Phenol, 4-fluoro-
- Formula: C6H5FO
- Molecular weight: 112.1017
- IUPAC Standard InChIKey: RHMPLDJJXGPMEX-UHFFFAOYSA-N
- CAS Registry Number: 371-41-5
- 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: Phenol, p-fluoro-; p-Fluorophenol; 4-Fluorophenol; Fluorophenol
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Condensed phase 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:
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 |
---|---|---|---|---|---|
ΔcH°solid | -2914.8 | kJ/mol | Ccb | Swarts, 1919 | Not corrected for CODATA value of ΔfH; ALS |
Constant pressure heat capacity of solid
Cp,solid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
144.6 | 298.15 | Lichanot, 1991 | T = 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
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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
DH - Eugene S. Domalski and Elizabeth D. Hearing
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 458. | K | N/A | PCR Inc., 1990 | BS |
Tboil | 458.7 | K | N/A | Weast and Grasselli, 1989 | BS |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 321.15 | K | N/A | Lichanot, 1991 | DH |
Tfus | 319. | K | N/A | Bergmann, Berkovic, et al., 1956 | Uncertainty assigned by TRC = 4. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 73.9 ± 1.4 | kJ/mol | C | Ribeiro da Silva and Ferreira, 2009 | AC |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
48.8 | 375. | A | Stephenson and Malanowski, 1987 | Based on data from 360. to 460. 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
By formula: Cl- + C6H5FO = (Cl- • C6H5FO)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 117. ± 8.4 | kJ/mol | TDEq | Cummings, French, et al., 1977 | gas phase; Re-anchored to data in French, Ikuta, et al., 1982.; B,M |
ΔrH° | 120. | kJ/mol | PHPMS | Paul and Kebarle, 1990 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 100. | J/mol*K | N/A | Paul and Kebarle, 1990 | gas phase; Entropy change calculated or estimated; M |
ΔrS° | 106. | J/mol*K | N/A | Cummings, French, et al., 1977 | gas phase; switching reaction(Cl-)C6H5OH, Entropy change calculated or estimated; French, Ikuta, et al., 1982; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 86.2 ± 8.4 | kJ/mol | TDEq | Cummings, French, et al., 1977 | gas phase; Re-anchored to data in French, Ikuta, et al., 1982.; B |
Free energy of reaction
ΔrG° (kJ/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
75.3 | 423. | PHPMS | Paul and Kebarle, 1990 | gas phase; Entropy change calculated or estimated; M |
80.8 | 300. | PHPMS | Cummings, French, et al., 1977 | gas phase; switching reaction(Cl-)C6H5OH, Entropy change calculated or estimated; French, Ikuta, et al., 1982; M |
By formula: I- + C6H5FO = (I- • C6H5FO)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 82.0 ± 7.5 | kJ/mol | IMRE | Paul and Kebarle, 1990 | gas phase; ΔGaff at 423 K; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 88. | J/mol*K | N/A | Paul and Kebarle, 1990 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 44.8 ± 4.2 | kJ/mol | IMRE | Paul and Kebarle, 1990 | gas phase; ΔGaff at 423 K; B |
Free energy of reaction
ΔrG° (kJ/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
43.9 | 423. | PHPMS | Paul and Kebarle, 1990 | gas phase; Entropy change calculated or estimated; M |
By formula: Br- + C6H5FO = (Br- • C6H5FO)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 97.5 ± 7.5 | kJ/mol | IMRE | Paul and Kebarle, 1990 | gas phase; ΔGaff at 423 K; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 96. | J/mol*K | N/A | Paul and Kebarle, 1990 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 56.9 ± 4.2 | kJ/mol | IMRE | Paul and Kebarle, 1990 | gas phase; ΔGaff at 423 K; B |
Free energy of reaction
ΔrG° (kJ/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
56.9 | 423. | PHPMS | Paul and Kebarle, 1990 | gas phase; Entropy change calculated or estimated; M |
C6H4FO- + =
By formula: C6H4FO- + H+ = C6H5FO
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1451. ± 8.8 | kJ/mol | G+TS | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale; B |
ΔrH° | 1455. ± 9.6 | kJ/mol | G+TS | Kebarle and McMahon, 1977 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1422. ± 8.4 | kJ/mol | IMRE | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale; B |
ΔrG° | 1426. ± 8.4 | kJ/mol | IMRE | Kebarle and McMahon, 1977 | gas phase; B |
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 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., 2002 | MM |
Gas basicity at 298K
Gas basicity (review) (kJ/mol) | Reference | Comment |
---|---|---|
