Acetophenone, 4'-nitro-

• Formula: C₈H₇NO₃
• Molecular weight: 165.1461
• IUPAC Standard InChI: InChI=1S/C8H7NO3/c1-6(10)7-2-4-8(5-3-7)9(11)12/h2-5H,1H3 Copy

  
• IUPAC Standard InChIKey: YQYGPGKTNQNXMH-UHFFFAOYSA-N Copy
• CAS Registry Number: 100-19-6
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
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• Other names: Ethanone, 1-(4-nitrophenyl)-; p-Acetylnitrobenzene; p-Nitroacetophenone; p-Nitrophenyl methyl ketone; 4'-Nitroacetophenone; 4-Nitroacetophenone; Paranitroacetophenone; Methyl-p-nitrophenyl ketone; PNAP; 4-Acetylnitrobenzene; 1-Acetyl-4-nitrobenzene; 1-(4-Nitrophenyl)ethan-1-one; Methyl 4-nitrophenyl ketone; NSC 41590; 1-(4-Nitrophenyl)ethanone
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• Information on this page:
  • Condensed phase thermochemistry data
  • Phase change data
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • References
  • Notes
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Phase change 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director

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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias

Data compiled as indicated in comments:
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
B - John E. Bartmess

Electron affinity determinations

Ionization energy determinations

Appearance energy determinations

IR Spectrum

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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, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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Additional Data

References

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

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

Seno, Tsuchiya, et al., 1975
Seno, M.; Tsuchiya, S.; Kise, H.; Asahara, T., Studies on bond character in phosphorus ylides by combustion heat and x-ray photoelectron spectroscopy, Bull. Chem. Soc. Jpn., 1975, 48, 2001-2005. [all data]

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]

Hajos, 1959
Hajos, A., Experiments in the Domain of chloroamphenicols VIII. Preparation of nitroacetophenones and nitrobenzaldehydes and various derivatives through oxidative oxime cleavage, Acta Chim. Acad. Sci. Hung., 1959, 21, 131. [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]

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]

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]

Mishima, Huh, et al., 1995
Mishima, M.; Huh, C.; Lee, H.W.; Nakamura, H.; Fujio, M.; Tsuno, Y., Electron affinities of acetophenones and methyl benzoates. Varying resonance demand of aromatic radical anions, Tetrahed. Lett., 1995, 36, 13, 2265, https://doi.org/10.1016/0040-4039(95)00267-G . [all data]

Kebarle and Chowdhury, 1987
Kebarle, P.; Chowdhury, S., Electron affinities and electron transfer reactions, Chem. Rev., 1987, 87, 513. [all data]

Foffani, Pignataro, et al., 1964
Foffani, A.; Pignataro, S.; Cantone, B.; Grasso, F., Ionization potentials and substituent effects for aromatic carbonyl compounds, Z. Physik. Chem. (Frankfurt), 1964, 42, 221. [all data]

Distefano, Granozzi, et al., 1987
Distefano, G.; Granozzi, G.; Olivato, P.R.; Guerrero, S.A., Hyperconjugative interactions in halogen-substituted carbonyls: Ultraviolet photoelectron spectroscopy of w-halogenoacetophenones, J. Chem. Soc. Perkin Trans. 2, 1987, 1459. [all data]

Gal, Geribaldi, et al., 1985
Gal, J.-F.; Geribaldi, S.; Pfister-Guillouzo, G.; Morris, D.G., Basicity of the carbonyl group. Part 12. Correlations between ionization potentials and lewis basicities in aromatic carbonyl compounds, J. Chem. Soc. Perkin Trans. 2, 1985, 103. [all data]

Egdell, Green, et al., 1975
Egdell, R.; Green, J.C.; Rao, C.N.R., Photoelectron spectra of substituted benzenes, Chem. Phys. Lett., 1975, 33, 600. [all data]

Chin and Harrison, 1969
Chin, M.S.; Harrison, A.G., Substituent effects on ion abundances and energetics in substituted acetophenones, Org. Mass Spectrom., 1969, 2, 1073. [all data]

Buchs, Rossetti, et al., 1964
Buchs, A.; Rossetti, G.P.; Susz, B.P., Etude, en fonction de la constante σp de Hammett, du spectre de masse d'acetophenones p-substituees, Helv. Chim. Acta, 1964, 47, 1563. [all data]

Grammaticakis, 1953
Grammaticakis, P., Contribution a l'etude de l'absorption dans l'U.-V. moyen et le visible des composes carbonyles aromatiques et de leurs derives. (2^e memoire), Bull. Soc. Chim. Fr., 1953, 20, 865-872. [all data]

Notes

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• Symbols used in this document:
  

  AE	Appearance energy
  EA	Electron affinity
  Tboil	Boiling point
  Tfus	Fusion (melting) point
  ΔcH°solid	Enthalpy of combustion of solid at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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