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 • Benzene, nitro-)

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

Quantity Value Units Method Reference Comment
Δr16.3 ± 1.0kcal/molTDAsChowdhury and Kebarle, 1986gas phase; B,M
Δr16.5kcal/molPHPMSPaul and Kebarle, 1991gas phase; from Ph. D. thesis of S. Chowdhury, Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr20.cal/mol*KN/APaul and Kebarle, 1991gas phase; from Ph. D. thesis of S. Chowdhury, Entropy change calculated or estimated; M
Δr19.4cal/mol*KPHPMSChowdhury and Kebarle, 1986gas phase; M
Quantity Value Units Method Reference Comment
Δr10.5 ± 1.6kcal/molTDAsChowdhury and Kebarle, 1986gas phase; B
Δr7.10kcal/molTDEqFrench, Ikuta, et al., 1982gas phase; B

Free energy of reaction

ΔrG° (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
Δr377.0 ± 3.1kcal/molG+TSCheng and Grabowski, 1989gas phase; between EtOH, iPrOH; B
Δr354.2 ± 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
Δr369.3 ± 3.0kcal/molIMRBCheng and Grabowski, 1989gas phase; between EtOH, iPrOH; B
Δr346.5 ± 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 • Benzene, nitro-)

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

Quantity Value Units Method Reference Comment
Δr15.0 ± 1.8kcal/molTDAsPaul and Kebarle, 1991gas phase; ΔGaff at 423 K; B,M
Quantity Value Units Method Reference Comment
Δr20.2cal/mol*KN/APaul and Kebarle, 1991gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr6.5 ± 1.0kcal/molTDAsPaul and Kebarle, 1991gas phase; ΔGaff at 423 K; B

Free energy of reaction

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

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

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

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Δr17.7kcal/molPHPMSMeot-Ner (Mautner) and El-Shall, 1986gas phase; M
Quantity Value Units Method Reference Comment
Δr21.2cal/mol*KPHPMSMeot-Ner (Mautner) and El-Shall, 1986gas phase; M

Free energy of reaction

ΔrG° (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 • Benzene, nitro-)

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

Quantity Value Units Method Reference Comment
Δr14.2 ± 2.0kcal/molTDAsGrimsrud, Chowdhury, et al., 1986gas phase; B,M
Quantity Value Units Method Reference Comment
Δr17.5cal/mol*KPHPMSGrimsrud, Chowdhury, et al., 1986gas phase; M
Quantity Value Units Method Reference Comment
Δr8.9 ± 2.0kcal/molTDAsGrimsrud, Chowdhury, et al., 1986gas phase; B

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

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

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Δr13.1kcal/molPHPMSEl-Shall and Meot-Ner (Mautner), 1987gas phase; M
Quantity Value Units Method Reference Comment
Δr26.3cal/mol*KPHPMSEl-Shall and Meot-Ner (Mautner), 1987gas phase; M

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

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

Quantity Value Units Method Reference Comment
Δr39.3kcal/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- • Benzene, nitro-)

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

Quantity Value Units Method Reference Comment
Δr14.9 ± 1.0kcal/molTDAsChowdhury and Kebarle, 1986gas phase; B
Quantity Value Units Method Reference Comment
Δr6.7 ± 1.6kcal/molTDAsChowdhury and Kebarle, 1986gas phase; B

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

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

Quantity Value Units Method Reference Comment
Δr14.9kcal/molPHPMSChowdhury and Kebarle, 1986gas phase; M
Quantity Value Units Method Reference Comment
Δr27.5cal/mol*KPHPMSChowdhury and Kebarle, 1986gas phase; M

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

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

Free energy of reaction

ΔrG° (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
Δr6.7 ± 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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