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
Δfgas-26.12 ± 0.26kcal/molCcrSabbah and Gouali, 1994Author was aware that data differs from previously reported values
Δfgas-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
Δfsolid-47.92 ± 0.24kcal/molCcrSabbah and Gouali, 1994Author was aware that data differs from previously reported values
Δfsolid-49.16 ± 0.41kcal/molCcbRibeiro Da Silva, Reis, et al., 1992 
Δfsolid-53.7kcal/molCcbSwarts, 1914See 14SWA2
Quantity Value Units Method Reference Comment
Δcsolid-687.2 ± 0.2kcal/molCcrSabbah and Gouali, 1994Author was aware that data differs from previously reported values
Δcsolid-685.95 ± 0.36kcal/molCcbRibeiro Da Silva, Reis, et al., 1992 
Δcsolid-688.4kcal/molCcbSwarts, 1914See 14SWA2

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
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Tfus368. ± 4.KAVGN/AAverage of 7 values; Individual data points
Quantity Value Units Method Reference Comment
Δvap20.5kcal/molBHeintz, Kapteina, et al., 2007AC
Quantity Value Units Method Reference Comment
Δsub21.80 ± 0.12kcal/molCSabbah and Gouali, 1994Author was aware that data differs from previously reported values; ALS
Δsub21.8 ± 0.1kcal/molCSabbah and Gouali, 1994, 2AC
Δsub23.9 ± 0.1kcal/molVRibeiro Da Silva, Reis, et al., 1992ALS
Δsub23.9 ± 0.1kcal/molN/ARibeiro Da Silva, Reis, et al., 1992AC

Reduced pressure boiling point

Tboil (K) Pressure (atm) Reference Comment
467.20.092Weast and Grasselli, 1989BS

Enthalpy of sublimation

ΔsubH (kcal/mol) Temperature (K) Method Reference Comment
23.5 ± 0.1321.MERibeiro Da Silva, Reis, et al., 1992AC
18.2319.5AStephenson and Malanowski, 1987Based on data from 305. to 334. K.; AC
21.9 ± 0.5328.VWolf and Weghofer, 1938ALS
21.9 ± 0.41325. to 336.N/ATrieschmann, 1935See also Wolf and Weghofer, 1938, 2 and Jones, 1960.; AC

Enthalpy of fusion

ΔfusH (kcal/mol) Temperature (K) Reference Comment
4.5880370.0Poeti, Fanelli, et al., 1982DH
4.316369.Musuc, Razus, et al., 2002AC
4.587371.2Acree, 1991See also Sabbah and Gouali, 1994, 2.; AC
4.59370.Poeti, Fanelli, et al., 1982AC
5.0908369.95Booss and Hauschildt, 1972DH

Entropy of fusion

ΔfusS (cal/mol*K) Temperature (K) Reference Comment
12.40370.0Poeti, Fanelli, et al., 1982DH
13.8369.95Booss and Hauschildt, 1972DH

Enthalpy of phase transition

ΔHtrs (kcal/mol) Temperature (K) Initial Phase Final Phase Reference Comment
0.0399356.crystaline, IIcrystaline, IWojcik and Marqueton, 1989DH
4.7706370.crystaline, IliquidWojcik and Marqueton, 1989DH

Entropy of phase transition

ΔStrs (cal/mol*K) Temperature (K) Initial Phase Final Phase Reference Comment
0.11356.crystaline, IIcrystaline, IWojcik and Marqueton, 1989DH
13.370.crystaline, IliquidWojcik and Marqueton, 1989DH

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-nitro- = (Bromine anion • Phenol, 3-nitro-)

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

Quantity Value Units Method Reference Comment
Δr27.4 ± 1.8kcal/molIMREPaul and Kebarle, 1990gas phase; ΔGaff at 423 K; B,M
Quantity Value Units Method Reference Comment
Δr23.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
Δr17.7 ± 1.0kcal/molIMREPaul and Kebarle, 1990gas phase; ΔGaff at 423 K; B

