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

Phenol, 4-fluoro-

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.


Condensed phase thermochemistry data

Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, 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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Deltacsolid-2914.8kJ/molCcbSwarts, 1919Not corrected for CODATA value of «DELTA»fH; ALS

Constant pressure heat capacity of solid

Cp,solid (J/mol*K) Temperature (K) Reference Comment
144.6298.15Lichanot, 1991T = 183 to 354 K. Cp(c) = 123.033 + 0.579T + 9.573x10-3T2 + 7.243x10-5T3 (T in °C) J/mol*K (-90 to 34°C). Cp value calculated from equation.; DH

Phase change data

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, 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 as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Kenneth Kroenlein director
AC - William E. Acree, Jr., James S. Chickos

Quantity Value Units Method Reference Comment
Tboil458.KN/APCR Inc., 1990BS
Tboil458.7KN/AWeast and Grasselli, 1989BS
Quantity Value Units Method Reference Comment
Tfus321.15KN/ALichanot, 1991DH
Tfus319.KN/ABergmann, Berkovic, et al., 1956Uncertainty assigned by TRC = 4. K; TRC
Quantity Value Units Method Reference Comment
Deltasub73.9 ± 1.4kJ/molCRibeiro da Silva and Ferreira, 2009AC

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
48.8375.AStephenson and Malanowski, 1987Based on data from 360. - 460. K.; AC

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


Reaction thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, 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 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

Chlorine anion + Phenol, 4-fluoro- = (Chlorine anion bullet Phenol, 4-fluoro-)

By formula: Cl- + C6H5FO = (Cl- bullet C6H5FO)

Quantity Value Units Method Reference Comment
Deltar117. ± 8.4kJ/molTDEqCummings, French, et al., 1977gas phase; Re-anchored to data in French, Ikuta, et al., 1982.; B,M
Deltar120.kJ/molPHPMSPaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar100.J/mol*KN/APaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
Deltar106.J/mol*KN/ACummings, French, et al., 1977gas phase; switching reaction(Cl-)C6H5OH, Entropy change calculated or estimated; French, Ikuta, et al., 1982; M
Quantity Value Units Method Reference Comment
Deltar86.2 ± 8.4kJ/molTDEqCummings, French, et al., 1977gas phase; Re-anchored to data in French, Ikuta, et al., 1982.; B

Free energy of reaction

DeltarG° (kJ/mol) T (K) Method Reference Comment
75.3423.PHPMSPaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
80.8300.PHPMSCummings, French, et al., 1977gas phase; switching reaction(Cl-)C6H5OH, Entropy change calculated or estimated; French, Ikuta, et al., 1982; M

Iodide + Phenol, 4-fluoro- = (Iodide bullet Phenol, 4-fluoro-)

By formula: I- + C6H5FO = (I- bullet C6H5FO)

Quantity Value Units Method Reference Comment
Deltar82.0 ± 7.5kJ/molIMREPaul and Kebarle, 1990gas phase; «DELTA»Gaff at 423 K; B,M
Quantity Value Units Method Reference Comment
Deltar88.J/mol*KN/APaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar44.8 ± 4.2kJ/molIMREPaul and Kebarle, 1990gas phase; «DELTA»Gaff at 423 K; B

Free energy of reaction

DeltarG° (kJ/mol) T (K) Method Reference Comment
43.9423.PHPMSPaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M

Bromine anion + Phenol, 4-fluoro- = (Bromine anion bullet Phenol, 4-fluoro-)

By formula: Br- + C6H5FO = (Br- bullet C6H5FO)

Quantity Value Units Method Reference Comment
Deltar97.5 ± 7.5kJ/molIMREPaul and Kebarle, 1990gas phase; «DELTA»Gaff at 423 K; B,M
Quantity Value Units Method Reference Comment
Deltar96.J/mol*KN/APaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar56.9 ± 4.2kJ/molIMREPaul and Kebarle, 1990gas phase; «DELTA»Gaff at 423 K; B

Free energy of reaction

DeltarG° (kJ/mol) T (K) Method Reference Comment
56.9423.PHPMSPaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M

C6H4FO- + Hydrogen cation = Phenol, 4-fluoro-

By formula: C6H4FO- + H+ = C6H5FO

Quantity Value Units Method Reference Comment
Deltar1451. ± 8.8kJ/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Deltar1455. ± 9.6kJ/molG+TSKebarle and McMahon, 1977gas phase; B
Quantity Value Units Method Reference Comment
Deltar1422. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Deltar1426. ± 8.4kJ/molIMREKebarle and McMahon, 1977gas phase; B

