Benzenamine, N,N,3-trimethyl-
- Formula: C9H13N
- Molecular weight: 135.2062
- IUPAC Standard InChI: InChI=1S/C9H13N/c1-8-5-4-6-9(7-8)10(2)3/h4-7H,1-3H3
- IUPAC Standard InChIKey: CWOMTHDOJCARBY-UHFFFAOYSA-N
- CAS Registry Number: 121-72-2
- 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: m-Toluidine, N,N-dimethyl-; m-Methyl-N,N-dimethylaniline; m,N,N-trimethylaniline; Benzene, 1-(dimethylamino)-3-methyl-; Dimethyl-m-toluidine; N,N-Dimethyl-m-methylaniline; N,N-Dimethyl-m-toluidine; N,N-Dimethyl-3-methylaniline; N,N,3-Trimethylaniline; N,N,3-Trimethylbenzenamine; N,N-Dimethyl-3-toluidine; Dimetil-m-toluidina; Benzeneamine,N,N,3-trimethyl-; 3-(Dimethylamino)toluene; NSC 1788; N,N-Dimethyl-m-ethylaniline
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Gas phase ion energetics data
Go To: Top, 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:
B - John E. Bartmess
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 |
|---|---|---|---|---|---|
| Proton affinity (review) | 225.2 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
| Quantity | Value | Units | Method | Reference | Comment |
| Gas basicity | 218.9 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 7.02 | EQ | Lias, Jackson, et al., 1985 | LBLHLM |
| 7.06 | PE | Cowling and Johnstone, 1973 | LLK |
| 7.35 | CTS | Farrell and Newton, 1965 | RDSH |
| 7.24 | PE | Kobayashi and Nagakura, 1974 | Vertical value; LLK |
| 7.24 | PE | Kobayashi and Nagakura, 1972 | Vertical value; LLK |
| 7.27 | PE | Kobayashi and Nagakura, 1972 | Vertical value; LLK |
De-protonation reactions
C9H12N- + =
By formula: C9H12N- + H+ = C9H13N
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 381.7 ± 5.1 | kcal/mol | G+TS | Caldwell and Bartmess | gas phase; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 375.0 ± 5.0 | kcal/mol | IMRB | Caldwell and Bartmess | gas phase; B |
References
Go To: Top, 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.
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]
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]
Farrell and Newton, 1965
Farrell, P.G.; Newton, J.,
Ionization potentials of aromatic amines,
J. Phys. Chem., 1965, 69, 3506. [all data]
Kobayashi and Nagakura, 1974
Kobayashi, T.; Nagakura, S.,
Photoelectron spectra of substituted benzenes,
Bull. Chem. Soc. Jpn., 1974, 47, 2563. [all data]
Kobayashi and Nagakura, 1972
Kobayashi, T.; Nagakura, S.,
Photoelectron spectra of anilines,
Chem. Lett., 1972, 1013. [all data]
Caldwell and Bartmess
Caldwell, G.; Bartmess, J.E.,
, Unpublished results. [all data]
Notes
Go To: Top, Gas phase ion energetics data, References
- Symbols used in this document:
ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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