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
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Phase change data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • 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

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

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

Gas phase ion energetics 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 evaluated as indicated in comments:
L - 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

Ionization energy determinations

De-protonation reactions

C₁₂H₁₀N^- +  =

By formula: C₁₂H₁₀N^- + H⁺ = C₁₂H₁₁N

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry 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.

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]

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]

Debies and Rabalais, 1974
Debies, T.P.; Rabalais, J.W., Photoelectron spectra of substituted benzenes. III. Bonding with Group V substituents, Inorg. Chem., 1974, 13, 308. [all data]

Potapov and Iskakov, 1971
Potapov, V.K.; Iskakov, L.I., Electronic structure and photoionization of aromatic amines, High Energy Chem., 1971, 5, 237, In original 264. [all data]

Vilesov and Zaitsev, 1964
Vilesov, F.I.; Zaitsev, V.M., Photoionization of phenyl derivatives of group 5 elements, Dokl. Akad. Nauk SSSR, 1964, 154, 886, In original 117. [all data]

Haink, Adams, et al., 1974
Haink, H.J.; Adams, J.E.; Huber, J.R., The electronic structure of aromatic amines: photoelectron spectroscopy of diphenylamine, iminobibenzyl, acridan and carbazole, Ber. Bunsen-Ges. Phys. Chem., 1974, 78, 436. [all data]

Notes

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• Symbols used in this document:
  

  IE (evaluated)	Recommended ionization energy
  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
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔrS°	Entropy of reaction at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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