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:
  • Phase change data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • Henry's Law data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
• Data at other public NIST sites:
  • Computational Chemistry Comparison and Benchmark Database
  • Gas Phase Kinetics Database
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Phase change 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:
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.
DH - Eugene S. Domalski and Elizabeth D. Hearing
AC - William E. Acree, Jr., James S. Chickos

Enthalpy of vaporization

Enthalpy of vaporization

Δ_vapH = A exp(-βT_r) (1 − T_r)^β
    Δ_vapH = Enthalpy of vaporization (at saturation pressure) (kJ/mol)
    T_r = reduced temperature (T / T_c)

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Entropy of vaporization

Antoine Equation Parameters

log₁₀(P) = A − (B / (T + C))
    P = vapor pressure (bar)
    T = temperature (K)

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Enthalpy of fusion

Entropy of fusion

Gas phase ion energetics data

Go To: Top, Phase change 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, 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.

Roberts, Emeleus, et al., 1939
Roberts, E.R.; Emeleus, H.J.; Briscoe, H.V.A., Preparation and Prop. of Ethyldideuteramine and Dimethyldeuteramine, J. Chem. Soc., 1939, 1939, 41. [all data]

Simon and Huter, 1935
Simon, A.; Huter, J., Vapor Pressure Curves, Melting Point and Chemical Constants of Dimethyl, Trimethyl- and Isobutylamines, Z. Elektrochem., 1935, 41, 28. [all data]

Simon and Huter, 1935, 2
Simon, A.; Huter, J., Z. Elektrochem., 1935, 41, 294. [all data]

Wiberg and Sutterlin, 1935
Wiberg, E.; Sutterlin, W., The Vapor Pressures and Melting Points of Dimethyl- and Trimethylamine Trimethylamines, Z. Elektrochem., 1935, 41, 151. [all data]

Timmermans and Mattaar, 1921
Timmermans, J.; Mattaar, J.F., Freezing points of orgainic substances VI. New experimental determinations., Bull. Soc. Chim. Belg., 1921, 30, 213. [all data]

Aston, Sagenkahn, et al., 1944
Aston, J.G.; Sagenkahn, M.L.; Szasz, G.J.; Moessen, G.W.; Zuhr, H.F., The Heat Capacity and Entropy, Heats of Fusion and Vaporization and the Vapor Pressure of Trimethylamine. The Entropy From Spectroscopic and Molecular Data, J. Am. Chem. Soc., 1944, 66, 1171. [all data]

Majer and Svoboda, 1985
Majer, V.; Svoboda, V., Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]

Kay and Young, 1974
Kay, W.B.; Young, C.L., Int. DATA Ser., Sel. Data Mixtures, Ser. A, 1974, No. 2, 154. [all data]

Day and Felsing, 1950
Day, H.O.; Felsing, W.A., Some Vapor Pressures and the Critical COnstants of Trimethylamine, J. Am. Chem. Soc., 1950, 72, 1698. [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]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

Aston, Sagenkahn, et al., 1944, 2
Aston, J.G.; Sagenkahn, M.L.; Szasa, G.J.; Moessen, G.W.; Zuhr, H.F., The heat capacity and entropy, heats of fusion and vaporization and the vapor pressure of trimethylamine. The entropy from spectroscopic and molecular data, J. Am. