Phenol, 4-amino-

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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
Δfgas-90.5 ± 1.2kJ/molCcrSabbah and Gouali, 1996Author was aware that data differs from previously reported values
Δfgas-81.5 ± 1.7kJ/molCcbNunez, Barral, et al., 1986 

Condensed 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
Δfsolid-194.1kJ/molCcrSabbah and Gouali, 1996Author was aware that data differs from previously reported values
Δfsolid-190.6 ± 0.9kJ/molCcbNunez, Barral, et al., 1986 
Δfsolid-168.kJ/molCcbLemoult, 1906Author value for hf298-condensed=-44 kcal/mol
Quantity Value Units Method Reference Comment
Δcsolid-3167.4 ± 0.9kJ/molCcrSabbah and Gouali, 1996Author was aware that data differs from previously reported values
Δcsolid-3170.9 ± 0.5kJ/molCcbNunez, Barral, et al., 1986 
Δcsolid-3194.kJ/molCcbLemoult, 1906Author value for hf298-condensed=-44 kcal/mol

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:
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
Tfus459.5KN/ABret-Dibat and Lichanot, 1989Uncertainty assigned by TRC = 0.5 K; TRC
Tfus457.KN/AKemula, Buchowski, et al., 1968Uncertainty assigned by TRC = 0.2 K; TRC
Tfus465.KN/ADunn, 1954Uncertainty assigned by TRC = 2. K; TRC
Tfus462.5KN/ADunn, 1954Uncertainty assigned by TRC = 1. K; TRC
Tfus463.4KN/ADunn, 1954Uncertainty assigned by TRC = 1. K; TRC
Quantity Value Units Method Reference Comment
Δsub103.63 ± 0.65kJ/molCSabbah and Gouali, 1996Author was aware that data differs from previously reported values; ALS
Δsub103.6 ± 0.7kJ/molCSabbah and Gouali, 1996AC
Δsub109.1 ± 1.4kJ/molCNunez, Barral, et al., 1986ALS
Δsub109.1 ± 1.4kJ/molCNunez, Barral, et al., 1986AC

Antoine Equation Parameters

log10(P) = A − (B / (T + C))
    P = vapor pressure (bar)
    T = temperature (K)

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Temperature (K) A B C Reference Comment
403.3 - 458.5-0.1507136.675-361.969Dunn, 1954, 2Coefficents calculated by NIST from author's data.

Enthalpy of sublimation

ΔsubH (kJ/mol) Temperature (K) Method Reference Comment
101.1 ± 0.7335.CSabbah and Gouali, 1996AC
111.0438.N/AStephenson and Malanowski, 1987Based on data from 423. - 459. K.; AC
92.1417.IDunn, 1954, 2Based on data from 403. - 430. K. See also Jones, 1960.; AC

Enthalpy of fusion

ΔfusH (kJ/mol) Temperature (K) Reference Comment
23.8455.2Rotich, Glass, et al., 2001AC
31.2459.5Domalski and Hearing, 1996See also Bret-Dibat and Lichanot, 1989, 2.; AC
26.0462.5Domalski and Hearing, 1996See also Sabbah and Gouali, 1996.; AC

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, 4-amino- = (Bromine anion • Phenol, 4-amino-)

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

Quantity Value Units Method Reference Comment
Δr81.6 ± 7.5kJ/molIMREPaul and Kebarle, 1990gas phase; ΔGaff at 423 K; B,M
Quantity Value Units Method Reference Comment
Δr96.J/mol*KN/APaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr41. ± 4.2kJ/molIMREPaul and Kebarle, 1990gas phase; ΔGaff at 423 K; B

Free energy of reaction

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

C6H6NO- + Hydrogen cation = Phenol, 4-amino-

By formula: C6H6NO- + H+ = C6H7NO

Quantity Value Units Method Reference Comment
Δr1475. ± 8.8kJ/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Δr1483. ± 9.6kJ/molG+TSKebarle and McMahon, 1977gas phase; B
Quantity Value Units Method Reference Comment
Δr1446. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Δr1454. ± 8.4kJ/molIMREKebarle and McMahon, 1977gas 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 compiled by: John E. Bartmess

