Diphenylamine
- Formula: C12H11N
- Molecular weight: 169.2224
- IUPAC Standard InChIKey: DMBHHRLKUKUOEG-UHFFFAOYSA-N
- CAS Registry Number: 122-39-4
- 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, N-phenyl-; Anilinobenzene; Benzene, (phenylamino)-; DFA; DPA; N-Phenylaniline; N-Phenylbenzeneamine; Aniline, N-phenyl-; Benzene, anilino-; Big Dipper; C.I. 10355; N-Phenylbenzenamine; N,N-Diphenylamine; No-Scald; Phenylaniline; Scaldip; Deccoscald 282; Difenylamin; N-Fenylanilin; No-Scald dpa 283; Naugalube 428L; NSC 215210
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Gas 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | 202. | kJ/mol | Ccb | Vriens and Hill, 1952 |
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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | 132. | kJ/mol | Ccb | Vriens and Hill, 1952 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -6426.2 | kJ/mol | Ccb | Vriens and Hill, 1952 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔfH°solid | 130.0 ± 1.5 | kJ/mol | Ccb | Medard, 1955 | Reanalyzed by Cox and Pilcher, 1970, Original value = 140.6 ± 1.5 kJ/mol; Heat of combustion corrected for pressure |
ΔfH°solid | 142.5 | kJ/mol | Ccb | Medard, 1954 | crystal phase; Heat of combustion corrected for pressure |
ΔfH°solid | 117.4 ± 2.1 | kJ/mol | Cm | Cole and Gilbert, 1951 | Reanalyzed by Cox and Pilcher, 1970, Original value = 116.9 kJ/mol |
ΔfH°solid | 131. | kJ/mol | Ccb | Schmidt and Becker, 1933 | |
ΔfH°solid | 109. | kJ/mol | Ccb | Lemoult, 1907 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -6424. ± 20. | kJ/mol | AVG | N/A | Average of 7 values; Individual data points |
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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
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 | 575.2 | K | N/A | Weast and Grasselli, 1989 | BS |
Tboil | 582.15 | K | N/A | Stillmann and Swain, 1899 | Uncertainty assigned by TRC = 2. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 326. ± 2. | K | AVG | N/A | Average of 21 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 931.15 | K | N/A | Glaser and Ruland, 1957 | Uncertainty assigned by TRC = 3. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 84.0997 | bar | N/A | Glaser and Ruland, 1957 | Uncertainty assigned by TRC = 4.053 bar; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 55.23 | kJ/mol | C | Glaser and Ruland, 1957 | ALS |
ΔvapH° | 69.9 | kJ/mol | V | Vriens and Hill, 1952 | ALS |
ΔvapH° | 70.0 | kJ/mol | N/A | Vriens and Hill, 1952 | DRB |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 110. | kJ/mol | GS | Surov, Terekhova, et al., 2009 | Based on data from 303. to 319. K.; AC |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
64.1 | 396. | A | Stephenson and Malanowski, 1987 | Based on data from 381. to 575. K. See also Stull, 1947.; AC |
54.2 | 588. | A | Stephenson and Malanowski, 1987 | Based on data from 573. to 673. 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 |
---|---|---|---|---|---|
381.5 to 575. | 5.09811 | 2729.385 | -39.207 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
110.0 ± 1.0 | 311. | GS | Surov, Terekhova, et al., 2009 | Based on data from 303. to 319. K.; AC |
96.7 ± 2.5 | 310. | QF | Aihara, 1953 | Based on data from 298. to 323. K. See also Cox and Pilcher, 1970, 2.; AC |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
19.9 | 326.1 | DSC | Surov, Terekhova, et al., 2009 | AC |
17.86 | 326.2 | N/A | Acree, 1991 | AC |
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 as indicated in comments:
MS - José A. Martinho Simões
B - John E. Bartmess
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
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
C16H34OP2Ru (solution) + (solution) = C28H43NP2Ru (solution) +
(solution)
By formula: C16H34OP2Ru (solution) + C12H11N (solution) = C28H43NP2Ru (solution) + H2O (solution)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 5.0 ± 0.4 | kJ/mol | EqS | Bryndza, Fong, et al., 1987 | solvent: Tetrahydrofuran; In a series of reactions involving similar ruthenium complexes, the reaction enthalpy was identified with the reaction Gibbs energy, since the entropy values are expected to be small Bryndza, Fong, et al., 1987. For this reaction, however a van't Hoff plot could be used. Temperature range: 293-328 K; MS |
ΔrH° | 19.7 | kJ/mol | EqS | Bryndza, Fong, et al., 1987 | solvent: Benzene; The reaction enthalpy was identified with the reaction Gibbs energy, since the the entropy is expected to be small Bryndza, Fong, et al., 1987; MS |
C12H10N- + =
By formula: C12H10N- + H+ = C12H11N
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1468. ± 8.8 | kJ/mol | G+TS | Taft and Bordwell, 1988 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1438. ± 8.4 | kJ/mol | IMRE | Taft and Bordwell, 1988 | gas phase; B |
(solution) + C5H11BrMg (solution) = C12H10BrMgN (solution) +
(solution)
By formula: C12H11N (solution) + C5H11BrMg (solution) = C12H10BrMgN (solution) + C5H12 (solution)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -118.8 | kJ/mol | RSC | Holm, 1983 | solvent: Diethyl ether; MS |
= C12H11N
By formula: C12H11N = C12H11N
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 260. ± 20. | kJ/mol | Cm | Suzuki, Kajii, et al., 1992 | solid phase; solvent: Methanol; ALS |
By formula: C12H11N + HNO2 = H2O + C12H10N2O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -62.84 | kJ/mol | Cm | Swientoslawski, 1910 | solid phase; ALS |
IR Spectrum
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Data compiled by: Coblentz Society, Inc.
