Aniline
- Formula: C6H7N
- Molecular weight: 93.1265
- IUPAC Standard InChIKey: PAYRUJLWNCNPSJ-UHFFFAOYSA-N
- CAS Registry Number: 62-53-3
- 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. - Isotopologues:
- Other names: Benzenamine; Aminobenzene; Aminophen; Anyvim; Benzene, amino-; Blue Oil; C.I. 76000; Phenylamine; Aniline Oil; Aniline reagent; Anilin; Anilina; Benzidam; C.I. Oxidation base 1; Cyanol; Huile D'aniline; Krystallin; Kyanol; NCI-C03736; Rcra waste number U012; UN 1547; Benzeneamine
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Condensed phase thermochemistry data
Go To: Top, 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 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°liquid | 31.3 ± 0.84 | kJ/mol | Ccb | Hatton, Hildenbrand, et al., 1962 | ALS |
ΔfH°liquid | 30. | kJ/mol | Ccb | Vriens and Hill, 1952 | ALS |
ΔfH°liquid | 30.8 | kJ/mol | Cm | Cole and Gilbert, 1951 | ALS |
ΔfH°liquid | 33. | kJ/mol | Ccb | Lemoult, 1907 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -3393.1 ± 1.0 | kJ/mol | Ccb | Hatton, Hildenbrand, et al., 1962 | ALS |
ΔcH°liquid | -3392. | kJ/mol | Ccb | Vriens and Hill, 1952 | ALS |
ΔcH°liquid | -3392.3 | kJ/mol | Cm | Cole and Gilbert, 1951 | ALS |
ΔcH°liquid | -3391. ± 13. | kJ/mol | Ccb | Anderson and Gilbert, 1942 | %hf calculated possible error by author; ALS |
ΔcH°liquid | -3411. | kJ/mol | Ccb | Lemoult, 1907 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 191.30 | J/mol*K | N/A | Hatton, Hildenbrand, et al., 1962 | DH |
S°liquid | 191.6 | J/mol*K | N/A | Parks, Huffman, et al., 1933 | Extrapolation below 90 K, 45.27 J/mol*K.; DH |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -3391. | kJ/mol | Ccb | Willis, 1947 | ALS |
Constant pressure heat capacity of liquid
Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
194.1 | 298. | Lesbats and Lichanot, 1987 | T = 200 to 300 K.; DH |
191.01 | 298.15 | Nichols and Wads, 1975 | DH |
193.7 | 298. | Deshpande and Bhatagadde, 1971 | T = 298 to 318 K.; DH |
192.05 | 298.15 | Hatton, Hildenbrand, et al., 1962 | T = 15 to 300 K. Cp(liq, cal/mol·K) = 33.71 + 0.0409T (15 to 300 K).; DH |
192.0 | 293. | Crtzen, Jost, et al., 1957 | DH |
197.5 | 323. | Hough, Mason, et al., 1950 | T = 323 to 453 K.; DH |
109.20 | 267.3 | Ziegler and Andrews, 1942 | T = 40.84 K.; DH |
183.7 | 288. | Radulescu and Jula, 1934 | DH |
178.8 | 298.15 | Ferguson and Miller, 1933 | T = 293 to 323 K. Data calculated from equation.; DH |
190.92 | 298.2 | Parks, Huffman, et al., 1933 | T = 94 to 298 K. Value is unsmoothed experimental datum.; DH |
193.38 | 298.2 | Lang, 1928 | T = 5 to 60°C.; DH |
192.5 | 298. | von Reis, 1881 | T = 290 to 465 K.; DH |
Phase change data
Go To: Top, 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 as indicated in comments:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
BS - Robert L. Brown and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 457. ± 2. | K | AVG | N/A | Average of 46 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 267.0 ± 0.3 | K | AVG | N/A | Average of 19 out of 24 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 267.13 | K | N/A | Hatton, Hildenbrand, et al., 1962, 2 | Uncertainty assigned by TRC = 0.02 K; from plot of 1/f vs T; TRC |
Ttriple | 267.300 | K | N/A | Ziegler and Andrews, 1942, 2 | Uncertainty assigned by TRC = 0.2 K; TRC |
Ttriple | 266.9 | K | N/A | Parks, Huffman, et al., 1933, 2 | Uncertainty assigned by TRC = 0.1 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 698.8 ± 0.4 | K | AVG | N/A | Average of 8 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 53.1 ± 0.2 | bar | AVG | N/A | Average of 6 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
ρc | 3.48 | mol/l | N/A | Lagutkin and Kuropatkin, 1981 | Uncertainty assigned by TRC = 0.05 mol/l; calculated from corr. Zc, and lit. values of Tc and Pc; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Zc | 0.26 | none | N/A | Lagutkin and Kuropatkin, 1981 | Uncertainty assigned by TRC = 0.003 none; Correlation based on literature values of 2nd vireal coeff.; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 54. ± 4. | kJ/mol | AVG | N/A | Average of 7 values; Individual data points |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
