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Benzene, nitro-

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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

Chlorine anion + Benzene, nitro- = (Chlorine anion bullet Benzene, nitro-)

By formula: Cl- + C6H5NO2 = (Cl- bullet C6H5NO2)

Quantity Value Units Method Reference Comment
Deltar16.3 ± 1.0kcal/molTDAsChowdhury and Kebarle, 1986gas phase; B,M
Deltar16.5kcal/molPHPMSPaul and Kebarle, 1991gas phase; from Ph. D. thesis of S. Chowdhury, Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar20.cal/mol*KN/APaul and Kebarle, 1991gas phase; from Ph. D. thesis of S. Chowdhury, Entropy change calculated or estimated; M
Deltar19.4cal/mol*KPHPMSChowdhury and Kebarle, 1986gas phase; M
Quantity Value Units Method Reference Comment
Deltar10.5 ± 1.6kcal/molTDAsChowdhury and Kebarle, 1986gas phase; B
Deltar7.10kcal/molTDEqFrench, Ikuta, et al., 1982gas phase; B

Free energy of reaction

DeltarG° (kcal/mol) T (K) Method Reference Comment
10.5300.PHPMSPaul and Kebarle, 1991gas phase; from Ph. D. thesis of S. Chowdhury, Entropy change calculated or estimated; M
7.7300.PHPMSFrench, Ikuta, et al., 1982gas phase; M

C6H4NO2- + Hydrogen cation = Benzene, nitro-

By formula: C6H4NO2- + H+ = C6H5NO2

Quantity Value Units Method Reference Comment
Deltar377.0 ± 3.1kcal/molG+TSCheng and Grabowski, 1989gas phase; between EtOH, iPrOH; B
Deltar354.2 ± 3.1kcal/molG+TSMeot-ner and Kafafi, 1988gas phase; acidity stronger than all levels of computation by 25 kcal/mol; B
Quantity Value Units Method Reference Comment
Deltar369.3 ± 3.0kcal/molIMRBCheng and Grabowski, 1989gas phase; between EtOH, iPrOH; B
Deltar346.5 ± 3.0kcal/molIMRBMeot-ner and Kafafi, 1988gas phase; acidity stronger than all levels of computation by 25 kcal/mol; B

Bromine anion + Benzene, nitro- = (Bromine anion bullet Benzene, nitro-)

By formula: Br- + C6H5NO2 = (Br- bullet C6H5NO2)

Quantity Value Units Method Reference Comment
Deltar15.0 ± 1.8kcal/molTDAsPaul and Kebarle, 1991gas phase; «DELTA»Gaff at 423 K; B,M
Quantity Value Units Method Reference Comment
Deltar20.2cal/mol*KN/APaul and Kebarle, 1991gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar6.5 ± 1.0kcal/molTDAsPaul and Kebarle, 1991gas phase; «DELTA»Gaff at 423 K; B

Free energy of reaction

DeltarG° (kcal/mol) T (K) Method Reference Comment
6.5423.PHPMSPaul and Kebarle, 1991gas phase; Entropy change calculated or estimated; M

C6H7N+ + Benzene, nitro- = (C6H7N+ bullet Benzene, nitro-)

By formula: C6H7N+ + C6H5NO2 = (C6H7N+ bullet C6H5NO2)

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Deltar17.7kcal/molPHPMSMeot-Ner (Mautner) and El-Shall, 1986gas phase; M
Quantity Value Units Method Reference Comment
Deltar21.2cal/mol*KPHPMSMeot-Ner (Mautner) and El-Shall, 1986gas phase; M

Free energy of reaction

DeltarG° (kcal/mol) T (K) Method Reference Comment
10.7324.PHPMSMeot-Ner (Mautner) and El-Shall, 1986gas phase; M

Nitrogen oxide anion + Benzene, nitro- = (Nitrogen oxide anion bullet Benzene, nitro-)

By formula: NO2- + C6H5NO2 = (NO2- bullet C6H5NO2)

Quantity Value Units Method Reference Comment
Deltar14.2 ± 2.0kcal/molTDAsGrimsrud, Chowdhury, et al., 1986gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar17.5cal/mol*KPHPMSGrimsrud, Chowdhury, et al., 1986gas phase; M
Quantity Value Units Method Reference Comment
Deltar8.9 ± 2.0kcal/molTDAsGrimsrud, Chowdhury, et al., 1986gas phase; B

C11H10+ + Benzene, nitro- = (C11H10+ bullet Benzene, nitro-)

By formula: C11H10+ + C6H5NO2 = (C11H10+ bullet C6H5NO2)

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Deltar13.1kcal/molPHPMSEl-Shall and Meot-Ner (Mautner), 1987gas phase; M
Quantity Value Units Method Reference Comment
Deltar26.3cal/mol*KPHPMSEl-Shall and Meot-Ner (Mautner), 1987gas phase; M

