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:
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
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Reaction thermochemistry data
Go To: Top, Mass spectrum (electron ionization), UV/Visible 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 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)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 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 |
| ΔrH° | 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- + =
By formula: C12H10N- + H+ = C12H11N
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1468. ± 8.8 | kJ/mol | G+TS | Taft and Bordwell, 1988 | gas phase; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1438. ± 8.4 | kJ/mol | IMRE | Taft and Bordwell, 1988 | gas phase; B |
(solution) + C5H11BrMg (solution) = C12H10BrMgN (solution) +
(solution)
By formula: C12H11N (solution) + C5H11BrMg (solution) = C12H10BrMgN (solution) + C5H12 (solution)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -118.8 | kJ/mol | RSC | Holm, 1983 | solvent: Diethyl ether; MS |
= C12H11N
By formula: C12H11N = C12H11N
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 260. ± 20. | kJ/mol | Cm | Suzuki, Kajii, et al., 1992 | solid phase; solvent: Methanol; ALS |
+
=
+
By formula: C12H11N + HNO2 = H2O + C12H10N2O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -62.84 | kJ/mol | Cm | Swientoslawski, 1910 | solid phase; ALS |
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
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Due to licensing restrictions, this spectrum cannot be downloaded.
| 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 |
UV/Visible spectrum
Go To: Top, Reaction thermochemistry data, 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: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina
Spectrum
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Additional Data
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| Source | Ramart-Lucas, Hoch, et al., 1949 |
|---|---|
| Owner | INEP CP RAS, NIST OSRD Collection (C) 2007 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
| Origin | INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS |
| Source reference | RAS UV No. 626 |
| Instrument | n.i.g. |
| Melting point | 52.9 |
| Boiling point | 302 |
References
Go To: Top, Reaction thermochemistry data, Mass spectrum (electron ionization), UV/Visible spectrum, Notes
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]
Ramart-Lucas, Hoch, et al., 1949
Ramart-Lucas, M.; Hoch, J.; Grumez, M.,
Deformation des orbites electroniques de l'azote par cyclisation (serie du benzotriazole et du phenyltriazole),
Bull. Soc. Chim. Fr., 1949, 16, 447-454. [all data]
Notes
Go To: Top, Reaction thermochemistry data, Mass spectrum (electron ionization), UV/Visible spectrum, References
- Symbols used in this document:
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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