Benzene, 1,4-dinitro-
- Formula: C6H4N2O4
- Molecular weight: 168.1070
- IUPAC Standard InChIKey: FYFDQJRXFWGIBS-UHFFFAOYSA-N
- 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
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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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°solid | -9.2 ± 0.1 | kcal/mol | Ccb | Lebedeva, Ryadnenko, et al., 1971 | Hfusion=8.0±0.3, see Lebedeva, Rjadnenko, et al., 1969; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -691.7 ± 0.1 | kcal/mol | Ccb | Lebedeva, Ryadnenko, et al., 1971 | Hfusion=8.0±0.3, see Lebedeva, Rjadnenko, et al., 1969; ALS |
ΔcH°solid | -693.7 | kcal/mol | Ccb | Garner and Abernethy, 1921 | ALS |
Constant pressure heat capacity of solid
Cp,solid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
39.9 | 325. | David, 1964 | T = 298 to 373 K. Mean value. T = uncertain.; DH |
47.80 | 298.15 | Ueberreiter and Orthmann, 1950 | T = 293 to 368 K. Equation only.; DH |
45.89 | 298. | Andrews, Lynn, et al., 1926 | T = 22 to 210°C.; DH |
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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tfus | 444.2 | K | N/A | Hwang, Tamura, et al., 1990 | Uncertainty assigned by TRC = 0.1 K; TRC |
Tfus | 446.65 | K | N/A | Booss and Hauschildt, 1972 | Uncertainty assigned by TRC = 0.2 K; TRC |
Tfus | 446.7 | K | N/A | Andrews, Lynn, et al., 1926, 2 | Uncertainty assigned by TRC = 0.3 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 22.5 ± 0.2 | kcal/mol | N/A | Verevkin, 1997 | AC |
ΔsubH° | 23.0 ± 0.60 | kcal/mol | TE | Ferro, Piacente, et al., 1976 | Based on data from 339. to 398. K.; AC |
Reduced pressure boiling point
Tboil (K) | Pressure (atm) | Reference | Comment |
---|---|---|---|
456.2 | 0.045 | Weast and Grasselli, 1989 | BS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
14.4 | 460. | A | Stephenson and Malanowski, 1987 | Based on data from 445. to 572. K. See also Dykyj, 1972.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
525. to 564.7 | 1.20878 | 167.313 | -429.356 | Maksimov, 1968 | Coefficents calculated by NIST from author's data. |
Enthalpy of sublimation
ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
21.2 ± 0.3 | 343. | V | Wolf and Weghofer, 1938 | ALS |
21.3 ± 0.41 | 343. | N/A | Trieschmann, 1935 | Based on data from 345. to 368. K. See also Wolf and Weghofer, 1938, 2 and Jones, 1960.; AC |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
4.202 | 446. | Musuc, Razus, et al., 2002 | AC |
6.721 | 446.7 | Acree, 1991 | AC |
6.7161 | 446.65 | Booss and Hauschildt, 1972 | DH |
6.7208 | 446.7 | Andrews, Lynn, et al., 1926 | DH |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
15.0 | 446.65 | Booss and Hauschildt, 1972 | DH |
15.0 | 446.7 | Andrews, Lynn, et al., 1926 | DH |
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: Br- + C6H4N2O4 = (Br- • C6H4N2O4)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 18.6 ± 1.8 | kcal/mol | IMRE | Paul and Kebarle, 1991 | gas phase; ΔGaff at 423 K, ΔSaff taken as that of mCF3-nitrobenzene..Br-; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 22. | cal/mol*K | N/A | Paul and Kebarle, 1991 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 9.2 ± 1.0 | kcal/mol | IMRE | Paul and Kebarle, 1991 | gas phase; ΔGaff at 423 K, ΔSaff taken as that of mCF3-nitrobenzene..Br-; B |
Free energy of reaction
ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
9.2 | 423. | PHPMS | Paul and Kebarle, 1991 | gas phase; Entropy change calculated or estimated; M |
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:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
B - John E. Bartmess
Electron affinity determinations
EA (eV) | Method | Reference | Comment |
---|---|---|---|
2.00 ± 0.10 | TDEq | Chowdury, Grimsrud, et al., 1986 | ΔGea(423 K) = -44.3 kcal/mol; ΔSea = -4.5 eu.; B |
0.02502 | N/A | Desfrancois, Periquet, et al., 1999 | quadrupole bound state; B |
1.995 ± 0.048 | IMRE | Fukuda and McIver, 1985 | ΔGea(355 K) = -44.4 kcal/mol; ΔSea =-4.5, est. from data in Chowdhury, Heinis, et al., 1986; B |
<3.100 ± 0.050 | PD | Mock and Grimsrud, 1989 | B |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
10.3 ± 0.1 | PE | Egdell, Green, et al., 1975 | LLK |
10.50 ± 0.02 | PI | Potapov, Kardash, et al., 1972 | LLK |
10.6 ± 0.1 | EI | Brown, 1970 | RDSH |
10.65 | PE | Palmer, Moyes, et al., 1979 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C6H4NO2+ | 12.5 ± 0.1 | NO2 | EI | Brown, 1970 | RDSH |
Ion clustering data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry 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. Searches may be limited to ion clustering reactions. A general reaction search form is also available.
Clustering reactions
By formula: Br- + C6H4N2O4 = (Br- • C6H4N2O4)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 18.6 ± 1.8 | kcal/mol | IMRE | Paul and Kebarle, 1991 | gas phase; ΔGaff at 423 K, ΔSaff taken as that of mCF3-nitrobenzene..Br-; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 22. | cal/mol*K | N/A | Paul and Kebarle, 1991 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 9.2 ± 1.0 | kcal/mol | IMRE | Paul and Kebarle, 1991 | gas phase; ΔGaff at 423 K, ΔSaff taken as that of mCF3-nitrobenzene..Br-; B |
Free energy of reaction
ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
9.2 | 423. | PHPMS | Paul and Kebarle, 1991 | gas phase; Entropy change calculated or estimated; M |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, 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]
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]
Chowdury, Grimsrud, et al., 1986
Chowdury, S.; Grimsrud, E.P.; Heinis, T.; Kebarle, P.,
Electron affinities of perfluorobenzene and perfluorophenyl compounds,
J. Am. Chem. Soc., 1986, 108, 3630. [all data]
Desfrancois, Periquet, et al., 1999
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]
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]
Chowdhury, Heinis, et al., 1986
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]
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]
Egdell, Green, et al., 1975
Egdell, R.; Green, J.C.; Rao, C.N.R.,
Photoelectron spectra of substituted benzenes,
Chem. Phys. Lett., 1975, 33, 600. [all data]
Potapov, Kardash, et al., 1972
Potapov, V.K.; Kardash, I.E.; Sorokin, V.V.; Sokolov, S.A.; Evlasheva, T.I.,
Photoionization of heteroaromatic compounds,
Khim. Vys. Energ., 1972, 6, 392. [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]
Palmer, Moyes, et al., 1979
Palmer, M.H.; Moyes, W.; Spiers, M.; Ridyard, J.N.A.,
The electronic structure of substituted benzenes; ab initio calculations and photoelectron spectra for nitrobenzene, the nitrotoluenes, dinitrobenzenes and fluoronitrobenzenes,
J. Mol. Struct., 1979, 55, 243. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, References
- Symbols used in this document:
AE Appearance energy Cp,solid Constant pressure heat capacity of solid EA Electron affinity T Temperature 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 ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy of reaction at standard conditions 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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