Benzenamine, N,N,3-trimethyl-
- Formula: C9H13N
- Molecular weight: 135.2062
- 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
Go To: Top, Condensed 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | 72.6 ± 7.3 | kJ/mol | Ccb | Riberio da Silva, Riberio da Silva, et al., 1996 |
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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | 14.4 ± 2.5 | kJ/mol | Ccb | Riberio da Silva, Riberio da Silva, et al., 1996 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -5413.9 ± 2.2 | kJ/mol | Ccb | Riberio da Silva, Riberio da Silva, et al., 1996 |
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
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 | 488.2 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
Tboil | 485.2 | K | N/A | Weast and Grasselli, 1989 | BS |
Tboil | 485. to 488. | K | N/A | Frinton Laboratories Inc., 1986 | BS |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 58.2 ± 6.9 | kJ/mol | V | Riberio da Silva, Riberio da Silva, et al., 1996 | ALS |
ΔvapH° | 58.2 | kJ/mol | N/A | Riberio da Silva, Riberio da Silva, et al., 1996 | DRB |
ΔvapH° | 58.2 ± 6.9 | kJ/mol | CGC | Riberio da Silva, Riberio da Silva, et al., 1996 | AC |
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) | 942.1 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 915.7 | kJ/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° | 1597. ± 21. | kJ/mol | G+TS | Caldwell and Bartmess | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1569. ± 21. | kJ/mol | IMRB | Caldwell and Bartmess | gas phase; B |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, 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.
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]
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [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]
Frinton Laboratories Inc., 1986
Frinton Laboratories Inc.,
Catalog Number 11, Frinton Laboratories Inc., Vineland, NJ, 1986, 99. [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]
Caldwell and Bartmess
Caldwell, G.; Bartmess, J.E.,
, Unpublished results. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
Tboil Boiling point ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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