Phenol, 4-nitro-
- Formula: C6H5NO3
- Molecular weight: 139.1088
- IUPAC Standard InChI: InChI=1S/C6H5NO3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8H
- IUPAC Standard InChIKey: BTJIUGUIPKRLHP-UHFFFAOYSA-N
- CAS Registry Number: 100-02-7
- 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: Phenol, p-nitro-; p-Hydroxynitrobenzene; p-Nitrophenol; Niphen; 4-Hydroxynitrobenzene; 4-Nitrophenol; NCI-C55992; Paranitrofenol; Paranitrofenolo; Paranitrophenol; 4-Nitrofenol; p-Nitrofenol; Rcra waste number U170; 1-Hydroxy-4-nitrobenzene; PNP; NSC 1317
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Gas phase ion energetics data
Go To: Top, References, Notes
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:
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 C6H5NO3+ (ion structure unspecified)
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 9.1 | PE | Kobayashi and Nagakura, 1975 | LLK |
| 7.38 | EI | Johnstone and Mellon, 1973 | LLK |
| 8.8 ± 0.1 | EI | Brown, 1970 | RDSH |
| 9.52 | EI | Crable and Kearns, 1962 | RDSH |
| 9.38 | PE | Kobayashi and Nagakura, 1975 | Vertical value; LLK |
Appearance energy determinations
| Ion | AE (eV) | Other Products | Method | Reference | Comment |
|---|---|---|---|---|---|
| C6H5O+ | 11.9 ± 0.1 | NO2 | EI | Brown, 1970 | RDSH |
| C6H5O2+ | 9.9 ± 0.1 | NO | EI | Brown, 1970 | RDSH |
De-protonation reactions
C6H4NO3- + =
By formula: C6H4NO3- + H+ = C6H5NO3
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1371. ± 8.8 | kJ/mol | G+TS | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1343. ± 8.4 | kJ/mol | IMRE | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale; B |
References
Go To: Top, Gas phase ion energetics data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Kobayashi and Nagakura, 1975
Kobayashi, T.; Nagakura, S.,
Photoelectron spectra of nitrophenols and nitroanisoles,
J. Electron Spectrosc. Relat. Phenom., 1975, 6, 421. [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]
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]
Fujio, McIver, et al., 1981
Fujio, M.; McIver, R.T., Jr.; Taft, R.W.,
Effects on the acidities of phenols from specific substituent-solvent interactions. Inherent substituent parameters from gas phase acidities,
J. Am. Chem. Soc., 1981, 103, 4017. [all data]
Notes
Go To: Top, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy 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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