomou, M.G., Negative Ion Chemical Ionization Mass Spectrometry - Binding of Molecules to Bromide and Iodide Anions, Org. Mass Spectrom., 1989, 24, 1, 8, https://doi.org/10.1002/oms.1210240103 . [all data]


Notes

Go To: Top, Ion clustering data, References