Home Symbol which looks like a small house Up Solid circle with an upward pointer in it

Diphenylamine

Data at NIST subscription sites:

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.


Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), 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
Deltafgas202.kJ/molCcbVriens and Hill, 1952 

Condensed phase thermochemistry data

Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), 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
Deltafliquid132.kJ/molCcbVriens and Hill, 1952 
Quantity Value Units Method Reference Comment
Deltacliquid-6426.2kJ/molCcbVriens and Hill, 1952 
Quantity Value Units Method Reference Comment
Deltafsolid130.0 ± 1.5kJ/molCcbMedard, 1955Reanalyzed by Cox and Pilcher, 1970, Original value = 140.6 ± 1.5 kJ/mol; Heat of combustion corrected for pressure
Deltafsolid142.5kJ/molCcbMedard, 1954crystal phase; Heat of combustion corrected for pressure
Deltafsolid117.4 ± 2.1kJ/molCmCole and Gilbert, 1951Reanalyzed by Cox and Pilcher, 1970, Original value = 116.9 kJ/mol
Deltafsolid131.kJ/molCcbSchmidt and Becker, 1933 
Deltafsolid109.kJ/molCcbLemoult, 1907 
Quantity Value Units Method Reference Comment
Deltacsolid-6424. ± 20.kJ/molAVGN/AAverage of 7 values; Individual data points

Phase change data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), 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, Kenneth Kroenlein 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
Tboil575.2KN/AWeast and Grasselli, 1989BS
Tboil582.15KN/AStillmann and Swain, 1899Uncertainty assigned by TRC = 2. K; TRC
Quantity Value Units Method Reference Comment
Tfus326. ± 2.KAVGN/AAverage of 21 values; Individual data points
Quantity Value Units Method Reference Comment
Tc931.15KN/AGlaser and Ruland, 1957Uncertainty assigned by TRC = 3. K; TRC
Quantity Value Units Method Reference Comment
Pc84.0997barN/AGlaser and Ruland, 1957Uncertainty assigned by TRC = 4.053 bar; TRC
Quantity Value Units Method Reference Comment
Deltavap55.23kJ/molCGlaser and Ruland, 1957ALS
Deltavap69.9kJ/molVVriens and Hill, 1952ALS
Deltavap70.0kJ/molN/AVriens and Hill, 1952DRB
Quantity Value Units Method Reference Comment
Deltasub110.kJ/molGSSurov, Terekhova, et al., 2009Based on data from 303. - 319. K.; AC

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
64.1396.AStephenson and Malanowski, 1987Based on data from 381. - 575. K. See also Stull, 1947.; AC
54.2588.AStephenson and Malanowski, 1987Based on data from 573. - 673. K.; AC

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
381.5 - 575.5.098112729.385-39.207Stull, 1947Coefficents calculated by NIST from author's data.

Enthalpy of sublimation

DeltasubH (kJ/mol) Temperature (K) Method Reference Comment
110.0 ± 1.0311.GSSurov, Terekhova, et al., 2009Based on data from 303. - 319. K.; AC
96.7 ± 2.5310.QFAihara, 1953Based on data from 298. - 323. K. See also Cox and Pilcher, 1970, 2.; AC

Enthalpy of fusion

DeltafusH (kJ/mol) Temperature (K) Method Reference Comment
19.9326.1DSCSurov, Terekhova, et al., 2009AC
17.86326.2N/AAcree, 1991AC

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


Reaction thermochemistry data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, IR Spectrum, Mass spectrum (electron ionization), 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:
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) + Diphenylamine (solution) = C28H43NP2Ru (solution) + Water (solution)

By formula: C16H34OP2Ru (solution) + C12H11N (solution) = C28H43NP2Ru (solution) + H2O (solution)

Quantity Value Units Method Reference Comment
Deltar5.0 ± 0.4kJ/molEqSBryndza, Fong, et al., 1987solvent: 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
Deltar19.7kJ/molEqSBryndza, Fong, et al., 1987solvent: 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- + Hydrogen cation = Diphenylamine

By formula: C12H10N- + H+ = C12H11N

Quantity Value Units Method Reference Comment
Deltar1468. ± 8.8kJ/molG+TSTaft and Bordwell, 1988gas phase; B
Quantity Value Units Method Reference Comment
Deltar1438. ± 8.4kJ/molIMRETaft and Bordwell, 1988gas phase; B

Diphenylamine (solution) + C5H11BrMg (solution) = C12H10BrMgN (solution) + Pentane (solution)

By formula: C12H11N (solution) + C5H11BrMg (solution) = C12H10BrMgN (solution) + C5H12 (solution)

Quantity Value Units Method Reference Comment
Deltar-118.8kJ/molRSCHolm, 1983solvent: Diethyl ether; MS

Diphenylamine = C12H11N

By formula: C12H11N = C12H11N

Quantity Value Units Method Reference Comment
Deltar260. ± 20.kJ/molCmSuzuki, Kajii, et al., 1992solid phase; solvent: Methanol; ALS

Diphenylamine + Nitrous acid = Water + N-Nitrosodiphenylamine

By formula: C12H11N + HNO2 = H2O + C12H10N2O

Quantity Value Units Method Reference Comment
Deltar-62.84kJ/molCmSwientoslawski, 1910solid phase; ALS

IR Spectrum

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Mass spectrum (electron ionization), References, Notes

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

Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.

Mass spectrum
For Zoom
1.) Enter the desired X axis range (e.g., 100, 200)
2.) Check here for automatic Y scaling
3.) Press here to zoom

Additional Data

View image of digitized spectrum (can be printed in landscape orientation).

View spectrum image in SVG format.

Download spectrum in JCAMP-DX format.

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

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


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