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Phenol, 3-chloro-

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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
Deltacliquid-2910.0 ± 8.4kJ/molCcbSmith, Bjellerup, et al., 1953Reanalyzed by Cox and Pilcher, 1970, Original value = -2907. ± 3. kJ/mol; "Supercooled"
Quantity Value Units Method Reference Comment
Deltacsolid-2890. ± 8.kJ/molCcbSmith, Bjellerup, et al., 1953powder at 291.7 °K

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
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny, director
AC - William E. Acree, Jr., James S. Chickos
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
Tboil487.2KN/AWeast and Grasselli, 1989BS
Quantity Value Units Method Reference Comment
Tfus305.8KN/APoeti, Faneli, et al., 1982Uncertainty assigned by TRC = 0.2 K; TRC
Quantity Value Units Method Reference Comment
Deltavap63.5 ± 0.3kJ/molGSVerevkin, Emel'yanenko, et al., 2007Based on data from 308. - 335. K.; AC
Quantity Value Units Method Reference Comment
Deltasub76.9 ± 0.3kJ/molGSVerevkin, Emel'yanenko, et al., 2007Based on data from 275. - 306. K.; AC

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
61.9322.GSVerevkin, Emel'yanenko, et al., 2007Based on data from 308. - 335. K.; AC
53.1332.AStephenson and Malanowski, 1987Based on data from 317. - 487. K. See also Stull, 1947.; AC

Antoine Equation Parameters

log10(P) = A − (B / (T + C))
    P = vapor pressure (bar)
    T = temperature (K)

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Temperature (K) A B C Reference Comment
317.4 - 487.4.670812074.632-42.359Stull, 1947Coefficents calculated by NIST from author's data.

Enthalpy of sublimation

DeltasubH (kJ/mol) Temperature (K) Method Reference Comment
53. ± 1.301.VWolf and Weghofer, 1938ALS

Enthalpy of fusion

DeltafusH (kJ/mol) Temperature (K) Reference Comment
14.905305.8Poeti, Fanelli, et al., 1982DH
14.91305.8Acree, 1991AC

Entropy of fusion

DeltafusS (J/mol*K) Temperature (K) Reference Comment
48.74305.8Poeti, Fanelli, et al., 1982DH

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

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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

C6H4ClO- + Hydrogen cation = Phenol, 3-chloro-

By formula: C6H4ClO- + H+ = C6H5ClO

Quantity Value Units Method Reference Comment
Deltar1430. ± 15.kJ/molG+TSFujio, McIver, et al., 1981gas phase; Exptl «DELTA»Hf(AH) more stable than group additivity by 6 kcal/mol; value altered from reference due to change in acidity scale; B
Deltar1433. ± 21.kJ/molG+TSKebarle and McMahon, 1977gas phase; B
Quantity Value Units Method Reference Comment
Deltar1402. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; Exptl «DELTA»Hf(AH) more stable than group additivity by 6 kcal/mol; value altered from reference due to change in acidity scale; B
Deltar1404. ± 8.4kJ/molIMREKebarle and McMahon, 1977gas phase; B

Bromine anion + Phenol, 3-chloro- = (Bromine anion bullet Phenol, 3-chloro-)

By formula: Br- + C6H5ClO = (Br- bullet C6H5ClO)

Quantity Value Units Method Reference Comment
Deltar101. ± 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; switching reaction,Thermochemical ladder(Br-)C6H5OH, Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar60.2 ± 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
60.2423.PHPMSPaul and Kebarle, 1990gas phase; switching reaction,Thermochemical ladder(Br-)C6H5OH, Entropy change calculated or estimated; M

Iodide + Phenol, 3-chloro- = (Iodide bullet Phenol, 3-chloro-)

By formula: I- + C6H5ClO = (I- bullet C6H5ClO)

Quantity Value Units Method Reference Comment
Deltar88.3 ± 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
Deltar51.0 ± 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
51.0423.PHPMSPaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M

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:
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
LL - Sharon G. Lias and Joel F. Liebman
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard

View reactions leading to C6H5ClO+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)8.655 ± 0.001eVN/AN/AL

