Phenol, 4-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-27.41 ± 0.29kcal/molCcrSabbah and Gouali, 1994Author was aware that data differs from previously reported values
Δfgas-28.13 ± 0.48kcal/molCcbFinch, Gardner, et al., 1983 

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 as indicated in comments:
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
Δfsolid-49.50 ± 0.26kcal/molCcrSabbah and Gouali, 1994Author was aware that data differs from previously reported values; ALS
Δfsolid-50.76 ± 0.24kcal/molCcbFinch, Gardner, et al., 1983ALS
Δfsolid-54.19kcal/molCcbRinkenbach, 1930Author hf298_condensed[kcal/mol]=-56.50; ALS
Δfsolid-50.0kcal/molCcbSwarts, 1914See 14SWA2; ALS
Quantity Value Units Method Reference Comment
Δcsolid-685.59 ± 0.24kcal/molCcrSabbah and Gouali, 1994Author was aware that data differs from previously reported values; ALS
Δcsolid-684.32 ± 0.13kcal/molCcbFinch, Gardner, et al., 1983ALS
Δcsolid-680.91kcal/molCcbRinkenbach, 1930Author hf298_condensed[kcal/mol]=-56.50; ALS
Δcsolid-687.0kcal/molCcbGarner and Abernethy, 1921ALS
Δcsolid-688.23kcal/molCcbSwarts, 1914See 14SWA2; ALS

Constant pressure heat capacity of solid

Cp,solid (cal/mol*K) Temperature (K) Reference Comment
34.4283.Campbell and Campbell, 1941T = 273 to 293 K. Value given as Cp = 0.248 cal/g over temperature range 0 to 20°C.; DH

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
Tboil552.2KN/AAldrich Chemical Company Inc., 1990BS
Quantity Value Units Method Reference Comment
Tfus385. ± 10.KAVGN/AAverage of 9 values; Individual data points
Quantity Value Units Method Reference Comment
Δsub22.08 ± 0.10kcal/molCSabbah and Gouali, 1994Author was aware that data differs from previously reported values; ALS
Δsub22.1kcal/molCSabbah and Gouali, 1994, 2AC
Δsub23.6 ± 0.2kcal/molMEParsons, Rochester, et al., 1971Based on data from 305. - 352. K.; AC

Enthalpy of sublimation

ΔsubH (kcal/mol) Temperature (K) Method Reference Comment
21.8 ± 0.4343.VWolf and Weghofer, 1938ALS
21.8 ± 0.41339. - 351.N/ATrieschmann, 1935See also Wolf and Weghofer, 1938, 2 and Jones, 1960.; AC

Enthalpy of fusion

ΔfusH (kcal/mol) Temperature (K) Reference Comment
7.1984385.15Singh and Kumar, 1986DH
4.3628387.0Poeti, Fanelli, et al., 1982DH
2.63386.4Musuc, Razus, et al., 2002AC
4.362388.2Domalski and Hearing, 1996See also Sabbah and Gouali, 1994, 2.; AC
4.6128368.75Booss and Hauschildt, 1972DH
5.8009387.Campbell and Campbell, 1941DH

Entropy of fusion

ΔfusS (cal/mol*K) Temperature (K) Reference Comment
18.7385.15Singh and Kumar, 1986DH
11.27387.0Poeti, Fanelli, et al., 1982DH
12.5368.75Booss and Hauschildt, 1972DH
15.0387.Campbell and Campbell, 1941DH

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

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

Quantity Value Units Method Reference Comment
Δr28.4 ± 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
Δr18.7 ± 1.0kcal/molIMREPaul and Kebarle, 1990gas phase; ΔGaff at 423 K; B

Free energy of reaction

ΔrG° (kcal/mol) T (K) Method Reference Comment
18.7423.PHPMSPaul and Kebarle, 1990gas phase; switching reaction,Thermochemical ladder(Br-)C6H5OH, Entropy change calculated or estimated; M

C6H4NO3- + Hydrogen cation = Phenol, 4-nitro-

By formula: C6H4NO3- + H+ = C6H5NO3

Quantity Value Units Method Reference Comment
Δr327.7 ± 2.1kcal/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Δr320.9 ± 2.0kcal/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B

IR Spectrum

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Mass spectrum (electron ionization), References, Notes

Data compiled by: Coblentz Society, Inc.

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


Mass spectrum (electron ionization)

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

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-NW-1737
NIST MS number 229414

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References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), 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]

Finch, Gardner, et al., 1983
Finch, A.; Gardner, P.J.; Wu, D., Studies on nitrophenols. Part IV. The standard enthalpies of combustion and formation of 1,2-dihydroxybenzene, 1,2- and 1,4-nitrophenol, Thermochim. Acta, 1983, 66, 333-342. [all data]

Rinkenbach, 1930
Rinkenbach, W.H., The heats of combustion and formation of aromatic nitro compounds, J. Am. Chem. Soc., 1930, 52, 115-120. [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]

Garner and Abernethy, 1921
Garner, W.E.; Abernethy, C.L., Heats of combustion and formation of nitro-compounds. Part I. - Benzene, toluene, phenol and methylaniline series, Proc. Roy. Soc. London A, 1921, 213-235. [all data]

Campbell and Campbell, 1941
Campbell, A.N.; Campbell, A.J.R., The system naphthalene-p-nitrophenol: an experimental investigation of all the variables in an equation of the freezing point curve, Can. J. Res., 1941, B19, 73-79. [all data]

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [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]

Parsons, Rochester, et al., 1971
Parsons, G.H.; Rochester, C.H.; Wood, C.E.C., Effect of 4-substitution on the thermodynamics of hydration of phenol and the phenoxide anion, J. Chem. Soc., B:, 1971, 533, https://doi.org/10.1039/j29710000533 . [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]

Singh and Kumar, 1986
Singh, N.B.; Kumar, P., Solidification behavior of the cinnamic acid-p-nitrophenol eutectic system, J. Chem. Eng. Data, 1986, 31, 406-408. [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]

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]

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]

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]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), References