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
View 3d structure (requires JavaScript / HTML 5) - 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 thermochemistry data
Go To: Top, Reaction thermochemistry data, Henry's Law data, 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | -27.41 ± 0.29 | kcal/mol | Ccr | Sabbah and Gouali, 1994 | Author was aware that data differs from previously reported values |
| ΔfH°gas | -28.13 ± 0.48 | kcal/mol | Ccb | Finch, Gardner, et al., 1983 |
Reaction 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 as indicated in comments:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.
Individual Reactions
+
= (
•
)
By formula: Br- + C6H5NO3 = (Br- • C6H5NO3)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 28.4 ± 1.8 | kcal/mol | IMRE | Paul and Kebarle, 1990 | gas phase; ΔGaff at 423 K; B,M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrS° | 23. | cal/mol*K | N/A | Paul and Kebarle, 1990 | gas phase; switching reaction,Thermochemical ladder(Br-)C6H5OH, Entropy change calculated or estimated; M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 18.7 ± 1.0 | kcal/mol | IMRE | Paul and Kebarle, 1990 | gas phase; ΔGaff at 423 K; B |
Free energy of reaction
| ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 18.7 | 423. | PHPMS | Paul and Kebarle, 1990 | gas phase; switching reaction,Thermochemical ladder(Br-)C6H5OH, Entropy change calculated or estimated; M |
C6H4NO3- + =
By formula: C6H4NO3- + H+ = C6H5NO3
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 327.7 ± 2.1 | kcal/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° | 320.9 ± 2.0 | kcal/mol | IMRE | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale; B |
Henry's Law 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: Rolf Sander
Henry's Law constant (water solution)
kH(T) = k°H exp(d(ln(kH))/d(1/T) ((1/T) - 1/(298.15 K)))
k°H = Henry's law constant for solubility in water at 298.15 K (mol/(kg*bar))
d(ln(kH))/d(1/T) = Temperature dependence constant (K)
| k°H (mol/(kg*bar)) | d(ln(kH))/d(1/T) (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 980. | 6000. | X | N/A | |
| 2.6×10+6 | 9100. | M | N/A | It is assumed here that the thermodynamic data in missing citation refers to the units [mol/dm3] and [atm] as standard states. |
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
| Column type | Active phase | Temperature (C) | I | Reference | Comment |
|---|---|---|---|---|---|
| Capillary | OV-1 | 190. | 1530. | Erdmann, Rochholz, et al., 1992 | Large deviations from similar measurements |
| Packed | E-301 | 150. | 1588. | Verevkin, Belen'kaya, et al., 1990 | He; Column length: 1.0 m |
| Packed | SE-30 | 204. | 1562. | Mitchell and Vernon, 1972 |
Kovats' RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | HP-5 | 1544.8 | Van Durme, Dewulf, et al., 2007 | Program: not specified |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | OV-101 | 1527.2 | Ferchichi and Messadi, 1994 | 4. K/min; Column length: 25. m; Column diameter: 0.2 mm; Tstart: 30. C; Tend: 250. C |
| Capillary | DB-5 | 1539. | Rostad and Pereira, 1986 | 30. m/0.26 mm/0.25 μm, He, 50. C @ 4. min, 6. K/min, 300. C @ 20. min |
Van Den Dool and Kratz RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | VF-5MS | 1546.1 | Tret'yakov, 2007 | 30. m/0.25 mm/0.25 μm, He; Program: Multi-step temperature program; T(initial)=60C; T(final)=270C |
Normal alkane RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | SE-54 | 1546. | Harland, Cumming, et al., 1986 | He, 50. C @ 2. min, 8. K/min, 250. C @ 12. min; Column length: 25. m; Column diameter: 0.32 mm |
