Benzenamine, N,N-diphenyl-
- Formula: C18H15N
- Molecular weight: 245.3184
- IUPAC Standard InChIKey: ODHXBMXNKOYIBV-UHFFFAOYSA-N
- CAS Registry Number: 603-34-9
- Chemical structure:
This structure is also available as a 2d Mol file - Other names: N,N-Diphenylaniline; Triphenylamine; N,N-Diphenylbenzenamine
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | 327. ± 4.2 | kJ/mol | Ccb | Steele, 1978 |
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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°solid | 235. ± 3. | kJ/mol | Ccb | Steele, 1978 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -9462. ± 3. | kJ/mol | Ccb | Steele, 1978 | ALS |
Constant pressure heat capacity of solid
Cp,solid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
297.5 | 298.5 | Smith and Andrews, 1931 | T = 102 to 346 K. Value is unsmoothed experimental datum.; DH |
Phase change 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 620.7 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 399.9 | K | N/A | Chickos, Braton, et al., 1991 | Uncertainty assigned by TRC = 1. K; TRC |
Tfus | 400.7 | K | N/A | Forward, Bowden, et al., 1949 | Uncertainty assigned by TRC = 0.6 K; TRC |
Tfus | 399. | K | N/A | Adkins, Zartman, et al., 1931 | Uncertainty assigned by TRC = 1.5 K; TRC |
Tfus | 399.65 | K | N/A | Smith and Andrews, 1931, 2 | Uncertainty assigned by TRC = 0.6 K; with Hg thelrmometer; TRC |
Tfus | 398.95 | K | N/A | Smith and Andrews, 1931, 2 | Uncertainty assigned by TRC = 0.5 K; with thermocouple; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 92. ± 3. | kJ/mol | V | Steele, 1978 | ALS |
ΔsubH° | 92.0 | kJ/mol | N/A | Steele, 1978 | DRB |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
65.2 | 488. | A | Stephenson and Malanowski, 1987 | Based on data from 473. to 640. K. See also Forward, Bowden, et al., 1949, 2.; AC |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
87.9 ± 1.3 | 337. | BG | Steele, 1978 | Based on data from 322. to 373. K. See also Stephenson and Malanowski, 1987.; AC |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
24.89 | 400.2 | Acree, 1993 | AC |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Mass spectrum (electron ionization), Gas Chromatography, 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:
HL - Edward P. Hunter and Sharon G. Lias
Data compiled as indicated in comments:
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 |
---|---|---|---|---|---|
Proton affinity (review) | 908.9 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 876.4 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
6.75 ± 0.01 | PE | Debies and Rabalais, 1974 | LLK |
6.80 ± 0.05 | PI | Potapov and Iskakov, 1971 | LLK |
6.86 ± 0.03 | PI | Vilesov and Zaitsev, 1964 | RDSH |
7.00 ± 0.05 | PE | Distefano, Pignataro, et al., 1975 | Vertical value; LLK |
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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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 | Japan AIST/NIMC Database- Spectrum MS-NW-1448 |
NIST MS number | 229683 |
Gas Chromatography
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics 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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Kovats' RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Packed | SE-30 | 2055. | Ramsey, Lee, et al., 1980 | He, Chromosorb G HP (80-100 mesh); Column length: 1.5 m; Program: not specified |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Other | Methyl Silicone | 2055. | Ardrey and Moffat, 1981 | Program: not specified |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Steele, 1978
Steele, W.V.,
The standard enthalpies of formation of the triphenyl compounds of the Group V elements. 1. Triphenylamine and the Ph-N bond-dissociation energy,
J. Chem. Thermodyn., 1978, 10, 441-444. [all data]
Smith and Andrews, 1931
Smith, R.H.; Andrews, D.H.,
Thermal energy studies. II. Phenyl derivatives of metals,
J. Am. Chem. Soc., 1931, 53, 3661-3667. [all data]
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]
Chickos, Braton, et al., 1991
Chickos, J.S.; Braton, C.M.; Hesse, D.G.; Liebman, J.F.,
Estimating entropies and enthalpies of fusion of organic compounds,
J. Org. Chem., 1991, 56, 3, 927, https://doi.org/10.1021/jo00003a007
. [all data]
Forward, Bowden, et al., 1949
Forward, M.V.; Bowden, S.T.; Jones, W.J.,
Physical Properties of Triphenyl Compounds of Group VB Elements,
J. Chem. Soc., 1949, 1949, 121-6. [all data]
Adkins, Zartman, et al., 1931
Adkins, H.; Zartman, W.H.; Cramer, H.,
The Hydrogention of Certain Branched Compounds Over Nickel,
J. Am. Chem. Soc., 1931, 53, 1425. [all data]
Smith and Andrews, 1931, 2
Smith, R.H.; Andrews, D.H.,
Thermal Energy Studies II. Phenyl Derivatives of Metals,
J. Am. Chem. Soc., 1931, 53, 3661-7. [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]
Forward, Bowden, et al., 1949, 2
Forward, M.V.; Bowden, S.T.; Jones, W.J.,
S 26. Physical properties of triphenyl compounds of group V B elements,
J. Chem. Soc., 1949, S121, https://doi.org/10.1039/jr949000s121
. [all data]
Acree, 1993
Acree, William E.,
Thermodynamic properties of organic compounds,
Thermochimica Acta, 1993, 219, 97-104, https://doi.org/10.1016/0040-6031(93)80486-T
. [all data]
Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G.,
Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update,
J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018
. [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]
Distefano, Pignataro, et al., 1975
Distefano, G.; Pignataro, S.; Szepes, L.; Borossay, J.,
Photoelectron spectroscopy study of the triphenyl derivatives of the group V elements,
J. Organomet. Chem., 1975, 102, 313. [all data]
Ramsey, Lee, et al., 1980
Ramsey, J.D.; Lee, T.D.; Osselton, M.D.; Moffat, A.C.,
Gas-liquid chromatographic retention indices of 296 non-drug substances on SE-30 or OV-1 likely to be encountered in toxicological analyses,
J. Chromatogr., 1980, 184, 2, 185-206, https://doi.org/10.1016/S0021-9673(00)85641-1
. [all data]
Ardrey and Moffat, 1981
Ardrey, R.E.; Moffat, A.C.,
Gas-liquid chromatographic retention indices of 1318 substances of toxicological interest on SE-30 or OV-1 stationary phase,
J. Chromatogr., 1981, 220, 3, 195-252, https://doi.org/10.1016/S0021-9673(00)81925-1
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, References
- Symbols used in this document:
Cp,solid Constant pressure heat capacity of solid Tboil Boiling point Tfus Fusion (melting) point ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔfusH Enthalpy of fusion ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions ΔvapH Enthalpy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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