Phenol, 3-nitro-
- Formula: C6H5NO3
- Molecular weight: 139.1088
- IUPAC Standard InChIKey: RTZZCYNQPHTPPL-UHFFFAOYSA-N
- CAS Registry Number: 554-84-7
- 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, m-nitro-; m-Nitrophenol; m-Hydroxynitrobenzene; 3-Hydroxynitrobenzene; 3-Nitrophenol; m-Nitrofenol; meta-Nitrophenol; 1-Hydroxy-3-nitrobenzene; NSC 1551
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Phase change data
Go To: Top, Henry's Law data, Gas phase ion energetics 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 as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
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 |
---|---|---|---|---|---|
Tfus | 368. ± 4. | K | AVG | N/A | Average of 7 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 85.9 | kJ/mol | B | Heintz, Kapteina, et al., 2007 | AC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 91.23 ± 0.49 | kJ/mol | C | Sabbah and Gouali, 1994 | Author was aware that data differs from previously reported values; ALS |
ΔsubH° | 91.2 ± 0.5 | kJ/mol | C | Sabbah and Gouali, 1994, 2 | AC |
ΔsubH° | 100.2 ± 0.6 | kJ/mol | V | Ribeiro Da Silva, Reis, et al., 1992 | ALS |
ΔsubH° | 100.2 ± 0.6 | kJ/mol | N/A | Ribeiro Da Silva, Reis, et al., 1992 | AC |
Reduced pressure boiling point
Tboil (K) | Pressure (bar) | Reference | Comment |
---|---|---|---|
467.2 | 0.093 | Weast and Grasselli, 1989 | BS |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
98.5 ± 0.6 | 321. | ME | Ribeiro Da Silva, Reis, et al., 1992 | AC |
76.2 | 319.5 | A | Stephenson and Malanowski, 1987 | Based on data from 305. to 334. K.; AC |
92. ± 2. | 328. | V | Wolf and Weghofer, 1938 | ALS |
91.6 ± 1.7 | 325. to 336. | N/A | Trieschmann, 1935 | See also Wolf and Weghofer, 1938, 2 and Jones, 1960.; AC |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
19.196 | 370.0 | Poeti, Fanelli, et al., 1982 | DH |
18.06 | 369. | Musuc, Razus, et al., 2002 | AC |
19.19 | 371.2 | Acree, 1991 | See also Sabbah and Gouali, 1994, 2.; AC |
19.2 | 370. | Poeti, Fanelli, et al., 1982 | AC |
21.300 | 369.95 | Booss and Hauschildt, 1972 | DH |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
51.88 | 370.0 | Poeti, Fanelli, et al., 1982 | DH |
57.6 | 369.95 | Booss and Hauschildt, 1972 | DH |
Enthalpy of phase transition
ΔHtrs (kJ/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
0.167 | 356. | crystaline, II | crystaline, I | Wojcik and Marqueton, 1989 | DH |
19.960 | 370. | crystaline, I | liquid | Wojcik and Marqueton, 1989 | DH |
Entropy of phase transition
ΔStrs (J/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
0.47 | 356. | crystaline, II | crystaline, I | Wojcik and Marqueton, 1989 | DH |
54. | 370. | crystaline, I | liquid | Wojcik and Marqueton, 1989 | DH |
Henry's Law data
Go To: Top, Phase change data, Gas phase ion energetics 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: 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 |
---|---|---|---|---|
500000. | X | N/A | Value given here as quoted by missing citation. |
Gas phase ion energetics data
Go To: Top, Phase change 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 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 |
---|---|---|---|
9.0 | PE | Kobayashi and Nagakura, 1975 | LLK |
9.33 | PE | Kobayashi and Nagakura, 1975 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
NO+ | 10.5 ± 0.2 | ? | EI | Beynon, Hopkinson, et al., 1969 | RDSH |
De-protonation reactions
C6H4NO3- + =
By formula: C6H4NO3- + H+ = C6H5NO3
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1399. ± 8.8 | kJ/mol | G+TS | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale; B |
ΔrH° | 1400. ± 11. | kJ/mol | G+TS | Kebarle and McMahon, 1977 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1370. ± 8.4 | kJ/mol | IMRE | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale; B |
ΔrG° | 1371. ± 8.4 | kJ/mol | IMRE | Kebarle and McMahon, 1977 | gas phase; B |
Gas Chromatography
Go To: Top, Phase change data, Henry's Law 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
Kovats' RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Packed | Apiezon L | 204. | 1514. | Mitchell and Vernon, 1972 | |
Packed | SE-52 | 204. | 1530. | Mitchell and Vernon, 1972 |
Van Den Dool and Kratz RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | VF-5MS | 1484.6 | Tret'yakov, 2007 | 30. m/0.25 mm/0.25 μm, He; Program: Multi-step temperature program; T(initial)=60C; T(final)=270C |
References
Go To: Top, Phase change data, Henry's Law data, Gas phase ion energetics data, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Heintz, Kapteina, et al., 2007
Heintz, A.; Kapteina, S.; Verevkin, S.P.,
Pairwise-Substitution Effects and Intramolecular Hydrogen Bonds in Nitrophenols and Methylnitrophenols. Thermochemical Measurements and ab Initio Calculations,
J. Phys. Chem. A, 2007, 111, 28, 6552-6562, https://doi.org/10.1021/jp0730388
. [all data]
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]
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]
Ribeiro Da Silva, Reis, et al., 1992
Ribeiro Da Silva, M.A.V.; Reis, A.M.M.V.; Monte, M.J.S.; Bartolo, M.M.S.S.F.; Rodrigues, J.A.R.G.O.,
Enthalpy of combustion, vapour pressures, and enthalpy of sublimation of 3-nitrophenol,
J. Chem. Thermodyn., 1992, 24, 653-659. [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]
Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw,
Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2
. [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]
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]
Acree, 1991
Acree, William E.,
Thermodynamic properties of organic compounds: enthalpy of fusion and melting point temperature compilation,
Thermochimica Acta, 1991, 189, 1, 37-56, https://doi.org/10.1016/0040-6031(91)87098-H
. [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]
Wojcik and Marqueton, 1989
Wojcik, G.; Marqueton, Y.,
The phase transition of m-nitrophenol,
Mol. Cryst. Liq. Cryst., 1989, 168, 247-254. [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]
Beynon, Hopkinson, et al., 1969
Beynon, J.H.; Hopkinson, J.A.; Lester, G.R.,
Mass spectrometry-the appearance potentials of "meta-stable peaks" in some aromatic nitro compounds - a chemical reaction in the mass spectrometer,
Intern. J. Mass Spectrom. Ion Phys., 1969, 2, 291. [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]
Kebarle and McMahon, 1977
Kebarle, P.; McMahon, T.B.,
Intrinsic Acidities of Substituted Phenols and Benzoic Acids Determined by Gas Phase Proton Transfer Equilibria,
J. Am. Chem. Soc., 1977, 99, 7, 2222, https://doi.org/10.1021/ja00449a032
. [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]
Tret'yakov, 2007
Tret'yakov, K.V.,
Retention Data. NIST Mass Spectrometry Data Center., NIST Mass Spectrometry Data Center, 2007. [all data]
Notes
Go To: Top, Phase change data, Henry's Law data, Gas phase ion energetics data, Gas Chromatography, References
- Symbols used in this document:
AE Appearance energy Tboil Boiling point Tfus Fusion (melting) point d(ln(kH))/d(1/T) Temperature dependence parameter for Henry's Law constant k°H Henry's Law constant at 298.15K ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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