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
- 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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Gas phase ion energetics data
Go To: Top, 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
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 |
References
Go To: Top, 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.
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, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy EA Electron affinity - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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