Phenol, 2-nitro-

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

  
• IUPAC Standard InChIKey: IQUPABOKLQSFBK-UHFFFAOYSA-N Copy
• CAS Registry Number: 88-75-5
• 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, o-nitro-; o-Hydroxynitrobenzene; o-Nitrophenol; 2-Hydroxynitrobenzene; 2-Nitrophenol; o-Nitrofenol; UN 1663
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Henry's Law data
  • Gas phase ion energetics data
  • Mass spectrum (electron ionization)
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • IR Spectrum
  • UV/Visible spectrum
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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

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

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

Enthalpy of vaporization

Antoine Equation Parameters

log₁₀(P) = A − (B / (T + C))
    P = vapor pressure (atm)
    T = temperature (K)

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Enthalpy of sublimation

Enthalpy of fusion

Entropy of fusion

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 by: John E. Bartmess

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

C₆H₄NO₃^- +  =

By formula: C₆H₄NO₃^- + H⁺ = C₆H₅NO₃

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

View reactions leading to C₆H₅NO₃⁺ (ion structure unspecified)

Ionization energy determinations

De-protonation reactions

C₆H₄NO₃^- +  =

By formula: C₆H₄NO₃^- + H⁺ = C₆H₅NO₃

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

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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Normal alkane RI, non-polar column, custom temperature program

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Normal alkane RI, polar column, custom temperature program

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

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References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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]

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]

Medard, 1954
Medard, L., Tables thermochimiques a l'usage des techniciens des substances explosives, Mem. Artillerie Fr. Sci. Tech. Armement, 1954, 28, 415-492. [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]

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]

Lecat, 1947
Lecat, M., Orthobaric Azeotropes of Sulfides, Bull. Cl. Sci., Acad. R. Belg., 1947, 33, 160-82. [all data]

Lecat, 1943
Lecat, M., Azeotropes of Ethyl Urethane and other Azeotropes, C. R. Hebd. Seances Acad. Sci., 1943, 217, 273. [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]

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]

Stull, 1947
Stull, Daniel R., Vapor Pressure of Pure Substances. Organic and Inorganic Compounds, Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022 . [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]

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]

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

Grzybowski, Lamparczyk, et al., 1980
Grzybowski, J.; Lamparczyk, H.; Nasal, A.; Radecki, A., Relationship between the retention indices of phenols on polar and non-polar stationary phases, J. Chromatogr., 1980, 196, 2, 217-223, https://doi.org/10.1016/S0021-9673(00)80441-0 . [all data]

Zhao C.X., Li, et al., 2006
Zhao C.X.; Li, X.N.; Liang Y.Z.; Fang H.Z.; Huang L.F.; Guo F.Q., Comparative analysis of chemical components of essential oils from different samples of Rhododendron with the help of chemometrics methods, Chemom. Intell. Lab. Syst., 2006, 82, 1-2, 218-228, https://doi.org/10.1016/j.chemolab.2005.08.008 . [all data]

Gerbino and Castello, 1995
Gerbino, T.C.; Castello, G., Prediction of programmed temperature retention indices on capillary columns of different polarities, J. Chromatogr. A, 1995, 699, 1-2, 161-171, https://doi.org/10.1016/0021-9673(95)00024-H . [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]

Yasuhara, Shiraishi, et al., 1997
Yasuhara, A.; Shiraishi, H.; Nishikawa, M.; Yamamoto, T.; Uehiro, T.; Nakasugi, O.; Okumura, T.; Kenmotsu, K.; Fukui, H.; Nagase, M.; Ono, Y.; Kawagoshi, Y.; Baba, K.; Noma, Y., Determination of organic components in leachates from hazardous waste disposal sites in Japan by gas chromatography-mass spectrometry, J. Chromatogr. A, 1997, 774, 1-2, 321-332, https://doi.org/10.1016/S0021-9673(97)00078-2 . [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]

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Peterson, K.L., Counter-Propagation Neural Networks in the Modeling and Prediction of Kovats Indices for Substituted Phenols, Anal. Chem., 1992, 64, 4, 379-386, https://doi.org/10.1021/ac00028a011 . [all data]

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Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, References

• Symbols used in this document:
  

  Tboil	Boiling point
  Tfus	Fusion (melting) point
  d(ln(kH))/d(1/T)	Temperature dependence parameter for Henry's Law constant
  k°H	Henry's Law constant at 298.15K
  ΔcH°solid	Enthalpy of combustion of solid at standard conditions
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfH°solid	Enthalpy of formation of solid at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔfusS	Entropy of fusion
  ΔrG°	Free energy of reaction at standard conditions
  ΔsubH	Enthalpy of sublimation
  ΔsubH°	Enthalpy of sublimation at standard conditions
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions

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