Acetophenone, 4'-nitro-
- Formula: C8H7NO3
- Molecular weight: 165.1461
- IUPAC Standard InChIKey: YQYGPGKTNQNXMH-UHFFFAOYSA-N
- 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
The 3d structure may be viewed using Java or Javascript. - 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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Condensed phase thermochemistry data
Go To: Top, Phase change data, 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 |
---|---|---|---|---|---|
ΔcH°solid | -3933. | kJ/mol | Ccb | Seno, Tsuchiya, et al., 1975 |
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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 475.2 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
Tboil | 421.7 | K | N/A | Weast and Grasselli, 1989 | BS |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 353.65 | K | N/A | Hajos, 1959 | Uncertainty assigned by TRC = 1.5 K; TRC |
Gas phase ion energetics data
Go To: Top, Condensed phase thermochemistry data, Phase change 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:
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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 824.3 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 792.5 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Electron affinity determinations
EA (eV) | Method | Reference | Comment |
---|---|---|---|
1.57 ± 0.10 | IMRE | Chowdhury, Kishi, et al., 1989 | ΔGea(423 K) = -34.8 kcal/mol, ΔS = -3 eu est; B |
1.539 ± 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 |
1.414 ± 0.087 | IMRE | Mishima, Huh, et al., 1995 | ΔGea(343 K)=-33.5 kcal/mol. Reanchored to EA(PhNO2), Kebarle and Chowdhury, 1987.; B |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
10.07 ± 0.02 | EI | Foffani, Pignataro, et al., 1964 | RDSH |
10.05 | PE | Distefano, Granozzi, et al., 1987 | Vertical value; LBLHLM |
9.98 | PE | Gal, Geribaldi, et al., 1985 | Vertical value; LBLHLM |
10.2 ± 0.1 | PE | Egdell, Green, et al., 1975 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C7H4NO3+ | 10.7 ± 0.1 | CH3 | EI | Chin and Harrison, 1969 | RDSH |
C7H4NO3+ | 10.32 | CH3 | EI | Buchs, Rossetti, et al., 1964 | RDSH |
Mass spectrum (electron ionization)
Go To: Top, Condensed phase thermochemistry data, Phase change 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
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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 | NIST Mass Spectrometry Data Center, 1990. |
NIST MS number | 118930 |
References
Go To: Top, Condensed phase thermochemistry data, Phase change 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.
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]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), References
- 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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