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
View 3d structure (requires JavaScript / HTML 5) - Other names: Benzonitrile, p-hydroxy-; p-Cyanophenol; p-Hydroxybenzonitrile; 4-Cyanophenol; 4-Hydroxybenzonitrile; 4-Hydroxybenzoic acid nitrile
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Condensed phase thermochemistry data
Go To: Top, Ion clustering 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°solid | -60.92 | kJ/mol | Ccb | Zavoianu, Ciocazanu, et al., 1988 | |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -3408. | kJ/mol | Ccb | Zavoianu, Ciocazanu, et al., 1988 |
Ion clustering data
Go To: Top, Condensed phase thermochemistry 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 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
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= (
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By formula: Br- + C7H5NO = (Br- • C7H5NO)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 116. ± 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° | 75.7 ± 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 |
|---|---|---|---|---|
| 75.7 | 423. | PHPMS | Paul and Kebarle, 1990 | gas phase; switching reaction,Thermochemical ladder(Br-)C6H5OH, Entropy change calculated or estimated; M |
+
= (
•
)
By formula: Cl- + C7H5NO = (Cl- • C7H5NO)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 147. ± 8.4 | kJ/mol | TDEq | Cummings, French, et al., 1977 | gas phase; Re-anchored to data in French, Ikuta, et al., 1982.; B,M,M |
| ΔrH° | 148. | kJ/mol | PHPMS | Paul and Kebarle, 1990 | gas phase; Entropy change calculated or estimated; M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrS° | 100. | J/mol*K | N/A | Paul and Kebarle, 1990 | gas phase; Entropy change calculated or estimated; M |
| ΔrS° | 120. | J/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° | 110. | J/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° | 114. ± 8.4 | kJ/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° (kJ/mol) | T (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 103. | 423. | PHPMS | Paul and Kebarle, 1990 | gas phase; Entropy change calculated or estimated; M |
| 110. | 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 |
| 108. | 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 |
+
= (
•
)
By formula: I- + C7H5NO = (I- • C7H5NO)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 99.6 ± 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° | 62.3 ± 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 |
|---|---|---|---|---|
| 62.3 | 423. | PHPMS | Paul and Kebarle, 1990 | gas phase; Entropy change calculated or estimated; M |
References
Go To: Top, Condensed phase thermochemistry data, Ion clustering data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Zavoianu, Ciocazanu, et al., 1988
Zavoianu, D.; Ciocazanu, I.; Moga-Gheorghe, S.; Bornaz, C.,
Structure and reactivity of nitriles. Heat of combustion and formation of some benzonitrile derivatives,
Rev. Chim. (Bucharest), 1988, 39, 487-489. [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]
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
Go To: Top, Condensed phase thermochemistry data, Ion clustering data, References
- Symbols used in this document:
T Temperature ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions 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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