Benzenamine, N,N,4-trimethyl-

• Formula: C₉H₁₃N
• Molecular weight: 135.2062
• IUPAC Standard InChI: InChI=1S/C9H13N/c1-8-4-6-9(7-5-8)10(2)3/h4-7H,1-3H3 Copy

  
• IUPAC Standard InChIKey: GYVGXEWAOAAJEU-UHFFFAOYSA-N Copy
• 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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• Information on this page:
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • Mass spectrum (electron ionization)
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Ion clustering data
  • IR Spectrum
  • UV/Visible spectrum
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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

C₉H₁₃N⁺ +  = (C₉H₁₃N⁺ • )

By formula: C₉H₁₃N⁺ + C₉H₁₃N = (C₉H₁₃N⁺ • C₉H₁₃N)

Bond type: Charge transfer bond (positive ion)

Free energy of reaction

C₉H₁₂N^- +  =

By formula: C₉H₁₂N^- + H⁺ = C₉H₁₃N

C₁₀H₁₀Fe⁺ +  = (C₁₀H₁₀Fe⁺ • )

By formula: C₁₀H₁₀Fe⁺ + C₉H₁₃N = (C₁₀H₁₀Fe⁺ • C₉H₁₃N)

= 0.5 + 0.5

By formula: C₈H₁₁N = 0.5C₇H₉N + 0.5C₉H₁₃N

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

Ionization energy determinations

De-protonation reactions

C₉H₁₂N^- +  =

By formula: C₉H₁₂N^- + H⁺ = C₉H₁₃N

Mass spectrum (electron ionization)

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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

Spectrum

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Additional Data

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

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Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Normal alkane RI, non-polar column, custom temperature program

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References

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

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]

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]

Still, Evans, et al., 1972
Still, R.H.; Evans, M.B.; Whitehead, A., Thermal Degradation of Polymers. V. Vacuum Pyrolysis of Poly (p-N,N-dimethylaminostyrene) . The Products Volatile at Pyrolysis Temperature, Liquid or Gaseous at Room Temperature, J. Appl. Polym. Sci., 1972, 16, 12, 3207-3221, https://doi.org/10.1002/app.1972.070161213 . [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]

Zenkevich, 2001
Zenkevich, I.G., Comparative Characterization of Conditions for Unambuguous Chromatographic Identification of Organic Compounds, Zh. Anal. Khim., 2001, 56, 9, 915-924. [all data]

Notes

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, References

• Symbols used in this document:
  

  IE (evaluated)	Recommended ionization energy
  T	Temperature
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔrS°	Entropy of reaction at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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