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
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Gas phase ion energetics data
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
• Options:
  • Switch to calorie-based units

Data at NIST subscription sites:

• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.

Gas phase thermochemistry data

Go To: Top, Gas phase ion energetics data, Gas Chromatography, 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

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, Gas Chromatography, 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
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

Gas Chromatography

Go To: Top, Gas phase thermochemistry 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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Kovats' RI, polar column, isothermal

View large format table.

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

View large format table.

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

View large format table.

References

Go To: Top, Gas phase 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]

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]

Caldwell and Bartmess
Caldwell, G.; Bartmess, J.E., , Unpublished results. [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, Gas phase thermochemistry data, Gas phase ion energetics data, Gas Chromatography, References

• Symbols used in this document:
  

  IE (evaluated)	Recommended ionization energy
  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
• The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
• Customer support for NIST Standard Reference Data products.