Phenol, 3-chloro-

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Reaction thermochemistry data

Go To: Top, Gas phase ion energetics data, Ion clustering data, Gas Chromatography, 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. 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
Δr341.8 ± 3.6kcal/molG+TSFujio, McIver, et al., 1981gas phase; Exptl ΔHf(AH) more stable than group additivity by 6 kcal/mol; value altered from reference due to change in acidity scale; B
Δr342.4 ± 5.0kcal/molG+TSKebarle and McMahon, 1977gas phase; B
Quantity Value Units Method Reference Comment
Δr335.0 ± 2.0kcal/molIMREFujio, McIver, et al., 1981gas phase; Exptl ΔHf(AH) more stable than group additivity by 6 kcal/mol; value altered from reference due to change in acidity scale; B
Δr335.5 ± 2.0kcal/molIMREKebarle and McMahon, 1977gas phase; B

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

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

Quantity Value Units Method Reference Comment
Δr24.1 ± 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; switching reaction,Thermochemical ladder(Br-)C6H5OH, Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr14.4 ± 1.0kcal/molIMREPaul and Kebarle, 1990gas phase; ΔGaff at 423 K; B

Free energy of reaction

ΔrG° (kcal/mol) T (K) Method Reference Comment
14.4423.PHPMSPaul and Kebarle, 1990gas phase; switching reaction,Thermochemical ladder(Br-)C6H5OH, Entropy change calculated or estimated; M

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

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

Quantity Value Units Method Reference Comment
Δr21.1 ± 1.8kcal/molIMREPaul and Kebarle, 1990gas phase; ΔGaff at 423 K; B,M
Quantity Value Units Method Reference Comment
Δr21.cal/mol*KN/APaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr12.2 ± 1.0kcal/molIMREPaul and Kebarle, 1990gas phase; ΔGaff at 423 K; B

Free energy of reaction

ΔrG° (kcal/mol) T (K) Method Reference Comment
12.2423.PHPMSPaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M

Gas phase ion energetics data

Go To: Top, Reaction thermochemistry data, Ion clustering data, Gas Chromatography, References, Notes

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
Δr341.8 ± 3.6kcal/molG+TSFujio, McIver, et al., 1981gas phase; Exptl ΔHf(AH) more stable than group additivity by 6 kcal/mol; value altered from reference due to change in acidity scale; B
Δr342.4 ± 5.0kcal/molG+TSKebarle and McMahon, 1977gas phase; B
Quantity Value Units Method Reference Comment
Δr335.0 ± 2.0kcal/molIMREFujio, McIver, et al., 1981gas phase; Exptl ΔHf(AH) more stable than group additivity by 6 kcal/mol; value altered from reference due to change in acidity scale; B
Δr335.5 ± 2.0kcal/molIMREKebarle and McMahon, 1977gas phase; B

Ion clustering data

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Gas Chromatography, 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 • Phenol, 3-chloro-)

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

Quantity Value Units Method Reference Comment
Δr24.1 ± 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; switching reaction,Thermochemical ladder(Br-)C6H5OH, Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr14.4 ± 1.0kcal/molIMREPaul and Kebarle, 1990gas phase; ΔGaff at 423 K; B

Free energy of reaction

ΔrG° (kcal/mol) T (K) Method Reference Comment
14.4423.PHPMSPaul and Kebarle, 1990gas phase; switching reaction,Thermochemical ladder(Br-)C6H5OH, Entropy change calculated or estimated; M

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

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

Quantity Value Units Method Reference Comment
Δr21.1 ± 1.8kcal/molIMREPaul and Kebarle, 1990gas phase; ΔGaff at 423 K; B,M
Quantity Value Units Method Reference Comment
Δr21.cal/mol*KN/APaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr12.2 ± 1.0kcal/molIMREPaul and Kebarle, 1990gas phase; ΔGaff at 423 K; B

Free energy of reaction

ΔrG° (kcal/mol) T (K) Method Reference Comment
12.2423.PHPMSPaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M

Gas Chromatography

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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

Kovats' RI, non-polar column, isothermal

View large format table.

