m-Nitroaniline
- Formula: C6H6N2O2
- Molecular weight: 138.1240
- IUPAC Standard InChI: InChI=1S/C6H6N2O2/c7-5-2-1-3-6(4-5)8(9)10/h1-4H,7H2
- IUPAC Standard InChIKey: XJCVRTZCHMZPBD-UHFFFAOYSA-N
- CAS Registry Number: 99-09-2
- 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: Benzenamine, 3-nitro-; Aniline, m-nitro-; m-Aminonitrobenzene; m-Nitroaminobenzene; m-Nitrophenylamine; Amarthol Fast Orange R Base; Azobase MNA; C.I. Azoic Diazo Component 7; C.I. 37030; Daito Orange Base R; Devol Orange R; Diazo Fast Orange R; Fast Orange Base R; Fast Orange M Base; Fast Orange MM Base; Fast Orange R Base; Fast Orange R Salt; Hiltonil Fast Orange R Base; MNA; Naphtoelan Orange R Base; Nitranilin; Orange Base Irga I; 1-Amino-3-nitrobenzene; 3-Nitroaniline; 3-Nitrobenzenamine; 3-Nitrobenzeneamine; 3-Nitrophenylamine; m-Nitraniline; 3-Aminonitrobenzene; NSC 9574
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Gas phase 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | 62.5 ± 1.8 | kJ/mol | Ccr | Nishiyama, Sakiyama, et al., 1983 |
Condensed phase 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:
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 |
|---|---|---|---|---|---|
| ΔfH°solid | -34.2 ± 1.2 | kJ/mol | Ccr | Nishiyama, Sakiyama, et al., 1983 | ALS |
| ΔfH°solid | -38. ± 0.4 | kJ/mol | Ccb | Lebedeva, Gutner, et al., 1971 | Hfusion=5.7±0.2, see Lebedeva, Rjadnenko, et al., 1969; ALS |
| ΔfH°solid | -28.3 | kJ/mol | Ccb | Medard and Thomas, 1957 | Heat of combustion corrected for pressure; ALS |
| ΔfH°solid | -63.47 | kJ/mol | Ccb | Rinkenbach, 1930 | Author hf298_condensed[kcal/mol]=-17.50; ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -3184.32 ± 0.88 | kJ/mol | Ccr | Nishiyama, Sakiyama, et al., 1983 | ALS |
| ΔcH°solid | -3180. ± 0.4 | kJ/mol | Ccb | Lebedeva, Gutner, et al., 1971 | Hfusion=5.7±0.2, see Lebedeva, Rjadnenko, et al., 1969; ALS |
| ΔcH°solid | -3190.3 | kJ/mol | Ccb | Medard and Thomas, 1957 | Heat of combustion corrected for pressure; ALS |
| ΔcH°solid | -3155.1 | kJ/mol | Ccb | Rinkenbach, 1930 | Author hf298_condensed[kcal/mol]=-17.50; ALS |
Constant pressure heat capacity of solid
| Cp,solid (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 158.84 | 298.15 | Nishiyama, Sakiyama, et al., 1983 | Cp given as 1.15 J/g*K.; DH |
| 186.6 | 323. | Satoh and Sogabe, 1941 | T = 0 to 100°C. Mean value.; DH |
| 168.2 | 298. | Andrews, Lynn, et al., 1926 | T = 22 to 210°C.; DH |
| 167.4 | 297.9 | Andrews, 1926 | T = 110 to 344 K. Value is unsmoothed experimental datum.; DH |
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 by: John E. Bartmess
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
C6H5N2O2- + =
By formula: C6H5N2O2- + H+ = C6H6N2O2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1474. ± 8.8 | kJ/mol | G+TS | Taft and Topsom, 1987 | gas phase |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1443. ± 8.4 | kJ/mol | IMRE | Taft and Topsom, 1987 | gas phase |
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 compiled as indicated in comments:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
View reactions leading to C6H6N2O2+ (ion structure unspecified)
Electron affinity determinations
| EA (eV) | Method | Reference | Comment |
|---|---|---|---|
| 0.95 ± 0.10 | IMRE | Chowdhury, Kishi, et al., 1989 | ΔGea(423 K) = -21.0 kcal/mol, ΔS = -2 eu est; B |
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 8.31 ± 0.02 | PI | Potapov, Kardash, et al., 1972 | LLK |
| 8.80 | EI | Crable and Kearns, 1962 | RDSH |
| 8.60 | PE | Khalil, Meeks, et al., 1973 | Vertical value; LLK |
Appearance energy determinations
| Ion | AE (eV) | Other Products | Method | Reference | Comment |
|---|---|---|---|---|---|
| C6H6N+ | 11.2 ± 0.1 | NO2 | EI | Brown, 1970 | RDSH |
| C6H6NO+ | 9.1 ± 0.1 | NO | EI | Brown, 1970 | RDSH |
De-protonation reactions
C6H5N2O2- + =
By formula: C6H5N2O2- + H+ = C6H6N2O2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1474. ± 8.8 | kJ/mol | G+TS | Taft and Topsom, 1987 | gas phase; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1443. ± 8.4 | kJ/mol | IMRE | Taft and Topsom, 1987 | gas phase; B |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, 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.
