Methylamine, N,N-dimethyl-

• Formula: C₃H₉N
• Molecular weight: 59.1103
• IUPAC Standard InChI: InChI=1S/C3H9N/c1-4(2)3/h1-3H3 Copy

  
• IUPAC Standard InChIKey: GETQZCLCWQTVFV-UHFFFAOYSA-N Copy
• CAS Registry Number: 75-50-3
• 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: Trimethylamine; Methanamine, N,N-dimethyl-; TMA; UN 1083; UN 1297
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Henry's Law data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
• Options:
  • Switch to SI 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.

Reaction thermochemistry data

Go To: Top, 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 as indicated in comments:
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
B - John E. Bartmess
RCD - Robert C. Dunbar
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: Li⁺ + C₃H₉N = (Li⁺ • C₃H₉N)

C₃H₁₀N⁺ +  = (C₃H₁₀N⁺ • )

By formula: C₃H₁₀N⁺ + C₃H₉N = (C₃H₁₀N⁺ • C₃H₉N)

C₃H₉Sn⁺ +  = (C₃H₉Sn⁺ • )

By formula: C₃H₉Sn⁺ + C₃H₉N = (C₃H₉Sn⁺ • C₃H₉N)

Free energy of reaction

(C₃H₁₀N⁺ •  • ) +  = (C₃H₁₀N⁺ • 2 • )

By formula: (C₃H₁₀N⁺ • H₂O • C₃H₉N) + H₂O = (C₃H₁₀N⁺ • 2H₂O • C₃H₉N)

Free energy of reaction

 +  = ( • )

By formula: K⁺ + C₃H₉N = (K⁺ • C₃H₉N)

C₃H₈N^- +  =

By formula: C₃H₈N^- + H⁺ = C₃H₉N

(C₃H₁₀N⁺ • ) +  = (C₃H₁₀N⁺ •  • )

By formula: (C₃H₁₀N⁺ • C₃H₉N) + CH₄O = (C₃H₁₀N⁺ • CH₄O • C₃H₉N)

Bond type: Hydrogen bonds of the type NH+-O between organics

(C₃H₁₀N⁺ • 2) +  = (C₃H₁₀N⁺ •  • 2)

By formula: (C₃H₁₀N⁺ • 2C₃H₉N) + H₂O = (C₃H₁₀N⁺ • H₂O • 2C₃H₉N)

Bond type: Hydrogen bond (positive ion to hydride)

(C₃H₁₀N⁺ •  • ) +  = (C₃H₁₀N⁺ • 2 • )

By formula: (C₃H₁₀N⁺ • CH₄O • C₃H₉N) + CH₄O = (C₃H₁₀N⁺ • 2CH₄O • C₃H₉N)

Bond type: Hydrogen bonds of the type NH+-O between organics

(C₃H₁₀N⁺ •  • ) +  = (C₃H₁₀N⁺ • 2 • )

By formula: (C₃H₁₀N⁺ • C₃H₉N • H₂O) + C₃H₉N = (C₃H₁₀N⁺ • 2C₃H₉N • H₂O)

(C₃H₁₀N⁺ • 2) +  = (C₃H₁₀N⁺ • 3)

By formula: (C₃H₁₀N⁺ • 2C₃H₉N) + C₃H₉N = (C₃H₁₀N⁺ • 3C₃H₉N)

(C₃H₁₀N⁺ • 3) +  = (C₃H₁₀N⁺ • 4)

By formula: (C₃H₁₀N⁺ • 3C₃H₉N) + C₃H₉N = (C₃H₁₀N⁺ • 4C₃H₉N)

(C₃H₁₀N⁺ • 4) +  = (C₃H₁₀N⁺ • 5)

By formula: (C₃H₁₀N⁺ • 4C₃H₉N) + C₃H₉N = (C₃H₁₀N⁺ • 5C₃H₉N)

(C₃H₁₀N⁺ • 5) +  = (C₃H₁₀N⁺ • 6)

