Benzonitrile, 4-hydroxy-
- Formula: C7H5NO
- Molecular weight: 119.1207
- IUPAC Standard InChI: InChI=1S/C7H5NO/c8-5-6-1-3-7(9)4-2-6/h1-4,9H
- IUPAC Standard InChIKey: CVNOWLNNPYYEOH-UHFFFAOYSA-N
- CAS Registry Number: 767-00-0
- 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: Benzonitrile, p-hydroxy-; p-Cyanophenol; p-Hydroxybenzonitrile; 4-Cyanophenol; 4-Hydroxybenzonitrile; 4-Hydroxybenzoic acid nitrile
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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
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Clustering reactions
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= (
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By formula: Br- + C7H5NO = (Br- • C7H5NO)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 27.8 ± 1.8 | kcal/mol | IMRE | Paul and Kebarle, 1990 | gas phase; ΔGaff at 423 K; B,M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrS° | 23. | cal/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° | 18.1 ± 1.0 | kcal/mol | IMRE | Paul and Kebarle, 1990 | gas phase; ΔGaff at 423 K; B |
Free energy of reaction
| ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 18.1 | 423. | PHPMS | Paul and Kebarle, 1990 | gas phase; switching reaction,Thermochemical ladder(Br-)C6H5OH, Entropy change calculated or estimated; M |
+
= (
•
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By formula: Cl- + C7H5NO = (Cl- • C7H5NO)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 35.1 ± 2.0 | kcal/mol | TDEq | Cummings, French, et al., 1977 | gas phase; Re-anchored to data in French, Ikuta, et al., 1982.; B,M,M |
| ΔrH° | 35.3 | kcal/mol | PHPMS | Paul and Kebarle, 1990 | gas phase; Entropy change calculated or estimated; M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrS° | 25. | cal/mol*K | N/A | Paul and Kebarle, 1990 | gas phase; Entropy change calculated or estimated; M |
| ΔrS° | 28. | cal/mol*K | N/A | Cummings, French, et al., 1977 | gas phase; switching reaction(Cl-)4-Cl-phenol, Entropy change calculated or estimated; French, Ikuta, et al., 1982; M |
| ΔrS° | 26. | cal/mol*K | N/A | Cummings, French, et al., 1977 | gas phase; switching reaction(Cl-)4-F-phenol, Entropy change calculated or estimated; French, Ikuta, et al., 1982; M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 27.3 ± 2.0 | kcal/mol | TDEq | Cummings, French, et al., 1977 | gas phase; Re-anchored to data in French, Ikuta, et al., 1982.; B |
Free energy of reaction
| ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 24.7 | 423. | PHPMS | Paul and Kebarle, 1990 | gas phase; Entropy change calculated or estimated; M |
| 26.2 | 300. | PHPMS | Cummings, French, et al., 1977 | gas phase; switching reaction(Cl-)4-Cl-phenol, Entropy change calculated or estimated; French, Ikuta, et al., 1982; M |
| 25.8 | 300. | PHPMS | Cummings, French, et al., 1977 | gas phase; switching reaction(Cl-)4-F-phenol, Entropy change calculated or estimated; French, Ikuta, et al., 1982; M |
+
= (
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By formula: I- + C7H5NO = (I- • C7H5NO)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 23.8 ± 1.8 | kcal/mol | IMRE | Paul and Kebarle, 1990 | gas phase; ΔGaff at 423 K; B,M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrS° | 21. | cal/mol*K | N/A | Paul and Kebarle, 1990 | gas phase; Entropy change calculated or estimated; M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 14.9 ± 1.0 | kcal/mol | IMRE | Paul and Kebarle, 1990 | gas phase; ΔGaff at 423 K; B |
Free energy of reaction
| ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 14.9 | 423. | PHPMS | Paul and Kebarle, 1990 | gas phase; Entropy change calculated or estimated; M |
References
Go To: Top, Ion clustering data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
Cummings, French, et al., 1977
Cummings, J.B.; French, M.A.; Kebarle, P.,
Effect of charge delocalization on hydrogen bonding to negative ions and solvation of negative ions. Substituted phenols and phenoxide ions,
J. Am. Chem. Soc., 1977, 99, 6999. [all data]
French, Ikuta, et al., 1982
French, M.A.; Ikuta, S.; Kebarle, P.,
Hydrogen bonding of O-H and C-H hydrogen donors to Cl-. Results from mass spectrometric measurement of the ion-molecule equilibria RH + Cl- = RHCl-,
Can. J. Chem., 1982, 60, 1907. [all data]
Notes
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- 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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