Nishiyama, Sakiyama, et al., 1983
Nishiyama, K.; Sakiyama, M.; Seki, S.,
Enthalpies of combustion of organic compounds. V. 3- and 4-nitroanilines,
Bull. Chem. Soc. Jpn., 1983, 56, 3171-3172. [all data]
Lebedeva, Gutner, et al., 1971
Lebedeva, N.D.; Gutner, N.M.; Ryadnenko, V.L.,
Heats of combustion and formation of certain aromatic amino-derivatives,
Russ. J. Phys. Chem. (Engl. Transl.), 1971, 45, 561-562. [all data]
Lebedeva, Rjadnenko, et al., 1969
Lebedeva, N.D.; Rjadnenko, B.L.; Gutner, N.M.,
Heats of formation of some N-containing organic compounds,
Int. Conf. Calorim. Therm. (Warsaw, Poland), 1969, 1-8. [all data]
Medard and Thomas, 1957
Medard, L.; Thomas, M.,
Chaleur de combustion de onze substances explosives ou apparentees a des explosifs,
Mem. Poudres, 1957, 39, 195-208. [all data]
Rinkenbach, 1930
Rinkenbach, W.H.,
The heats of combustion and formation of aromatic nitro compounds,
J. Am. Chem. Soc., 1930, 52, 115-120. [all data]
Satoh and Sogabe, 1941
Satoh, S.; Sogabe, T.,
The heat capacities of some organic compounds containing nitrogen and the atomic heat of nitrogen. (3), Sci.,
Pap. Inst. Phys. Chem. Res. (Tokyo), 1941, 38, 238-245. [all data]
Andrews, Lynn, et al., 1926
Andrews, D.H.; Lynn, G.; Johnston, J.,
The heat capacities and heat of crystallization of some isomeric aromatic compounds,
J. Am. Chem. Soc., 1926, 48, 1274-1287. [all data]
Andrews, 1926
Andrews, D.H.,
The specific heats of some isomers of the type ortho, meta and para C6H4XY from 110 to 340K,
J. Am. Chem. Soc., 1926, 48, 1287-1298. [all data]
Taft and Topsom, 1987
Taft, R.W.; Topsom, R.D.,
The Nature and Analysis of Substituent Effects,
Prog. Phys. Org. Chem., 1987, 16, 1. [all data]
Chowdhury, Kishi, et al., 1989
Chowdhury, S.; Kishi, H.; Dillow, G.W.; Kebarle, P.,
Electron Affinities of Substituted Nitrobenzenes,
Can. J. Chem., 1989, 67, 4, 603, https://doi.org/10.1139/v89-091
. [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]
Crable and Kearns, 1962
Crable, G.F.; Kearns, G.L.,
Effect of substituent groups on the ionization potentials of benzenes,
J. Phys. Chem., 1962, 66, 436. [all data]
Khalil, Meeks, et al., 1973
Khalil, O.S.; Meeks, J.L.; McGlynn, S.P.,
Electronic spectroscopy of highly polar aromatics. VII. Photoelectron spectra of nitroanilines,
J. Am. Chem. Soc., 1973, 95, 5876. [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]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy Cp,solid Constant pressure heat capacity of solid EA Electron affinity ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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