Data compiled by: Timothy J. Johnson, Tanya L. Myers, Yin-Fong Su, Russell G. Tonkyn, Molly Rose K. Kelly-Gorham, and Tyler O. Danby
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR 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
View image of digitized spectrum (can be printed in landscape orientation).
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 | NIST Mass Spectrometry Data Center, 1990. |
NIST MS number | 113400 |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
Medard, 1955
Medard, L.,
La chaleur de combustion de la diphenylamine et l'energie de la liaison n - n,
J. Chem. Phys., 1955, 52, 467-472. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]
Medard, 1954
Medard, L.,
Tables thermochimiques a l'usage des techniciens des substances explosives,
Mem. Artillerie Fr. Sci. Tech. Armement, 1954, 28, 415-492. [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]
Schmidt and Becker, 1933
Schmidt, V.A.; Becker, F.,
Die Bildungswarme von Nitrocellulofen, Nitroglycerin und anderen widuigen Beltandteilen von Treibmitteln,
Z. Gesamte Schiess Sprengstoffwes., 1933, 33, 280-282. [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]
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]
Stillmann and Swain, 1899
Stillmann, J.M.; Swain, R.E.,
The melting heat of naphthylamine and diphenylamine in relation to their lowering of molecular freezing point,
Z. Phys. Chem., Stoechiom. Verwandtschaftsl., 1899, 29, 705. [all data]
Glaser and Ruland, 1957
Glaser, F.; Ruland, H.,
Untersuchungsen über dampfdruckkurven und kritische daten einiger technisch wichtiger organischer substanzen,
Chem. Ing. Techn., 1957, 29, 772. [all data]
Surov, Terekhova, et al., 2009
Surov, Artem O.; Terekhova, Irina V.; Bauer-Brandl, Annette; Perlovich, German L.,
Thermodynamic and Structural Aspects of Some Fenamate Molecular Crystals,
Crystal Growth & Design, 2009, 9, 7, 3265-3272, https://doi.org/10.1021/cg900002q
. [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]
Aihara, 1953
Aihara, A.,
J. Chem. Soc. Jpn. Pure Chem. Sect., 1953, 74, 437. [all data]
Cox and Pilcher, 1970, 2
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press Inc., London, 1970, 643. [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]
Bryndza, Fong, et al., 1987
Bryndza, H.E.; Fong, L.K.; Paciello, R.A.; Tam, W.; Bercaw, J.E.,
J. Am. Chem. Soc., 1987, 109, 1444. [all data]
Taft and Bordwell, 1988
Taft, R.W.; Bordwell, F.G.,
Structural and Solvent Effects Evaluated from Acidities Measured in Dimethyl Sulfoxide and in the Gas Phase,
Acc. Chem. Res., 1988, 21, 12, 463, https://doi.org/10.1021/ar00156a005
. [all data]
Holm, 1983
Holm, T.,
Acta Chem. Scand. B, 1983, 37, 797. [all data]
Suzuki, Kajii, et al., 1992
Suzuki, T.; Kajii, Y.; Shibuya, K.; Obi, K.,
Photocyclization of diphenylamine studied by time-resolved thermal lensing. Heat of reaction, energetics, and reactivity of intermediates,
Bull. Chem. Soc. Jpn., 1992, 65, 1084-1088. [all data]
Swientoslawski, 1910
Swientoslawski, W.,
Thermochemische Untersuchungen der organischen Verbindungen. Dritte Mitteilung. Stickstoffhaltige Verbindungen.,
Z. Phys. Chem., 1910, 72, 49-83. [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), References
- Symbols used in this document:
Pc Critical pressure Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔfusH Enthalpy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy of reaction at standard conditions ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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