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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Reaction thermochemistry 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 compiled as indicated in comments:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
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Individual 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 |
+
= (
•
)
By formula: Br- + C6H5ClO = (Br- • C6H5ClO)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 101. ± 7.5 | kJ/mol | IMRE | Paul and Kebarle, 1990 | gas phase; ΔGaff at 423 K; B,M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrS° | 96. | J/mol*K | N/A | Paul and Kebarle, 1990 | gas phase; switching reaction,Thermochemical ladder(Br-)C6H5OH, Entropy change calculated or estimated; M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 60.2 ± 4.2 | kJ/mol | IMRE | Paul and Kebarle, 1990 | gas phase; ΔGaff at 423 K; B |
Free energy of reaction
| ΔrG° (kJ/mol) | T (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 60.2 | 423. | PHPMS | Paul and Kebarle, 1990 | gas phase; switching reaction,Thermochemical ladder(Br-)C6H5OH, Entropy change calculated or estimated; M |
+
= (
•
)
By formula: I- + C6H5ClO = (I- • C6H5ClO)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 88.3 ± 7.5 | kJ/mol | IMRE | Paul and Kebarle, 1990 | gas phase; ΔGaff at 423 K; B,M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrS° | 88. | J/mol*K | N/A | Paul and Kebarle, 1990 | gas phase; Entropy change calculated or estimated; M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 51.0 ± 4.2 | kJ/mol | IMRE | Paul and Kebarle, 1990 | gas phase; ΔGaff at 423 K; B |
Free energy of reaction
| ΔrG° (kJ/mol) | T (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 51.0 | 423. | PHPMS | Paul and Kebarle, 1990 | gas phase; Entropy change calculated or estimated; M |
References
Go To: Top, Reaction thermochemistry data, 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]
Notes
Go To: Top, Reaction thermochemistry data, References
- Symbols used in this document:
T Temperature ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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