Benzene, 1,4-dinitro-

• Formula: C₆H₄N₂O₄
• Molecular weight: 168.1070
• IUPAC Standard InChI: InChI=1S/C6H4N2O4/c9-7(10)5-1-2-6(4-3-5)8(11)12/h1-4H Copy

  
• IUPAC Standard InChIKey: FYFDQJRXFWGIBS-UHFFFAOYSA-N Copy
• CAS Registry Number: 100-25-4
• 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: Benzene, p-dinitro-; p-Dinitrobenzene; 1,4-Dinitrobenzene; para-Dinitrobenzene; Dithane a-4; UN 1597
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Condensed phase thermochemistry data
  • Phase change data
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
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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 solid

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

Reduced pressure boiling point

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 sublimation

Enthalpy of fusion

Entropy of fusion

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

Lee's RI, non-polar column, custom temperature program

View large format table.

References

Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas Chromatography, Notes

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

Lebedeva, Ryadnenko, et al., 1971
Lebedeva, N.D.; Ryadnenko, V.L.; Kuznetsova, I.N., Heats of combustion and enthalpies of formation of certain aromatic nitro-derivatives, Russ. J. Phys. Chem. (Engl. Transl.), 1971, 45, 549. [all data]

Lebedeva, Rjadnenko, et al., 1969
Lebedeva, N.D.; Rjadnenko, B.L.; Gutner, N.M., Heats of formation of some N-containing organic compounds, Int. Conf. Calorim. Therm. (Warsaw, Poland), 1969, 1-8. [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]

David, 1964
David, D.J., Determination of specific heat and heat of fusion by differential thermal analysis. Study of theory and operating parameters, Anal. Chem., 1964, 36, 2162-2166. [all data]

Ueberreiter and Orthmann, 1950
Ueberreiter, K.; Orthmann, H.-J., Specifische Wärme, spezifisches Volumen, Temperatur- und Wärme-leittähigkeit einiger disubstituierter Benzole und polycyclischer Systeme, Z. Natursforsch. 5a, 1950, 101-108. [all data]

Andrews, Lynn, et al., 1926
Andrews, D.H.; Lynn, G.; Johnston, J., The heat capacities and heat of crystallization of some isomeric aromatic compounds, J. Am. Chem. Soc., 1926, 48, 1274-1287. [all data]

Hwang, Tamura, et al., 1990
Hwang, D.-R.; Tamura, M.; Yoshida, T.; Tanaka, N.; Hosoya, F., Estimation of ΔH°f of nitro derivatives of benzene and toluene using AM1 and DSC, J. Energ. Mater., 1990, 8, 85-98. [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]

Andrews, Lynn, et al., 1926, 2
Andrews, D.H.; Lynn, G.; Johnston, J., The Heat Capacities and Heat of Crystallization of Some Isomeric Aromatic Compounds, J. Am. Chem. Soc., 1926, 48, 1274. [all data]

Verevkin, 1997
Verevkin, Sergey P., Thermochemistry of nitro compounds. Experimental standard enthalpies of formation and improved group-additivity values, Thermochimica Acta, 1997, 307, 1, 17-25, https://doi.org/10.1016/S0040-6031(97)00359-6 . [all data]

Ferro, Piacente, et al., 1976
Ferro, D.; Piacente, V.; Gigli, R.; D'Ascenzo, G., Determination of the vapour pressures of o-, m-, and p-dinitrobenzene by the torsion-effusion method, The Journal of Chemical Thermodynamics, 1976, 8, 12, 1137-1143, https://doi.org/10.1016/0021-9614(76)90120-8 . [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]

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

Maksimov, 1968
Maksimov, Yu, Steam Pressures of Nitroaromatic Compouds at Different Temperatures, Zh. Fiz. Khim., 1968, 42, 2921-2925. [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]

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]

Eckel and Kind, 2003
Eckel, W.P.; Kind, T., Use of boiling point-Lee retention index correlation for rapid review of gas chromatography-mass spectrometry data, Anal. Chim. Acta., 2003, 494, 1-2, 235-243, https://doi.org/10.1016/j.aca.2003.08.003 . [all data]

Notes

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• Symbols used in this document:
  

  Cp,solid	Constant pressure heat capacity of solid
  Tboil	Boiling point
  Tfus	Fusion (melting) point
  ΔcH°solid	Enthalpy of combustion of solid at standard conditions
  ΔfH°solid	Enthalpy of formation of solid at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔfusS	Entropy of fusion
  ΔsubH	Enthalpy of sublimation
  ΔsubH°	Enthalpy of sublimation at standard conditions
  ΔvapH	Enthalpy of vaporization

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