Benzenamine, N,N,4-trimethyl-
- Formula: C9H13N
- Molecular weight: 135.2062
- IUPAC Standard InChIKey: GYVGXEWAOAAJEU-UHFFFAOYSA-N
- CAS Registry Number: 99-97-8
- 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: p-Toluidine, N,N-dimethyl-; p-Methyl-N,N-dimethylaniline; p,N,N-trimethylaniline; Dimethyl-p-toluidine; N,N-Dimethyl-p-toluidine; N,N-Dimethyl-p-tolylamine; N,N-Dimethyl-4-methylaniline; N,N,4-Trimethylbenzenamine; N,N-Dimethyl-4-toluidine; N,N,4-Trimethylaniline; Dimetil-p-toluidina; Benzeneamine,N,N,4-trimethyl-; 1-(Dimethylamino)-4-methylbenzene; NSC 1785; p-(Dimethylamino)toluene
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, 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 | 68.9 ± 7.4 | 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 | 11.7 ± 2.7 | kJ/mol | Ccb | Riberio da Silva, Riberio da Silva, et al., 1996 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -5411.2 ± 2.4 | 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
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 | 484.2 | K | N/A | Weast and Grasselli, 1989 | BS |
Tboil | 483.15 | K | N/A | Broxton, Deady, et al., 1970 | Uncertainty assigned by TRC = 2. K; TRC |
Tboil | 484.3 | K | N/A | Perkin, 1896 | Uncertainty assigned by TRC = 1. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 57.2 ± 6.9 | kJ/mol | V | Riberio da Silva, Riberio da Silva, et al., 1996 | ALS |
ΔvapH° | 57.2 | kJ/mol | N/A | Riberio da Silva, Riberio da Silva, et al., 1996 | DRB |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
60.7 | 338. | A | Stephenson and Malanowski, 1987 | Based on data from 323. to 483. K. See also Stull, 1947.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
323.3 to 482.7 | 3.71671 | 1364.255 | -116.036 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
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 as indicated in comments:
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
B - John E. Bartmess
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
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
By formula: C9H13N+ + C9H13N = (C9H13N+ • C9H13N)
Bond type: Charge transfer bond (positive ion)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 70.7 | kJ/mol | PHPMS | Meot-Ner (Mautner) and El-Shall, 1986 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | (110.) | J/mol*K | N/A | Meot-Ner (Mautner) and El-Shall, 1986 | gas phase; Entropy change calculated or estimated; M |
Free energy of reaction
ΔrG° (kJ/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
34. | 331. | PHPMS | Meot-Ner (Mautner) and El-Shall, 1986 | gas phase; Entropy change calculated or estimated; M |
C9H12N- + =
By formula: C9H12N- + H+ = C9H13N
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1614. ± 21. | kJ/mol | G+TS | Caldwell and Bartmess | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1586. ± 21. | kJ/mol | IMRB | Caldwell and Bartmess | gas phase; B |
By formula: C10H10Fe+ + C9H13N = (C10H10Fe+ • C9H13N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 51.0 | kJ/mol | PHPMS | Meot-Ner (Mautner), 1989 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 86.2 | J/mol*K | PHPMS | Meot-Ner (Mautner), 1989 | gas phase; M |
By formula: C8H11N = 0.5C7H9N + 0.5C9H13N
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -1. | kJ/mol | Kin | Kachurin, Matvienko, et al., 1980 | liquid phase; ALS |
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
L - 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 |
---|---|---|---|---|---|
IE (evaluated) | 6.93 ± 0.02 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 950.0 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 918.1 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
6.93 | EQ | Lias, Jackson, et al., 1985 | LBLHLM |
6.95 ± 0.05 | EQ | Mautner(Meot-Ner), Nelsen, et al., 1984 | LBLHLM |
6.9 ± 0.1 | PE | Egdell, Green, et al., 1975 | LLK |
6.95 | PE | Cowling and Johnstone, 1973 | LLK |
7.33 | CTS | Farrell and Newton, 1965 | RDSH |
7.27 | PE | Kobayashi and Nagakura, 1974 | Vertical value; LLK |
7.48 | PE | Baker, May, et al., 1968 | Vertical value; RDSH |
De-protonation reactions
C9H12N- + =
By formula: C9H12N- + H+ = C9H13N
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1614. ± 21. | kJ/mol | G+TS | Caldwell and Bartmess | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1586. ± 21. | kJ/mol | IMRB | Caldwell and Bartmess | gas phase; B |
Ion clustering 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: Michael M. Meot-Ner (Mautner) and Sharon G. Lias
Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.