Lee's RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | DB-5 | 260.4 | Donnelly, Abdel-Hamid, et al., 1993 | 30. m/0.32 mm/0.25 μm, He, 40. C @ 3. min, 8. K/min, 285. C @ 29.5 min |
| Capillary | DB-5 | 262.33 | Rostad and Pereira, 1986 | 30. m/0.26 mm/0.25 μm, He, 50. C @ 4. min, 6. K/min, 300. C @ 20. min |
References
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Henry's Law data, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Sabbah and Gouali, 1994
Sabbah, R.; Gouali, M.,
Energetics of intra- and inter-molecular bonds in the three nitrophenols,
Aust. J. Chem., 1994, 47, 1651-1660. [all data]
Finch, Gardner, et al., 1983
Finch, A.; Gardner, P.J.; Wu, D.,
Studies on nitrophenols. Part IV. The standard enthalpies of combustion and formation of 1,2-dihydroxybenzene, 1,2- and 1,4-nitrophenol,
Thermochim. Acta, 1983, 66, 333-342. [all data]
Paul and Kebarle, 1990
Paul, G.J.C.; Kebarle, P.,
Stabilities in the Gas Phase of the Hydrogen Bonded Complexes, YC6H4OH-X-, of Substituted Phenols, YC6H4OH, with the Halide Anions X-(Cl-, Br-),
Can. J. Chem., 1990, 68, 11, 2070, https://doi.org/10.1139/v90-316
. [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]
Erdmann, Rochholz, et al., 1992
Erdmann, F.; Rochholz, G.; Schütz, H.,
Retention-indices on OV-1 of approximately 170 commonly used pesticides,
Mikrochim. Acta, 1992, 106, 3-6, 219-226, https://doi.org/10.1007/BF01242093
. [all data]
Verevkin, Belen'kaya, et al., 1990
Verevkin, S.P.; Belen'kaya, R.S.; Rozhnov, A.M.; Matyushina, V.P.,
Investigation of the chromatographic behaviour of alkylnitrophenols,
Zh. Anal. Khim., 1990, 45, 1786-1790. [all data]
Mitchell and Vernon, 1972
Mitchell, P.T.; Vernon, F.,
Gas-Liquid Chromatography of Nitrophenols and Methyl Derivatives,
J. Chromatogr., 1972, 65, 3, 487-491, https://doi.org/10.1016/S0021-9673(00)84994-8
. [all data]
Van Durme, Dewulf, et al., 2007
Van Durme, J.; Dewulf, J.; Sysmans, W.; Leys, C.; Van Langenhove, H.,
Abatement and degradation pathways of toluene in indoor air by positive corona discharge,
Chemosphere, 2007, 68, 10, 1821-1829, https://doi.org/10.1016/j.chemosphere.2007.03.053
. [all data]
Ferchichi and Messadi, 1994
Ferchichi, L.; Messadi, D.,
Simulations de la rétention et de l'effecacité de colonne en chromatographie en phase gazeuse à température programmée: théorie et application,
Analusis, 1994, 22, 392-399. [all data]
Rostad and Pereira, 1986
Rostad, C.E.; Pereira, W.E.,
Kovats and Lee retention indices determined by gas chromatography/mass spectrometry for organic compounds of environmental interest,
J. Hi. Res. Chromatogr. Chromatogr. Comm., 1986, 9, 6, 328-334, https://doi.org/10.1002/jhrc.1240090603
. [all data]
Tret'yakov, 2007
Tret'yakov, K.V.,
Retention Data. NIST Mass Spectrometry Data Center., NIST Mass Spectrometry Data Center, 2007. [all data]
Harland, Cumming, et al., 1986
Harland, B.J.; Cumming, R.I.; Gillings, E.,
The Kovats indexes of some organic micropollutants on an SE54 capillary column,
EUR, I Org. Micropollut. Aquat. Environ., 1986, EUR 10388, 123-127. [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]
Notes
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Henry's Law data, Gas Chromatography, References
- Symbols used in this document:
T Temperature d(ln(kH))/d(1/T) Temperature dependence parameter for Henry's Law constant k°H Henry's Law constant at 298.15K ΔfH°gas Enthalpy of formation of gas at standard conditions ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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