Free energy of reaction

ΔrG° (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 • Phenol, 3-nitro-)

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

Quantity Value Units Method Reference Comment
Δr23.2 ± 1.8kcal/molIMREPaul and Kebarle, 1990gas phase; ΔGaff at 423 K; B,M
Quantity Value Units Method Reference Comment
Δr21.cal/mol*KN/APaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr14.3 ± 1.0kcal/molIMREPaul and Kebarle, 1990gas phase; ΔGaff at 423 K; B

Free energy of reaction

ΔrG° (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
Δr334.3 ± 2.1kcal/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Δr334.6 ± 2.6kcal/molG+TSKebarle and McMahon, 1977gas phase; B
Quantity Value Units Method Reference Comment
Δr327.5 ± 2.0kcal/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Δr327.7 ± 2.0kcal/molIMREKebarle and McMahon, 1977gas phase; B

Henry's Law 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: Rolf Sander

Henry's Law constant (water solution)

kH(T) = H exp(d(ln(kH))/d(1/T) ((1/T) - 1/(298.15 K)))
H = Henry's law constant for solubility in water at 298.15 K (mol/(kg*bar))
d(ln(kH))/d(1/T) = Temperature dependence constant (K)

H (mol/(kg*bar)) d(ln(kH))/d(1/T) (K) Method Reference Comment
500000. XN/AValue given here as quoted by missing citation.

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law 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]

Heintz, Kapteina, et al., 2007
Heintz, A.; Kapteina, S.; Verevkin, S.P., Pairwise-Substitution Effects and Intramolecular Hydrogen Bonds in Nitrophenols and Methylnitrophenols. Thermochemical Measurements and ab Initio Calculations, J. Phys. Chem. A, 2007, 111, 28, 6552-6562, https://doi.org/10.1021/jp0730388 . [all data]

Sabbah and Gouali, 1994, 2
Sabbah, R.; Gouali, M., Energetics of Intra- and Inter-molecular Bonds in the Three Nitrophenols, Aust. J. Chem., 1994, 47, 9, 1651-621, https://doi.org/10.1071/CH9941651 . [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]

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]

Wolf and Weghofer, 1938
Wolf, K.L.; Weghofer, H., Uber sublimationswarmen, Z. Phys. Chem., 1938, 39, 194-208. [all data]

Trieschmann, 1935
Trieschmann, H.G., , Ph.D. Dissertation, Inst. Fur Phys. Chem. and Electrochem. der Universitat Kiel, Germany, 1935. [all data]

Wolf and Weghofer, 1938, 2
Wolf, K.L.; Weghofer, H.Z., Z. Phys. Chem. Abt. B, 1938, 39, 194. [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]

Poeti, Fanelli, et al., 1982
Poeti, G.; Fanelli, E.; Braghetti, M., A differential scanning calorimetric study of some phenol derivatives, J. Therm. Anal., 1982, 24(2), 273-279. [all data]

Musuc, Razus, et al., 2002
Musuc, A.M.; Razus, D.; Oancea, D., Analele Universitatii Bucuresti Chimie, 2002, 11, 2, 147. [all data]

Acree, 1991
Acree, William E., Thermodynamic properties of organic compounds: enthalpy of fusion and melting point temperature compilation, Thermochimica Acta, 1991, 189, 1, 37-56, https://doi.org/10.1016/0040-6031(91)87098-H . [all data]

Booss and Hauschildt, 1972
Booss, H.J.; Hauschildt, K.R., Die Schmelzenthalpie des Benzils und 4-Nitrophenols, Z. Anal. Chem., 1972, 261(1), 32. [all data]

Wojcik and Marqueton, 1989
Wojcik, G.; Marqueton, Y., The phase transition of m-nitrophenol, Mol. Cryst. Liq. Cryst., 1989, 168, 247-254. [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, Phase change data, Reaction thermochemistry data, Henry's Law data, References