Benzene, 1,3-dinitro-

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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

Bromine anion + Benzene, 1,3-dinitro- = (Bromine anion • Benzene, 1,3-dinitro-)

By formula: Br- + C6H4N2O4 = (Br- • C6H4N2O4)

Quantity Value Units Method Reference Comment
Δr84.9 ± 7.5kJ/molIMREPaul and Kebarle, 1991gas phase; ΔGaff at 423 K, ΔSaff taken as that of mCF3-nitrobenzene..Br-; B,M
Quantity Value Units Method Reference Comment
Δr92.J/mol*KN/APaul and Kebarle, 1991gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr45.6 ± 4.2kJ/molIMREPaul and Kebarle, 1991gas 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
45.6423.PHPMSPaul and Kebarle, 1991gas phase; Entropy change calculated or estimated; M

Nitrogen oxide anion + Benzene, 1,3-dinitro- = (Nitrogen oxide anion • Benzene, 1,3-dinitro-)

By formula: NO2- + C6H4N2O4 = (NO2- • C6H4N2O4)

Quantity Value Units Method Reference Comment
Δr88.7 ± 8.4kJ/molTDAsGrimsrud, Chowdhury, et al., 1986gas phase; B,M
Quantity Value Units Method Reference Comment
Δr94.6J/mol*KPHPMSGrimsrud, Chowdhury, et al., 1986gas phase; M
Quantity Value Units Method Reference Comment
Δr60.2 ± 8.4kJ/molTDAsGrimsrud, Chowdhury, et al., 1986gas phase; B

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 evaluated as indicated in comments:
L - Sharon G. Lias

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

Quantity Value Units Method Reference Comment
IE (evaluated)10.4eVN/AN/AL

Electron affinity determinations

EA (eV) Method Reference Comment
1.66 ± 0.10IMREChowdhury, Heinis, et al., 1986ΔGea(423 K) = -36.9 kcal/mol; ΔSea (estimated) = -3.2 eu.; B
0.067996N/ADesfrancois, Periquet, et al., 1999dipole bound state; B
<1.650 ± 0.050PDMock and Grimsrud, 1989B
1.652 ± 0.048IMREFukuda and McIver, 1985ΔGea(355 K) = -37.0 kcal/mol; ΔSea =-3.2, est. from data in Chowdhury, Heinis, et al., 1986; B

Ionization energy determinations

IE (eV) Method Reference Comment
10.43 ± 0.02PIKotov and Potapov, 1972LLK
10.6 ± 0.1EIBrown, 1970RDSH
10.40PEPalmer, Moyes, et al., 1979Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C6H4NO2+12.3 ± 0.1NO2EIBrown, 1970RDSH

Ion clustering 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. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

Clustering reactions

Bromine anion + Benzene, 1,3-dinitro- = (Bromine anion • Benzene, 1,3-dinitro-)

By formula: Br- + C6H4N2O4 = (Br- • C6H4N2O4)

Quantity Value Units Method Reference Comment
Δr84.9 ± 7.5kJ/molIMREPaul and Kebarle, 1991gas phase; ΔGaff at 423 K, ΔSaff taken as that of mCF3-nitrobenzene..Br-; B,M
Quantity Value Units Method Reference Comment
Δr92.J/mol*KN/APaul and Kebarle, 1991gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr45.6 ± 4.2kJ/molIMREPaul and Kebarle, 1991gas 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
45.6423.PHPMSPaul and Kebarle, 1991gas phase; Entropy change calculated or estimated; M

Nitrogen oxide anion + Benzene, 1,3-dinitro- = (Nitrogen oxide anion • Benzene, 1,3-dinitro-)

By formula: NO2- + C6H4N2O4 = (NO2- • C6H4N2O4)

Quantity Value Units Method Reference Comment
Δr88.7 ± 8.4kJ/molTDAsGrimsrud, Chowdhury, et al., 1986gas phase; B,M
Quantity Value Units Method Reference Comment
Δr94.6J/mol*KPHPMSGrimsrud, Chowdhury, et al., 1986gas phase; M
Quantity Value Units Method Reference Comment
Δr60.2 ± 8.4kJ/molTDAsGrimsrud, Chowdhury, et al., 1986gas phase; B

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director


References

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Notes

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

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]

Grimsrud, Chowdhury, et al., 1986
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]

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]

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]

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]

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]

Kotov and Potapov, 1972
Kotov, B.V.; Potapov, V.K., Ionization potentials of strong organic electron acceptors, Khim. Vys. Energ., 1972, 6, 375. [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, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, References