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:
  • Phase change data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Henry's Law data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
  • X-ray Photoelectron Spectroscopy Database, version 5.0
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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 (bar)
    T = temperature (K)

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Enthalpy of fusion

Entropy of fusion

Reaction thermochemistry data

Go To: Top, Phase change data, Gas phase ion energetics data, References, Notes

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^-

Gas phase ion energetics data

Go To: Top, Phase change data, Reaction thermochemistry data, References, Notes

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

Data evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
LL - Sharon G. Lias and Joel F. Liebman

Electron affinity determinations

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

C₆H₄NO₂^- +  =

By formula: C₆H₄NO₂^- + H⁺ = C₆H₅NO₂

References

Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Notes

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

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]

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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]

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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]

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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]

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Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [all data]

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Desfrancois, C.; Periquet, V.; Lyapustina, S.A.; Lippa, T.P.; Robinson, D.W.; Bowen, K.H.; Nonaka, H.; Compton, Electron Binding to Valence and Multipole states of Molecules: Nitrobenzene, para- and meta-dinitrobenzenes, J. Chem. Phys., 1999, 111, 10, 4569, https://doi.org/10.1063/1.479218 . [all data]

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Chowdhury, S.; Heinis, T.; Grimsrud, E.P.; Kebarle, P., Entropy Changes and Electron Affinities from Gas-Phase Electron Transfer Equilibria: A^- + B = A + B^-, J. Phys. Chem., 1986, 90, 12, 2747, https://doi.org/10.1021/j100403a037 . [all data]

Chen, Wiley, et al., 1994
Chen, E.C.M.; Wiley, J.R.; Batten, C.F.; Wentworth, W.E., Determination of the Electron Affinities of Molecules Using Negative Ion Mass Spectrometry, J. Phys. Chem., 1994, 98, 1, 88, https://doi.org/10.1021/j100052a016 . [all data]

Chen, Chen, et al., 1992
Chen, E.C.M.; Chen, E.S.; Milligan, M.S.; Wentworth, W.E.; Wiley, J.R., Experimental Determination of the Electron Affinities of Nitrobenzene, Nitrotoluenes, Pentafluoronitrobenzene, and Isotopic Nitrobenzenes an, J. Phys. Chem., 1992, 96, 5, 2385, https://doi.org/10.1021/j100184a069 . [all data]

Fukuda and McIver, 1985
Fukuda, E.K.; McIver, R.T., Jr., Relative electron affinities of substituted benzophenones, nitrobenzenes, and quinones. [Anchored to EA(SO₂) from 74CEL/BEN], J. Am. Chem. Soc., 1985, 107, 2291. [all data]

Mock and Grimsrud, 1989
Mock, R.S.; Grimsrud, E.P., Gas-Phase Electron Photodetachment Spectroscopy of the Molecular Anions of Nitroaromatic Hydrocarbons at Atmospheric Pressure, J. Am. Chem. Soc., 1989, 111, 8, 2861, https://doi.org/10.1021/ja00190a020 . [all data]

Henglein and Muccini, 1959
Henglein, A.; Muccini, G.A., Negative Ion-Molecule Reactions, J. Chem. Phys., 1959, 31, 5, 1426, https://doi.org/10.1063/1.1730618 . [all data]

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Lifshitz, C.; Tiernan, T.O.; Hughes, B.M., Electron affinities from endothermic negative-ion charge transfer reactions. IV. SF₆, selected fluorocarbons, and other polyatomic molecules, J. Chem. Phys., 1973, 59, 3182. [all data]

Compton, Christophorou, et al., 1966
Compton, R.N.; Christophorou, L.G.; Hurst, G.S.; Reinhardt, P.W., Nondissociative Electron Capture in Complex Molecules and Negative Ion Lifetimes, J. Chem. Phys., 1966, 45, 12, 4634, https://doi.org/10.1063/1.1727547 . [all data]

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Klasinc, L.; Kovac, B.; Gusten, H., Photoelectron spectra of acenes. Electronic structure and substituent effects, Pure Appl. Chem., 1983, 55, 289. [all data]

Katsumata, Shiromaru, et al., 1982
Katsumata, S.; Shiromaru, H.; Mitani, K.; Iwata, S.; Kimura, K., Photoelectron angular distribution and assignments of photoelectron spectra of nitrogen dioxide, nitromethane and nitrobenzene, Chem. Phys., 1982, 69, 423. [all data]

Allam, Migahed, et al., 1982
Allam, S.H.; Migahed, M.D.; El-Khodary, A., Electron impact ionization and dissociation of deuterated and non-deuterated methanol, methyl cyanide, nitromethane and nitrobenzene, Egypt. J. Phys., 1982, 13, 167. [all data]

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Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki, T.; Iwata, S., Ionization energies, Ab initio assignments, and valence electronic structure for 200 molecules in Handbook of HeI Photoelectron Spectra of Fundamental Organic Compounds, Japan Scientific Soc. Press, Tokyo, 1981. [all data]

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Matyuk, V.M.; Potapov, V.K.; Prokhoda, A.L., Photoexcitation and photoionisation of nitro- derivatives of benzene and toluene, Russ. J. Phys. Chem., 1979, 53, 538. [all data]

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Behan, J.M.; Johnstone, R.A.W.; Bentley, T.W., An evaluation of empirical methods for calculating the ionization potentials of substituted benzenes, Org. Mass Spectrom., 1976, 11, 207. [all data]

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McLafferty, F.W.; Bente, P.F., III; Kornfeld, R.; Tsai, S.-C.; Howe, I., Collisional activation spectra of organic ions, J. Am. Chem. Soc., 1973, 95, 2120. [all data]

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Notes

Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, References

• Symbols used in this document:
  

  AE	Appearance energy
  EA	Electron affinity
  IE (evaluated)	Recommended ionization energy
  T	Temperature
  Tboil	Boiling point
  Tfus	Fusion (melting) point
  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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