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 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | 17.4 ± 1.7 | kcal/mol | Ccb | Riberio da Silva, Riberio da Silva, et al., 1996 |
Reaction 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 by: John E. Bartmess
Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.
Individual 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 |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 375.0 ± 5.0 | kcal/mol | IMRB | Caldwell and Bartmess | gas phase |
Gas phase ion energetics 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 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 |
Gas Chromatography
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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
Kovats' RI, polar column, isothermal
| Column type | Active phase | Temperature (C) | I | Reference | Comment |
|---|---|---|---|---|---|
| Packed | Carbowax 20M | 150. | 1653.2 | Ellis and Still, 1979 | Chromosorb W, AW-DMCS |
| Packed | Carbowax 20M | 150. | 1653.6 | Ellis and Still, 1979 | Chromosorb W, AW-DMCS |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | OV-1 | 1164.6 | Gautzsch and Zinn, 1996 | 8. K/min; Tstart: 35. C; Tend: 300. C |
Normal alkane RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | SPB-1 | 1174. | Thomas and Bassols, 1992 | 5. K/min; Column length: 60. m; Tstart: 80. C; Tend: 230. C |
Normal alkane RI, polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | Supelcowax | 1664. | Thomas and Bassols, 1992 | 5. K/min; Column length: 60. m; Tstart: 80. C; Tend: 230. C |
References
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
Caldwell and Bartmess
Caldwell, G.; Bartmess, J.E.,
, Unpublished results. [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]
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]
Ellis and Still, 1979
Ellis, T.S.; Still, R.H.,
Thermal degradation of polymers. XXI. Vacuum pyrolysis of poly(m-N,N-dimethylaminostyrene); the products volatile at pyrolysis temperature, liquid at room temperature,
J. Appl. Polym. Sci., 1979, 23, 10, 2837-2854, https://doi.org/10.1002/app.1979.070231002
. [all data]
Gautzsch and Zinn, 1996
Gautzsch, R.; Zinn, P.,
Use of incremental models to estimate the retention indexes of aromatic compounds,
Chromatographia, 1996, 43, 3/4, 163-176, https://doi.org/10.1007/BF02292946
. [all data]
Thomas and Bassols, 1992
Thomas, A.F.; Bassols, F.,
Occurrence of pyridines and other bases in orange oil,
J. Agric. Food Chem., 1992, 40, 11, 2236-2243, https://doi.org/10.1021/jf00023a037
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Gas Chromatography, References
- Symbols used in this document:
ΔfH°gas Enthalpy of formation of gas at standard conditions 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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