Nitric oxide anion + Benzene, nitro- = (Nitric oxide anion bullet Benzene, nitro-)

By formula: NO- + C6H5NO2 = (NO- bullet C6H5NO2)

Quantity Value Units Method Reference Comment
Deltar39.3kcal/molICRReents and Freiser, 1981gas phase; switching reaction,Thermochemical ladder(NO+)C2H5OH, Entropy change calculated or estimated; Farid and McMahon, 1978; M

F6S- + Benzene, nitro- = (F6S- bullet Benzene, nitro-)

By formula: F6S- + C6H5NO2 = (F6S- bullet C6H5NO2)

Quantity Value Units Method Reference Comment
Deltar14.9 ± 1.0kcal/molTDAsChowdhury and Kebarle, 1986gas phase; B
Quantity Value Units Method Reference Comment
Deltar6.7 ± 1.6kcal/molTDAsChowdhury and Kebarle, 1986gas phase; B

F6S- + Benzene, nitro- = (F6S- bullet Benzene, nitro-)

By formula: F6S- + C6H5NO2 = (F6S- bullet C6H5NO2)

Quantity Value Units Method Reference Comment
Deltar14.9kcal/molPHPMSChowdhury and Kebarle, 1986gas phase; M
Quantity Value Units Method Reference Comment
Deltar27.5cal/mol*KPHPMSChowdhury and Kebarle, 1986gas phase; M

Perfluoro(methylcyclohexane) anion + Benzene, nitro- = (Perfluoro(methylcyclohexane) anion bullet Benzene, nitro-)

By formula: C7F14- + C6H5NO2 = (C7F14- bullet C6H5NO2)

Free energy of reaction

DeltarG° (kcal/mol) T (K) Method Reference Comment
6.7300.PHPMSChowdhury and Kebarle, 1986gas phase; M

Perfluoro(methylcyclohexane) anion + Benzene, nitro- = C13H5F14NO2-

By formula: C7F14- + C6H5NO2 = C13H5F14NO2-

Quantity Value Units Method Reference Comment
Deltar6.7 ± 1.0kcal/molIMREChowdhury and Kebarle, 1986gas phase; B

References

Go To: Top, Reaction thermochemistry data, Notes

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

Chowdhury and Kebarle, 1986
Chowdhury, S.; Kebarle, P., Role of Binding Energies in A-.B and A.B- Complexes in the Kinetics of Gas Phase Electron Transfer Reactions:A- + B = A + B- Involving Perfluoro Compounds: SF6, C6F11CF3, J. Chem. Phys., 1986, 85, 9, 4989, https://doi.org/10.1063/1.451687 . [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]

French, Ikuta, et al., 1982
French, M.A.; Ikuta, S.; Kebarle, P., Hydrogen bonding of O-H and C-H hydrogen donors to Cl-. Results from mass spectrometric measurement of the ion-molecule equilibria RH + Cl- = RHCl-, Can. J. Chem., 1982, 60, 1907. [all data]

Cheng and Grabowski, 1989
Cheng, X.; Grabowski, J.J., Gas-phase Acidity of Nitrobenzene from Flowing Afterglow Bracketing Studies, Rapid Commun. Mass Spectrom., 1989, 3, 2, 34-36, https://doi.org/10.1002/rcm.1290030207 . [all data]

Meot-ner and Kafafi, 1988
Meot-ner, M.; Kafafi, S.A., Carbon Acidities of Aromatic Compounds, J. Am. Chem. Soc., 1988, 110, 19, 6297, https://doi.org/10.1021/ja00227a003 . [all data]

Meot-Ner (Mautner) and El-Shall, 1986
Meot-Ner (Mautner), M.; El-Shall, M.S., Ionic Charge Transfer Complexes. 1. Cationic Complexes with Delocalized and Partially Localized pi Systems, J. Am. Chem. Soc., 1986, 108, 15, 4386, https://doi.org/10.1021/ja00275a026 . [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]

El-Shall and Meot-Ner (Mautner), 1987
El-Shall, M.S.; Meot-Ner (Mautner), M., Ionic Charge Transfer Complexes. 3. Delocalised pi Systems as Electron Acceptors and Donors, J. Phys. Chem., 1987, 91, 5, 1088, https://doi.org/10.1021/j100289a017 . [all data]

Reents and Freiser, 1981
Reents, W.D.; Freiser, B.S., Gas-Phase Binding Energies and Spectroscopic Properties of NO+ Charge-Transfer Complexes, J. Am. Chem. Soc., 1981, 103, 2791. [all data]

Farid and McMahon, 1978
Farid, R.; McMahon, T.B., Gas-Phase Ion-Molecule Reactions of Alkyl Nitrites by Ion Cyclotron Resonance Spectroscopy, Int. J. Mass Spectrom. Ion Phys., 1978, 27, 2, 163, https://doi.org/10.1016/0020-7381(78)80037-0 . [all data]


Notes

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