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, Gas phase ion energetics data, 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
Δcsolid-2914.8kJ/molCcbSwarts, 1919Not corrected for CODATA value of ΔfH; 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, Gas phase ion energetics data, 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, Chris Muzny 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
Δsub73.9 ± 1.4kJ/molCRibeiro da Silva and Ferreira, 2009AC

Enthalpy of vaporization

ΔvapH (kJ/mol) Temperature (K) Method Reference Comment
48.8375.AStephenson and Malanowski, 1987Based on data from 360. to 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:


Gas phase ion energetics data

Go To: Top, Condensed phase thermochemistry data, Phase change data, 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
Δr1451. ± 8.8kJ/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Δr1455. ± 9.6kJ/molG+TSKebarle and McMahon, 1977gas phase; B
Quantity Value Units Method Reference Comment
Δr1422. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Δr1426. ± 8.4kJ/molIMREKebarle and McMahon, 1977gas phase; B

References

Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, 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]

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]

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]


Notes

Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, References