m-Nitroaniline
- Formula: C6H6N2O2
- Molecular weight: 138.1240
- IUPAC Standard InChIKey: XJCVRTZCHMZPBD-UHFFFAOYSA-N
- CAS Registry Number: 99-09-2
- 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: Benzenamine, 3-nitro-; Aniline, m-nitro-; m-Aminonitrobenzene; m-Nitroaminobenzene; m-Nitrophenylamine; Amarthol Fast Orange R Base; Azobase MNA; C.I. Azoic Diazo Component 7; C.I. 37030; Daito Orange Base R; Devol Orange R; Diazo Fast Orange R; Fast Orange Base R; Fast Orange M Base; Fast Orange MM Base; Fast Orange R Base; Fast Orange R Salt; Hiltonil Fast Orange R Base; MNA; Naphtoelan Orange R Base; Nitranilin; Orange Base Irga I; 1-Amino-3-nitrobenzene; 3-Nitroaniline; 3-Nitrobenzenamine; 3-Nitrobenzeneamine; 3-Nitrophenylamine; m-Nitraniline; 3-Aminonitrobenzene; NSC 9574
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible 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 | 62.5 ± 1.8 | kJ/mol | Ccr | Nishiyama, Sakiyama, 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 | -34.2 ± 1.2 | kJ/mol | Ccr | Nishiyama, Sakiyama, et al., 1983 | ALS |
ΔfH°solid | -38. ± 0.4 | kJ/mol | Ccb | Lebedeva, Gutner, et al., 1971 | Hfusion=5.7±0.2, see Lebedeva, Rjadnenko, et al., 1969; ALS |
ΔfH°solid | -28.3 | kJ/mol | Ccb | Medard and Thomas, 1957 | Heat of combustion corrected for pressure; ALS |
ΔfH°solid | -63.47 | kJ/mol | Ccb | Rinkenbach, 1930 | Author hf298_condensed[kcal/mol]=-17.50; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -3184.32 ± 0.88 | kJ/mol | Ccr | Nishiyama, Sakiyama, et al., 1983 | ALS |
ΔcH°solid | -3180. ± 0.4 | kJ/mol | Ccb | Lebedeva, Gutner, et al., 1971 | Hfusion=5.7±0.2, see Lebedeva, Rjadnenko, et al., 1969; ALS |
ΔcH°solid | -3190.3 | kJ/mol | Ccb | Medard and Thomas, 1957 | Heat of combustion corrected for pressure; ALS |
ΔcH°solid | -3155.1 | kJ/mol | Ccb | Rinkenbach, 1930 | Author hf298_condensed[kcal/mol]=-17.50; ALS |
Constant pressure heat capacity of solid
Cp,solid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
158.84 | 298.15 | Nishiyama, Sakiyama, et al., 1983 | Cp given as 1.15 J/g*K.; DH |
186.6 | 323. | Satoh and Sogabe, 1941 | T = 0 to 100°C. Mean value.; DH |
168.2 | 298. | Andrews, Lynn, et al., 1926 | T = 22 to 210°C.; DH |
167.4 | 297.9 | Andrews, 1926 | T = 110 to 344 K. Value is unsmoothed experimental datum.; 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:
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 | 386. ± 3. | K | AVG | N/A | Average of 8 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 97. ± 1. | kJ/mol | V | Malaspina, Gigli, et al., 1973 | ALS |
ΔsubH° | 96.5 ± 0.3 | kJ/mol | C | Malaspina, Gigli, et al., 1973 | AC |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
64.9 | 458. | A | Ferro and Piacente, 1985 | Based on data from 443. to 578. K.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
392.5 to 578.9 | 5.84615 | 3308.304 | -12.776 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
93.6 ± 0.7 | 351. | ME | Malaspina, Gigli, et al., 1973 | Based on data from 320. to 384. K.; AC |
94.6 ± 0.3 | 351. | C | Malaspina, Gigli, et al., 1973 | Based on data from 320. to 384. K.; AC |
97.6 | 316. | ME | Hoyer and Peperle, 1958 | Based on data from 288. to 343. K. See also Cox and Pilcher, 1970.; AC |
97.5 ± 4.2 | 288. | V | Hoyer and Peperle, 1958, 2 | Reanalyzed by Pedley, Naylor, et al., 1986, Original value = 95.0 kJ/mol; ALS |
88.7 ± 2.5 | 332. to 341. | N/A | Wolf and Weghofer, 1938 | See also Jones, 1960 and Trieschmann, 1935.; AC |
89. ± 2. | 342. | V | Wolf and Weghofer, 1938, 2 | ALS |
88.3 ± 1.7 | 332. to 341. | TE | Wolf and Trieschmann, 1934 | AC |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
23.689 | 387. | Singh, Gupta, et al., 1990 | DH |
23.68 | 387.2 | Domalski and Hearing, 1996 | AC |
23.600 | 384.95 | Booss and Hauschildt, 1972 | DH |
23.680 | 385.0 | Andrews, Lynn, et al., 1926 | DH |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
61.3 | 384.95 | Booss and Hauschildt, 1972 | DH |
61.5 | 385.0 | Andrews, Lynn, et al., 1926 | 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 by: John E. Bartmess
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
C6H5N2O2- + =
By formula: C6H5N2O2- + H+ = C6H6N2O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1474. ± 8.8 | kJ/mol | G+TS | Taft and Topsom, 1987 | gas phase |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1443. ± 8.4 | kJ/mol | IMRE | Taft and Topsom, 1987 | gas phase |
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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Gas Phase Spectrum
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Additional Data
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Owner | NIST Standard Reference Data Program Collection (C) 2018 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | NIST Mass Spectrometry Data Center |
State | gas |
Instrument | HP-GC/MS/IRD |
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, UV/Visible 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
Spectrum
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Additional Data
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Due to licensing restrictions, this spectrum cannot be downloaded.
Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | D.HENNEBERG, MAX-PLANCK INSTITUTE, MULHEIM, WEST GERMANY |
NIST MS number | 63856 |
UV/Visible 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: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina
Spectrum
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Additional Data
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Source | Grammaticakis, 1951 |
---|---|
Owner | INEP CP RAS, NIST OSRD Collection (C) 2007 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
Origin | INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS |
Source reference | RAS UV No. 137 |
Instrument | n.i.g. |
Melting point | 114 |
Boiling point | 306 dec |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Nishiyama, Sakiyama, et al., 1983
Nishiyama, K.; Sakiyama, M.; Seki, S.,
Enthalpies of combustion of organic compounds. V. 3- and 4-nitroanilines,
Bull. Chem. Soc. Jpn., 1983, 56, 3171-3172. [all data]
Lebedeva, Gutner, et al., 1971
Lebedeva, N.D.; Gutner, N.M.; Ryadnenko, V.L.,
Heats of combustion and formation of certain aromatic amino-derivatives,
Russ. J. Phys. Chem. (Engl. Transl.), 1971, 45, 561-562. [all data]
Lebedeva, Rjadnenko, et al., 1969
Lebedeva, N.D.; Rjadnenko, B.L.; Gutner, N.M.,
Heats of formation of some N-containing organic compounds,
Int. Conf. Calorim. Therm. (Warsaw, Poland), 1969, 1-8. [all data]
Medard and Thomas, 1957
Medard, L.; Thomas, M.,
Chaleur de combustion de onze substances explosives ou apparentees a des explosifs,
Mem. Poudres, 1957, 39, 195-208. [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]
Satoh and Sogabe, 1941
Satoh, S.; Sogabe, T.,
The heat capacities of some organic compounds containing nitrogen and the atomic heat of nitrogen. (3), Sci.,
Pap. Inst. Phys. Chem. Res. (Tokyo), 1941, 38, 238-245. [all data]
Andrews, Lynn, et al., 1926
Andrews, D.H.; Lynn, G.; Johnston, J.,
The heat capacities and heat of crystallization of some isomeric aromatic compounds,
J. Am. Chem. Soc., 1926, 48, 1274-1287. [all data]
Andrews, 1926
Andrews, D.H.,
The specific heats of some isomers of the type ortho, meta and para C6H4XY from 110 to 340K,
J. Am. Chem. Soc., 1926, 48, 1287-1298. [all data]
Malaspina, Gigli, et al., 1973
Malaspina, L.; Gigli, R.; Bardi, G.; De Maria, G.,
Simultaneous determination by Knudsen effusion microcalorimetry of the vapour pressure and the enthalpy of sublimation of p- and m-nitroaniline,
J. Chem. Thermodyn., 1973, 5, 699-706. [all data]
Ferro and Piacente, 1985
Ferro, D.; Piacente, V.,
Heat of vaporization of o-, m- and p-nitroaniline,
Thermochimica Acta, 1985, 90, 387-389, https://doi.org/10.1016/0040-6031(85)87121-5
. [all data]
Stull, 1947
Stull, Daniel R.,
Vapor Pressure of Pure Substances. Organic and Inorganic Compounds,
Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022
. [all data]
Hoyer and Peperle, 1958
Hoyer, H.; Peperle, W.,
Z. Elektrochem., 1958, 62, 61. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press Inc., London, 1970, 643. [all data]
Hoyer and Peperle, 1958, 2
Hoyer, H.; Peperle, W.,
Dampfdrunkmessungen an organischen substanzen und ihre sublimationswarmen,
Z. Electrochem., 1958, 62, 61-66. [all data]
Pedley, Naylor, et al., 1986
Pedley, J.B.; Naylor, R.D.; Kirby, S.P.,
Thermochemical Data of Organic Compounds, Chapman and Hall, New York, 1986, 1-792. [all data]
Wolf and Weghofer, 1938
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]
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.,
Uber sublimationswarmen,
Z. Phys. Chem., 1938, 39, 194-208. [all data]
Wolf and Trieschmann, 1934
Wolf, K.L.; Trieschmann, H.G.,
Z. Phys. Chem. Abt. B, 1934, 27, 376. [all data]
Singh, Gupta, et al., 1990
Singh, R.N.; Gupta, J.P.; Singh, N.; Singh, N.P.; Singh, O.P.; Singh, N.B.; Hopkins, R.H.; Mazelsky, R.,
Growth conditions of organic non-linear optical crystals,
Thermochim. Acta, 1990, 165(2), 297-299. [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]
Taft and Topsom, 1987
Taft, R.W.; Topsom, R.D.,
The Nature and Analysis of Substituent Effects,
Prog. Phys. Org. Chem., 1987, 16, 1. [all data]
Grammaticakis, 1951
Grammaticakis, P.,
Contribution a l'etude de l'absorption dans l'ultraviolet moyen et le visible des arylamines isomeres et de leurs derives N substitues (Premier memoire),
Bull. Soc. Chim. Fr., 1951, 18, 220-226. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, References
- Symbols used in this document:
Cp,solid Constant pressure heat capacity of solid 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 ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions ΔvapH Enthalpy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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