Phenol, 3-chloro-
- Formula: C6H5ClO
- Molecular weight: 128.556
- IUPAC Standard InChIKey: HORNXRXVQWOLPJ-UHFFFAOYSA-N
- CAS Registry Number: 108-43-0
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript. - Other names: Phenol, m-chloro-; m-Chlorophenol; 3-Chlorophenol; 3-Hydroxychlorobenzene; meta-Chlorophenol; m-Chlorophenic acid; NSC 59700
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Gas phase ion energetics data
Go To: Top, 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 ± 0.001 | eV | N/A | N/A | L |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.655 ± 0.001 | LS | Cockett, Takahashi, et al., 1991 | Cis isomer; LL |
8.682 ± 0.001 | LS | Cockett, Takahashi, et al., 1991 | Trans isomer; LL |
8.65 ± 0.03 | S | Oikawa, Abe, et al., 1985 | LBLHLM |
De-protonation reactions
C6H4ClO- + =
By formula: C6H4ClO- + H+ = C6H5ClO
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1430. ± 15. | kJ/mol | G+TS | Fujio, McIver, et al., 1981 | gas phase; Exptl ΔHf(AH) more stable than group additivity by 6 kcal/mol; value altered from reference due to change in acidity scale; B |
ΔrH° | 1433. ± 21. | kJ/mol | G+TS | Kebarle and McMahon, 1977 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1402. ± 8.4 | kJ/mol | IMRE | Fujio, McIver, et al., 1981 | gas phase; Exptl ΔHf(AH) more stable than group additivity by 6 kcal/mol; value altered from reference due to change in acidity scale; B |
ΔrG° | 1404. ± 8.4 | kJ/mol | IMRE | Kebarle and McMahon, 1977 | gas phase; B |
Gas Chromatography
Go To: Top, 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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Kovats' RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | SE-30 | 160. | 1157. | Evans and Haken, 1989 | Column length: 25. m; Column diameter: 0.32 mm |
Capillary | SE-30 | 140. | 1159. | Korhonen, 1984 | |
Capillary | SE-30 | 160. | 1157. | Korhonen, 1984 | |
Capillary | SE-30 | 180. | 1161. | Korhonen, 1984 | |
Packed | Methyl Silicone | 150. | 1189. | Radecki, Grzybowski, et al., 1979 |
Kovats' RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Packed | SE-30 | 1194. | Grzybowski, Lamparczyk, et al., 1980 | Chromosorb W HMDS (80-100 mesh); Column length: 2.9 m; Program: not specified |
Kovats' RI, polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | FFAP | 160. | 2371. | Evans and Haken, 1989 | Column length: 25. m; Column diameter: 0.35 mm |
Capillary | FFAP | 160. | 2371. | Korhonen, 1984 | |
Capillary | FFAP | 180. | 2371. | Korhonen, 1984 | |
Capillary | FFAP | 200. | 2380. | Korhonen, 1984 |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | OV-1 | 1171.0 | Gautzsch and Zinn, 1996 | 8. K/min; Tstart: 35. C; Tend: 300. C |
Capillary | SE-30 | 1169. | Korhonen, 1984 | 10. K/min; Tstart: 100. C |
Capillary | SE-30 | 1165. | Korhonen, 1984 | 2. K/min; Tstart: 100. C |
Capillary | SE-30 | 1167. | Korhonen, 1984 | 6. K/min; Tstart: 100. C |
Van Den Dool and Kratz RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | VF-5MS | 1203.3 | Tret'yakov, 2007 | 30. m/0.25 mm/0.25 μm, He; Program: Multi-step temperature program; T(initial)=60C; T(final)=270C |
Capillary | 5 % Phenyl methyl siloxane | 1198. | Yasuhara, Shiraishi, et al., 1997 | 25. 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
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | FFAP | 2364. | Korhonen, 1984 | 10. K/min; Tstart: 100. C |
Capillary | FFAP | 2333. | Korhonen, 1984 | 2. K/min; Tstart: 100. C |
Capillary | FFAP | 2350. | Korhonen, 1984 | 6. K/min; Tstart: 100. C |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Ultra-1 | 1170. | Okumura, 1991 | 25. m/0.32 mm/0.25 μm, He, 3. K/min; Tstart: 80. C; Tend: 260. C |
Capillary | SE-54 | 1207. | Harland, Cumming, et al., 1986 | He, 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
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Methyl Silicone | 1159. | Yu and Zazhi, 2005 | Program: not specified |
Capillary | PTE-5 | 1200. | Nakano, Fujimori, et al., 1992 | 25. m/0.20 mm/0.33 μm; Program: 50 0C (2 min) 30 0C/min -> 200 0C 8 0C/min -> 280 0C (10 min) |
Capillary | Ultra-2 | 1203. | Nakano, Fujimori, et al., 1992 | 25. m/0.20 mm/0.33 μm; Program: 50 0C (2 min) 30 0C/min -> 200 0C 8 0C/min -> 280 0C (10 min) |
Capillary | SE-30 | 1194. | Peterson, 1992 | Program: not specified |
Capillary | OV-1 | 1173. | Waggott and Davies, 1984 | Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified |
Normal alkane RI, polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Superox 0.6; Carbowax 20M | 2345. | Waggott and Davies, 1984 | Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified |
Capillary | Superox 0.6; Carbowax 20M | 2378. | Waggott and Davies, 1984 | Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified |
Capillary | Carbowax 400, Carbowax 20M, Carbowax 1540, Carbowax 4000, Superox 06, PEG 20M, etc. | 2345. | Waggott and Davies, 1984 | Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified |
References
Go To: Top, Gas phase ion energetics data, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
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]
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, Gas phase ion energetics data, Gas Chromatography, References
- Symbols used in this document:
IE (evaluated) Recommended ionization energy ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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