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Phenol, 3-amino-

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Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Deltafgas-23.6 ± 0.38kcal/molCcrSabbah and Gouali, 1996Author was aware that data differs from previously reported values
Deltafgas-21.4 ± 0.38kcal/molCcbNunez, Barral, et al., 1986 

Condensed phase thermochemistry data

Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Deltafsolid-47.85 ± 0.29kcal/molCcrSabbah and Gouali, 1996Author was aware that data differs from previously reported values
Deltafsolid-46.39 ± 0.24kcal/molCcbNunez, Barral, et al., 1986 
Quantity Value Units Method Reference Comment
Deltacsolid-755.54 ± 0.29kcal/molCcrSabbah and Gouali, 1996Author was aware that data differs from previously reported values
Deltacsolid-757.0 ± 0.1kcal/molCcbNunez, 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
Tfus394.KN/ABret-Dibat and Lichanot, 1989Crystal phase 1 phase; Uncertainty assigned by TRC = 0.5 K; TRC
Tfus397. - 399.KN/ABuckingham and Donaghy, 1982BS
Tfus396.KN/AKemula, Buchowski, et al., 1968Uncertainty assigned by TRC = 0.2 K; TRC
Quantity Value Units Method Reference Comment
Deltasub24.3 ± 0.2kcal/molCSabbah and Gouali, 1996Author was aware that data differs from previously reported values; ALS
Deltasub24.3 ± 0.2kcal/molCSabbah and Gouali, 1996AC
Deltasub25.02 ± 0.29kcal/molCNunez, Barral, et al., 1986ALS
Deltasub25.02 ± 0.29kcal/molCNunez, Barral, et al., 1986AC

Reduced pressure boiling point

Tboil (K) Pressure (atm) Reference Comment
437.20.014Weast and Grasselli, 1989BS
437.0.014Buckingham and Donaghy, 1982BS

Enthalpy of sublimation

DeltasubH (kcal/mol) Temperature (K) Method Reference Comment
23.6 ± 0.2335.CSabbah and Gouali, 1996AC

Enthalpy of fusion

DeltafusH (kcal/mol) Temperature (K) Reference Comment
5.4892396.Singh, Gupta, et al., 1990DH
5.246396.8Huang, 2003See also Huang, Tang, et al., 2005.; AC
5.71390.7Rotich, Glass, et al., 2001AC
5.492399.Rai and George, 1991AC

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


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

Bromine anion + Phenol, 3-amino- = (Bromine anion bullet Phenol, 3-amino-)

By formula: Br- + C6H7NO = (Br- bullet C6H7NO)

Quantity Value Units Method Reference Comment
Deltar20.3 ± 1.8kcal/molIMREPaul and Kebarle, 1990gas phase; «DELTA»Gaff at 423 K; B,M
Quantity Value Units Method Reference Comment
Deltar23.cal/mol*KN/APaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar10.6 ± 1.0kcal/molIMREPaul and Kebarle, 1990gas phase; «DELTA»Gaff at 423 K; B

Free energy of reaction

DeltarG° (kcal/mol) T (K) Method Reference Comment
10.6423.PHPMSPaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M

C6H6NO- + Hydrogen cation = Phenol, 3-amino-

By formula: C6H6NO- + H+ = C6H7NO

Quantity Value Units Method Reference Comment
Deltar350.5 ± 2.1kcal/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Deltar351.2 ± 2.3kcal/molG+TSKebarle and McMahon, 1977gas phase; B
Quantity Value Units Method Reference Comment
Deltar343.7 ± 2.0kcal/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Deltar344.3 ± 2.0kcal/molIMREKebarle and McMahon, 1977gas phase; B

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, 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)214.8kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity207.2kcal/molN/AHunter and Lias, 1998HL

De-protonation reactions

C6H6NO- + Hydrogen cation = Phenol, 3-amino-

By formula: C6H6NO- + H+ = C6H7NO

Quantity Value Units Method Reference Comment
Deltar350.5 ± 2.1kcal/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Deltar351.2 ± 2.3kcal/molG+TSKebarle and McMahon, 1977gas phase; B
Quantity Value Units Method Reference Comment
Deltar343.7 ± 2.0kcal/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Deltar344.3 ± 2.0kcal/molIMREKebarle and McMahon, 1977gas phase; B

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

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

Bromine anion + Phenol, 3-amino- = (Bromine anion bullet Phenol, 3-amino-)

By formula: Br- + C6H7NO = (Br- bullet C6H7NO)

Quantity Value Units Method Reference Comment
Deltar20.3 ± 1.8kcal/molIMREPaul and Kebarle, 1990gas phase; «DELTA»Gaff at 423 K; B,M
Quantity Value Units Method Reference Comment
Deltar23.cal/mol*KN/APaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar10.6 ± 1.0kcal/molIMREPaul and Kebarle, 1990gas phase; «DELTA»Gaff at 423 K; B

Free energy of reaction

DeltarG° (kcal/mol) T (K) Method Reference Comment
10.6423.PHPMSPaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M

IR Spectrum

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, Mass spectrum (electron ionization), UV/Visible spectrum, 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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Gas Phase Spectrum

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IR spectrum
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Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.

Additional Data

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Owner NIST Standard Reference Data Program
Collection (C) 2018 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin Sadtler Research Labs Under US-EPA Contract
State gas

This IR spectrum is from the NIST/EPA Gas-Phase Infrared Database .


Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, UV/Visible spectrum, 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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Mass 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

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


UV/Visible spectrum

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), 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 by: Victor Talrose, Alexander N. Yermakov, Alexy A. Usov, Antonina A. Goncharova, Axlexander N. Leskin, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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UVVis 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, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, 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

View large format table.

Column type Active phase I Reference Comment
PackedSE-301335.Grzybowski, Lamparczyk, et al., 1980Chromosorb W HMDS (80-100 mesh); Column length: 2.9 m; Program: not specified

Normal alkane RI, non-polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
CapillarySE-301335.Peterson, 1992Program: not specified
CapillaryOV-1, SE-30, Methyl silicone, SP-2100, OV-101, DB-1, etc.1335.Waggott and Davies, 1984Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, 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, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, References