m-Nitroaniline
- Formula: C6H6N2O2
- Molecular weight: 138.1240
- 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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Reaction thermochemistry data
Go To: Top, Gas phase ion energetics 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: 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° | 352.3 ± 2.1 | kcal/mol | G+TS | Taft and Topsom, 1987 | gas phase |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 345.0 ± 2.0 | kcal/mol | IMRE | Taft and Topsom, 1987 | gas phase |
Gas phase ion energetics data
Go To: Top, 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:
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° | 352.3 ± 2.1 | kcal/mol | G+TS | Taft and Topsom, 1987 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 345.0 ± 2.0 | kcal/mol | IMRE | Taft and Topsom, 1987 | gas phase; B |
References
Go To: Top, 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.
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, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy EA Electron affinity 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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