Benzenamine, N,N-dimethyl-
- Formula: C8H11N
- Molecular weight: 121.1796
- IUPAC Standard InChIKey: JLTDJTHDQAWBAV-UHFFFAOYSA-N
- CAS Registry Number: 121-69-7
- 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: Aniline, N,N-dimethyl-; (Dimethylamino)benzene; Dimethylaniline; Dimethylphenylamine; N,N-Dimethylaniline; Versneller NL 63/10; N,N-Dimethylbenzenamine; Dwumetyloanilina; N,N-(Dimethylamino)benzene; N,N-Dimethylphenylamine; NCI-C56428; N,N-Dimethylbenzeneamine; UN 2253; NL 63-10P; NSC 7195; N,N-dimethylanilin
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Gas phase thermochemistry data
Go To: Top, 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | 24.02 ± 0.81 | kcal/mol | Ccb | Furukawa, Sakiyama, et al., 1982 | |
ΔfH°gas | 20.1 | kcal/mol | Ccb | Vriens and Hill, 1952 |
Phase change data
Go To: Top, Gas phase thermochemistry 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 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 | 466. ± 3. | K | AVG | N/A | Average of 10 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 275. ± 2. | K | AVG | N/A | Average of 8 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 687.5 ± 0.6 | K | AVG | N/A | Average of 6 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 35.8 ± 0.5 | atm | AVG | N/A | Average of 7 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 12.4 ± 0.6 | kcal/mol | AVG | N/A | Average of 6 values; Individual data points |
Reduced pressure boiling point
Tboil (K) | Pressure (atm) | Reference | Comment |
---|---|---|---|
350.2 | 0.017 | Weast and Grasselli, 1989 | BS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
12.8 ± 0.1 | 304. | N/A | Verevkin, 1997 | Based on data from 284. to 323. K.; AC |
11.8 | 378. | A | Stephenson and Malanowski, 1987 | Based on data from 363. to 418. K.; AC |
11.4 | 317. | A | Stephenson and Malanowski, 1987 | Based on data from 302. to 467. K. See also Stull, 1947.; AC |
10.60 | 465.7 | V | Mathews and Fehlandt, 1931 | ALS |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
302.7 to 466.3 | 4.82432 | 2117.236 | -27.606 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
344.17 to 469.93 | 4.84147 | 2132.497 | -26.116 | Nelson and Wales, 1925 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
2.763 | 275.6 | Ahmed and Eades, 1972 | AC |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Phase change 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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
L - 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 |
---|---|---|---|---|---|
IE (evaluated) | 7.12 ± 0.02 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 224.9 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 217.3 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
7.15 | PE | Behan, Johnstone, et al., 1976 | LLK |
7.78 | EI | Hansen and Undheim, 1975 | LLK |
7.10 ± 0.02 | PE | Maier and Turner, 1973 | LLK |
7.42 | CTS | Kobayashi, Kobayashi, et al., 1973 | LLK |
7.11 | PE | Cowling and Johnstone, 1973 | LLK |
7.13 ± 0.04 | PI | Potapov and Iskakov, 1971 | LLK |
7.2 | CTS | Finch, 1964 | RDSH |
7.10 ± 0.05 | PI | Akopyan and Vilesov, 1964 | RDSH |
7.31 | CTS | Kinoshita, 1962 | RDSH |
7.2 | CTS | Foster, 1959 | RDSH |
7.14 ± 0.03 | PI | Vilesov and Terenin, 1957 | RDSH |
7.35 | PE | Kobayashi, 1978 | Vertical value; LLK |
7.92 | PE | Kobayashi and Nagakura, 1974 | Vertical value; LLK |
7.6 | PE | Schafer and Schweig, 1972 | Vertical value; LLK |
7.37 | PE | Kobayashi and Nagakura, 1972 | Vertical value; LLK |
7.51 | PE | Baker, May, et al., 1968 | Vertical value; RDSH |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C6H5+ | 15.7 ± 0.1 | ? | EI | Gowenlock, Jones, et al., 1961 | RDSH |
C8H10N+ | 10.56 ± 0.05 | H | PI | Potapov and Iskakov, 1971 | LLK |
C8H10N+ | 10.75 ± 0.05 | H | PI | Akopyan and Vilesov, 1964 | RDSH |
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, Phase change data, 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 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 | 118735 |
