Benzene, nitro-

• Formula: C₆H₅NO₂
• Molecular weight: 123.1094
• IUPAC Standard InChI: InChI=1S/C6H5NO2/c8-7(9)6-4-2-1-3-5-6/h1-5H Copy

  
• IUPAC Standard InChIKey: LQNUZADURLCDLV-UHFFFAOYSA-N Copy
• CAS Registry Number: 98-95-3
• 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.
• Isotopologues:
  • Nitrobenzene-D5
• Other names: Essence of Mirbane; Essence of Myrbane; Mirbane oil; Nitrobenzene; Nitrobenzol; Oil of Mirbane; Oil of Myrbane; Nitrobenzeen; Nitrobenzen; NCI-C60082; Rcra waste number U169; UN 1662; NSC 9573
• 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
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • References
  • Notes
• Other data available:
  • Henry's Law data
  • Gas phase ion energetics data
  • Ion clustering data
  • UV/Visible spectrum
  • Gas Chromatography
• Data at other public NIST sites:
  • Computational Chemistry Comparison and Benchmark Database
  • Gas Phase Kinetics Database
  • X-ray Photoelectron Spectroscopy Database, version 5.0
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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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Constant pressure heat capacity of liquid

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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
BS - Robert L. Brown and Stephen E. Stein
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 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 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

 +  = ( • )

By formula: Cl^- + C₆H₅NO₂ = (Cl^- • C₆H₅NO₂)

Free energy of reaction

C₆H₄NO₂^- +  =

By formula: C₆H₄NO₂^- + H⁺ = C₆H₅NO₂

 +  = ( • )

By formula: Br^- + C₆H₅NO₂ = (Br^- • C₆H₅NO₂)

Free energy of reaction

C₆H₇N⁺ +  = (C₆H₇N⁺ • )

By formula: C₆H₇N⁺ + C₆H₅NO₂ = (C₆H₇N⁺ • C₆H₅NO₂)

Bond type: Charge transfer bond (positive ion)

Free energy of reaction

 +  = ( • )

By formula: NO₂^- + C₆H₅NO₂ = (NO₂^- • C₆H₅NO₂)

C₁₁H₁₀⁺ +  = (C₁₁H₁₀⁺ • )

By formula: C₁₁H₁₀⁺ + C₆H₅NO₂ = (C₁₁H₁₀⁺ • C₆H₅NO₂)

Bond type: Charge transfer bond (positive ion)

 +  = ( • )

By formula: NO^- + C₆H₅NO₂ = (NO^- • C₆H₅NO₂)

F₆S^- +  = (F₆S^- • )

By formula: F₆S^- + C₆H₅NO₂ = (F₆S^- • C₆H₅NO₂)

F₆S^- +  = (F₆S^- • )

By formula: F₆S^- + C₆H₅NO₂ = (F₆S^- • C₆H₅NO₂)

 +  = ( • )

By formula: C₇F₁₄^- + C₆H₅NO₂ = (C₇F₁₄^- • C₆H₅NO₂)

Free energy of reaction

 +  = C₁₃H₅F₁₄NO₂^-

By formula: C₇F₁₄^- + C₆H₅NO₂ = C₁₃H₅F₁₄NO₂^-

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• SOLUTION (10% IN CCl4 FOR 4000-1330 CM^-1, 10% IN CS2 FOR 1330-600 CM^-1); BECKMAN IR-7 (GRATING); DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm^-1 resolution

Data compiled by: Tanya L. Myers, Russell G. Tonkyn, Ashley M. Oeck, Tyler O. Danby, John S. Loring, Matthew S. Taubman, Stephen W. Sharpe, Jerome C. Birnbaum, and Timothy J. Johnson

• liquid; Bruker Tensor 27 FTIR; 0.4821395 cm^-1 resolution

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

• gas

Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, References, Notes

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

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.

Lebedeva, Katin, et al., 1971
Lebedeva, N.D.; Katin, Y.A.; Akhmedova, G.Y., Standard enthalpy of formation of nitrobenzene, Russ. J. Phys. Chem. (Engl. Transl.), 1971, 45, 1192-1193. [all data]

Pedley, Naylor, et al., 1986
Pedley, J.B.; Naylor, R.D.; Kirby, S.P., Thermochemical Data of Organic Compounds, Chapman and Hall, New York, 1986, 1-792. [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]

Parks, Todd, et al., 1936
Parks, G.S.; Todd, S.S.; Moore, W.A., Thermal data on organic compounds. XVI. Some heat capacity, entropy and free energy data for typical benzene derivatives and heterocyclic compounds, J. Am. Chem. Soc., 1936, 58, 398-401. [all data]

