Phenol, 3-amino-
- Formula: C6H7NO
- Molecular weight: 109.1259
- IUPAC Standard InChIKey: CWLKGDAVCFYWJK-UHFFFAOYSA-N
- CAS Registry Number: 591-27-5
- 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: m-Hydroxyaniline; Phenol, m-amino-; m-Aminophenol; m-Hydroxyaminobenzene; m-Hydroxyphenylamine; C.I. Oxidation Base 7; C.I. 76545; Fouramine EG; Fourrine EG; Fourrine 65; Furro EG; Futramine EG; Nako TEG; Pelagol EG; Renal EG; Tertral EG; Ursol EG; Zoba EG; 1-Amino-3-hydroxybenzene; 3-Aminophenol; 3-Hydroxyaniline; m-Aminofenol; Basf ursol eg; 3-Amino-1-hydroxybenzene; 3-Hydroxybenzenamine; NSC 1546
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Gas phase thermochemistry 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -23.6 ± 0.38 | kcal/mol | Ccr | Sabbah and Gouali, 1996 | Author was aware that data differs from previously reported values |
ΔfH°gas | -21.4 ± 0.38 | kcal/mol | Ccb | Nunez, Barral, et al., 1986 |
Phase change 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:
BS - Robert L. Brown and Stephen E. Stein
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
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tfus | 394. | K | N/A | Bret-Dibat and Lichanot, 1989 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.5 K; TRC |
Tfus | 397. to 399. | K | N/A | Buckingham and Donaghy, 1982 | BS |
Tfus | 396. | K | N/A | Kemula, Buchowski, et al., 1968 | Uncertainty assigned by TRC = 0.2 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 24.3 ± 0.2 | kcal/mol | C | Sabbah and Gouali, 1996 | Author was aware that data differs from previously reported values; ALS |
ΔsubH° | 24.3 ± 0.2 | kcal/mol | C | Sabbah and Gouali, 1996 | AC |
ΔsubH° | 25.02 ± 0.29 | kcal/mol | C | Nunez, Barral, et al., 1986 | ALS |
ΔsubH° | 25.02 ± 0.29 | kcal/mol | C | Nunez, Barral, et al., 1986 | AC |
Reduced pressure boiling point
Tboil (K) | Pressure (atm) | Reference | Comment |
---|---|---|---|
437.2 | 0.014 | Weast and Grasselli, 1989 | BS |
437. | 0.014 | Buckingham and Donaghy, 1982 | BS |
Enthalpy of sublimation
ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
23.6 ± 0.2 | 335. | C | Sabbah and Gouali, 1996 | AC |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
5.4892 | 396. | Singh, Gupta, et al., 1990 | DH |
5.246 | 396.8 | Huang, 2003 | See also Huang, Tang, et al., 2005.; AC |
5.71 | 390.7 | Rotich, Glass, et al., 2001 | AC |
5.492 | 399. | Rai and George, 1991 | AC |
Reaction thermochemistry 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
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° | 20.3 ± 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° | 10.6 ± 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 |
---|---|---|---|---|
10.6 | 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° | 350.5 ± 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° | 351.2 ± 2.3 | kcal/mol | G+TS | Kebarle and McMahon, 1977 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 343.7 ± 2.0 | kcal/mol | IMRE | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale; B |
ΔrG° | 344.3 ± 2.0 | kcal/mol | IMRE | Kebarle and McMahon, 1977 | gas phase; B |
Gas phase ion energetics 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 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) | 214.8 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 207.2 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
De-protonation reactions
C6H6NO- + =
By formula: C6H6NO- + H+ = C6H7NO
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 350.5 ± 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° | 351.2 ± 2.3 | kcal/mol | G+TS | Kebarle and McMahon, 1977 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 343.7 ± 2.0 | kcal/mol | IMRE | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale; B |
ΔrG° | 344.3 ± 2.0 | kcal/mol | IMRE | Kebarle and McMahon, 1977 | gas phase; B |
Mass spectrum (electron ionization)
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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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
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Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | Japan AIST/NIMC Database- Spectrum MS-IW-4311 |
NIST MS number | 228498 |
UV/Visible spectrum
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Spectrum
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Additional Data
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Source | Vanderhaege and Derudder, 1952 |
---|---|
Owner | INEP CP RAS, NIST OSRD Collection (C) 2007 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
Origin | INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS |
Source reference | RAS UV No. 184 |
Instrument | n.i.g. |
Melting point | 123 |
Boiling point | 464/ 11 mm |
Gas Chromatography
Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, 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, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Packed | SE-30 | 1335. | 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 | 1335. | Peterson, 1992 | Program: not specified |
Capillary | OV-1, SE-30, Methyl silicone, SP-2100, OV-101, DB-1, etc. | 1335. | Waggott and Davies, 1984 | Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified |
References
Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, 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]
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]
Buckingham and Donaghy, 1982
Buckingham, J.; Donaghy, S.M.,
Dictionary of Organic Compounds: Fifth Edition, Chapman and Hall, New York, 1982, 1. [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]
Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]
Singh, Gupta, et al., 1990
Singh, R.N.; Gupta, J.P.; Singh, N.; Singh, N.P.; Singh, O.P.; Singh, N.B.; Hopkins, R.H.; Mazelsky, R.,
Growth conditions of organic non-linear optical crystals,
Thermochim. Acta, 1990, 165(2), 297-299. [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]
Rai and George, 1991
Rai, U.S.; George, Santhi,
Some Physicochemical Studies on Binary Organic Eutectics and 1:2 Molecular Complexes,
Cryst. Res. Technol., 1991, 26, 4, 511-519, https://doi.org/10.1002/crat.2170260426
. [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]
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]
Vanderhaege and Derudder, 1952
Vanderhaege, H.; Derudder, G.,
Bull. soc. chim. Belges, 1952, 61, 310. [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]
Waggott and Davies, 1984
Waggott, A.; Davies, I.W.,
Identification of organic pollutants using linear temperature programmed retention indices (LTPRIs) - Part II, 1984, retrieved from http://dwi.defra.gov.uk/research/completed-research/reports/dwi0383.pdf. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, References
- Symbols used in this document:
T Temperature Tboil Boiling point Tfus Fusion (melting) point ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfusH Enthalpy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy 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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