Phenol, 4-amino-
- Formula: C6H7NO
- Molecular weight: 109.1259
- IUPAC Standard InChI: InChI=1S/C6H7NO/c7-5-1-3-6(8)4-2-5/h1-4,8H,7H2
- IUPAC Standard InChIKey: PLIKAWJENQZMHA-UHFFFAOYSA-N
- CAS Registry Number: 123-30-8
- 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, p-amino-; p-Aminophenol; p-Hydroxyaniline; p-Hydroxyphenylamine; Activol; Azol; Benzofur P; BASF Ursol P Base; C.I. Oxidation Base 6; C.I. 76550; Certinal; Citol; Durafur Brown RB; Fouramine P; Fourrine P Base; Fourrine 84; Furro P base; Nako Brown R; Paranol; Pelagol Grey P Base; Pelagol P Base; Renal AC; Rodinal; Tertral P Base; Unal; Ursol P; Ursol P Base; Zoba Brown P Base; 1-Amino-4-hydroxybenzene; 4-Amino-1-hydroxybenzene; 4-Aminophenol; 4-Hydroxyaniline; p-Aminofenol; C.I. Oxidation Base 6A; PAP; UN 2512; 4-Aminobenzenol; Kodelon; Para-aminophenol; Paramidophenol; Takatol; NSC 1545; Furro P (Salt/Mix); Futramine P (Salt/Mix); Pelagol CP (Salt/Mix); Pelagol Grey CP (Salt/Mix); Peltol P (Salt/Mix); Durafur Brown R (Salt/Mix)
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Reaction 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | -21.6 ± 0.29 | kcal/mol | Ccr | Sabbah and Gouali, 1996 | Author was aware that data differs from previously reported values |
| ΔfH°gas | -19.5 ± 0.41 | kcal/mol | Ccb | Nunez, Barral, et al., 1986 |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, Reaction 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°solid | -46.39 | kcal/mol | Ccr | Sabbah and Gouali, 1996 | Author was aware that data differs from previously reported values |
| ΔfH°solid | -45.6 ± 0.2 | kcal/mol | Ccb | Nunez, Barral, et al., 1986 | |
| ΔfH°solid | -40.1 | kcal/mol | Ccb | Lemoult, 1906 | Author value for hf298-condensed=-44 kcal/mol |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -757.0 ± 0.2 | kcal/mol | Ccr | Sabbah and Gouali, 1996 | Author was aware that data differs from previously reported values |
| ΔcH°solid | -757.9 ± 0.1 | kcal/mol | Ccb | Nunez, Barral, et al., 1986 | |
| ΔcH°solid | -763.3 | kcal/mol | Ccb | Lemoult, 1906 | Author value for hf298-condensed=-44 kcal/mol |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, 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. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.
Individual Reactions
+
= (
•
)
By formula: Br- + C6H7NO = (Br- • C6H7NO)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 19.5 ± 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; Entropy change calculated or estimated; M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 9.8 ± 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 |
|---|---|---|---|---|
| 9.8 | 423. | PHPMS | Paul and Kebarle, 1990 | gas phase; Entropy change calculated or estimated; M |
C6H6NO- + =
By formula: C6H6NO- + H+ = C6H7NO
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 352.5 ± 2.1 | kcal/mol | G+TS | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale; B |
| ΔrH° | 354.5 ± 2.3 | kcal/mol | G+TS | Kebarle and McMahon, 1977 | gas phase; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 345.6 ± 2.0 | kcal/mol | IMRE | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale; B |
| ΔrG° | 347.6 ± 2.0 | kcal/mol | IMRE | Kebarle and McMahon, 1977 | gas phase; B |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Sabbah and Gouali, 1996
Sabbah, R.; Gouali, M.,
Energetique des liaisons inter et intramoleculaires dans les trois isomeres de l'aminophenol,
Can. J. Chem., 1996, 74, 500-507. [all data]
Nunez, Barral, et al., 1986
Nunez, L.; Barral, L.; Largo, S.G.; Pilcher, G.,
Enthalpies of combustion of the three aminophenols,
J. Chem. Thermodyn., 1986, 18, 575-579. [all data]
Lemoult, 1906
Lemoult, M.P.,
Thermochimie. - Chaleur de combustion et de formation de quelques composes cycliques azotes,
Compt. Rend., 1906, 143, 772-775. [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]
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 thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, References
- Symbols used in this document:
T Temperature ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°gas Enthalpy of formation of gas 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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