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
IUPAC Standard InChIKey: DMBHHRLKUKUOEG-UHFFFAOYSA-N
CAS Registry Number: 122-39-4
Chemical structure:
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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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Reaction thermochemistry data

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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

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Individual Reactions

C₁₆H₃₄OP₂Ru (solution) + Diphenylamine (solution) = C₂₈H₄₃NP₂Ru (solution) + (solution)

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

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	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
Δ_rH°	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^- + = Diphenylamine

By formula: C₁₂H₁₀N^- + H⁺ = C₁₂H₁₁N

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	1468. ± 8.8	kJ/mol	G+TS	Taft and Bordwell, 1988	gas phase; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	1438. ± 8.4	kJ/mol	IMRE	Taft and Bordwell, 1988	gas phase; B

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

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

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-118.8	kJ/mol	RSC	Holm, 1983	solvent: Diethyl ether; MS

Diphenylamine = C₁₂H₁₁N

By formula: C₁₂H₁₁N = C₁₂H₁₁N

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	260. ± 20.	kJ/mol	Cm	Suzuki, Kajii, et al., 1992	solid phase; solvent: Methanol; ALS

Diphenylamine + = +

By formula: C₁₂H₁₁N + HNO₂ = H₂O + C₁₂H₁₀N₂O

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-62.84	kJ/mol	Cm	Swientoslawski, 1910	solid phase; ALS

References

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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

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Symbols used in this document:

Δ_rG° Free energy of reaction at standard conditions

Δ_rH° Enthalpy of reaction at standard conditions

Δ_rS° Entropy of reaction at standard conditions
Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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Δ_rG°	Free energy of reaction at standard conditions
Δ_rH°	Enthalpy of reaction at standard conditions
Δ_rS°	Entropy of reaction at standard conditions