By formula: (C₃H₁₀N⁺ • 5C₃H₉N) + C₃H₉N = (C₃H₁₀N⁺ • 6C₃H₉N)

 +  = ( • )

By formula: Na⁺ + C₃H₉N = (Na⁺ • C₃H₉N)

Free energy of reaction

(C₃H₁₀N⁺ • ) +  = (C₃H₁₀N⁺ • 2)

By formula: (C₃H₁₀N⁺ • C₃H₉N) + C₃H₉N = (C₃H₁₀N⁺ • 2C₃H₉N)

2 =  + 

By formula: 2C₂H₇N = CH₅N + C₃H₉N

Gas phase ion energetics data

Go To: Top, Reaction thermochemistry data, 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

Appearance energy determinations

De-protonation reactions

C₃H₈N^- +  =

By formula: C₃H₈N^- + H⁺ = C₃H₉N

References

Go To: Top, Reaction thermochemistry 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.

Woodin and Beauchamp, 1978
Woodin, R.L.; Beauchamp, J.L., Bonding of Li+ to Lewis Bases in the Gas Phase. Reversals in Methyl Substituent Effects for Different Reference Acids, J. Am. Chem. Soc., 1978, 100, 2, 501, https://doi.org/10.1021/ja00470a024 . [all data]

Dzidic and Kebarle, 1970
Dzidic, I.; Kebarle, P., Hydration of the Alkali Ions in the Gas Phase. Enthalpies and Entropies of Reactions M+(H2O)n-1 + H2O = M+(H2O)n, J. Phys. Chem., 1970, 74, 7, 1466, https://doi.org/10.1021/j100702a013 . [all data]

Staley and Beauchamp, 1975
Staley, R.H.; Beauchamp, J.L., Intrinsic Acid - Base Properties of Molecules. Binding Energies of Li+ to pi - and n - Donor Bases, J. Am. Chem. Soc., 1975, 97, 20, 5920, https://doi.org/10.1021/ja00853a050 . [all data]

El-Shall, Daly, et al., 1992
El-Shall, M.S.; Daly, G.M.; Gao, J.; Meot-Ner (Mautner), M.; Sieck, L.W., How Sensitive are Cluster Compositions to Energetics? A Joint Beam Expansion/ Thermochemical Study of Water - Methanol - Trimethylamine Clusters, J. Phys. Chem., 1992, 96, 2, 507, https://doi.org/10.1021/j100181a002 . [all data]

Meot-Ner (Mautner), 1992
Meot-Ner (Mautner), M., Intermolecular Forces in Organic Clusters, J. Am. Chem. Soc., 1992, 114, 9, 3312, https://doi.org/10.1021/ja00035a024 . [all data]

Wei, Tzeng, et al., 1991
Wei, S.; Tzeng, W.B.; Castleman, A.W., Structure of protonated solvation complexes - ammonia trimethylamine cluster ions and their metastable decompositions, J. Phys. Chem., 1991, 95, 2, 585, https://doi.org/10.1021/j100155a019 . [all data]

Yamdagni and Kebarle, 1973
Yamdagni, R.; Kebarle, P., Gas - Phase Basicites of Amines. Hydrogen Bonding in Proton - Bound Amine Dimers and Proton - Induced Cyclization of alpha, omega - Diamines, J. Am. Chem. Soc., 1973, 95, 11, 3504, https://doi.org/10.1021/ja00792a010 . [all data]

Stone and Splinter, 1984
Stone, J.A.; Splinter, D.E., A high-pressure mass spectrometric study of the binding of (CH₃)₃Sn⁺ to lewis bases in the gas phase, Int. J. Mass Spectrom. Ion Processes, 1984, 59, 169. [all data]

Davidson and Kebarle, 1976
Davidson, W.R.; Kebarle, P., Binding Energies and Stabilities of Potassium Ion Complexes from Studies of Gas Phase Ion Equilibria K+ + M = K+.M, J. Am. Chem. Soc., 1976, 98, 20, 6133, https://doi.org/10.1021/ja00436a011 . [all data]

