p-Nitroaniline
- Formula: C6H6N2O2
- Molecular weight: 138.1240
- IUPAC Standard InChI: InChI=1S/C6H6N2O2/c7-5-1-3-6(4-2-5)8(9)10/h1-4H,7H2
- IUPAC Standard InChIKey: TYMLOMAKGOJONV-UHFFFAOYSA-N
- CAS Registry Number: 100-01-6
- 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, 4-nitro-; Aniline, p-nitro-; p-Aminonitrobenzene; p-Nitrophenylamine; Azoamine Red Zh; C.I. Azoic Diazo Component 37; C.I. Developer 17; C.I. 37035; Developer P; Devol Red GG; Fast Red Base GG; Fast Red Base 2J; Fast Red GG Base; Fast Red MP Base; Fast Red P Base; Fast Red 2G Base; Naphtoelan Red GG Base; Nitrazol CF extra; PNA; Red 2G Base; Shinnippon Fast Red GG Base; 1-Amino-4-nitrobenzene; 4-Nitraniline; 4-Nitroaniline; 4-Nitrobenzenamine; p-Nitraniline; Aniline, 4-nitro-; Azofix Red GG Salt; Azoic Diazo Component 37; Diazo Fast Red GG; Fast Red GG Salt; Fast Red P Salt; Fast Red Salt GG; Fast Red Salt 2J; Fast Red 2G Salt; NCI-C60786; p-Nitroanilina; Paranitroaniline; Rcra waste number P077; 4-Aminonitrobenzene; Azoamine Red 2H; NSC 9797
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | 55.2 ± 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 | -45.6 ± 1.2 | kJ/mol | Ccr | Nishiyama, Sakiyama, et al., 1983 | ALS |
| ΔfH°solid | -43.1 ± 0.8 | kJ/mol | Ccb | Lebedeva, Gutner, et al., 1971 | Hfusion=5.1±0.2, see Lebedeva, Rjadnenko, et al., 1969; ALS |
| ΔfH°solid | -38.5 ± 3.2 | kJ/mol | Ccb | Medard and Thomas, 1954 | Heat of combustion corrected for pressure; ALS |
| ΔfH°solid | -41.5 | kJ/mol | Cm | Cole and Gilbert, 1951 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -3172.98 ± 0.90 | kJ/mol | Ccr | Nishiyama, Sakiyama, et al., 1983 | ALS |
| ΔcH°solid | -3176. ± 0.8 | kJ/mol | Ccb | Lebedeva, Gutner, et al., 1971 | Hfusion=5.1±0.2, see Lebedeva, Rjadnenko, et al., 1969; ALS |
| ΔcH°solid | -3180.0 ± 3.2 | kJ/mol | Ccb | Medard and Thomas, 1954 | Heat of combustion corrected for pressure; ALS |
| ΔcH°solid | -3177.1 | kJ/mol | Cm | Cole and Gilbert, 1951 | ALS |
Constant pressure heat capacity of solid
| Cp,solid (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 154.2 | 298.15 | Nishiyama, Sakiyama, et al., 1983 | Cp given as 1.116 J/g*K.; DH |
| 184.9 | 323. | Satoh and Sogabe, 1941 | T = 0 to 100°C. Mean value.; DH |
| 169.0 | 298. | Andrews, Lynn, et al., 1926 | T = 22 to 195°C.; DH |
| 165.7 | 297.9 | Andrews, 1926 | T = 110 to 344 K. Value is unsmoothed experimental datum.; DH |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry 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: 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° | 1437. ± 8.8 | kJ/mol | G+TS | Taft and Topsom, 1987 | gas phase; value altered from reference due to change in acidity scale |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1407. ± 8.4 | kJ/mol | IMRE | Taft and Topsom, 1987 | gas phase; value altered from reference due to change in acidity scale |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, 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, 1954
Medard, L.; Thomas, M.,
Chaleurs de combustion de vingt-quatre substances explosives ou apparentees a des explosifs,
Mem. Poudres, 1954, 36, 97-127. [all data]
Cole and Gilbert, 1951
Cole, L.G.; Gilbert, E.C.,
The heats of combustion of some nitrogen compounds and the apparent energy of the N-N bond,
J. Am. Chem. Soc., 1951, 73, 5423-5427. [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]
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]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, References
- Symbols used in this document:
Cp,solid Constant pressure heat capacity of solid 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 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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