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2-Propanol, 1,1,1,3,3,3-hexafluoro-

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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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos

Quantity Value Units Method Reference Comment
Tboil331.KN/APCR Inc., 1990BS
Tboil332.2KN/AWeast and Grasselli, 1989BS
Quantity Value Units Method Reference Comment
Deltavap9.938kcal/molVRochester and Symonds, 1973ALS
Deltavap9.94kcal/molMMRochester and Symonds, 1973Based on data from 294. - 330. K.; AC

Enthalpy of vaporization

DeltavapH (kcal/mol) Temperature (K) Method Reference Comment
9.61309.A,MMStephenson and Malanowski, 1987Based on data from 294. - 330. K. See also Rochester and Symonds, 1973.; AC
11.3284.N/AVan Ness, Soczek, et al., 1967Based on data from 273. - 296. K.; 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

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 + 2-Propanol, 1,1,1,3,3,3-hexafluoro- = (Fluorine anion bullet 2-Propanol, 1,1,1,3,3,3-hexafluoro-)

By formula: F- + C3H2F6O = (F- bullet C3H2F6O)

Quantity Value Units Method Reference Comment
Deltar47.0 ± 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
Quantity Value Units Method Reference Comment
Deltar38.9 ± 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

Chlorine anion + 2-Propanol, 1,1,1,3,3,3-hexafluoro- = (Chlorine anion bullet 2-Propanol, 1,1,1,3,3,3-hexafluoro-)

By formula: Cl- + C3H2F6O = (Cl- bullet C3H2F6O)

Quantity Value Units Method Reference Comment
Deltar26.5kcal/molICRLarson and McMahon, 1984gas phase; switching reaction(Cl-)(CF3)2CH3COH, Entropy change calculated or estimated, DG>, «DELTA»rH>; Larson and McMahon, 1984, 2; M
Quantity Value Units Method Reference Comment
Deltar25.0cal/mol*KN/ALarson and McMahon, 1984gas phase; switching reaction(Cl-)(CF3)2CH3COH, Entropy change calculated or estimated, DG>, «DELTA»rH>; Larson and McMahon, 1984, 2; M
Quantity Value Units Method Reference Comment
Deltar19.0kcal/molICRLarson and McMahon, 1984gas phase; switching reaction(Cl-)(CF3)2CH3COH, Entropy change calculated or estimated, DG>, «DELTA»rH>; Larson and McMahon, 1984, 2; M

CN- + 2-Propanol, 1,1,1,3,3,3-hexafluoro- = (CN- bullet 2-Propanol, 1,1,1,3,3,3-hexafluoro-)

By formula: CN- + C3H2F6O = (CN- bullet C3H2F6O)

Quantity Value Units Method Reference Comment
Deltar25.0 ± 3.5kcal/molIMRELarson and McMahon, 1987gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar26.cal/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
Deltar16.8 ± 2.3kcal/molIMRELarson and McMahon, 1987gas phase; B,M

C3HF6O- + Hydrogen cation = 2-Propanol, 1,1,1,3,3,3-hexafluoro-

By formula: C3HF6O- + H+ = C3H2F6O

Quantity Value Units Method Reference Comment
Deltar345.0 ± 2.1kcal/molG+TSTaft, Koppel, et al., 1990gas phase; B
Quantity Value Units Method Reference Comment
Deltar338.4 ± 2.0kcal/molIMRETaft, Koppel, et al., 1990gas phase; B
Deltar340.40kcal/molIMRBKoppel, Pikver, et al., 1981gas phase; B

Iodide + 2-Propanol, 1,1,1,3,3,3-hexafluoro- = (Iodide bullet 2-Propanol, 1,1,1,3,3,3-hexafluoro-)

By formula: I- + C3H2F6O = (I- bullet C3H2F6O)

Quantity Value Units Method Reference Comment
Deltar23.9 ± 1.0kcal/molTDAsCaldwell, Masucci, et al., 1989gas phase; B,M

Henry's Law 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: Rolf Sander

Henry's Law constant (water solution)

kH(T) = H exp(d(ln(kH))/d(1/T) ((1/T) - 1/(298.15 K)))
H = Henry's law constant for solubility in water at 298.15 K (mol/kg*bar)
d(ln(kH))/d(1/T) = Temperature dependence constant (K)

H (mol/kg*bar) d(ln(kH))/d(1/T) (K) Method Reference
24.6700.MN/A

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)164.1kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity156.8kcal/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
11.94PEKoppel, Molder, et al., 1983LBLHLM
12.23PERobin and Kuebler, 1973Vertical value; LLK