Ionization energy determinations

IE (eV) Method Reference Comment
8.655 ± 0.001LSCockett, Takahashi, et al., 1991Cis isomer; LL
8.682 ± 0.001LSCockett, Takahashi, et al., 1991Trans isomer; LL
8.65 ± 0.03SOikawa, Abe, et al., 1985LBLHLM

De-protonation reactions

C6H4ClO- + Hydrogen cation = Phenol, 3-chloro-

By formula: C6H4ClO- + H+ = C6H5ClO

Quantity Value Units Method Reference Comment
Deltar1430. ± 15.kJ/molG+TSFujio, McIver, et al., 1981gas phase; Exptl «DELTA»Hf(AH) more stable than group additivity by 6 kcal/mol; value altered from reference due to change in acidity scale; B
Deltar1433. ± 21.kJ/molG+TSKebarle and McMahon, 1977gas phase; B
Quantity Value Units Method Reference Comment
Deltar1402. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; Exptl «DELTA»Hf(AH) more stable than group additivity by 6 kcal/mol; value altered from reference due to change in acidity scale; B
Deltar1404. ± 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), 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, 3-chloro- = (Bromine anion bullet Phenol, 3-chloro-)

By formula: Br- + C6H5ClO = (Br- bullet C6H5ClO)

Quantity Value Units Method Reference Comment
Deltar101. ± 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; switching reaction,Thermochemical ladder(Br-)C6H5OH, Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar60.2 ± 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
60.2423.PHPMSPaul and Kebarle, 1990gas phase; switching reaction,Thermochemical ladder(Br-)C6H5OH, Entropy change calculated or estimated; M

Iodide + Phenol, 3-chloro- = (Iodide bullet Phenol, 3-chloro-)

By formula: I- + C6H5ClO = (I- bullet C6H5ClO)

Quantity Value Units Method Reference Comment
Deltar88.3 ± 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
Deltar51.0 ± 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
51.0423.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), 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, 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 A.E.WILLIAMS ICI DYESTUFFS DIVISION. BLACKLEY.
NIST MS number 2761

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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.

Smith, Bjellerup, et al., 1953
Smith, L.; Bjellerup, L.; Krook, S.; Westermark, H., Heats of combustion of organic chloro compounds determined by the "quartz wool" method, Acta Chem. Scand., 1953, 7, 65. [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [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]

Poeti, Faneli, et al., 1982
Poeti, G.; Faneli, E.; Braghetti, M.J., A differential scanning calorimetric study of some phenol derivatives, Therm. Anal., 1982, 24, 2, 273, https://doi.org/10.1007/BF01913681 . [all data]

Verevkin, Emel'yanenko, et al., 2007
Verevkin, Sergey P.; Emel'yanenko, Vladimir N.; Klamt, Andreas, Thermochemistry of Chlorobenzenes and Chlorophenols: Ambient Temperature Vapor Pressures and Enthalpies of Phase Transitions, J. Chem. Eng. Data, 2007, 52, 2, 499-510, https://doi.org/10.1021/je060429r . [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]

Stull, 1947
Stull, Daniel R., Vapor Pressure of Pure Substances. Organic and Inorganic Compounds, Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022 . [all data]

Wolf and Weghofer, 1938
Wolf, K.L.; Weghofer, H., Uber sublimationswarmen, Z. Phys. Chem., 1938, 39, 194-208. [all data]

Poeti, Fanelli, et al., 1982
Poeti, G.; Fanelli, E.; Braghetti, M., A differential scanning calorimetric study of some phenol derivatives, J. Therm. Anal., 1982, 24(2), 273-279. [all data]

Acree, 1991
Acree, William E., Thermodynamic properties of organic compounds: enthalpy of fusion and melting point temperature compilation, Thermochimica Acta, 1991, 189, 1, 37-56, https://doi.org/10.1016/0040-6031(91)87098-H . [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]

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]

Cockett, Takahashi, et al., 1991
Cockett, M.C.R.; Takahashi, M.; Okuyama, K.; Kimura, K., REMPI threshold photoelectron spectra of the cis and trans rotational isomers of jet-cooled m-chlorophenol, Chem. Phys. Lett., 1991, 187, 250. [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]


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