Phenol, 2-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: Eugene S. Domalski and Elizabeth D. Hearing

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
188.7283.Bramley, 1916Mean value, 0 to 20°C.

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
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Tboil448.1KN/AWeast and Grasselli, 1989BS
Tboil448.9KN/AFort and Moore, 1965Uncertainty assigned by TRC = 0.4 K; TRC
Tboil450.0KN/ALecat, 1947Uncertainty assigned by TRC = 0.7 K; TRC
Tboil448.15KN/ABramley, 1916, 2Uncertainty assigned by TRC = 3. K; TRC
Quantity Value Units Method Reference Comment
Tfus283.0KN/APoeti, Faneli, et al., 1982Uncertainty assigned by TRC = 0.2 K; TRC
Tfus282.KN/ADreisbach, 1955Uncertainty assigned by TRC = 0.02 K; TRC
Tfus281.15KN/ABramley, 1916, 2Uncertainty assigned by TRC = 2. K; TRC
Tfus281.15KN/ABramley, 1916, 3Uncertainty assigned by TRC = 0.2 K; TRC
Quantity Value Units Method Reference Comment
Δvap52.3 ± 0.2kJ/molGSVerevkin, Emel'yanenko, et al., 2007Based on data from 288. to 321. K.; AC

Enthalpy of vaporization

ΔvapH (kJ/mol) Temperature (K) Method Reference Comment
51.9305.GSVerevkin, Emel'yanenko, et al., 2007Based on data from 288. to 321. K.; AC
47.0352.N/AGabaldon, Marzal, et al., 1995Based on data from 337. to 447. K.; AC
47.2369.AStephenson and Malanowski, 1987Based on data from 354. to 448. K.; AC
50.1348.AStephenson and Malanowski, 1987Based on data from 333. to 449. K. See also Kiva, Nadutkina, et al., 1974.; AC
45.2300.N/AStull, 1947Based on data from 285. to 447. K.; AC

Enthalpy of fusion

ΔfusH (kJ/mol) Temperature (K) Reference Comment
12.523283.0Poeti, Fanelli, et al., 1982DH
12.52283.Acree, 1991AC

Entropy of fusion

ΔfusS (J/mol*K) Temperature (K) Reference Comment
44.25283.0Poeti, 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

Bromine anion + Phenol, 2-chloro- = (Bromine anion • Phenol, 2-chloro-)

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

Quantity Value Units Method Reference Comment
Δr88.7 ± 7.5kJ/molIMREPaul and Kebarle, 1990gas phase; ΔGaff at 423 K; B,M
Quantity Value Units Method Reference Comment
Δr96.J/mol*KN/APaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr48.1 ± 4.2kJ/molIMREPaul and Kebarle, 1990gas phase; ΔGaff at 423 K; B

Free energy of reaction

ΔrG° (kJ/mol) T (K) Method Reference Comment
48.1423.PHPMSPaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M

C6H4ClO- + Hydrogen cation = Phenol, 2-chloro-

By formula: C6H4ClO- + H+ = C6H5ClO

Quantity Value Units Method Reference Comment
Δr1437. ± 9.6kJ/molG+TSKebarle and McMahon, 1977gas phase; B
Quantity Value Units Method Reference Comment
Δr1410. ± 8.4kJ/molIMREKebarle and McMahon, 1977gas 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
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

View reactions leading to C6H5ClO+ (ion structure unspecified)

Ionization energy determinations

IE (eV) Method Reference Comment
9.28EICrable and Kearns, 1962RDSH

De-protonation reactions

C6H4ClO- + Hydrogen cation = Phenol, 2-chloro-

By formula: C6H4ClO- + H+ = C6H5ClO

Quantity Value Units Method Reference Comment
Δr1437. ± 9.6kJ/molG+TSKebarle and McMahon, 1977gas phase; B
Quantity Value Units Method Reference Comment
Δr1410. ± 8.4kJ/molIMREKebarle and McMahon, 1977gas 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

Bromine anion + Phenol, 2-chloro- = (Bromine anion • Phenol, 2-chloro-)

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

Quantity Value Units Method Reference Comment
Δr88.7 ± 7.5kJ/molIMREPaul and Kebarle, 1990gas phase; ΔGaff at 423 K; B,M
Quantity Value Units Method Reference Comment
Δr96.J/mol*KN/APaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr48.1 ± 4.2kJ/molIMREPaul and Kebarle, 1990gas phase; ΔGaff at 423 K; B

Free energy of reaction

ΔrG° (kJ/mol) T (K) Method Reference Comment
48.1423.PHPMSPaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M

References

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

Bramley, 1916
Bramley, A., The study of binary mixtures. Part IV. Heats of reaction and specific heats, J. Chem. Soc. (London), 1916, 109, 496-515. [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]

Fort and Moore, 1965
Fort, R.J.; Moore, W.R., Adiabatic compressibilities of binary liquid mixtures, Trans. Faraday Soc., 1965, 61, 2102. [all data]

Lecat, 1947
Lecat, M., Orthobaric Azeotropes of Sulfides, Bull. Cl. Sci., Acad. R. Belg., 1947, 33, 160-82. [all data]

Bramley, 1916, 2
Bramley, A., XXXVI.--The Study of Binary Mixtures. Part II. The Densities and Viscosities of Mixtures Containing Substituted Phenols., J. Chem. Soc., 1916, 109, 434. [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]

Dreisbach, 1955
Dreisbach, R.R., Physical Properties of Chemical Compounds, Advances in Chemistry Series No. 15, Am. Chem. Soc.: Washington, D. C., 1955. [all data]

Bramley, 1916, 3
Bramley, A., The Studyu of Binary Mixtures. Part III. Freezing Point Curves, J. Chem. Soc., 1916, 109, 469. [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]

Gabaldon, Marzal, et al., 1995
Gabaldon, Carmen; Marzal, Paula; Monton, Juan B., Vapor-Liquid Equilibria of the 1-Butanol + o-Chlorophenol System. Effects of Association in the Vapor Phase, J. Chem. Eng. Data, 1995, 40, 1, 190-193, https://doi.org/10.1021/je00017a039 . [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]

Kiva, Nadutkina, et al., 1974
Kiva, N.N.; Nadutkina, S.I.; Ivanova, L.V.; Bogdanov, V.S., Russ. J. Phys. Chem., 1974, 148, 297. [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]

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]

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]

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]

Crable and Kearns, 1962
Crable, G.F.; Kearns, G.L., Effect of substituent groups on the ionization potentials of benzenes, J. Phys. Chem., 1962, 66, 436. [all data]


Notes

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