p-Nitroaniline
- Formula: C6H6N2O2
- Molecular weight: 138.1240
- IUPAC Standard InChIKey: TYMLOMAKGOJONV-UHFFFAOYSA-N
- CAS Registry Number: 100-01-6
- 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, 4-nitro-; Aniline, p-nitro-; p-Aminonitrobenzene; p-Nitrophenylamine; Azoamine Red Zh; C.I. Azoic Diazo Component 37; C.I. Developer 17; C.I. 37035; Developer P; Devol Red GG; Fast Red Base GG; Fast Red Base 2J; Fast Red GG Base; Fast Red MP Base; Fast Red P Base; Fast Red 2G Base; Naphtoelan Red GG Base; Nitrazol CF extra; PNA; Red 2G Base; Shinnippon Fast Red GG Base; 1-Amino-4-nitrobenzene; 4-Nitraniline; 4-Nitroaniline; 4-Nitrobenzenamine; p-Nitraniline; Aniline, 4-nitro-; Azofix Red GG Salt; Azoic Diazo Component 37; Diazo Fast Red GG; Fast Red GG Salt; Fast Red P Salt; Fast Red Salt GG; Fast Red Salt 2J; Fast Red 2G Salt; NCI-C60786; p-Nitroanilina; Paranitroaniline; Rcra waste number P077; 4-Aminonitrobenzene; Azoamine Red 2H; NSC 9797
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Gas phase thermochemistry data
Go To: Top, Gas phase ion energetics data, Mass spectrum (electron ionization), 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 |
---|---|---|---|---|---|
ΔfH°gas | 13.2 ± 0.43 | kcal/mol | Ccr | Nishiyama, Sakiyama, et al., 1983 |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Mass spectrum (electron ionization), References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
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)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 207.0 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 199.4 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Electron affinity determinations
EA (eV) | Method | Reference | Comment |
---|---|---|---|
0.75 ± 0.10 | LPES | Smith, Buonaugurio, et al., 2013 | Vertical Detachment Energy: 1.1 eV; B |
0.915 ± 0.087 | IMRE | Huh, Kang, et al., 1999 | ΔG(EA) 343K; anchored to ΔG value. Including anchor ΔS, EA is ca. 0.4 kcal/mol more bound.; B |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.43 | EI | Johnstone and Mellon, 1973 | LLK |
8.34 ± 0.01 | PI | Potapov, Kardash, et al., 1972 | LLK |
8.6 ± 0.1 | EI | Brown, 1970 | RDSH |
8.85 | 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+ | 11.5 ± 0.1 | NO2 | EI | Brown, 1970 | RDSH |
C6H6NO+ | 9.6 ± 0.1 | NO | EI | Brown, 1970 | RDSH |
De-protonation reactions
C6H5N2O2- + =
By formula: C6H5N2O2- + H+ = C6H6N2O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 343.5 ± 2.1 | kcal/mol | G+TS | Taft and Topsom, 1987 | gas phase; value altered from reference due to change in acidity scale; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 336.2 ± 2.0 | kcal/mol | IMRE | Taft and Topsom, 1987 | gas phase; value altered from reference due to change in acidity scale; B |
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, 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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
Due to licensing restrictions, this spectrum cannot be downloaded.
Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | Japan AIST/NIMC Database- Spectrum MS-NW-1703 |
NIST MS number | 229522 |
References
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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]
Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G.,
Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update,
J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018
. [all data]
Smith, Buonaugurio, et al., 2013
Smith, B.H.; Buonaugurio, A.; Chen, J.; Collins, E.; Bowen, K.H.; Compton, R.N.; Sommerfeld, T.,
Negative ions of p-nitroaniline: Photodetachment, collisions, and ab initio calculations,
J. Chem. Phys., 2013, 138, 23, 234304, https://doi.org/10.1063/1.4810869
. [all data]
Huh, Kang, et al., 1999
Huh, C.; Kang, C.H.; Lee, H.W.; Nakamura, H.; Mishima, M.; Tsuno, Y.; Yamataka, H.,
Thermodynamic stabilities and resonance demand of aromatic radical anions in the gas phase,
Bull. Chem. Soc. Japan, 1999, 72, 5, 1083-1091, https://doi.org/10.1246/bcsj.72.1083
. [all data]
Johnstone and Mellon, 1973
Johnstone, R.A.W.; Mellon, F.A.,
Effects of induction and resonance in the calculation of ionization potentials of substituted benzenes by perturbation molecular orbital theory,
J. Chem. Soc. Faraday Trans. 2, 1973, 69, 36. [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]
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]
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]
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]
Notes
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), References
- Symbols used in this document:
AE Appearance energy EA Electron affinity ΔfH°gas Enthalpy of formation of gas 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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