Column type Active phase Temperature (C) I Reference Comment
CapillarySE-30160.1157.Evans and Haken, 1989Column length: 25. m; Column diameter: 0.32 mm
CapillarySE-30140.1159.Korhonen, 1984 
CapillarySE-30160.1157.Korhonen, 1984 
CapillarySE-30180.1161.Korhonen, 1984 
PackedMethyl Silicone150.1189.Radecki, Grzybowski, et al., 1979 

Kovats' RI, non-polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
PackedSE-301194.Grzybowski, Lamparczyk, et al., 1980Chromosorb W HMDS (80-100 mesh); Column length: 2.9 m; Program: not specified

Kovats' RI, polar column, isothermal

View large format table.

Column type Active phase Temperature (C) I Reference Comment
CapillaryFFAP160.2371.Evans and Haken, 1989Column length: 25. m; Column diameter: 0.35 mm
CapillaryFFAP160.2371.Korhonen, 1984 
CapillaryFFAP180.2371.Korhonen, 1984 
CapillaryFFAP200.2380.Korhonen, 1984 

Van Den Dool and Kratz RI, non-polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryOV-11171.0Gautzsch and Zinn, 19968. K/min; Tstart: 35. C; Tend: 300. C
CapillarySE-301169.Korhonen, 198410. K/min; Tstart: 100. C
CapillarySE-301165.Korhonen, 19842. K/min; Tstart: 100. C
CapillarySE-301167.Korhonen, 19846. K/min; Tstart: 100. C

Van Den Dool and Kratz RI, non-polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
CapillaryVF-5MS1203.3Tret'yakov, 200730. m/0.25 mm/0.25 μm, He; Program: Multi-step temperature program; T(initial)=60C; T(final)=270C
Capillary5 % Phenyl methyl siloxane1198.Yasuhara, Shiraishi, et al., 199725. m/0.31 mm/0.52 μm, He; Program: 50C(2min) => (20C/min) => 120C => (7C/min) => 310C(10min)

Van Den Dool and Kratz RI, polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryFFAP2364.Korhonen, 198410. K/min; Tstart: 100. C
CapillaryFFAP2333.Korhonen, 19842. K/min; Tstart: 100. C
CapillaryFFAP2350.Korhonen, 19846. K/min; Tstart: 100. C

Normal alkane RI, non-polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryUltra-11170.Okumura, 199125. m/0.32 mm/0.25 μm, He, 3. K/min; Tstart: 80. C; Tend: 260. C
CapillarySE-541207.Harland, Cumming, et al., 1986He, 50. C @ 2. min, 8. K/min, 250. C @ 12. min; Column length: 25. m; Column diameter: 0.32 mm

Normal alkane RI, non-polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
CapillaryMethyl Silicone1159.Yu and Zazhi, 2005Program: not specified
CapillaryPTE-51200.Nakano, Fujimori, et al., 199225. m/0.20 mm/0.33 μm; Program: 50 0C (2 min) 30 0C/min -> 200 0C 8 0C/min -> 280 0C (10 min)
CapillaryUltra-21203.Nakano, Fujimori, et al., 199225. m/0.20 mm/0.33 μm; Program: 50 0C (2 min) 30 0C/min -> 200 0C 8 0C/min -> 280 0C (10 min)
CapillarySE-301194.Peterson, 1992Program: not specified
CapillaryOV-11173.Waggott and Davies, 1984Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified

Normal alkane RI, polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
CapillarySuperox 0.6; Carbowax 20M2345.Waggott and Davies, 1984Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified
CapillarySuperox 0.6; Carbowax 20M2378.Waggott and Davies, 1984Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified
CapillaryCarbowax 400, Carbowax 20M, Carbowax 1540, Carbowax 4000, Superox 06, PEG 20M, etc.2345.Waggott and Davies, 1984Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified

References

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, Gas Chromatography, Notes

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

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]

Evans and Haken, 1989
Evans, M.B.; Haken, J.K., Dispersion and selectivity indices in gas chromatography. IV. Chlorinated aromatic compounds, J. Chromatogr., 1989, 468, 373-382, https://doi.org/10.1016/S0021-9673(00)96332-5 . [all data]