View reactions leading to C6H7NO+ (ion structure unspecified)

De-protonation reactions

C6H6NO- + Hydrogen cation = Phenol, 4-amino-

By formula: C6H6NO- + H+ = C6H7NO

Quantity Value Units Method Reference Comment
Δr1475. ± 8.8kJ/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Δr1483. ± 9.6kJ/molG+TSKebarle and McMahon, 1977gas phase
Quantity Value Units Method Reference Comment
Δr1446. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Δr1454. ± 8.4kJ/molIMREKebarle and McMahon, 1977gas phase

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, 4-amino- = (Bromine anion • Phenol, 4-amino-)

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

Quantity Value Units Method Reference Comment
Δr81.6 ± 7.5kJ/molIMREPaul and Kebarle, 1990gas phase; ΔGaff at 423 K; B,M
Quantity Value Units Method Reference Comment
Δr96.J/mol*KN/APaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr41. ± 4.2kJ/molIMREPaul and Kebarle, 1990gas phase; ΔGaff at 423 K; B

Free energy of reaction

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

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director


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, Gas Chromatography, NIST Free Links, 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

View image of digitized spectrum (can be printed in landscape orientation).

Due to licensing restrictions, this spectrum cannot be downloaded.

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-NW-1627
NIST MS number 228504

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.


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), NIST Free Links, 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-301314.Grzybowski, Lamparczyk, et al., 1980Chromosorb W HMDS (80-100 mesh); Column length: 2.9 m; Program: not specified

Van Den Dool and Kratz RI, non-polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
PackedSE-301265.Peng, Ding, et al., 1988He, Supelcoport and Chromosorb, 40. C @ 4. min, 10. K/min, 250. C @ 60. min; Column length: 3.05 m
PackedSE-301265.Peng, Ding, et al., 1988He, Supelcoport and Chromosorb, 40. C @ 4. min, 10. K/min, 250. C @ 60. min; Column length: 3.05 m

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

View large format table.

Column type Active phase I Reference Comment
CapillarySE-301314.Peterson, 1992Program: not specified
CapillaryOV-1, SE-30, Methyl silicone, SP-2100, OV-101, DB-1, etc.1314.Waggott and Davies, 1984Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified
OtherMethyl Silicone1265.Ardrey and Moffat, 1981Program: 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), Gas Chromatography, NIST Free Links, 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]

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]

Dunn, 1954
Dunn, S.A., Some physical properties of p-aminophenol, J. Am. Chem. Soc., 1954, 76, 6191. [all data]

Dunn, 1954, 2
Dunn, S.A., Some Physical Properties of p-Aminophenol, J. Am. Chem. Soc., 1954, 76, 23, 6191-6192, https://doi.org/10.1021/ja01652a096 . [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

Jones, 1960
Jones, A.H., Sublimation Pressure Data for Organic Compounds., J. Chem. Eng. Data, 1960, 5, 2, 196-200, https://doi.org/10.1021/je60006a019 . [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]

Bret-Dibat and Lichanot, 1989, 2
Bret-Dibat, P.; Lichanot, A., Thermodynamic properties of positional isomers of disubstituted benzene in condensed phase, Thermochim. Acta, 1989, 147(2), 261-271. [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]

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]

Peng, Ding, et al., 1988
Peng, C.T.; Ding, S.F.; Hua, R.L.; Yang, Z.C., Prediction of Retention Indexes I. Structure-Retention Index Relationship on Apolar Columns, J. Chromatogr., 1988, 436, 137-172, https://doi.org/10.1016/S0021-9673(00)94575-8 . [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]

Ardrey and Moffat, 1981
Ardrey, R.E.; Moffat, A.C., Gas-liquid chromatographic retention indices of 1318 substances of toxicological interest on SE-30 or OV-1 stationary phase, J. Chromatogr., 1981, 220, 3, 195-252, https://doi.org/10.1016/S0021-9673(00)81925-1 . [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), Gas Chromatography, NIST Free Links, References