N,N-Diethylaniline
- Formula: C10H15N
- Molecular weight: 149.2328
- IUPAC Standard InChIKey: GGSUCNLOZRCGPQ-UHFFFAOYSA-N
- CAS Registry Number: 91-66-7
- 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,N-diethyl-; Aniline, N,N-diethyl-; Diethylaniline; Diethylphenylamine; N,N-Diethylaminobenzene; N,N-Diethylbenzenamine; DEA; Diaethylanilin; N,N-Diethylanilin; Phenyldiethylamine; UN 2432; (Diethylamino)benzene; N-Phenyldiethylamine; NSC 7205
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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 | 490. ± 2. | K | AVG | N/A | Average of 13 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 251.85 | K | N/A | Radwan and Hanna, 1976 | Uncertainty assigned by TRC = 0.2 K; TRC |
Tfus | 251.85 | K | N/A | Timmermans, 1921 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.3 K; the stable form; TRC |
Tfus | 238.75 | K | N/A | Timmermans, 1921 | Crystal phase 2 phase; Uncertainty assigned by TRC = 0.5 K; identified as an unstable form; TRC |
Tfus | 235.1 | K | N/A | Timmermans, 1911 | Uncertainty assigned by TRC = 0.3 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 60.3 ± 6.9 | kJ/mol | V | Riberio da Silva, Riberio da Silva, et al., 1996 | ALS |
ΔvapH° | 60.3 | kJ/mol | N/A | Riberio da Silva, Riberio da Silva, et al., 1996 | DRB |
ΔvapH° | 56.5 | kJ/mol | V | Vriens and Hill, 1952 | ALS |
ΔvapH° | 56.0 | kJ/mol | N/A | Vriens and Hill, 1952 | DRB |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
54.5 | 358. | A | Stephenson and Malanowski, 1987 | Based on data from 343. to 493. K.; AC |
46.32 | 488.2 | V | Mathews and Fehlandt, 1931 | ALS |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
323. to 491.6 | 5.38274 | 2652.751 | 4.172 | Nelson and Wales, 1925 | Coefficents calculated by NIST from author's data. |
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:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias
Data compiled as indicated in comments:
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
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) | 6.98 ± 0.05 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 959.8 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 927.9 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
6.98 | EQ | Lias, Jackson, et al., 1985 | LBLHLM |
6.98 ± 0.05 | EQ | Mautner(Meot-Ner), Nelsen, et al., 1984 | LBLHLM |
6.95 ± 0.02 | PE | Maier and Turner, 1973 | LLK |
6.99 | CTS | Farrell and Newton, 1965 | RDSH |
7.15 | CTS | Briegleb and Czekalla, 1959 | RDSH |
7.51 | PE | Baker, May, et al., 1968 | Vertical value; RDSH |
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.
Radwan and Hanna, 1976
Radwan, M.H.; Hanna, A.A.,
Binary Azeotropes Containing Butyric Acid,
J. Chem. Eng. Data, 1976, 21, 285-8. [all data]
Timmermans, 1921
Timmermans, J.,
The Freezing Points of Organic Substances IV. New Exp. Determinations,
Bull. Soc. Chim. Belg., 1921, 30, 62. [all data]
Timmermans, 1911
Timmermans, J.,
Researches on the freezing point of organic liquid compounds,
Bull. Soc. Chim. Belg., 1911, 25, 300. [all data]
Riberio da Silva, Riberio da Silva, et al., 1996
Riberio da Silva, M.A.V.; Riberio da Silva, M.D.M.C.; Monteiro, M.F.B.M.; Gomes, M.L.A.C.N.; Chickos, J.S.; Smith, A.P.; Liebman, J.F.,
Thermochemical studies for determination of the molar enthalpy of formation of aniline derivatives,
Struct. Chem., 1996, 7, 367-373. [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]
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]
Mathews and Fehlandt, 1931
Mathews, J.H.; Fehlandt, P.R.,
The heats of vaporization of some organic compounds,
J. Am. Chem. Soc., 1931, 53, 3212-32. [all data]
Nelson and Wales, 1925
Nelson, O.A.; Wales, H.,
Vapor Pressures and Boiling Points of Mono- and Dimthylanilines and Mono- and Diethylanilines,
J. Am. Chem. Soc., 1925, 47, 3, 867-872, https://doi.org/10.1021/ja01680a040
. [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]
Lias, Jackson, et al., 1985
Lias, S.G.; Jackson, J.-A.A.; Argentar, H.; Liebman, J.F.,
Substituted N,N-dialkylanilines: Relative ionization energies and proton affinities through determinations of ion-molecule reaction equilibrium constants,
J. Org. Chem., 1985, 50, 333. [all data]
Mautner(Meot-Ner), Nelsen, et al., 1984
Mautner(Meot-Ner), M.; Nelsen, S.F.; Willi, M.R.; Frigo, T.B.,
Special effects of an unusually large neutral to radical cation geometry change. Adiabatic ionization energies and proton affinities of alkylhydrazines,
J. Am. Chem. Soc., 1984, 106, 7384. [all data]
Maier and Turner, 1973
Maier, J.P.; Turner, D.W.,
Steric inhibition of resonance studied by molecular photoelectron spectroscopy Part 3. Anilines, Phenols and Related Compounds,
J. Chem. Soc. Faraday Trans. 2, 1973, 69, 521. [all data]
Farrell and Newton, 1965
Farrell, P.G.; Newton, J.,
Ionization potentials of aromatic amines,
J. Phys. Chem., 1965, 69, 3506. [all data]
Briegleb and Czekalla, 1959
Briegleb, G.; Czekalla, J.,
Die Bestimmung von lonisierungsenergien aus den Spektren von Elektronenubergangskomplexen,
Z.Elektrochem., 1959, 63, 6. [all data]
Baker, May, et al., 1968
Baker, A.D.; May, D.P.; Turner, D.W.,
Molecular photoelectron spectroscopy. Part VII. The vertical ionisation potentials of benzene and some of its monosubstituted and 1,4-disubstituted derivatives,
J. Chem. Soc. B, 1968, 22. [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 Tboil Boiling point Tfus Fusion (melting) point 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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