51.0 ± 0.2 | 360. | EB | Steele, Chirico, et al., 2002 | Based on data from 350. to 499. K.; AC |
48.0 ± 0.2 | 400. | EB | Steele, Chirico, et al., 2002 | Based on data from 350. to 499. K.; AC |
45.2 ± 0.2 | 440. | EB | Steele, Chirico, et al., 2002 | Based on data from 350. to 499. K.; AC |
42.2 ± 0.4 | 480. | EB | Steele, Chirico, et al., 2002 | Based on data from 350. to 499. K.; AC |
45.8 | 444. | N/A | Lee, Chen, et al., 1992 | Based on data from 421. to 591. K.; AC |
52.2 | 288. | A | Stephenson and Malanowski, 1987 | Based on data from 273. to 338. K.; AC |
53.6 | 319. | A | Stephenson and Malanowski, 1987 | Based on data from 304. to 485. K.; AC |
48.6 | 388. | A | Stephenson and Malanowski, 1987 | Based on data from 373. to 458. K.; AC |
46.3 | 470. | A | Stephenson and Malanowski, 1987 | Based on data from 455. to 523. K.; AC |
42.44 | 457.2 | N/A | Majer and Svoboda, 1985 | |
51.4 | 350. | N/A | Maher and Smith, 1979 | Based on data from 313. to 386. K.; AC |
52.9 | 293. | N/A | Ravdel and Danilov, 1968 | Based on data from 288. to 298. K.; AC |
54.0 | 319. | N/A | Hatton, Hildenbrand, et al., 1962 | Based on data from 304. to 457. K.; AC |
53.0 | 333. | C | Hatton, Hildenbrand, et al., 1962 | AC |
Enthalpy of vaporization
ΔvapH =
A exp(-βTr) (1 − Tr)β
ΔvapH =
Enthalpy of vaporization (at saturation pressure)
(kJ/mol)
Tr = reduced temperature (T / Tc)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | A (kJ/mol) | β | Tc (K) | Reference | Comment |
---|---|---|---|---|---|
298. to 333. | 80.66 | 0.3744 | 699. | Majer and Svoboda, 1985 |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
304. to 457. | 4.34541 | 1661.858 | -74.048 | Hatton, Hildenbrand, et al., 1962 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
10.539 | 267.13 | Hatton, Hildenbrand, et al., 1962 | DH |
10.54 | 267.1 | Ahmed and Eades, 1972 | See also Domalski and Hearing, 1996.; AC |
10.92 | 267.3 | Ziegler and Andrews, 1942 | AC |
10.556 | 266.8 | Parks, Huffman, et al., 1933 | DH |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
39.57 | 266.8 | Parks, Huffman, et al., 1933 | DH |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Hatton, Hildenbrand, et al., 1962
Hatton, W.E.; Hildenbrand, D.L.; Sinke, G.C.; Stull, D.R.,
Chemical thermodynamic properties of aniline,
J. Chem. Eng. Data, 1962, 7, 229-231. [all data]
Vriens and Hill, 1952
Vriens, G.N.; Hill, A.G.,
Equilibria of several reactions of aromatic amines,
Ind. Eng. Chem., 1952, 44, 2732-27. [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]
Lemoult, 1907
Lemoult, M.P.,
Recherches theoriques et experimentales sur les chaleurs de combustion et de formation des composes organiques,
Ann. Chim. Phys., 1907, 12, 395-432. [all data]
Anderson and Gilbert, 1942
Anderson, C.M.; Gilbert, E.C.,
The apparent energy of the N-N bond as calculated from heats of combustion,
J. Am. Chem. Soc., 1942, 64, 2369-2372. [all data]
Parks, Huffman, et al., 1933
Parks, G.S.; Huffman, H.M.; Barmore, M.,
Thermal data on organic compounds. XI. The heat capacities,
entropies and free energies of ten compounds containing oxygen or nitrogen. J. Am. Chem. Soc., 1933, 55, 2733-2740. [all data]
Willis, 1947
Willis, J.B.,
The heats of combustion of some organic bases and their salts. The resonance energies of acridine and phenazine,
Trans. Faraday Soc., 1947, 43, 97-102. [all data]
Lesbats and Lichanot, 1987
Lesbats, C.; Lichanot, A.,
Capacites calorifiques de durcisseurs amines et resines epoxydes,
Thermochim. Acta, 1987, 109, 317-329. [all data]
Nichols and Wads, 1975
Nichols, N.; Wads, I.,
Thermochemistry of solutions of biochemical model compounds. 3. Some benzene derivatives in aqueous solution,
J. Chem. Thermodynam., 1975, 7, 329-336. [all data]
Deshpande and Bhatagadde, 1971
Deshpande, D.D.; Bhatagadde, L.G.,
Heat capacities at constant volume, free volumes, and rotational freedom in some liquids,
Aust. J. Chem., 1971, 24, 1817-1822. [all data]
Crtzen, Jost, et al., 1957
Crtzen, J.L.; Jost, W.; Sieg, L.,