Gas phase ion energetics data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, 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 as indicated in comments:
B - John E. Bartmess
MM - Michael M. Meot-Ner (Mautner)
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

View reactions leading to C6H5FO+ (ion structure unspecified)

Proton affinity at 298K

Proton affinity (kJ/mol) Reference Comment
775.Bogdanov, van Duijn, et al., 2002MM

Gas basicity at 298K

Gas basicity (review) (kJ/mol) Reference Comment
747.Bogdanov, van Duijn, et al., 2002MM

Ionization energy determinations

IE (eV) Method Reference Comment
8.79 ± 0.02PEMaier, Marthaler, et al., 1980Vertical value; LLK
8.77PEPalmer, Moyes, et al., 1979Vertical value; LLK

De-protonation reactions

C6H4FO- + Hydrogen cation = Phenol, 4-fluoro-

By formula: C6H4FO- + H+ = C6H5FO

Quantity Value Units Method Reference Comment
Deltar1451. ± 8.8kJ/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Deltar1455. ± 9.6kJ/molG+TSKebarle and McMahon, 1977gas phase; B
Quantity Value Units Method Reference Comment
Deltar1422. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Deltar1426. ± 8.4kJ/molIMREKebarle and McMahon, 1977gas phase; B

Ion clustering data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, 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 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

Bromine anion + Phenol, 4-fluoro- = (Bromine anion bullet Phenol, 4-fluoro-)

By formula: Br- + C6H5FO = (Br- bullet C6H5FO)

Quantity Value Units Method Reference Comment
Deltar97.5 ± 7.5kJ/molIMREPaul and Kebarle, 1990gas phase; «DELTA»Gaff at 423 K; B,M
Quantity Value Units Method Reference Comment
Deltar96.J/mol*KN/APaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar56.9 ± 4.2kJ/molIMREPaul and Kebarle, 1990gas phase; «DELTA»Gaff at 423 K; B

Free energy of reaction

DeltarG° (kJ/mol) T (K) Method Reference Comment
56.9423.PHPMSPaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M

Chlorine anion + Phenol, 4-fluoro- = (Chlorine anion bullet Phenol, 4-fluoro-)

By formula: Cl- + C6H5FO = (Cl- bullet C6H5FO)

Quantity Value Units Method Reference Comment
Deltar117. ± 8.4kJ/molTDEqCummings, French, et al., 1977gas phase; Re-anchored to data in French, Ikuta, et al., 1982.; B,M
Deltar120.kJ/molPHPMSPaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar100.J/mol*KN/APaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
Deltar106.J/mol*KN/ACummings, French, et al., 1977gas phase; switching reaction(Cl-)C6H5OH, Entropy change calculated or estimated; French, Ikuta, et al., 1982; M
Quantity Value Units Method Reference Comment
Deltar86.2 ± 8.4kJ/molTDEqCummings, French, et al., 1977gas phase; Re-anchored to data in French, Ikuta, et al., 1982.; B

Free energy of reaction

DeltarG° (kJ/mol) T (K) Method Reference Comment
75.3423.PHPMSPaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
80.8300.PHPMSCummings, French, et al., 1977gas phase; switching reaction(Cl-)C6H5OH, Entropy change calculated or estimated; French, Ikuta, et al., 1982; M

Iodide + Phenol, 4-fluoro- = (Iodide bullet Phenol, 4-fluoro-)

By formula: I- + C6H5FO = (I- bullet C6H5FO)

Quantity Value Units Method Reference Comment
Deltar82.0 ± 7.5kJ/molIMREPaul and Kebarle, 1990gas phase; «DELTA»Gaff at 423 K; B,M
Quantity Value Units Method Reference Comment
Deltar88.J/mol*KN/APaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar44.8 ± 4.2kJ/molIMREPaul and Kebarle, 1990gas phase; «DELTA»Gaff at 423 K; B

Free energy of reaction

DeltarG° (kJ/mol) T (K) Method Reference Comment
43.9423.PHPMSPaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M

IR Spectrum

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, NIST Free Links, References, Notes

Data compiled by: Coblentz Society, Inc.

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


Mass spectrum (electron ionization)

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, UV/Visible spectrum, Gas Chromatography, 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

Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.

Mass spectrum
For Zoom
1.) Enter the desired X axis range (e.g., 100, 200)
2.) Check here for automatic Y scaling
3.) Press here to zoom

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.
Origin Chemical Concepts
NIST MS number 156519

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.


UV/Visible spectrum

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.

UVVis spectrum
For Zoom
1.) Enter the desired X axis range (e.g., 100, 200)
2.) Check here for automatic Y scaling
3.) Press here to zoom

Additional Data

View image of digitized spectrum (can be printed in landscape orientation).

