p-Nitroaniline

• Formula: C₆H₆N₂O₂
• Molecular weight: 138.1240
• IUPAC Standard InChI: InChI=1S/C6H6N2O2/c7-5-1-3-6(4-2-5)8(9)10/h1-4H,7H2 Copy

  
• IUPAC Standard InChIKey: TYMLOMAKGOJONV-UHFFFAOYSA-N Copy
• 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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• Information on this page:
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
  • X-ray Photoelectron Spectroscopy Database, version 5.0
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Gas phase ion energetics data

Go To: Top, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, 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)

Electron affinity determinations

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

C₆H₅N₂O₂^- +  =

By formula: C₆H₅N₂O₂^- + H⁺ = C₆H₆N₂O₂

IR Spectrum

Go To: Top, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, References, Notes

Data compiled by: Coblentz Society, Inc.

• Not specified, most likely a prism, grating, or hybrid spectrometer.; (NO SPECTRUM, ONLY SCANNED IMAGE IS AVAILABLE)

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

• gas

Mass spectrum (electron ionization)

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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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Additional Data

UV/Visible spectrum

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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: Victor Talrose, Alexander N. Yermakov, Alexy A. Usov, Antonina A. Goncharova, Axlexander N. Leskin, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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Additional Data

Gas Chromatography

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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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Kovats' RI, non-polar column, isothermal

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Lee's RI, non-polar column, temperature ramp

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Lee's RI, non-polar column, custom temperature program

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References

Go To: Top, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, Notes

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

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]

Kumler, 1946
Kumler, W.D., J. Am. Chem. Soc., 1946, 68, 1184. [all data]

Oszczapowicz, Osek, et al., 1985
Oszczapowicz, J.; Osek, J.; Ciszkowski, K.; Krawczyk, W.; Ostrowski, M., Retention Indices of Dimethylbenzamidines and Benzylideneamines on a Non-Polar Column, J. Chromatogr., 1985, 330, 79-85, https://doi.org/10.1016/S0021-9673(01)81964-6 . [all data]

Oszczapowicz, Osek, et al., 1984
Oszczapowicz, J.; Osek, J.; Dolecka, E., Retention indices of dimethylformamidines, dimethylacetamidines and tetramethylguanidines on a non-polar column, J. Chromatogr., 1984, 315, 95-100, https://doi.org/10.1016/S0021-9673(01)90727-7 . [all data]

Donnelly, Abdel-Hamid, et al., 1993
Donnelly, J.R.; Abdel-Hamid, M.S.; Jeter, J.L.; Gurka, D.F., Application of gas chromatographic retention properties to the identification of environmental contaminants, J. Chromatogr., 1993, 642, 1-2, 409-415, https://doi.org/10.1016/0021-9673(93)80106-I . [all data]

Eckel and Kind, 2003
Eckel, W.P.; Kind, T., Use of boiling point-Lee retention index correlation for rapid review of gas chromatography-mass spectrometry data, Anal. Chim. Acta., 2003, 494, 1-2, 235-243, https://doi.org/10.1016/j.aca.2003.08.003 . [all data]

Notes

Go To: Top, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, 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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