Phenol, 3-chloro-
- Formula: C6H5ClO
- Molecular weight: 128.556
- IUPAC Standard InChI: InChI=1S/C6H5ClO/c7-5-2-1-3-6(8)4-5/h1-4,8H
- 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, 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 |
References
Go To: Top, Gas phase ion energetics data, 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]
Notes
Go To: Top, Gas phase ion energetics data, 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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