Diphenylamine
- Formula: C12H11N
- Molecular weight: 169.2224
- 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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Phase change data
Go To: Top, Gas phase ion energetics data, 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:
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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 575.2 | K | N/A | Weast and Grasselli, 1989 | BS |
Tboil | 582.15 | K | N/A | Stillmann and Swain, 1899 | Uncertainty assigned by TRC = 2. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 326. ± 2. | K | AVG | N/A | Average of 21 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 931.15 | K | N/A | Glaser and Ruland, 1957 | Uncertainty assigned by TRC = 3. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 83.0000 | atm | N/A | Glaser and Ruland, 1957 | Uncertainty assigned by TRC = 4.000 atm; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 13.20 | kcal/mol | C | Glaser and Ruland, 1957 | ALS |
ΔvapH° | 16.7 | kcal/mol | V | Vriens and Hill, 1952 | ALS |
ΔvapH° | 16.7 | kcal/mol | N/A | Vriens and Hill, 1952 | DRB |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 26.3 | kcal/mol | GS | Surov, Terekhova, et al., 2009 | Based on data from 303. to 319. K.; AC |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
15.3 | 396. | A | Stephenson and Malanowski, 1987 | Based on data from 381. to 575. K. See also Stull, 1947.; AC |
13.0 | 588. | A | Stephenson and Malanowski, 1987 | Based on data from 573. to 673. K.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
381.5 to 575. | 5.09240 | 2729.385 | -39.207 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Enthalpy of sublimation
ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
26.29 ± 0.24 | 311. | GS | Surov, Terekhova, et al., 2009 | Based on data from 303. to 319. K.; AC |
23.1 ± 0.60 | 310. | QF | Aihara, 1953 | Based on data from 298. to 323. K. See also Cox and Pilcher, 1970.; AC |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
4.76 | 326.1 | DSC | Surov, Terekhova, et al., 2009 | AC |
4.269 | 326.2 | N/A | Acree, 1991 | AC |
Gas phase ion energetics data
Go To: Top, Phase change data, References, Notes
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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 7.19 ± 0.05 | eV | N/A | N/A | L |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
7.18 ± 0.01 | PE | Debies and Rabalais, 1974 | LLK |
7.14 ± 0.03 | PI | Potapov and Iskakov, 1971 | LLK |
7.25 ± 0.03 | PI | Vilesov and Zaitsev, 1964 | RDSH |
7.44 | PE | Haink, Adams, et al., 1974 | Vertical value; LLK |
De-protonation reactions
C12H10N- + =
By formula: C12H10N- + H+ = C12H11N
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 350.8 ± 2.1 | kcal/mol | G+TS | Taft and Bordwell, 1988 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 343.8 ± 2.0 | kcal/mol | IMRE | Taft and Bordwell, 1988 | gas phase; B |
References
Go To: Top, Phase change 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.
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]
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]
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]
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]
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]
Notes
Go To: Top, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
IE (evaluated) Recommended ionization energy Pc Critical pressure Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point ΔfusH Enthalpy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy 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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