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 (cal/mol*K) Temperature (K) Reference Comment
45.10283.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
Δvap12.5 ± 0.05kcal/molGSVerevkin, Emel'yanenko, et al., 2007Based on data from 288. to 321. K.; AC

Enthalpy of vaporization

ΔvapH (kcal/mol) Temperature (K) Method Reference Comment
12.4305.GSVerevkin, Emel'yanenko, et al., 2007Based on data from 288. to 321. K.; AC
11.2352.N/AGabaldon, Marzal, et al., 1995Based on data from 337. to 447. K.; AC
11.3369.AStephenson and Malanowski, 1987Based on data from 354. to 448. K.; AC
12.0348.AStephenson and Malanowski, 1987Based on data from 333. to 449. K. See also Kiva, Nadutkina, et al., 1974.; AC
10.8300.N/AStull, 1947Based on data from 285. to 447. K.; AC

Enthalpy of fusion

ΔfusH (kcal/mol) Temperature (K) Reference Comment
2.9931283.0Poeti, Fanelli, et al., 1982DH
2.992283.Acree, 1991AC

Entropy of fusion

ΔfusS (cal/mol*K) Temperature (K) Reference Comment
10.58283.0Poeti, 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
Δr21.2 ± 1.8kcal/molIMREPaul and Kebarle, 1990gas phase; ΔGaff at 423 K; B,M
Quantity Value Units Method Reference Comment
Δr23.cal/mol*KN/APaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr11.5 ± 1.0kcal/molIMREPaul and Kebarle, 1990gas phase; ΔGaff at 423 K; B

Free energy of reaction

ΔrG° (kcal/mol) T (K) Method Reference Comment
11.5423.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
Δr343.4 ± 2.3kcal/molG+TSKebarle and McMahon, 1977gas phase; B
Quantity Value Units Method Reference Comment
Δr337.1 ± 2.0kcal/molIMREKebarle and McMahon, 1977gas phase; B

Henry's Law 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: Rolf Sander

Henry's Law constant (water solution)

kH(T) = H exp(d(ln(kH))/d(1/T) ((1/T) - 1/(298.15 K)))
H = Henry's law constant for solubility in water at 298.15 K (mol/(kg*bar))
d(ln(kH))/d(1/T) = Temperature dependence constant (K)

H (mol/(kg*bar)) d(ln(kH))/d(1/T) (K) Method Reference
120.4600.XN/A

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
Δr343.4 ± 2.3kcal/molG+TSKebarle and McMahon, 1977gas phase; B
Quantity Value Units Method Reference Comment
Δr337.1 ± 2.0kcal/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
Δr21.2 ± 1.8kcal/molIMREPaul and Kebarle, 1990gas phase; ΔGaff at 423 K; B,M
Quantity Value Units Method Reference Comment
Δr23.cal/mol*KN/APaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr11.5 ± 1.0kcal/molIMREPaul and Kebarle, 1990gas phase; ΔGaff at 423 K; B

Free energy of reaction

ΔrG° (kcal/mol) T (K) Method Reference Comment
11.5423.PHPMSPaul and Kebarle, 1990gas 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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Mass 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 NIST Mass Spectrometry Data Center, 1990.
NIST MS number 114927

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


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, Alexander N. Yermakov, Alexy A. Usov, Antonina A. Goncharova, Axlexander N. Leskin, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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UVVis spectrum
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Additional Data

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Source Perkampus, 1966
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. 19791
Instrument Zeiss PMQ II
Boiling point 175-176

References

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Notes

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]

Perkampus, 1966
Perkampus, H.-H., UV atlas of organic compounds, 1966, 2, D9/28. [all data]


Notes

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, References