Reddy, 1986
Reddy, K.S., Isentropic compressibilities of binary liquid mixtures at 303.15 and 313.15 K, J. Chem. Eng. Data, 1986, 31, 238-240. [all data]

Lainez, Rodrigo, et al., 1985
Lainez, A.; Rodrigo, M.; Roux, A.H.; Grolier, J.-P.E.; Wilhelm, E., Relations between structure and thermodynamic properties. Heat capacities of polar substances (nitrobenzene and benzonitrile) in alkane solutions, Calorim. Anal. Therm., 1985, 16, 153-158. [all data]

Pacor, 1967
Pacor, P., Applicability of the DuPont 900 DTA apparatus in quantitative differential thermal analysis, Anal. Chim. Acta, 1967, 37, 200-208. [all data]

Rastorguev and Ganiev, 1967
Rastorguev, Yu.L.; Ganiev, Yu.A., Study of the heat capacity of selected solvents, Izv. Vyssh. Uchebn. Zaved. Neft Gaz. 10, 1967, No.1, 79-82. [all data]

Lutskii and Panova, 1958
Lutskii, A.E.; Panova, A.N., Specific heat of liquid nitrobenzene, Zhur. Fiz. Khim., 1958, 32, 2183-2185. [all data]

Mazur, 1939
Mazur, J., Über die spezifische Wärme des Nitrobenzols, Acta Phys. Pol., 1939, 7, 290-304. [all data]

Mazur, 1939, 2
Mazur, J., Über die spezifische Wärme des Äthyläthers, des Nitrobenzols und des Schwefelkohlenstoffs, Z. Physik., 1939, 113, 710-720. [all data]

Parks and Todd, 1934
Parks, G.S.; Todd, S.S., Some heat capacity data for liquid nitrobenzene, no indication of allotropy, J. Chem. Phys., 1934, 2, 440-441. [all data]

Willams and Daniels, 1924
Willams, J.W.; Daniels, F., The specific heats of certain organic liquids at elevated temperatures, J. Am. Chem. Soc., 1924, 46, 903-917. [all data]

von Reis, 1881
von Reis, M.A., Die specifische Wärme flüssiger organischer Verbindungen und ihre Beziehung zu deren Moleculargewicht, Ann. Physik [3], 1881, 13, 447-464. [all data]

Chickos, Hosseini, et al., 1995
Chickos, James S.; Hosseini, Sarah; Hesse, Donald G., Determination of vaporization enthalpies of simple organic molecules by correlations of changes in gas chromatographic net retention times, Thermochimica Acta, 1995, 249, 41-62, https://doi.org/10.1016/0040-6031(95)90670-3 . [all data]

Kusano and Wadso, 1971
Kusano, K.; Wadso, I., Enthalpy of vaporization of some organic substances at 25.0°C and test of calorimeter, Bull. Chem. Soc. Jpn., 1971, 44, 1705-17. [all data]

Kusano and Wadsö, 1971
Kusano, Kazuhito; Wadsö, Ingemar, Enthalpy of Vaporization of Some Organic Substances at 25.0°C and Test of Calorimeter, Bull. Chem. Soc. Jpn., 1971, 44, 6, 1705-1707, https://doi.org/10.1246/bcsj.44.1705 . [all data]

Lebedeva, Katin, et al., 1971, 2
Lebedeva, N.D.; Katin, Y.A.; Akhmedova, G.Y., Russ. J. Phys. Chem., 1971, 45, 8, 1192. [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]

Dykyj, 1972
Dykyj, J., Petrochemia, 1972, 12, 1, 13. [all data]

Lynch and Wilke, 1960
Lynch, E.J.; Wilke, C.R., Vapor Pressure of Nitrobenzene at Low Temperatures., J. Chem. Eng. Data, 1960, 5, 3, 300-300, https://doi.org/10.1021/je60007a018 . [all data]

Zaraiskii, 1985
Zaraiskii, A.P., Zh. Fiz. Khim., 1985, 59, 2087. [all data]

Sklyarenko, Markin, et al., 1958
Sklyarenko, S.I.; Markin, B.I.; Belyaeva, L.B., Zh. Fiz. Khim., 1958, 32, 1916. [all data]

Oliver and Grisard, 1952
Oliver, George D.; Grisard, J.W., Thermal Data, Vapor Pressure and Entropy of Bromine Trifluoride ¹, J. Am. Chem. Soc., 1952, 74, 11, 2705-2707, https://doi.org/10.1021/ja01131a003 . [all data]

Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E., The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [all data]

Toral and Moles, 1933
Toral, M.T.; Moles, E., An. R. Soc. Esp. Fis. Quim., 1933, 31, 735. [all data]

Brown, 1952
Brown, I., Liquid-Vapour Equilibria. III. The Systems Benzene-n-Heptane, n-Hexane-Chlorobenzene, and cycloHexane-Nitrobenzene, Aust. J. Sci. Res. Ser. A:, 1952, 5, 530-540. [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]

Chowdhury and Kebarle, 1986
Chowdhury, S.; Kebarle, P., Role of Binding Energies in A^-.B and A.B^- Complexes in the Kinetics of Gas Phase Electron Transfer Reactions:A^- + B = A + B^- Involving Perfluoro Compounds: SF₆, C₆F₁₁CF₃, J. Chem. Phys., 1986, 85, 9, 4989, https://doi.org/10.1063/1.451687 . [all data]

Paul and Kebarle, 1991
Paul, G.J.C.; Kebarle, P., Stabilities of Complexes of Br- with Substituted Benzenes (SB) Based on Determinations of the Gas-Phase Equilibria Br- + SB = (BrSB)-, J. Am. Chem. Soc., 1991, 113, 4, 1148, https://doi.org/10.1021/ja00004a014 . [all data]

French, Ikuta, et al., 1982
French, M.A.; Ikuta, S.; Kebarle, P., Hydrogen bonding of O-H and C-H hydrogen donors to Cl^-. Results from mass spectrometric measurement of the ion-molecule equilibria RH + Cl^- = RHCl^-, Can. J. Chem., 1982, 60, 1907. [all data]

Cheng and Grabowski, 1989
Cheng, X.; Grabowski, J.J., Gas-phase Acidity of Nitrobenzene from Flowing Afterglow Bracketing Studies, Rapid Commun. Mass Spectrom., 1989, 3, 2, 34-36, https://doi.org/10.1002/rcm.1290030207 . [all data]

Meot-ner and Kafafi, 1988
Meot-ner, M.; Kafafi, S.A., Carbon Acidities of Aromatic Compounds, J. Am. Chem. Soc., 1988, 110, 19, 6297, https://doi.org/10.1021/ja00227a003 . [all data]

Meot-Ner (Mautner) and El-Shall, 1986
Meot-Ner (Mautner), M.; El-Shall, M.S., Ionic Charge Transfer Complexes. 1. Cationic Complexes with Delocalized and Partially Localized pi Systems, J. Am. Chem. Soc., 1986, 108, 15, 4386, https://doi.org/10.1021/ja00275a026 . [all data]

Grimsrud, Chowdhury, et al., 1986
Grimsrud, E.P.; Chowdhury, S.; Kebarle, P., Gas Phase Reactions of NO₂^- with Nitrobenzenes and Quinones. Electron Transfer, Clusters, and Formation of Phenoxide and Quinoxide Negative Ions. Use of NO₂ as a NICI Reagent Gas., Int. J. Mass Spectrom. Ion Proc., 1986, 68, 1-2, 57, https://doi.org/10.1016/0168-1176(86)87068-9 . [all data]

El-Shall and Meot-Ner (Mautner), 1987
El-Shall, M.S.; Meot-Ner (Mautner), M., Ionic Charge Transfer Complexes. 3. Delocalised pi Systems as Electron Acceptors and Donors, J. Phys. Chem., 1987, 91, 5, 1088, https://doi.org/10.1021/j100289a017 . [all data]

Reents and Freiser, 1981
Reents, W.D.; Freiser, B.S., Gas-Phase Binding Energies and Spectroscopic Properties of NO+ Charge-Transfer Complexes, J. Am. Chem. Soc., 1981, 103, 2791. [all data]

Farid and McMahon, 1978
Farid, R.; McMahon, T.B., Gas-Phase Ion-Molecule Reactions of Alkyl Nitrites by Ion Cyclotron Resonance Spectroscopy, Int. J. Mass Spectrom. Ion Phys., 1978, 27, 2, 163, https://doi.org/10.1016/0020-7381(78)80037-0 . [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

• Symbols used in this document:
  

  Cp,liquid	Constant pressure heat capacity of liquid
  S°liquid	Entropy of liquid at standard conditions
  T	Temperature
  Tboil	Boiling point
  Tfus	Fusion (melting) point
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfH°liquid	Enthalpy of formation of liquid at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔfusS	Entropy of fusion
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔrS°	Entropy of reaction 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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