Phenol, 4-nitro-
- Formula: C6H5NO3
- Molecular weight: 139.1088
- 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 thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering 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: 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 |
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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°solid | -49.50 ± 0.26 | kcal/mol | Ccr | Sabbah and Gouali, 1994 | Author was aware that data differs from previously reported values; ALS |
ΔfH°solid | -50.76 ± 0.24 | kcal/mol | Ccb | Finch, Gardner, et al., 1983 | ALS |
ΔfH°solid | -54.19 | kcal/mol | Ccb | Rinkenbach, 1930 | Author hf298_condensed[kcal/mol]=-56.50; ALS |
ΔfH°solid | -50.0 | kcal/mol | Ccb | Swarts, 1914 | See 14SWA2; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -685.59 ± 0.24 | kcal/mol | Ccr | Sabbah and Gouali, 1994 | Author was aware that data differs from previously reported values; ALS |
ΔcH°solid | -684.32 ± 0.13 | kcal/mol | Ccb | Finch, Gardner, et al., 1983 | ALS |
ΔcH°solid | -680.91 | kcal/mol | Ccb | Rinkenbach, 1930 | Author hf298_condensed[kcal/mol]=-56.50; ALS |
ΔcH°solid | -687.0 | kcal/mol | Ccb | Garner and Abernethy, 1921 | ALS |
ΔcH°solid | -688.23 | kcal/mol | Ccb | Swarts, 1914 | See 14SWA2; ALS |
Constant pressure heat capacity of solid
Cp,solid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
34.4 | 283. | Campbell and Campbell, 1941 | T = 273 to 293 K. Value given as Cp = 0.248 cal/g over temperature range 0 to 20°C.; DH |
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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 552.2 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 385. ± 10. | K | AVG | N/A | Average of 9 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 22.08 ± 0.10 | kcal/mol | C | Sabbah and Gouali, 1994 | Author was aware that data differs from previously reported values; ALS |
ΔsubH° | 22.1 | kcal/mol | C | Sabbah and Gouali, 1994, 2 | AC |
ΔsubH° | 23.6 ± 0.2 | kcal/mol | ME | Parsons, Rochester, et al., 1971 | Based on data from 305. to 352. K.; AC |
Enthalpy of sublimation
ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
21.8 ± 0.4 | 343. | V | Wolf and Weghofer, 1938 | ALS |
21.8 ± 0.41 | 339. to 351. | N/A | Trieschmann, 1935 | See also Wolf and Weghofer, 1938, 2 and Jones, 1960.; AC |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
7.1984 | 385.15 | Singh and Kumar, 1986 | DH |
4.3628 | 387.0 | Poeti, Fanelli, et al., 1982 | DH |
2.63 | 386.4 | Musuc, Razus, et al., 2002 | AC |
4.362 | 388.2 | Domalski and Hearing, 1996 | See also Sabbah and Gouali, 1994, 2.; AC |
4.6128 | 368.75 | Booss and Hauschildt, 1972 | DH |
5.8009 | 387. | Campbell and Campbell, 1941 | DH |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
18.7 | 385.15 | Singh and Kumar, 1986 | DH |
11.27 | 387.0 | Poeti, Fanelli, et al., 1982 | DH |
12.5 | 368.75 | Booss and Hauschildt, 1972 | DH |
15.0 | 387. | Campbell and Campbell, 1941 | DH |
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 |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Ion clustering 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 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° | 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 |
Ion clustering data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry 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 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. Searches may be limited to ion clustering reactions. A general reaction search form is also available.
Clustering 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 |
IR Spectrum
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, References, Notes
Data compiled by: Coblentz Society, Inc.
- SOLID (OIL MULL); BAIRD (GRATING); 2 cm-1 resolution
- SOLUTION (ETHYL ETHER); Not specified, most likely a prism, grating, or hybrid spectrometer.; DIGITIZED BY NIST FROM HARD COPY; 4 cm-1 resolution
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, 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]
Rinkenbach, 1930
Rinkenbach, W.H.,
The heats of combustion and formation of aromatic nitro compounds,
J. Am. Chem. Soc., 1930, 52, 115-120. [all data]
Swarts, 1914
Swarts, F.,
Sur la chaleur de combustion de quelques derives nitres aromatlques,
Recl. Trav. Chim. Pays-Bas, 1914, 33, 281-298. [all data]
Garner and Abernethy, 1921
Garner, W.E.; Abernethy, C.L.,
Heats of combustion and formation of nitro-compounds. Part I. - Benzene, toluene, phenol and methylaniline series,
Proc. Roy. Soc. London A, 1921, 213-235. [all data]
Campbell and Campbell, 1941
Campbell, A.N.; Campbell, A.J.R.,
The system naphthalene-p-nitrophenol: an experimental investigation of all the variables in an equation of the freezing point curve,
Can. J. Res., 1941, B19, 73-79. [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]
Sabbah and Gouali, 1994, 2
Sabbah, R.; Gouali, M.,
Energetics of Intra- and Inter-molecular Bonds in the Three Nitrophenols,
Aust. J. Chem., 1994, 47, 9, 1651-621, https://doi.org/10.1071/CH9941651
. [all data]
Parsons, Rochester, et al., 1971
Parsons, G.H.; Rochester, C.H.; Wood, C.E.C.,
Effect of 4-substitution on the thermodynamics of hydration of phenol and the phenoxide anion,
J. Chem. Soc., B:, 1971, 533, https://doi.org/10.1039/j29710000533
. [all data]
Wolf and Weghofer, 1938
Wolf, K.L.; Weghofer, H.,
Uber sublimationswarmen,
Z. Phys. Chem., 1938, 39, 194-208. [all data]
Trieschmann, 1935
Trieschmann, H.G.,
, Ph.D. Dissertation, Inst. Fur Phys. Chem. and Electrochem. der Universitat Kiel, Germany, 1935. [all data]
Wolf and Weghofer, 1938, 2
Wolf, K.L.; Weghofer, H.Z.,
Z. Phys. Chem. Abt. B, 1938, 39, 194. [all data]
Jones, 1960
Jones, A.H.,
Sublimation Pressure Data for Organic Compounds.,
J. Chem. Eng. Data, 1960, 5, 2, 196-200, https://doi.org/10.1021/je60006a019
. [all data]
Singh and Kumar, 1986
Singh, N.B.; Kumar, P.,
Solidification behavior of the cinnamic acid-p-nitrophenol eutectic system,
J. Chem. Eng. Data, 1986, 31, 406-408. [all data]
Poeti, Fanelli, et al., 1982
Poeti, G.; Fanelli, E.; Braghetti, M.,
A differential scanning calorimetric study of some phenol derivatives,
J. Therm. Anal., 1982, 24(2), 273-279. [all data]
Musuc, Razus, et al., 2002
Musuc, A.M.; Razus, D.; Oancea, D.,
Analele Universitatii Bucuresti Chimie, 2002, 11, 2, 147. [all data]
Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D.,
Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III,
J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985
. [all data]
Booss and Hauschildt, 1972
Booss, H.J.; Hauschildt, K.R.,
Die Schmelzenthalpie des Benzils und 4-Nitrophenols,
Z. Anal. Chem., 1972, 261(1), 32. [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]
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]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, References
- Symbols used in this document:
AE Appearance energy Cp,solid Constant pressure heat capacity of solid T Temperature Tboil Boiling point Tfus Fusion (melting) point ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy of reaction at standard conditions ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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