Phenol, 3-fluoro-
- Formula: C6H5FO
- Molecular weight: 112.1017
- IUPAC Standard InChIKey: SJTBRFHBXDZMPS-UHFFFAOYSA-N
- CAS Registry Number: 372-20-3
- 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, m-fluoro-; m-Fluorophenol; 3-Fluorophenol; 3-Fluorphenol
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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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔcH°liquid | -696.6 | kcal/mol | Ccb | Swarts, 1919 | Not corrected for CODATA value of ΔfH |
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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 451.2 | K | N/A | Weast and Grasselli, 1989 | BS |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 14.4 ± 0.2 | kcal/mol | C | Ribeiro da Silva and Ferreira, 2009 | AC |
Reduced pressure boiling point
Tboil (K) | Pressure (atm) | Reference | Comment |
---|---|---|---|
370. to 376. | 0.061 | PCR Inc., 1990 | BS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
12.0 | 388. | A | Stephenson and Malanowski, 1987 | Based on data from 373. to 451. 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
C6H4FO- + =
By formula: C6H4FO- + H+ = C6H5FO
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 343.6 ± 2.1 | kcal/mol | G+TS | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale; B |
ΔrH° | 343.6 ± 2.8 | kcal/mol | D-EA | Hernandez-Gill, Wentworth, et al., 1984 | gas phase; B |
ΔrH° | 344.5 ± 2.3 | kcal/mol | G+TS | Kebarle and McMahon, 1977 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 336.8 ± 2.0 | kcal/mol | IMRE | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale; B |
ΔrG° | 336.7 ± 2.9 | kcal/mol | H-TS | Hernandez-Gill, Wentworth, et al., 1984 | gas phase; B |
ΔrG° | 337.6 ± 2.0 | kcal/mol | IMRE | Kebarle and McMahon, 1977 | gas phase; B |
By formula: I- + C6H5FO = (I- • C6H5FO)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 19.4 ± 1.8 | kcal/mol | IMRE | Paul and Kebarle, 1990 | gas phase; ΔGaff at 423 K; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 21. | cal/mol*K | N/A | Paul and Kebarle, 1990 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 10.5 ± 1.0 | kcal/mol | IMRE | Paul and Kebarle, 1990 | gas phase; ΔGaff at 423 K; B |
Free energy of reaction
ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
10.7 | 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° | 23.4 ± 1.8 | kcal/mol | IMRE | Paul and Kebarle, 1990 | gas phase; ΔGaff at 423 K; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 23. | cal/mol*K | N/A | Paul and Kebarle, 1990 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 13.7 ± 1.0 | kcal/mol | IMRE | Paul and Kebarle, 1990 | gas phase; ΔGaff at 423 K; B |
Free energy of reaction
ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
13.7 | 423. | PHPMS | Paul and Kebarle, 1990 | gas phase; Entropy change calculated or estimated; M |
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), 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)
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
View reactions leading to C6H5FO+ (ion structure unspecified)
Proton affinity at 298K
Proton affinity (kcal/mol) | Reference | Comment |
---|---|---|
192. | Bogdanov, van Duijn, et al., 2002 | MM |
Gas basicity at 298K
Gas basicity (review) (kcal/mol) | Reference | Comment |
---|---|---|
185. | Bogdanov, van Duijn, et al., 2002 | MM |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.73 ± 0.03 | S | Oikawa, Abe, et al., 1985 | LBLHLM |
9.05 ± 0.02 | PE | Maier, Marthaler, et al., 1980 | Vertical value; LLK |
8.99 | 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° | 343.6 ± 2.1 | kcal/mol | G+TS | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale; B |
ΔrH° | 343.6 ± 2.8 | kcal/mol | D-EA | Hernandez-Gill, Wentworth, et al., 1984 | gas phase; B |
ΔrH° | 344.5 ± 2.3 | kcal/mol | G+TS | Kebarle and McMahon, 1977 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 336.8 ± 2.0 | kcal/mol | IMRE | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale; B |
ΔrG° | 336.7 ± 2.9 | kcal/mol | H-TS | Hernandez-Gill, Wentworth, et al., 1984 | gas phase; B |
ΔrG° | 337.6 ± 2.0 | kcal/mol | IMRE | Kebarle and McMahon, 1977 | gas 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), 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
By formula: Br- + C6H5FO = (Br- • C6H5FO)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 23.4 ± 1.8 | kcal/mol | IMRE | Paul and Kebarle, 1990 | gas phase; ΔGaff at 423 K; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 23. | cal/mol*K | N/A | Paul and Kebarle, 1990 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 13.7 ± 1.0 | kcal/mol | IMRE | Paul and Kebarle, 1990 | gas phase; ΔGaff at 423 K; B |
Free energy of reaction
ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
13.7 | 423. | PHPMS | Paul and Kebarle, 1990 | gas phase; Entropy change calculated or estimated; M |
By formula: I- + C6H5FO = (I- • C6H5FO)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 19.4 ± 1.8 | kcal/mol | IMRE | Paul and Kebarle, 1990 | gas phase; ΔGaff at 423 K; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 21. | cal/mol*K | N/A | Paul and Kebarle, 1990 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 10.5 ± 1.0 | kcal/mol | IMRE | Paul and Kebarle, 1990 | gas phase; ΔGaff at 423 K; B |
Free energy of reaction
ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
10.7 | 423. | PHPMS | Paul and Kebarle, 1990 | gas phase; Entropy change calculated or estimated; 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: Coblentz Society, Inc.
Condensed Phase Spectrum
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Notice: Except where noted, spectra from this collection were measured on dispersive instruments, often in carefully selected solvents, and hence may differ in detail from measurements on FTIR instruments or in other chemical environments. More information on the manner in which spectra in this collection were collected can be found here.
Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.
Additional Data
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Owner | COBLENTZ SOCIETY Collection (C) 2018 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | DOW CHEMICAL COMPANY |
Source reference | COBLENTZ NO. 6449 |
Date | 1954/07/19 |
Name(s) | 3-fluorophenol |
State | SOLUTION (10% CCl4 FOR 2-7.6, 10% CS2 FOR 7.6-15.9 MICRON) |
Instrument | BAIRD (PRISM) |
Instrument parameters | NaCl PRISM |
Path length | 0.012 CM, 0.011 CM SPECTRAL CONTAMINATION DUE TO CCl4 AROUND 1550 CM-1 |
Resolution | 2 |
Sampling procedure | TRANSMISSION |
Data processing | DIGITIZED BY NIST FROM HARD COPY |
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, 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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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 | Japan AIST/NIMC Database- Spectrum MS-IW-2227 |
NIST MS number | 227813 |
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), 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]
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]
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]
PCR Inc., 1990
PCR Inc.,
Research Chemicals Catalog 1990-1991, PCR Inc., Gainesville, FL, 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]
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]
Hernandez-Gill, Wentworth, et al., 1984
Hernandez-Gill, N.; Wentworth, W.E.; Chen, E.C.M.,
Electron affinities of fluorinated phenoxy radicals,
J. Phys. Chem., 1984, 88, 6181. [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]
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]
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]
Oikawa, Abe, et al., 1985
Oikawa, A.; Abe, H.; Mikami, N.; Ito, M.,
Electronic spectra and ionization potentials of rotational isomers of severaldDisubstituted benzenes,
Chem. Phys. Lett., 1985, 116, 50. [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]
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), References
- Symbols used in this document:
T Temperature Tboil Boiling point ΔcH°liquid Enthalpy of combustion of liquid 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 ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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