Phenol, o-amino-
- Formula: C6H7NO
- Molecular weight: 109.1259
- IUPAC Standard InChIKey: CDAWCLOXVUBKRW-UHFFFAOYSA-N
- CAS Registry Number: 95-55-6
- 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: o-Hydroxyaniline; Phenol, 2-amino-; o-Aminophenol; o-Hydroxyphenylamine; Benzofur GG; BASF Ursol 3GA; C.I. Oxidation Base 17; C.I. 76520; Fouramine OP; Nako Yellow 3GA; Paradone Olive Green B; Pelagol Grey GG; Pelagol 3GA; Zoba 3GA; 1-Amino-2-hydroxybenzene; 1-Hydroxy-2-aminobenzene; 2-Aminophenol; 2-Hydroxyaniline; Benzene, 1-hydroxy-2-amine-; Nako Yellow ga; 2-Amino-1-hydroxybenzene; 2-Hydroxyanaline; Questiomycin B; 2-Aminophenyl alcohol; NSC 1534
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Phase change data
Go To: Top, Gas phase ion energetics data, Gas Chromatography, 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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tfus | 447.4 | K | N/A | Bret-Dibat and Lichanot, 1989 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.5 K; TRC |
Tfus | 446.7 | K | N/A | Kemula, Buchowski, et al., 1968 | Uncertainty assigned by TRC = 0.2 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 96.9 ± 0.6 | kJ/mol | C | Sabbah and Gouali, 1996 | Author was aware that data differs from previously reported values; ALS |
ΔsubH° | 96.9 ± 0.6 | kJ/mol | C | Sabbah and Gouali, 1996 | AC |
ΔsubH° | 103.9 ± 0.9 | kJ/mol | C | Nunez, Barral, et al., 1986 | ALS |
ΔsubH° | 103.9 ± 0.9 | kJ/mol | C | Nunez, Barral, et al., 1986 | AC |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
93.5 ± 0.8 | 332. | C | Sabbah and Gouali, 1996 | AC |
95.3 ± 0.7 | 337. | C | Sabbah and Gouali, 1996 | AC |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
21.72 | 447.6 | Huang, 2003 | See also Huang, Tang, et al., 2005.; AC |
31.4 | 443.2 | Rotich, Glass, et al., 2001 | AC |
34.0 | 447.4 | Domalski and Hearing, 1996 | AC |
Gas phase ion energetics data
Go To: Top, Phase change data, Gas Chromatography, 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:
HL - Edward P. Hunter and Sharon G. Lias
Data compiled as indicated in comments:
B - John E. Bartmess
View reactions leading to C6H7NO+ (ion structure unspecified)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 898.8 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 866.9 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
De-protonation reactions
C6H6NO- + =
By formula: C6H6NO- + H+ = C6H7NO
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1460. ± 8.8 | kJ/mol | G+TS | Kebarle and McMahon, 1977 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1428. ± 8.4 | kJ/mol | IMRE | Kebarle and McMahon, 1977 | gas phase; B |
Gas Chromatography
Go To: Top, Phase change data, Gas phase ion energetics 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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Kovats' RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Packed | SE-30 | 180. | 1251. | Dolecka, Raczynska, et al., 1988 | He, Chromosorb W AW; Column length: 2. m |
Kovats' RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Packed | SE-30 | 1242. | Grzybowski, Lamparczyk, et al., 1980 | Chromosorb W HMDS (80-100 mesh); Column length: 2.9 m; Program: not specified |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | SE-30 | 1242. | Peterson, 1992 | Program: not specified |
References
Go To: Top, Phase change data, Gas phase ion energetics data, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Bret-Dibat and Lichanot, 1989
Bret-Dibat, P.; Lichanot, A.,
Proprietes thermodynamiques des isomeres de position de benzenes disubstitues en phase condensee,
Thermochim. Acta, 1989, 147, 2, 261, https://doi.org/10.1016/0040-6031(89)85181-0
. [all data]
Kemula, Buchowski, et al., 1968
Kemula, W.; Buchowski, H.; Pawlowski, W.,
Effect of the position of substituents in an aromatic ring on R(f) and partition coefficients: II. aromatic amines,
Rocz. Chem., 1968, 42, 1951. [all data]
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]
Huang, 2003
Huang, C.-Y.,
, M.S. Thesis, Chinese Culture University, 2003. [all data]
Huang, Tang, et al., 2005
Huang, Chih-Yung; Tang, Muoi; Chen, Yan-Ping,
Solid-Liquid Equilibria for 3-Aminophenol + 2-Aminophenol, 4-(Acetylamino)toluene + 2-(Acetylamino)toluene, and 3,4,5-Trimethoxybenzoic Acid + 2,4,5-Trimethoxybenzoic Acid,
J. Chem. Eng. Data, 2005, 50, 1, 40-43, https://doi.org/10.1021/je049878m
. [all data]
Rotich, Glass, et al., 2001
Rotich, M.K.; Glass, B.D.; Brown, M.E.,
Journal of Thermal Analysis and Calorimetry, 2001, 64, 2, 681-688, https://doi.org/10.1023/A:1011584125859
. [all data]
Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D.,
Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III,
J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985
. [all data]
Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G.,
Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update,
J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018
. [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]
Dolecka, Raczynska, et al., 1988
Dolecka, E.; Raczynska, E.D.; Drapala, T.,
Retention indices and basicity of N1N1-dimethyl-N2-phenylformamidines ortho-substituent effect,
J. Chem. Soc. Perkin Trans. 2:, 1988, 3, 257-260, https://doi.org/10.1039/p29880000257
. [all data]
Grzybowski, Lamparczyk, et al., 1980
Grzybowski, J.; Lamparczyk, H.; Nasal, A.; Radecki, A.,
Relationship between the retention indices of phenols on polar and non-polar stationary phases,
J. Chromatogr., 1980, 196, 2, 217-223, https://doi.org/10.1016/S0021-9673(00)80441-0
. [all data]
Peterson, 1992
Peterson, K.L.,
Counter-Propagation Neural Networks in the Modeling and Prediction of Kovats Indices for Substituted Phenols,
Anal. Chem., 1992, 64, 4, 379-386, https://doi.org/10.1021/ac00028a011
. [all data]
Notes
Go To: Top, Phase change data, Gas phase ion energetics data, Gas Chromatography, References
- Symbols used in this document:
Tfus Fusion (melting) point ΔfusH Enthalpy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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