Clustering reactions
By formula: C9H13N+ + C9H13N = (C9H13N+ • C9H13N)
Bond type: Charge transfer bond (positive ion)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 70.7 | kJ/mol | PHPMS | Meot-Ner (Mautner) and El-Shall, 1986 | gas phase; Entropy change calculated or estimated |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | (110.) | J/mol*K | N/A | Meot-Ner (Mautner) and El-Shall, 1986 | gas phase; Entropy change calculated or estimated |
Free energy of reaction
ΔrG° (kJ/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
34. | 331. | PHPMS | Meot-Ner (Mautner) and El-Shall, 1986 | gas phase; Entropy change calculated or estimated |
By formula: C10H10Fe+ + C9H13N = (C10H10Fe+ • C9H13N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 51.0 | kJ/mol | PHPMS | Meot-Ner (Mautner), 1989 | gas phase |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 86.2 | J/mol*K | PHPMS | Meot-Ner (Mautner), 1989 | gas phase |
IR Spectrum
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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
Gas Phase Spectrum
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Additional Data
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Owner | NIST Standard Reference Data Program Collection (C) 2018 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | Sadtler Research Labs Under US-EPA Contract |
State | gas |
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, UV/Visible spectrum, 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 | Japan AIST/NIMC Database- Spectrum MS-NW- 584 |
NIST MS number | 229670 |
UV/Visible spectrum
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, 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.
Spectrum
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Additional Data
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Source | Bol'shakov, et al., 1969 |
---|---|
Owner | INEP CP RAS, NIST OSRD Collection (C) 2007 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
Origin | INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS |
Source reference | RAS UV No. 20179 |
Instrument | SF-4 |
Boiling point | 211 |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, 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]
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]
Broxton, Deady, et al., 1970
Broxton, T.J.; Deady, L.W.; Katritzky, A.R.; Liu, A.; Topsom, R.D.,
Infrared Intensities as a Quantitative Measure of Intermolecular Inter- actions XII. π-Distortions in teh Ground States of Some p-Alkylbenzenes,
J. Am. Chem. Soc., 1970, 92, 6845. [all data]
Perkin, 1896
Perkin, W.H.,
LXIX. On Magnetic Rotatory Power, especially of Aromatic Compounds,
J. Chem. Soc., 1896, 69, 1025-1257. [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]
Meot-Ner (Mautner) and El-Shall, 1986
Meot-Ner (Mautner), M.; El-Shall, M.S.,
Ionic Charge Transfer Complexes. 1. Cationic Complexes with Delocalized and Partially Localized pi Systems,
J. Am. Chem. Soc., 1986, 108, 15, 4386, https://doi.org/10.1021/ja00275a026
. [all data]
Caldwell and Bartmess
Caldwell, G.; Bartmess, J.E.,
, Unpublished results. [all data]
Meot-Ner (Mautner), 1989
Meot-Ner (Mautner), M.,
Ion DChemistry of Ferrocene. Thermochemistry of Ionization and Protonation and Solvent Clustering. Slow and Entropy - Driven Proton - Transfer Kinetics,
J. Am. Chem. Soc., 1989, 111, 8, 2830, https://doi.org/10.1021/ja00190a014
. [all data]
Kachurin, Matvienko, et al., 1980
Kachurin, O.I.; Matvienko, N.M.; Chekhuta, V.G.,
N-Methylated p-toluidines,
Russ. Chem. Rev., 1980, 46, 64-67. [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]
Egdell, Green, et al., 1975
Egdell, R.; Green, J.C.; Rao, C.N.R.,
Photoelectron spectra of substituted benzenes,
Chem. Phys. Lett., 1975, 33, 600. [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]
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]
Bol'shakov, et al., 1969
Bol'shakov, G.F., et al.,
Ultraviolet spectra of heteroorganic compounds, 1969, 167. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, References
- Symbols used in this document:
IE (evaluated) Recommended ionization energy T Temperature 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 ΔrS° Entropy of reaction at standard conditions 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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