747. | Bogdanov, van Duijn, et al., 2002 | MM |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.79 ± 0.02 | PE | Maier, Marthaler, et al., 1980 | Vertical value; LLK |
8.77 | PE | Palmer, Moyes, et al., 1979 | Vertical value; LLK |
De-protonation reactions
C6H4FO- + =
By formula: C6H4FO- + H+ = C6H5FO
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1451. ± 8.8 | kJ/mol | G+TS | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale; B |
ΔrH° | 1455. ± 9.6 | kJ/mol | G+TS | Kebarle and McMahon, 1977 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1422. ± 8.4 | kJ/mol | IMRE | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale; B |
ΔrG° | 1426. ± 8.4 | kJ/mol | IMRE | Kebarle and McMahon, 1977 | gas 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
By formula: Br- + C6H5FO = (Br- • C6H5FO)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 97.5 ± 7.5 | kJ/mol | IMRE | Paul and Kebarle, 1990 | gas phase; ΔGaff at 423 K; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 96. | J/mol*K | N/A | Paul and Kebarle, 1990 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 56.9 ± 4.2 | kJ/mol | IMRE | Paul and Kebarle, 1990 | gas phase; ΔGaff at 423 K; B |
Free energy of reaction
ΔrG° (kJ/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
56.9 | 423. | PHPMS | Paul and Kebarle, 1990 | gas phase; Entropy change calculated or estimated; M |
By formula: Cl- + C6H5FO = (Cl- • C6H5FO)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 117. ± 8.4 | kJ/mol | TDEq | Cummings, French, et al., 1977 | gas phase; Re-anchored to data in French, Ikuta, et al., 1982.; B,M |
ΔrH° | 120. | kJ/mol | PHPMS | Paul and Kebarle, 1990 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 100. | J/mol*K | N/A | Paul and Kebarle, 1990 | gas phase; Entropy change calculated or estimated; M |
ΔrS° | 106. | J/mol*K | N/A | Cummings, French, et al., 1977 | gas phase; switching reaction(Cl-)C6H5OH, Entropy change calculated or estimated; French, Ikuta, et al., 1982; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 86.2 ± 8.4 | kJ/mol | TDEq | Cummings, French, et al., 1977 | gas phase; Re-anchored to data in French, Ikuta, et al., 1982.; B |
Free energy of reaction
ΔrG° (kJ/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
75.3 | 423. | PHPMS | Paul and Kebarle, 1990 | gas phase; Entropy change calculated or estimated; M |
80.8 | 300. | PHPMS | Cummings, French, et al., 1977 | gas phase; switching reaction(Cl-)C6H5OH, Entropy change calculated or estimated; French, Ikuta, et al., 1982; M |
By formula: I- + C6H5FO = (I- • C6H5FO)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 82.0 ± 7.5 | kJ/mol | IMRE | Paul and Kebarle, 1990 | gas phase; ΔGaff at 423 K; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 88. | J/mol*K | N/A | Paul and Kebarle, 1990 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 44.8 ± 4.2 | kJ/mol | IMRE | Paul and Kebarle, 1990 | gas phase; ΔGaff at 423 K; B |
Free energy of reaction
ΔrG° (kJ/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
43.9 | 423. | PHPMS | Paul and Kebarle, 1990 | gas phase; Entropy change calculated or estimated; M |
IR Spectrum
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Data compiled by: Coblentz Society, Inc.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Mass spectrum (electron ionization)
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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
Spectrum
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Additional Data
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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 |
UV/Visible 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: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina
Spectrum
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Additional Data
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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
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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
Kovats' RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Packed | Apiezon L | 180. | 955. | Vernon and Edwards, 1975 | N2, 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
- Symbols used in this document:
Cp,solid Constant pressure heat capacity of solid T Temperature Tboil Boiling point Tfus Fusion (melting) point ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy of reaction at standard conditions ΔsubH° Enthalpy of sublimation at standard conditions ΔvapH Enthalpy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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