References
Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Furukawa, Sakiyama, et al., 1982
Furukawa, J.; Sakiyama, M.; Seki, S.; Saito, Y.; Kusano, K.,
Standard enthalpies of combustion and vaporization of N,N-dimethylaniline,
Bull. Chem. Soc. Jpn., 1982, 55, 3329-3330. [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]
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]
Verevkin, 1997
Verevkin, Sergey P.,
Thermochemistry of amines: experimental standard molar enthalpies of formation of some aliphatic and aromatic amines,
The Journal of Chemical Thermodynamics, 1997, 29, 8, 891-899, https://doi.org/10.1006/jcht.1997.0212
. [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]
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]
Ahmed and Eades, 1972
Ahmed, A.M.I.; Eades, R.G.,
Proton relaxation in solid aniline and some methyl derivatives,
J. Chem. Soc., Faraday Trans. 2, 1972, 68, 2017, https://doi.org/10.1039/f29726802017
. [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]
Behan, Johnstone, et al., 1976
Behan, J.M.; Johnstone, R.A.W.; Bentley, T.W.,
An evaluation of empirical methods for calculating the ionization potentials of substituted benzenes,
Org. Mass Spectrom., 1976, 11, 207. [all data]
Hansen and Undheim, 1975
Hansen, P.E.; Undheim, K.,
Mass spectrometry of onium compounds. XXIX. Ionisation potential in structure analysis of valence isomers,
Acta Chem. Scand., Ser. B, 1975, 29, 221. [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]
Kobayashi, Kobayashi, et al., 1973
Kobayashi, H.; Kobayashi, M.; Kaizu, Y.,
Molecular complexes of arenetricarbonylchromium,
Bull. Chem. Soc. Jpn., 1973, 46, 3109. [all data]
Cowling and Johnstone, 1973
Cowling, S.A.; Johnstone, R.A.W.,
Photoelectron spectroscopy: The effects of steric inhibition to resonance in anilines,
J. Electron Spectrosc. Relat. Phenom., 1973, 2, 161. [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]
Finch, 1964
Finch, A.C.M.,
Charge-transfer spectra and the ionization energy of azulene,
J. Chem. Soc., 1964, 2272. [all data]
Akopyan and Vilesov, 1964
Akopyan, M.E.; Vilesov, F.I.,
Excited states of positive ions and dissociative photoionization of aromatic amines,
Dokl. Akad. Nauk SSSR, 1964, 158, 1386, In original 965. [all data]
Kinoshita, 1962
Kinoshita, M.,
The absorption spectra of the molecular complexes of aromatic compounds with p-bromanil,
Bull. Chem. Soc. Japan, 1962, 35, 1609. [all data]
Foster, 1959
Foster, R.,
Ionization potentials of electron donors,
Nature (London), 1959, 183, 1253. [all data]
Vilesov and Terenin, 1957
Vilesov, F.I.; Terenin, A.N.,
The photoionization of the vapors of certain organic compounds,
Dokl. Akad. Nauk SSSR, 1957, 115, 744, In original 539. [all data]
Kobayashi, 1978
Kobayashi, T.,
A simple general tendency in photoelectron angular distributions of some monosubstituted benzenes,
Phys. Lett., 1978, 69, 105. [all data]
Kobayashi and Nagakura, 1974
Kobayashi, T.; Nagakura, S.,
Photoelectron spectra of substituted benzenes,
Bull. Chem. Soc. Jpn., 1974, 47, 2563. [all data]
Schafer and Schweig, 1972
Schafer, W.; Schweig, A.,
Zur Konjugation in aromatischen Aminen und Phosphanen,
Angew. Chem., 1972, 84, 898. [all data]
Kobayashi and Nagakura, 1972
Kobayashi, T.; Nagakura, S.,
Photoelectron spectra of anilines,
Chem. Lett., 1972, 1013. [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]
Gowenlock, Jones, et al., 1961
Gowenlock, B.G.; Jones, P.P.; Majer, J.R.,
Bond dissociation energies in some molecules containing alkyl substituted CH3, NH2, and OH,
J. Chem. Soc. Faraday Trans., 1961, 57, 23. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), References
- Symbols used in this document:
AE Appearance energy IE (evaluated) Recommended ionization energy Pc Critical pressure Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfusH Enthalpy of fusion 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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