p-Nitroaniline
- Formula: C6H6N2O2
- Molecular weight: 138.1240
- 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, Phase change 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | 13.2 ± 0.43 | kcal/mol | Ccr | Nishiyama, Sakiyama, et al., 1983 |
Phase change data
Go To: Top, Gas phase thermochemistry 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 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 | 420. ± 5. | K | AVG | N/A | Average of 8 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 24.1 ± 0.3 | kcal/mol | AVG | N/A | Average of 8 values; Individual data points |
Reduced pressure boiling point
Tboil (K) | Pressure (atm) | Reference | Comment |
---|---|---|---|
533.2 | 0.132 | Aldrich Chemical Company Inc., 1990 | BS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
18.6 | 488. | A | Stephenson and Malanowski, 1987 | Based on data from 473. to 538. K.; AC |
16.7 | 430. | N/A | Stull, 1947 | Based on data from 415. to 609. K.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
415.6 to 609. | 6.94545 | 4591.888 | 52.016 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Enthalpy of sublimation
ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
26.12 | 333. | ME | Hoyer and Peperle, 1958 | Based on data from 303. to 363. K. See also Cox and Pilcher, 1970.; AC |
26.1 ± 1.0 | 303. | V | Hoyer and Peperle, 1958, 2 | Reanalyzed by Pedley, Naylor, et al., 1986, Original value = 25.5 kcal/mol; ALS |
23.3 ± 0.41 | 356. | ME | Majury, 1956 | Based on data from 346. to 366. K.; AC |
23.6 ± 0.60 | 361. | TE | Wolf and Weghofer, 1938 | See also Jones, 1960.; AC |
23.6 ± 0.6 | 361. | V | Wolf and Weghofer, 1938, 2 | ALS |
24.69 ± 0.41 | 362. | N/A | Wolf and Trieschmann, 1934 | Based on data from 357. to 367. K.; AC |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
5.041 | 420.2 | Domalski and Hearing, 1996 | AC |
5.0550 | 420.65 | Booss and Hauschildt, 1972 | DH |
5.0406 | 420.7 | Andrews, Lynn, et al., 1926 | DH |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
12.0 | 420.65 | Booss and Hauschildt, 1972 | DH |
12.0 | 420.7 | Andrews, Lynn, et al., 1926 | DH |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Phase change data, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
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 C6H6N2O2+ (ion structure unspecified)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 207.0 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 199.4 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Electron affinity determinations
EA (eV) | Method | Reference | Comment |
---|---|---|---|
0.75 ± 0.10 | LPES | Smith, Buonaugurio, et al., 2013 | Vertical Detachment Energy: 1.1 eV; B |
0.915 ± 0.087 | IMRE | Huh, Kang, et al., 1999 | ΔG(EA) 343K; anchored to ΔG value. Including anchor ΔS, EA is ca. 0.4 kcal/mol more bound.; B |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.43 | EI | Johnstone and Mellon, 1973 | LLK |
8.34 ± 0.01 | PI | Potapov, Kardash, et al., 1972 | LLK |
8.6 ± 0.1 | EI | Brown, 1970 | RDSH |
8.85 | EI | Crable and Kearns, 1962 | RDSH |
8.60 | PE | Khalil, Meeks, et al., 1973 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C6H6N+ | 11.5 ± 0.1 | NO2 | EI | Brown, 1970 | RDSH |
C6H6NO+ | 9.6 ± 0.1 | NO | EI | Brown, 1970 | RDSH |
De-protonation reactions
C6H5N2O2- + =
By formula: C6H5N2O2- + H+ = C6H6N2O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 343.5 ± 2.1 | kcal/mol | G+TS | Taft and Topsom, 1987 | gas phase; value altered from reference due to change in acidity scale; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 336.2 ± 2.0 | kcal/mol | IMRE | Taft and Topsom, 1987 | gas phase; value altered from reference due to change in acidity scale; B |
References
Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics 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]
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 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]
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]
Majury, 1956
Majury, T.G.,
Chem. Ind., 1956, 17, 349. [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]
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]
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]
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]
Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G.,
Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update,
J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018
. [all data]
Smith, Buonaugurio, et al., 2013
Smith, B.H.; Buonaugurio, A.; Chen, J.; Collins, E.; Bowen, K.H.; Compton, R.N.; Sommerfeld, T.,
Negative ions of p-nitroaniline: Photodetachment, collisions, and ab initio calculations,
J. Chem. Phys., 2013, 138, 23, 234304, https://doi.org/10.1063/1.4810869
. [all data]
Huh, Kang, et al., 1999
Huh, C.; Kang, C.H.; Lee, H.W.; Nakamura, H.; Mishima, M.; Tsuno, Y.; Yamataka, H.,
Thermodynamic stabilities and resonance demand of aromatic radical anions in the gas phase,
Bull. Chem. Soc. Japan, 1999, 72, 5, 1083-1091, https://doi.org/10.1246/bcsj.72.1083
. [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]
Potapov, Kardash, et al., 1972
Potapov, V.K.; Kardash, I.E.; Sorokin, V.V.; Sokolov, S.A.; Evlasheva, T.I.,
Photoionization of heteroaromatic compounds,
Khim. Vys. Energ., 1972, 6, 392. [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]
Khalil, Meeks, et al., 1973
Khalil, O.S.; Meeks, J.L.; McGlynn, S.P.,
Electronic spectroscopy of highly polar aromatics. VII. Photoelectron spectra of nitroanilines,
J. Am. Chem. Soc., 1973, 95, 5876. [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, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy EA Electron affinity Tboil Boiling point Tfus Fusion (melting) point ΔfH°gas Enthalpy of formation of gas 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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