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Benzene, nitro-

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Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Deltafgas68.53 ± 0.67kJ/molCcbLebedeva, Katin, et al., 1971Reanalyzed by Pedley, Naylor, et al., 1986, Original value = 65.77 ± 0.42 kJ/mol

Condensed phase thermochemistry data

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, 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:
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
Deltafliquid12.5 ± 0.54kJ/molCcbLebedeva, Katin, et al., 1971Reanalyzed by Pedley, Naylor, et al., 1986, Original value = 9.71 ± 0.42 kJ/mol; ALS
Deltafliquid-16.kJ/molCcbSwarts, 1914See 14SWA2; ALS
Quantity Value Units Method Reference Comment
Deltacliquid-3088.08 ± 0.42kJ/molCcbLebedeva, Katin, et al., 1971ALS
Deltacliquid-3096.kJ/molCcbGarner and Abernethy, 1921ALS
Deltacliquid-3073.8kJ/molCcbSwarts, 1914See 14SWA2; ALS
Quantity Value Units Method Reference Comment
liquid224.3J/mol*KN/AParks, Todd, et al., 1936Extrapolation below 90 K, 62.13 J/mol*K.; DH

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
177.3303.15Reddy, 1986T = 303.15, 313.15 K.; DH
181.13298.15Lainez, Rodrigo, et al., 1985DH
176.303.Pacor, 1967DH
180.2293.Rastorguev and Ganiev, 1967T = 293 to 373 K.; DH
188.7335.5Lutskii and Panova, 1958T = 62 to 141°C. Value is unsmoothed experimental datum.; DH
179.95293.15Mazur, 1939T = 5 to 20°C.; DH
179.9293.Mazur, 1939, 2T = 5 to 20°C.; DH
186.69298.1Parks, Todd, et al., 1936T = 90 to 300 K.; DH
186.73298.Parks and Todd, 1934T = 273 to 299 K.; DH
177.4303.Willams and Daniels, 1924T = 303 to 358 K. Equation only.; DH
177.8298.von Reis, 1881T = 291 to 486 K.; DH

Reaction thermochemistry data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, 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

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

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

Quantity Value Units Method Reference Comment
Deltar68.2 ± 4.2kJ/molTDAsChowdhury and Kebarle, 1986gas phase; B,M
Deltar69.0kJ/molPHPMSPaul and Kebarle, 1991gas phase; from Ph. D. thesis of S. Chowdhury, Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar84.J/mol*KN/APaul and Kebarle, 1991gas phase; from Ph. D. thesis of S. Chowdhury, Entropy change calculated or estimated; M
Deltar81.2J/mol*KPHPMSChowdhury and Kebarle, 1986gas phase; M
Quantity Value Units Method Reference Comment
Deltar43.9 ± 6.7kJ/molTDAsChowdhury and Kebarle, 1986gas phase; B
Deltar29.7kJ/molTDEqFrench, Ikuta, et al., 1982gas phase; B

Free energy of reaction

DeltarG° (kJ/mol) T (K) Method Reference Comment
43.9300.PHPMSPaul and Kebarle, 1991gas phase; from Ph. D. thesis of S. Chowdhury, Entropy change calculated or estimated; M
32.300.PHPMSFrench, Ikuta, et al., 1982gas phase; M

C6H4NO2- + Hydrogen cation = Benzene, nitro-

By formula: C6H4NO2- + H+ = C6H5NO2

Quantity Value Units Method Reference Comment
Deltar1577. ± 13.kJ/molG+TSCheng and Grabowski, 1989gas phase; between EtOH, iPrOH; B
Deltar1482. ± 13.kJ/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
Deltar1545. ± 13.kJ/molIMRBCheng and Grabowski, 1989gas phase; between EtOH, iPrOH; B
Deltar1450. ± 13.kJ/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
Deltar62.8 ± 7.5kJ/molTDAsPaul and Kebarle, 1991gas phase; «DELTA»Gaff at 423 K; B,M
Quantity Value Units Method Reference Comment
Deltar84.5J/mol*KN/APaul and Kebarle, 1991gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar27. ± 4.2kJ/molTDAsPaul and Kebarle, 1991gas phase; «DELTA»Gaff at 423 K; B

Free energy of reaction

DeltarG° (kJ/mol) T (K) Method Reference Comment
27.423.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
Deltar74.1kJ/molPHPMSMeot-Ner (Mautner) and El-Shall, 1986gas phase; M
Quantity Value Units Method Reference Comment
Deltar88.7J/mol*KPHPMSMeot-Ner (Mautner) and El-Shall, 1986gas phase; M