De-protonation reactions

C3HF6O- + Hydrogen cation = 2-Propanol, 1,1,1,3,3,3-hexafluoro-

By formula: C3HF6O- + H+ = C3H2F6O

Quantity Value Units Method Reference Comment
Deltar345.0 ± 2.1kcal/molG+TSTaft, Koppel, et al., 1990gas phase; B
Quantity Value Units Method Reference Comment
Deltar338.4 ± 2.0kcal/molIMRETaft, Koppel, et al., 1990gas phase; B
Deltar340.40kcal/molIMRBKoppel, Pikver, et al., 1981gas phase; 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

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- + 2-Propanol, 1,1,1,3,3,3-hexafluoro- = (CN- bullet 2-Propanol, 1,1,1,3,3,3-hexafluoro-)

By formula: CN- + C3H2F6O = (CN- bullet C3H2F6O)

Quantity Value Units Method Reference Comment
Deltar25.0 ± 3.5kcal/molIMRELarson and McMahon, 1987gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar26.cal/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
Deltar16.8 ± 2.3kcal/molIMRELarson and McMahon, 1987gas phase; B,M

Chlorine anion + 2-Propanol, 1,1,1,3,3,3-hexafluoro- = (Chlorine anion bullet 2-Propanol, 1,1,1,3,3,3-hexafluoro-)

By formula: Cl- + C3H2F6O = (Cl- bullet C3H2F6O)

Quantity Value Units Method Reference Comment
Deltar26.5kcal/molICRLarson and McMahon, 1984gas phase; switching reaction(Cl-)(CF3)2CH3COH, Entropy change calculated or estimated, DG>, «DELTA»rH>; Larson and McMahon, 1984, 2; M
Quantity Value Units Method Reference Comment
Deltar25.0cal/mol*KN/ALarson and McMahon, 1984gas phase; switching reaction(Cl-)(CF3)2CH3COH, Entropy change calculated or estimated, DG>, «DELTA»rH>; Larson and McMahon, 1984, 2; M
Quantity Value Units Method Reference Comment
Deltar19.0kcal/molICRLarson and McMahon, 1984gas phase; switching reaction(Cl-)(CF3)2CH3COH, Entropy change calculated or estimated, DG>, «DELTA»rH>; Larson and McMahon, 1984, 2; M

Fluorine anion + 2-Propanol, 1,1,1,3,3,3-hexafluoro- = (Fluorine anion bullet 2-Propanol, 1,1,1,3,3,3-hexafluoro-)

By formula: F- + C3H2F6O = (F- bullet C3H2F6O)

Quantity Value Units Method Reference Comment
Deltar47.0 ± 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
Quantity Value Units Method Reference Comment
Deltar38.9 ± 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

Iodide + 2-Propanol, 1,1,1,3,3,3-hexafluoro- = (Iodide bullet 2-Propanol, 1,1,1,3,3,3-hexafluoro-)

By formula: I- + C3H2F6O = (I- bullet C3H2F6O)

Quantity Value Units Method Reference Comment
Deltar23.9 ± 1.0kcal/molTDAsCaldwell, Masucci, et al., 1989gas phase; B,M

IR Spectrum

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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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Gas Phase Spectrum

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IR spectrum
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Additional Data

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Owner NIST Standard Reference Data Program
Collection (C) 2018 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin Sadtler Research Labs Under US-EPA Contract
State gas

This IR spectrum is from the NIST/EPA Gas-Phase Infrared Database .


Mass spectrum (electron ionization)

Go To: Top, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, NIST Free Links, 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.
Origin NIST Mass Spectrometry Data Center, 1998.
NIST MS number 290914

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


References

Go To: Top, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), NIST Free Links, Notes

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

PCR Inc., 1990
PCR Inc., Research Chemicals Catalog 1990-1991, PCR Inc., Gainesville, FL, 1990, 1. [all data]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]

Rochester and Symonds, 1973
Rochester, C.H.; Symonds, J.R., Thermodynamic studies of fluoroalchols Part 1.-Vapour pressures and enthalpies of vaporization, J. Chem. Soc. Faraday Trans. 1, 1973, 69, 1267. [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]

Van Ness, Soczek, et al., 1967
Van Ness, Hendrick C.; Soczek, C.A.; Peloquin, G.L.; Machado, R.L., Thermodynamic excess properties of three alcohol-hydrocarbon systems, J. Chem. Eng. Data, 1967, 12, 2, 217-224, https://doi.org/10.1021/je60033a017 . [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]

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]

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]

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]

Koppel, Pikver, et al., 1981
Koppel, I.; Pikver, R.; Sugis, A.; Suurmaa, E.; Lippmaa, E., FTICR Study of Structure and Solvent Effects on Basicity of Some Anions in the Gas Phase, Org. Reac., 1981, 18, 3. [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]

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]

Robin and Kuebler, 1973
Robin, M.B.; Kuebler, N.A., Excited electronic states of the simple alcohols, J. Electron Spectrosc. Relat. Phenom., 1973, 1, 13. [all data]


Notes

Go To: Top, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), NIST Free Links, References