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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
Deltafgas-21.6 ± 0.29kcal/molCcrSabbah and Gouali, 1996Author was aware that data differs from previously reported values
Deltafgas-19.5 ± 0.41kcal/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
Deltafsolid-46.39kcal/molCcrSabbah and Gouali, 1996Author was aware that data differs from previously reported values
Deltafsolid-45.6 ± 0.2kcal/molCcbNunez, Barral, et al., 1986 
Deltafsolid-40.1kcal/molCcbLemoult, 1906Author value for hf298-condensed=-44 kcal/mol
Quantity Value Units Method Reference Comment
Deltacsolid-757.0 ± 0.2kcal/molCcrSabbah and Gouali, 1996Author was aware that data differs from previously reported values
Deltacsolid-757.9 ± 0.1kcal/molCcbNunez, Barral, et al., 1986 
Deltacsolid-763.3kcal/molCcbLemoult, 1906Author value for hf298-condensed=-44 kcal/mol

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 bullet Phenol, 4-amino-)

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

Quantity Value Units Method Reference Comment
Deltar19.5 ± 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
Deltar9.8 ± 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
9.8423.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
Deltar352.5 ± 2.1kcal/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Deltar354.5 ± 2.3kcal/molG+TSKebarle and McMahon, 1977gas phase; B
Quantity Value Units Method Reference Comment
Deltar345.6 ± 2.0kcal/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Deltar347.6 ± 2.0kcal/molIMREKebarle and McMahon, 1977gas 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