View spectrum image in SVG format.

Download spectrum in JCAMP-DX format.

Source Forbes, 1959
Owner INEP CP RAS, NIST OSRD
Collection (C) 2007 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS
Source reference RAS UV No. 5905
Instrument Unicam SP 500 or Beckman DU
Melting point 48
Boiling point 185.5

Gas Chromatography

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible 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

Kovats' RI, non-polar column, isothermal

View large format table.

Column type Active phase Temperature (C) I Reference Comment
PackedApiezon L180.955.Vernon and Edwards, 1975N2, Celite; Column length: 1. m

References

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, NIST Free Links, Notes

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

Swarts, 1919
Swarts, F., Etudes thermochimiques sur les combinaisons organiques fluorees, J. Chim. Phys., 1919, 17, 3-70. [all data]

Lichanot, 1991
Lichanot, A., Heat capacities of fluroaniline, fluorophenol and difluorobenzene in condensed phase, Thermochim. Acta, 1991, 177, 265-272. [all data]

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]

Bergmann, Berkovic, et al., 1956
Bergmann, E.D.; Berkovic, S.; Ikan, R., A New Method for the Preparation of Aromatic Fluorine Compounds, J. Am. Chem. Soc., 1956, 78, 6037-9. [all data]

Ribeiro da Silva and Ferreira, 2009
Ribeiro da Silva, Manuel A.V.; Ferreira, Ana I.M.C. Lobo, Experimental and Computational Thermochemical Study of the Three Monofluorophenol Isomers «8224», J. Chem. Eng. Data, 2009, 54, 9, 2517-2526, https://doi.org/10.1021/je9000872 . [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]

Cummings, French, et al., 1977
Cummings, J.B.; French, M.A.; Kebarle, P., Effect of charge delocalization on hydrogen bonding to negative ions and solvation of negative ions. Substituted phenols and phenoxide ions, J. Am. Chem. Soc., 1977, 99, 6999. [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]

Paul and Kebarle, 1990
Paul, G.J.C.; Kebarle, P., Stabilities in the Gas Phase of the Hydrogen Bonded Complexes, YC6H4OH-X-, of Substituted Phenols, YC6H4OH, with the Halide Anions X-(Cl-, Br-), Can. J. Chem., 1990, 68, 11, 2070, https://doi.org/10.1139/v90-316 . [all data]

Fujio, McIver, et al., 1981
Fujio, M.; McIver, R.T., Jr.; Taft, R.W., Effects on the acidities of phenols from specific substituent-solvent interactions. Inherent substituent parameters from gas phase acidities, J. Am. Chem. Soc., 1981, 103, 4017. [all data]

Kebarle and McMahon, 1977
Kebarle, P.; McMahon, T.B., Intrinsic Acidities of Substituted Phenols and Benzoic Acids Determined by Gas Phase Proton Transfer Equilibria, J. Am. Chem. Soc., 1977, 99, 7, 2222, https://doi.org/10.1021/ja00449a032 . [all data]

Bogdanov, van Duijn, et al., 2002
Bogdanov, B.; van Duijn, D.; Ingemann, S.; Hammerum, S., Protonation of fluorophenols and fluoroanisoles in the gas phase: experiment and theory, Phys. Chem. Chem. Phys., 2002, 4, 2904. [all data]

Maier, Marthaler, et al., 1980
Maier, J.P.; Marthaler, O.; Mohraz, M., Emission spectra of the cations of some fluorosubstituted phenols in the gaseous phase, J. Electron Spectrosc. Relat. Phenom., 1980, 19, 11. [all data]

Palmer, Moyes, et al., 1979
Palmer, M.H.; Moyes, W.; Speirs, M.; Ridyard, J.N.A., The electronic structure of substituted benzenes; ab initio calculations and photoelectron spectra for phenol, the methyl- and fluoro-derivatives, and the dihydroxybenzenes, J. Mol. Struct., 1979, 52, 293. [all data]

Forbes, 1959
Forbes, W.F., Light absorption studies. Part XVI. The ultraviolet absorption spectra of fluorobenzenes, Can. J. Chem., 1959, 37, 1977-1985. [all data]

Vernon and Edwards, 1975
Vernon, F.; Edwards, G.T., Gas-liquid chromatography on fluorinated stationary phases. II. Fluorinated compounds containing a functional group, J. Chromatogr., 1975, 114, 1, 87-93, https://doi.org/10.1016/S0021-9673(00)85245-0 . [all data]


Notes

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, NIST Free Links, References