Diphenylamine

• Formula: C₁₂H₁₁N
• Molecular weight: 169.2224
• IUPAC Standard InChI: InChI=1S/C12H11N/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h1-10,13H Copy

  
• IUPAC Standard InChIKey: DMBHHRLKUKUOEG-UHFFFAOYSA-N Copy
• 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
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Mass spectrum (electron ionization)
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Gas phase ion energetics data
  • IR Spectrum
  • UV/Visible spectrum
  • Gas Chromatography
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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

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

Enthalpy of vaporization

Antoine Equation Parameters

log₁₀(P) = A − (B / (T + C))
    P = vapor pressure (bar)
    T = temperature (K)

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Enthalpy of sublimation

Enthalpy of fusion

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)

C₁₂H₁₀N^- +  =

By formula: C₁₂H₁₀N^- + H⁺ = C₁₂H₁₁N

 (solution) + C₅H₁₁BrMg (solution) = C₁₂H₁₀BrMgN (solution) +  (solution)

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

= C₁₂H₁₁N

By formula: C₁₂H₁₁N = C₁₂H₁₁N

 +  =  + 

By formula: C₁₂H₁₁N + HNO₂ = H₂O + C₁₂H₁₀N₂O

Mass spectrum (electron ionization)

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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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Additional Data

References

Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, 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]

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
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, Phase change data, Reaction thermochemistry data, Mass spectrum (electron ionization), References

• Symbols used in this document:
  

  Pc	Critical pressure
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  ΔfH°gas	Enthalpy of formation of gas 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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