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Diphenylamine

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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

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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

References

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

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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