Benzene, 1,2-dinitro-
- Formula: C6H4N2O4
- Molecular weight: 168.1070
- IUPAC Standard InChIKey: IZUKQUVSCNEFMJ-UHFFFAOYSA-N
- CAS Registry Number: 528-29-0
- 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, o-dinitro-; o-Dinitrobenzene; 1,2-Dinitrobenzene; ortho-Dinitrobenzene; 1,2-Dinitrobenzol; UN 1597
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Phase change data
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), 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:
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 | 387.7 | K | N/A | Hwang, Tamura, et al., 1990 | Uncertainty assigned by TRC = 0.1 K; TRC |
Tfus | 390.05 | K | N/A | Booss and Hauschildt, 1972 | Uncertainty assigned by TRC = 0.2 K; TRC |
Tfus | 390. | K | N/A | White, Biggs, et al., 1940 | Uncertainty assigned by TRC = 2. K; TRC |
Tfus | 390.1 | K | N/A | Andrews, Lynn, et al., 1926 | Uncertainty assigned by TRC = 0.2 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 95.5 ± 0.9 | kJ/mol | GS | Verevkin, 1997 | Based on data from 323. to 353. K.; AC |
ΔsubH° | 87.9 ± 2.1 | kJ/mol | TE | Ferro, Piacente, et al., 1976 | Based on data from 343. to 397. K.; AC |
Reduced pressure boiling point
Tboil (K) | Pressure (bar) | Reference | Comment |
---|---|---|---|
592.2 | 1.03 | Aldrich Chemical Company Inc., 1990 | BS |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
60.0 | 469. | A | Stephenson and Malanowski, 1987 | Based on data from 454. to 593. K. See also Dykyj, 1972.; AC |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
93.1 ± 0.9 | 338. | GS | Verevkin, 1997 | Based on data from 323. to 353. K.; AC |
82.9 | 358. | N/A | Stephenson and Malanowski, 1987 | Based on data from 343. to 387. K.; AC |
87. ± 1. | 333. | V | Wolf and Weghofer, 1938 | ALS |
86.6 ± 1.2 | 309. | N/A | Trieschmann, 1935 | Based on data from 328. to 338. K. See also Wolf and Weghofer, 1938, 2 and Jones, 1960.; AC |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
22.84 | 396.1 | Domalski and Hearing, 1996 | AC |
22.750 | 390.05 | Booss and Hauschildt, 1972 | DH |
22.840 | 396.1 | Andrews, Lynn, et al., 1926, 2 | DH |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
58.3 | 390.05 | Booss and Hauschildt, 1972 | DH |
58.6 | 396.1 | Andrews, Lynn, et al., 1926, 2 | DH |
Reaction thermochemistry data
Go To: Top, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), 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: Br- + C6H4N2O4 = (Br- • C6H4N2O4)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 87.9 ± 7.5 | kJ/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° | 92. | J/mol*K | N/A | Paul and Kebarle, 1991 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 48.5 ± 4.2 | kJ/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° (kJ/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
48.5 | 423. | PHPMS | Paul and Kebarle, 1991 | gas phase; Entropy change calculated or estimated; M |
Gas phase ion energetics data
Go To: Top, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), 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:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
B - John E. Bartmess
Electron affinity determinations
EA (eV) | Method | Reference | Comment |
---|---|---|---|
1.65 ± 0.10 | IMRE | Chowdhury, Heinis, et al., 1986 | ΔGea(423 K) = -36.9 kcal/mol; ΔSea (estimated) = -3.2 eu.; B |
<1.770 ± 0.050 | PD | Mock and Grimsrud, 1989 | B |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
10.71 | PE | Palmer, Moyes, et al., 1979 | Vertical value; LLK |
IR Spectrum
Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), References, Notes
Data compiled by: Coblentz Society, Inc.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Mass spectrum (electron ionization)
Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics 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
View image of digitized spectrum (can be printed in landscape orientation).
Due to licensing restrictions, this spectrum cannot be downloaded.
Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | NIST Mass Spectrometry Data Center, 1992 |
NIST MS number | 125419 |
References
Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics 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.
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]
White, Biggs, et al., 1940
White, A.H.; Biggs, B.S.; Morgan, S.O.,
Dielectric Evidence for Molecular Rotation in the Crystals of Certain Benzene Derivatives,
J. Am. Chem. Soc., 1940, 62, 16-25. [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. [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]
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 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]
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]
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]
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, 1274-1287. [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]
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]
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, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), References
- Symbols used in this document:
EA Electron affinity 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 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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