Free energy of reaction

DeltarG° (kJ/mol) T (K) Method Reference Comment
44.8324.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
Deltar59.4 ± 8.4kJ/molTDAsGrimsrud, Chowdhury, et al., 1986gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar73.2J/mol*KPHPMSGrimsrud, Chowdhury, et al., 1986gas phase; M
Quantity Value Units Method Reference Comment
Deltar37. ± 8.4kJ/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
Deltar54.8kJ/molPHPMSEl-Shall and Meot-Ner (Mautner), 1987gas phase; M
Quantity Value Units Method Reference Comment
Deltar110.J/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
Deltar164.kJ/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
Deltar62.3 ± 4.2kJ/molTDAsChowdhury and Kebarle, 1986gas phase; B
Quantity Value Units Method Reference Comment
Deltar28. ± 6.7kJ/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
Deltar62.3kJ/molPHPMSChowdhury and Kebarle, 1986gas phase; M
Quantity Value Units Method Reference Comment
Deltar115.J/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° (kJ/mol) T (K) Method Reference Comment
28.300.PHPMSChowdhury and Kebarle, 1986gas phase; M

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

By formula: C7F14- + C6H5NO2 = C13H5F14NO2-

Quantity Value Units Method Reference Comment
Deltar28. ± 4.2kJ/molIMREChowdhury and Kebarle, 1986gas phase; B

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Notes

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

Lebedeva, Katin, et al., 1971
Lebedeva, N.D.; Katin, Y.A.; Akhmedova, G.Y., Standard enthalpy of formation of nitrobenzene, Russ. J. Phys. Chem. (Engl. Transl.), 1971, 45, 1192-1193. [all data]

Pedley, Naylor, et al., 1986
Pedley, J.B.; Naylor, R.D.; Kirby, S.P., Thermochemical Data of Organic Compounds, Chapman and Hall, New York, 1986, 1-792. [all data]

Swarts, 1914
Swarts, F., Sur la chaleur de combustion de quelques derives nitres aromatlques, Recl. Trav. Chim. Pays-Bas, 1914, 33, 281-298. [all data]

Garner and Abernethy, 1921
Garner, W.E.; Abernethy, C.L., Heats of combustion and formation of nitro-compounds. Part I. - Benzene, toluene, phenol and methylaniline series, Proc. Roy. Soc. London A, 1921, 213-235. [all data]

Parks, Todd, et al., 1936
Parks, G.S.; Todd, S.S.; Moore, W.A., Thermal data on organic compounds. XVI. Some heat capacity, entropy and free energy data for typical benzene derivatives and heterocyclic compounds, J. Am. Chem. Soc., 1936, 58, 398-401. [all data]

Reddy, 1986
Reddy, K.S., Isentropic compressibilities of binary liquid mixtures at 303.15 and 313.15 K, J. Chem. Eng. Data, 1986, 31, 238-240. [all data]

Lainez, Rodrigo, et al., 1985
Lainez, A.; Rodrigo, M.; Roux, A.H.; Grolier, J.-P.E.; Wilhelm, E., Relations between structure and thermodynamic properties. Heat capacities of polar substances (nitrobenzene and benzonitrile) in alkane solutions, Calorim. Anal. Therm., 1985, 16, 153-158. [all data]

Pacor, 1967
Pacor, P., Applicability of the DuPont 900 DTA apparatus in quantitative differential thermal analysis, Anal. Chim. Acta, 1967, 37, 200-208. [all data]

Rastorguev and Ganiev, 1967
Rastorguev, Yu.L.; Ganiev, Yu.A., Study of the heat capacity of selected solvents, Izv. Vyssh. Uchebn. Zaved. Neft Gaz. 10, 1967, No.1, 79-82. [all data]

Lutskii and Panova, 1958
Lutskii, A.E.; Panova, A.N., Specific heat of liquid nitrobenzene, Zhur. Fiz. Khim., 1958, 32, 2183-2185. [all data]

Mazur, 1939
Mazur, J., Über die spezifische Wärme des Nitrobenzols, Acta Phys. Pol., 1939, 7, 290-304. [all data]

Mazur, 1939, 2
Mazur, J., Über die spezifische Wärme des Äthyläthers, des Nitrobenzols und des Schwefelkohlenstoffs, Z. Physik., 1939, 113, 710-720. [all data]

Parks and Todd, 1934
Parks, G.S.; Todd, S.S., Some heat capacity data for liquid nitrobenzene, no indication of allotropy, J. Chem. Phys., 1934, 2, 440-441. [all data]

Willams and Daniels, 1924
Willams, J.W.; Daniels, F., The specific heats of certain organic liquids at elevated temperatures, J. Am. Chem. Soc., 1924, 46, 903-917. [all data]

von Reis, 1881
von Reis, M.A., Die specifische Wärme flüssiger organischer Verbindungen und ihre Beziehung zu deren Moleculargewicht, Ann. Physik [3], 1881, 13, 447-464. [all data]

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

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, References