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-109.3 ± 1.1kJ/molCcrSabbah and Gouali, 1994Author was aware that data differs from previously reported values
Δfgas-105.5 ± 1.8kJ/molCcbRibeiro Da Silva, Reis, et al., 1992 

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
Δvap85.9kJ/molBHeintz, Kapteina, et al., 2007AC
Quantity Value Units Method Reference Comment
Δsub91.23 ± 0.49kJ/molCSabbah and Gouali, 1994Author was aware that data differs from previously reported values; ALS
Δsub91.2 ± 0.5kJ/molCSabbah and Gouali, 1994, 2AC
Δsub100.2 ± 0.6kJ/molVRibeiro Da Silva, Reis, et al., 1992ALS
Δsub100.2 ± 0.6kJ/molN/ARibeiro Da Silva, Reis, et al., 1992AC

Reduced pressure boiling point

Tboil (K) Pressure (bar) Reference Comment
467.20.093Weast and Grasselli, 1989BS

Enthalpy of sublimation

ΔsubH (kJ/mol) Temperature (K) Method Reference Comment
98.5 ± 0.6321.MERibeiro Da Silva, Reis, et al., 1992AC
76.2319.5AStephenson and Malanowski, 1987Based on data from 305. to 334. K.; AC
92. ± 2.328.VWolf and Weghofer, 1938ALS
91.6 ± 1.7325. to 336.N/ATrieschmann, 1935See also Wolf and Weghofer, 1938, 2 and Jones, 1960.; AC

Enthalpy of fusion

ΔfusH (kJ/mol) Temperature (K) Reference Comment
19.196370.0Poeti, Fanelli, et al., 1982DH
18.06369.Musuc, Razus, et al., 2002AC
19.19371.2Acree, 1991See also Sabbah and Gouali, 1994, 2.; AC
19.2370.Poeti, Fanelli, et al., 1982AC
21.300369.95Booss and Hauschildt, 1972DH

Entropy of fusion

ΔfusS (J/mol*K) Temperature (K) Reference Comment
51.88370.0Poeti, Fanelli, et al., 1982DH
57.6369.95Booss and Hauschildt, 1972DH

Enthalpy of phase transition

ΔHtrs (kJ/mol) Temperature (K) Initial Phase Final Phase Reference Comment
0.167356.crystaline, IIcrystaline, IWojcik and Marqueton, 1989DH
19.960370.crystaline, IliquidWojcik and Marqueton, 1989DH

Entropy of phase transition

ΔStrs (J/mol*K) Temperature (K) Initial Phase Final Phase Reference Comment
0.47356.crystaline, IIcrystaline, IWojcik and Marqueton, 1989DH
54.370.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:


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 as indicated in comments:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

View reactions leading to C6H5NO3+ (ion structure unspecified)

Ionization energy determinations

IE (eV) Method Reference Comment
9.0PEKobayashi and Nagakura, 1975LLK
9.33PEKobayashi and Nagakura, 1975Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
NO+10.5 ± 0.2?EIBeynon, Hopkinson, et al., 1969RDSH

De-protonation reactions

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

By formula: C6H4NO3- + H+ = C6H5NO3

Quantity Value Units Method Reference Comment
Δr1399. ± 8.8kJ/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Δr1400. ± 11.kJ/molG+TSKebarle and McMahon, 1977gas phase; B
Quantity Value Units Method Reference Comment
Δr1370. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Δr1371. ± 8.4kJ/molIMREKebarle and McMahon, 1977gas phase; B

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

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

Quantity Value Units Method Reference Comment
Δr115. ± 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; switching reaction,Thermochemical ladder(Br-)C6H5OH, Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr74.1 ± 4.2kJ/molIMREPaul and Kebarle, 1990gas phase; ΔGaff at 423 K; B

Free energy of reaction

ΔrG° (kJ/mol) T (K) Method Reference Comment
74.1423.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
Δr97.1 ± 7.5kJ/molIMREPaul and Kebarle, 1990gas phase; ΔGaff at 423 K; B,M
Quantity Value Units Method Reference Comment
Δr88.J/mol*KN/APaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr59.8 ± 4.2kJ/molIMREPaul and Kebarle, 1990gas phase; ΔGaff at 423 K; B

Free energy of reaction

ΔrG° (kJ/mol) T (K) Method Reference Comment
59.8423.PHPMSPaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M

IR Spectrum

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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

Gas Phase Spectrum

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IR spectrum
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Additional Data

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Owner NIST Standard Reference Data Program
Collection (C) 2018 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin Sadtler Research Labs Under US-EPA Contract
State gas

This IR spectrum is from the NIST/EPA Gas-Phase Infrared Database .


Gas Chromatography

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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

Kovats' RI, non-polar column, isothermal

View large format table.

Column type Active phase Temperature (C) I Reference Comment
PackedApiezon L204.1514.Mitchell and Vernon, 1972 
PackedSE-52204.1530.Mitchell and Vernon, 1972 

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

View large format table.

Column type Active phase I Reference Comment
CapillaryVF-5MS1484.6Tret'yakov, 200730. m/0.25 mm/0.25 μm, He; Program: Multi-step temperature program; T(initial)=60C; T(final)=270C

References

Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Gas Chromatography, 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]

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]

Kobayashi and Nagakura, 1975
Kobayashi, T.; Nagakura, S., Photoelectron spectra of nitrophenols and nitroanisoles, J. Electron Spectrosc. Relat. Phenom., 1975, 6, 421. [all data]

Beynon, Hopkinson, et al., 1969
Beynon, J.H.; Hopkinson, J.A.; Lester, G.R., Mass spectrometry-the appearance potentials of "meta-stable peaks" in some aromatic nitro compounds - a chemical reaction in the mass spectrometer, Intern. J. Mass Spectrom. Ion Phys., 1969, 2, 291. [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]

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]

Mitchell and Vernon, 1972
Mitchell, P.T.; Vernon, F., Gas-Liquid Chromatography of Nitrophenols and Methyl Derivatives, J. Chromatogr., 1972, 65, 3, 487-491, https://doi.org/10.1016/S0021-9673(00)84994-8 . [all data]

Tret'yakov, 2007
Tret'yakov, K.V., Retention Data. NIST Mass Spectrometry Data Center., NIST Mass Spectrometry Data Center, 2007. [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Gas Chromatography, References