Benzaldehyde, 4-nitro-
- Formula: C7H5NO3
- Molecular weight: 151.1195
- IUPAC Standard InChIKey: BXRFQSNOROATLV-UHFFFAOYSA-N
- CAS Registry Number: 555-16-8
- 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: Benzaldehyde, p-nitro-; p-Formylnitrobenzene; p-Nitrobenzaldehyde; 4-Nitrobenzaldehyde
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Phase change data
Go To: Top, Gas phase ion energetics data, IR 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 compiled by: Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tfus | 377.15 | K | N/A | Hajos, 1959 | Uncertainty assigned by TRC = 2. K |
Tfus | 375.15 | K | N/A | Hajos, 1959 | Uncertainty assigned by TRC = 2.5 K |
Tfus | 380. | K | N/A | Timmermans, 1935 | Uncertainty assigned by TRC = 2. K |
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
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) | 190.0 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 182.4 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Electron affinity determinations
EA (eV) | Method | Reference | Comment |
---|---|---|---|
1.691 ± 0.087 | IMRE | Chowdhury, Kishi, et al., 1989 | ΔGea(423 K) = -37.7 kcal/mol, ΔS = -3 eu est.; B |
1.652 ± 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 |
1.635 ± 0.087 | IMRE | Mishima, Huh, et al., 1993 | ΔGea(343 K)=-29.4 kcal/mol. Reanchored to EA(PhNO2), Kebarle and Chowdhury, 1987.; B |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
10.27 ± 0.01 | PE | Gal, Geribaldi, et al., 1985 | LBLHLM |
10.27 ± 0.01 | EI | Foffani, Pignataro, et al., 1964 | RDSH |
10.37 | PE | Gal, Geribaldi, et al., 1985 | Vertical value; LBLHLM |
IR 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: Coblentz Society, Inc.
Condensed Phase Spectrum
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Notice: Except where noted, spectra from this collection were measured on dispersive instruments, often in carefully selected solvents, and hence may differ in detail from measurements on FTIR instruments or in other chemical environments. More information on the manner in which spectra in this collection were collected can be found here.
Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.
Additional Data
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Owner | COPYRIGHT (C) 1988 by COBLENTZ SOCIETY INC. Collection (C) 2018 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | DOW CHEMICAL COMPANY |
Source reference | COBLENTZ NO. 8654 |
Date | 1963/05/17 |
Name(s) | 4-nitrobenzaldehyde |
State | SOLUTION (CCl4 FOR 3800-1330, CS2 FOR 1330-400 CM-1) |
Instrument | DOW KBr FOREPRISM-GRATING |
Instrument parameters | BLAZED AT 3.5, 12.0, 20.0 MICRON AND CHANGED AT 5.0, 7.5, 14.9 MICRON |
Path length | 0.011 CM, 0.010 CM SPECTRAL CONTAMINATION DUE TO CS2 AROUND 850, AND CCl4 AROUND 1550 CM-1 |
Resolution | 2 |
Sampling procedure | TRANSMISSION |
Data processing | DIGITIZED BY COBLENTZ SOCIETY (BATCH I) FROM HARD COPY |
Gas Chromatography
Go To: Top, Phase change data, Gas phase ion energetics data, IR Spectrum, 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
Kovats' RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Packed | OV-101 | 140. | 1291.8 | Righezza, Hassani, et al., 1996 | N2, Chromosorb G HP; Column length: 5. m |
Packed | OV-101 | 160. | 1302.2 | Hassani and Meklati, 1992 | N2, Chromosorb G HP; Column length: 5. m |
References
Go To: Top, Phase change data, Gas phase ion energetics data, IR Spectrum, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
Timmermans, 1935
Timmermans, J.,
Researches in Stoichiometry. I. The Heat of Fusion of Organic Compounds.,
Bull. Soc. Chim. Belg., 1935, 44, 17-40. [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., 1993
Mishima, M.; Huh, C.; Nakamura, H.; Fujio, M.; Tsuno, Y.,
Electron Affinities of Benzaldehydes. Substituent Effects on Stabilities of Aromatic Radical Anions.,
Tetrahed. Lett., 1993, 34, 26, 4223, https://doi.org/10.1016/S0040-4039(00)60533-6
. [all data]
Kebarle and Chowdhury, 1987
Kebarle, P.; Chowdhury, S.,
Electron affinities and electron transfer reactions,
Chem. Rev., 1987, 87, 513. [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]
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]
Righezza, Hassani, et al., 1996
Righezza, M.; Hassani, A.; Meklati, B.Y.; Chrétien, J.R.,
Quantitative structure-retention relationships (QSRR) of congeneric aromatics series studied on phenyl OV phases in gas chromatography,
J. Chromatogr. A, 1996, 723, 1, 77-91, https://doi.org/10.1016/0021-9673(95)00816-0
. [all data]
Hassani and Meklati, 1992
Hassani, A.; Meklati, B.Y.,
Gas chromatographic behaviour of monosubstituted benzenes, benzaldehydes and acetophenones on OV polymethylphenyl-silicone stationary phases,
Chromatographia, 1992, 33, 5/6, 267-271, https://doi.org/10.1007/BF02276193
. [all data]
Notes
Go To: Top, Phase change data, Gas phase ion energetics data, IR Spectrum, Gas Chromatography, References
- Symbols used in this document:
EA Electron affinity Tfus Fusion (melting) point - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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