Phenol, 4-nitro-

• Formula: C₆H₅NO₃
• Molecular weight: 139.1088
• IUPAC Standard InChI: InChI=1S/C6H5NO3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8H Copy

  
• IUPAC Standard InChIKey: BTJIUGUIPKRLHP-UHFFFAOYSA-N Copy
• CAS Registry Number: 100-02-7
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
  The 3d structure may be viewed using Java or Javascript.
• Other names: Phenol, p-nitro-; p-Hydroxynitrobenzene; p-Nitrophenol; Niphen; 4-Hydroxynitrobenzene; 4-Nitrophenol; NCI-C55992; Paranitrofenol; Paranitrofenolo; Paranitrophenol; 4-Nitrofenol; p-Nitrofenol; Rcra waste number U170; 1-Hydroxy-4-nitrobenzene; PNP; NSC 1317
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Henry's Law data
  • Gas phase ion energetics data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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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)

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

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

Appearance energy determinations

De-protonation reactions

C₆H₄NO₃^- +  =

By formula: C₆H₄NO₃^- + H⁺ = C₆H₅NO₃

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

 +  = ( • )

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

Free energy of reaction

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• SOLID (OIL MULL); BAIRD (GRATING); 2 cm^-1 resolution
• SOLUTION (ETHYL ETHER); Not specified, most likely a prism, grating, or hybrid spectrometer.; DIGITIZED BY NIST FROM HARD COPY; 4 cm^-1 resolution

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

• gas; HP-GC/MS/IRD

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

UV/Visible 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: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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Additional Data

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

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Kovats' RI, non-polar column, custom temperature program

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

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

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Normal alkane RI, non-polar column, temperature ramp

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Lee's RI, non-polar column, temperature ramp

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References

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

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

Johnstone and Mellon, 1973
Johnstone, R.A.W.; Mellon, F.A., Effects of induction and resonance in the calculation of ionization potentials of substituted benzenes by perturbation molecular orbital theory, J. Chem. Soc. Faraday Trans. 2, 1973, 69, 36. [all data]

Brown, 1970
Brown, P., Kinetic studies in mass spectrometry. IX. Competing [M-NO₂] and [M-NO] reactions in substituted nitrobenzenes. Approximate activation energies from ionization and appearance potentials, Org. Mass Spectrom., 1970, 4, 533. [all data]

Crable and Kearns, 1962
Crable, G.F.; Kearns, G.L., Effect of substituent groups on the ionization potentials of benzenes, J. Phys. Chem., 1962, 66, 436. [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]

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]

Grammaticakis, 1951
Grammaticakis, P., Contribution a l'etude de l'absorption dans l'ultraviolet moyen et le visible des arylamines isomeres et de leurs derives N substitues (Premier memoire), Bull. Soc. Chim. Fr., 1951, 18, 220-226. [all data]

Erdmann, Rochholz, et al., 1992
Erdmann, F.; Rochholz, G.; Schütz, H., Retention-indices on OV-1 of approximately 170 commonly used pesticides, Mikrochim. Acta, 1992, 106, 3-6, 219-226, https://doi.org/10.1007/BF01242093 . [all data]

Verevkin, Belen'kaya, et al., 1990
Verevkin, S.P.; Belen'kaya, R.S.; Rozhnov, A.M.; Matyushina, V.P., Investigation of the chromatographic behaviour of alkylnitrophenols, Zh. Anal. Khim., 1990, 45, 1786-1790. [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]

Van Durme, Dewulf, et al., 2007
Van Durme, J.; Dewulf, J.; Sysmans, W.; Leys, C.; Van Langenhove, H., Abatement and degradation pathways of toluene in indoor air by positive corona discharge, Chemosphere, 2007, 68, 10, 1821-1829, https://doi.org/10.1016/j.chemosphere.2007.03.053 . [all data]

Ferchichi and Messadi, 1994
Ferchichi, L.; Messadi, D., Simulations de la rétention et de l'effecacité de colonne en chromatographie en phase gazeuse à température programmée: théorie et application, Analusis, 1994, 22, 392-399. [all data]

Rostad and Pereira, 1986
Rostad, C.E.; Pereira, W.E., Kovats and Lee retention indices determined by gas chromatography/mass spectrometry for organic compounds of environmental interest, J. Hi. Res. Chromatogr. Chromatogr. Comm., 1986, 9, 6, 328-334, https://doi.org/10.1002/jhrc.1240090603 . [all data]

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

Harland, Cumming, et al., 1986
Harland, B.J.; Cumming, R.I.; Gillings, E., The Kovats indexes of some organic micropollutants on an SE54 capillary column, EUR, I Org. Micropollut. Aquat. Environ., 1986, EUR 10388, 123-127. [all data]

Donnelly, Abdel-Hamid, et al., 1993
Donnelly, J.R.; Abdel-Hamid, M.S.; Jeter, J.L.; Gurka, D.F., Application of gas chromatographic retention properties to the identification of environmental contaminants, J. Chromatogr., 1993, 642, 1-2, 409-415, https://doi.org/10.1016/0021-9673(93)80106-I . [all data]

Notes

Go To: Top, Henry's Law data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, References

• Symbols used in this document:
  

  AE	Appearance energy
  T	Temperature
  d(ln(kH))/d(1/T)	Temperature dependence parameter for Henry's Law constant
  k°H	Henry's Law constant at 298.15K
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔrS°	Entropy of reaction at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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