Gleichgewichtsmessungen im System Anilin-N-Methylanilin, N-N-Dimethylanilin, 1,2-Äthandiol,
Z. Elektrochem., 1957, 61, 230-246. [all data]
Hough, Mason, et al., 1950
Hough, E.W.; Mason, D.M.; Sage, B.H.,
Heat capacities of several organic liquids,
J. Am. Chem. Soc., 1950, 72, 5775-5777. [all data]
Ziegler and Andrews, 1942
Ziegler, W.T.; Andrews, D.H.,
The heat capacity of benzene-d6,
J. Am. Chem. Soc., 1942, 64, 2482-2485. [all data]
Radulescu and Jula, 1934
Radulescu, D.; Jula, O.,
Beiträge zur Bestimmung der Abstufung der Polarität des Aminstickstoffes in den organischen Verbindungen,
Z. Phys. Chem., 1934, B26, 390-393. [all data]
Ferguson and Miller, 1933
Ferguson, A.; Miller, J.T.,
A method for the determination of the specific heats of liquids, and a determination of the specific heats of aniline and benzene over the approximate range 20°C to 50°C,
Proc. Phys. Soc. London, 1933, 45, 194-207. [all data]
Lang, 1928
Lang, H.R.,
On the measurement of the variation of the specific heat of aniline with temperature, using the continuous flow electric method,
Proc. Roy. Soc. (London), 1928, A118, 138-156. [all data]
von Reis, 1881
von Reis, M.A.,
Die specifische Wärme flüssiger organischer Verbindungen und ihre Beziehung zu deren Moleculargewicht,
Ann. Physik [3], 1881, 13, 447-464. [all data]
Hatton, Hildenbrand, et al., 1962, 2
Hatton, W.E.; Hildenbrand, D.L.; Sinke, G.C.; Stull, D.R.,
Chemical Thermodynamic Properties of Aniline,
J. Chem. Eng. Data, 1962, 7, 229. [all data]
Ziegler and Andrews, 1942, 2
Ziegler, W.T.; Andrews, D.H.,
The heat capacity of benzene-d6,
J. Am. Chem. Soc., 1942, 64, 2482. [all data]
Parks, Huffman, et al., 1933, 2
Parks, G.S.; Huffman, H.M.; Barmore, M.,
Thermal Data on Organic Compounds. XI. The Heat Capacities, Entropies and Free Energies of Ten Compounds Containing Oxygen or Nitrogen,
J. Am. Chem. Soc., 1933, 55, 7, 2733, https://doi.org/10.1021/ja01334a016
. [all data]
Lagutkin and Kuropatkin, 1981
Lagutkin, O.D.; Kuropatkin, E.I.,
Critical coefficient of compressibility and critical dens. of aniline,
Zh. Fiz. Khim., 1981, 55, 1329. [all data]
Steele, Chirico, et al., 2002
Steele, W.V.; Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A.,
Vapor Pressure, Heat Capacity, and Density along the Saturation Line: Measurements for Benzenamine, Butylbenzene, sec -Butylbenzene, tert -Butylbenzene, 2,2-Dimethylbutanoic Acid, Tridecafluoroheptanoic Acid, 2-Butyl-2-ethyl-1,3-propanediol, 2,2,4-Trimethyl-1,3-pentanediol, and 1-Chloro-2-propanol,
J. Chem. Eng. Data, 2002, 47, 4, 648-666, https://doi.org/10.1021/je010083e
. [all data]
Lee, Chen, et al., 1992
Lee, Chang Ha; Chen, Quen; Mohamed, Rahoma S.; Holder, Gerald D.,
Vapor-liquid equilibria in the system of toluene/aniline, aniline/naphthalene, and naphthalene/quinoline,
J. Chem. Eng. Data, 1992, 37, 2, 179-183, https://doi.org/10.1021/je00006a011
. [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]
Majer and Svoboda, 1985
Majer, V.; Svoboda, V.,
Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]
Maher and Smith, 1979
Maher, Patrick J.; Smith, Buford D.,
A new total pressure vapor-liquid equilibrium apparatus. The ethanol + aniline system at 313.15, 350.81, and 386.67 K,
J. Chem. Eng. Data, 1979, 24, 1, 16-22, https://doi.org/10.1021/je60080a022
. [all data]
Ravdel and Danilov, 1968
Ravdel, A.A.; Danilov, V.V.,
Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol., 1968, 11, 6, 642. [all data]
Ahmed and Eades, 1972
Ahmed, A.M.I.; Eades, R.G.,
Proton relaxation in solid aniline and some methyl derivatives,
J. Chem. Soc., Faraday Trans. 2, 1972, 68, 2017, https://doi.org/10.1039/f29726802017
. [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]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid Pc Critical pressure S°liquid Entropy of liquid at standard conditions Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point Ttriple Triple point temperature Zc Critical compressability factor ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions ρc Critical density - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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