Davidson and Kebarle, 1976, 2
Davidson, W.R.; Kebarle, P., Ionic Solvation by Aprotic Solvents. Gas Phase Solvation of the Alkali Ions by Acetonitrile, J. Am. Chem. Soc., 1976, 98, 20, 6125, https://doi.org/10.1021/ja00436a010 . [all data]

MacKay and Bohme, 1978
MacKay, G.I.; Bohme, D.K., Proton-Transfer Reactions in Nitromethane at 297K, Int. J. Mass Spectrom. Ion Phys., 1978, 26, 4, 327, https://doi.org/10.1016/0020-7381(78)80052-7 . [all data]

McMahon and Ohanessian, 2000
McMahon, T.B.; Ohanessian, G., An Experimental and Ab Initio Study of the Nature of the Binding in Gas-Phase Complexes of Sodium Ions, Chem. Eur. J., 2000, 6, 16, 2931, https://doi.org/10.1002/1521-3765(20000818)6:16<2931::AID-CHEM2931>3.0.CO;2-7 . [all data]

Issoire and Long, 1960
Issoire, J.; Long, C., Etude de la thermodynamique chimique de la reaction de formation des methylamines, Bull. Soc. Chim. France, 1960, 2004-2012. [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]

Aue and Bowers, 1979
Aue, D.H.; Bowers, M.T., Chapter 9. Stabilities of positive ions from equilibrium gas phase basicity measurements in Ions Chemistry,, ed. M.T. Bowers, 1979. [all data]

Baldwin, Loudon, et al., 1977
Baldwin, M.A.; Loudon, A.G.; Webb, K.S.; Cardnell, P.C., Charge location and fragmentation under electron impact. V-The ionization potentials of (methylated) phosphoramides, guanidines, formamides, acetamides, ureas and thioureas, Org. Mass Spectrom., 1977, 12, 279. [all data]

Aue, Webb, et al., 1976
Aue, D.H.; Webb, H.M.; Bowers, M.T., Quantitative proton affinities, ionization potentials, and hydrogen affinities of alkylamines, J. Am. Chem. Soc., 1976, 98, 311. [all data]

Vovna and Vilesov, 1974
Vovna, V.I.; Vilesov, F.I., Photoelectron spectra the structure of molecular orbitals of methyl amines, Opt. Spectrosc., 1974, 36, 251. [all data]

Akopyan and Loginov, 1974
Akopyan, M.E.; Loginov, Yu.V., Photoelectron spectra of trimethylamine derivatives, Opt. Spectrosc., 1974, 37, 250, In original 442. [all data]

Maier and Turner, 1973
Maier, J.P.; Turner, D.W., Steric inhibition of resonance studied by molecular photoelectron spectroscopy Part 3. Anilines, Phenols and Related Compounds, J. Chem. Soc. Faraday Trans. 2, 1973, 69, 521. [all data]

Adamchuk, Dmitriev, et al., 1972
Adamchuk, V.K.; Dmitriev, A.B.; Prudnikova, G.V.; Sorokin, L.S., Photoionization of low-volatility molecules in a Geiger counter, Opt. Spectrosc., 1972, 33, 191, In original 358. [all data]

Cornford, Frost, et al., 1971
Cornford, A.B.; Frost, D.C.; Herring, F.G.; McDowell, C.A., Electronic levels of methyl amines by photoelectron spectroscopy and an i.n.d.o. calculation, Can. J. Chem., 1971, 49, 1135. [all data]

Watanabe and Mottl, 1957
Watanabe, K.; Mottl, J.R., Ionization potentials of ammonia and some amines, J. Chem. Phys., 1957, 26, 1773. [all data]

Elbel, Dieck, et al., 1982
Elbel, S.; Dieck, H.T.; Demuth, R., Photoelectron sSpectra of group V compounds. IX. The relative perfluoroalkyl substituent effect, J. Fluorine Chem., 1982, 19, 349. [all data]