Korhonen, 1984
Korhonen, I.O.O., Gas-liquid chromatographic analyses. XXXI. Retention increments of isomeric chlorophenols on low-polarity (SE-30) and polar (FFAP) capillary columns, J. Chromatogr., 1984, 315, 185-200, https://doi.org/10.1016/S0021-9673(01)90736-8 . [all data]

Radecki, Grzybowski, et al., 1979
Radecki, A.; Grzybowski, J.; Lamparczyk, H.; Nasal, A., Relationships between retention indices and substituent constants of phenols on polar stationary phases, J. Hi. Res. Chromatogr. Chromatogr. Comm., 1979, 2, 9, 581-582, https://doi.org/10.1002/jhrc.1240020911 . [all data]

Grzybowski, Lamparczyk, et al., 1980
Grzybowski, J.; Lamparczyk, H.; Nasal, A.; Radecki, A., Relationship between the retention indices of phenols on polar and non-polar stationary phases, J. Chromatogr., 1980, 196, 2, 217-223, https://doi.org/10.1016/S0021-9673(00)80441-0 . [all data]

Gautzsch and Zinn, 1996
Gautzsch, R.; Zinn, P., Use of incremental models to estimate the retention indexes of aromatic compounds, Chromatographia, 1996, 43, 3/4, 163-176, https://doi.org/10.1007/BF02292946 . [all data]

Tret'yakov, 2007
Tret'yakov, K.V., Retention Data. NIST Mass Spectrometry Data Center., NIST Mass Spectrometry Data Center, 2007. [all data]

Yasuhara, Shiraishi, et al., 1997
Yasuhara, A.; Shiraishi, H.; Nishikawa, M.; Yamamoto, T.; Uehiro, T.; Nakasugi, O.; Okumura, T.; Kenmotsu, K.; Fukui, H.; Nagase, M.; Ono, Y.; Kawagoshi, Y.; Baba, K.; Noma, Y., Determination of organic components in leachates from hazardous waste disposal sites in Japan by gas chromatography-mass spectrometry, J. Chromatogr. A, 1997, 774, 1-2, 321-332, https://doi.org/10.1016/S0021-9673(97)00078-2 . [all data]

Okumura, 1991
Okumura, T., retention indices of environmental chemicals on methyl silicone capillary column, Journal of Environmental Chemistry (Japan), 1991, 1, 2, 333-358, https://doi.org/10.5985/jec.1.333 . [all data]

Harland, Cumming, et al., 1986
Harland, B.J.; Cumming, R.I.; Gillings, E., The Kovats indexes of some organic micropollutants on an SE54 capillary column, EUR, I Org. Micropollut. Aquat. Environ., 1986, EUR 10388, 123-127. [all data]

Yu and Zazhi, 2005
Yu, H.; Zazhi, J., Relationship between chromatogram retention index and toxicity of chlorinated phenols and chlorinated benzenes to Guppy, J. Enviropn. Health (Chinese), 2005, 22, 6, 441-444. [all data]

Nakano, Fujimori, et al., 1992
Nakano, T.; Fujimori, K.; Takaishi, Y.; Okuno, T., GC/MS-SIM analysis of polychlorobenzenes, polychlorophenols and polychloronaphthalenes, Report of the Environmental Science Institute of Hyogo Prefecture, 1992, 24, 30-37. [all data]

Peterson, 1992
Peterson, K.L., Counter-Propagation Neural Networks in the Modeling and Prediction of Kovats Indices for Substituted Phenols, Anal. Chem., 1992, 64, 4, 379-386, https://doi.org/10.1021/ac00028a011 . [all data]

Waggott and Davies, 1984
Waggott, A.; Davies, I.W., Identification of organic pollutants using linear temperature programmed retention indices (LTPRIs) - Part II, 1984, retrieved from http://dwi.defra.gov.uk/research/completed-research/reports/dwi0383.pdf. [all data]


Notes

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, Gas Chromatography, References