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Phenol, 3-nitro-

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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-26.12 ± 0.26kcal/molCcrSabbah and Gouali, 1994Author was aware that data differs from previously reported values
Deltafgas-25.22 ± 0.43kcal/molCcbRibeiro Da Silva, Reis, et al., 1992 

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-47.92 ± 0.24kcal/molCcrSabbah and Gouali, 1994Author was aware that data differs from previously reported values
Deltafsolid-49.16 ± 0.41kcal/molCcbRibeiro Da Silva, Reis, et al., 1992 
Deltafsolid-53.7kcal/molCcbSwarts, 1914See 14SWA2
Quantity Value Units Method Reference Comment
Deltacsolid-687.2 ± 0.2kcal/molCcrSabbah and Gouali, 1994Author was aware that data differs from previously reported values
Deltacsolid-685.95 ± 0.36kcal/molCcbRibeiro Da Silva, Reis, et al., 1992 
Deltacsolid-688.4kcal/molCcbSwarts, 1914See 14SWA2

Reaction thermochemistry data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry 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 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-nitro- = (Bromine anion bullet Phenol, 3-nitro-)

By formula: Br- + C6H5NO3 = (Br- bullet C6H5NO3)

Quantity Value Units Method Reference Comment
Deltar27.4 ± 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; switching reaction,Thermochemical ladder(Br-)C6H5OH, Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar17.7 ± 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
17.7423.PHPMSPaul and Kebarle, 1990gas phase; switching reaction,Thermochemical ladder(Br-)C6H5OH, Entropy change calculated or estimated; M

Iodide + Phenol, 3-nitro- = (Iodide bullet Phenol, 3-nitro-)

By formula: I- + C6H5NO3 = (I- bullet C6H5NO3)

Quantity Value Units Method Reference Comment
Deltar23.2 ± 1.8kcal/molIMREPaul and Kebarle, 1990gas phase; «DELTA»Gaff at 423 K; B,M
Quantity Value Units Method Reference Comment
Deltar21.cal/mol*KN/APaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar14.3 ± 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
14.3423.PHPMSPaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M

C6H4NO3- + Hydrogen cation = Phenol, 3-nitro-

By formula: C6H4NO3- + H+ = C6H5NO3

Quantity Value Units Method Reference Comment
Deltar334.3 ± 2.1kcal/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Deltar334.6 ± 2.6kcal/molG+TSKebarle and McMahon, 1977gas phase; B
Quantity Value Units Method Reference Comment
Deltar327.5 ± 2.0kcal/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Deltar327.7 ± 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, 1994
Sabbah, R.; Gouali, M., Energetics of intra- and inter-molecular bonds in the three nitrophenols, Aust. J. Chem., 1994, 47, 1651-1660. [all data]

Ribeiro Da Silva, Reis, et al., 1992
Ribeiro Da Silva, M.A.V.; Reis, A.M.M.V.; Monte, M.J.S.; Bartolo, M.M.S.S.F.; Rodrigues, J.A.R.G.O., Enthalpy of combustion, vapour pressures, and enthalpy of sublimation of 3-nitrophenol, J. Chem. Thermodyn., 1992, 24, 653-659. [all data]

Swarts, 1914
Swarts, F., Sur la chaleur de combustion de quelques derives nitres aromatlques, Recl. Trav. Chim. Pays-Bas, 1914, 33, 281-298. [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