Kobayashi, 1978
Kobayashi, T., A simple general tendency in photoelectron angular distributions of some monosubstituted benzenes, Phys. Lett., 1978, 69, 105. [all data]

Daamen and Oskam, 1978
Daamen, H.; Oskam, A., Bonding properties of some monosubstituted chromium and tungsten hexacarbonyls M(CO)₅L (L=amine, substituted pyridine, azine), Inorg. Chim. Acta, 1978, 26, 81. [all data]

Kimura and Osafune, 1975
Kimura, K.; Osafune, K., Sum rule consideration on valence orbital ionization energies in methyl amines, Mol. Phys., 1975, 29, 1073. [all data]

Aue, Webb, et al., 1975
Aue, D.H.; Webb, H.M.; Bowers, M.T., Proton affinities, ionization potentials, and hydrogen affinities of nitrogen and oxygen bases. Hybridization effects, J. Am. Chem. Soc., 1975, 97, 4137. [all data]

Elbel, Bergmann, et al., 1974
Elbel, S.; Bergmann, H.; EnBlin, W., Photoelectron spectra of the trimethyl compounds of the Group V elements, J. Chem. Soc. Faraday Trans. 2., 1974, 70, 555. [all data]

Schafer and Schweig, 1972
Schafer, W.; Schweig, A., Zur Konjugation in aromatischen Aminen und Phosphanen, Angew. Chem., 1972, 84, 898. [all data]

Lloyd and Lynaugh, 1972
Lloyd, D.R.; Lynaugh, N., Photoelectron studies of boron compounds. Part 3. Complexes of borane with Lewis bases, J. Chem. Soc. Faraday Trans. 2, 1972, 68, 947. [all data]

Cradock, Ebsworth, et al., 1972
Cradock, S.; Ebsworth, E.A.V.; Savage, W.J.; Whiteford, R.A., Photoelectron spectra of some methyl, silyl and germyl amines, phosphines and arsines, J. Chem. Soc. Faraday Trans. 2, 1972, 68, 934. [all data]

SenSharma and Franklin, 1973
SenSharma, D.K.; Franklin, J.L., Heat of formation of free radicals by mass spectrometry, J. Am. Chem. Soc., 1973, 95, 6562. [all data]

Gowenlock, Jones, et al., 1961
Gowenlock, B.G.; Jones, P.P.; Majer, J.R., Bond dissociation energies in some molecules containing alkyl substituted CH₃, NH₂, and OH, J. Chem. Soc. Faraday Trans., 1961, 57, 23. [all data]

Loudon and Webb, 1977
Loudon, A.G.; Webb, K.S., The nature of the [C₂H₆N]⁺ and [CH₄N]⁺ ions formed by electron impact on methylated formamides, acetamides, ureas, thioureas and hexamethylphosphoramide, Org. Mass Spectrom., 1977, 12, 283. [all data]

Solka and Russell, 1974
Solka, B.H.; Russell, M.E., Energetics of formation of some structural isomers of gaseous C₂H₅O⁺ C₂H₆N⁺ ions, J. Phys. Chem., 1974, 78, 1268. [all data]

Fisher and Henderson, 1967
Fisher, I.P.; Henderson, E., Mass spectrometry of free radicals, J. Chem. Soc. Faraday Trans., 1967, 63, 1342. [all data]

Lossing, Lam, et al., 1981
Lossing, F.P.; Lam, Y.-T.; Maccoll, A., Gas phase heats of formation of alkyl immonium ions, Can. J. Chem., 1981, 59, 2228. [all data]

Taft, Martin, et al., 1965
Taft, R.W.; Martin, R.H.; Lampe, F.W., Stabilization energies of substituted methyl cations. The effect of strong demand on the resonance order, J. Am. Chem. Soc., 1965, 87, 2490. [all data]

Notes

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, References

• Symbols used in this document:
  

  AE	Appearance energy
  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
• 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.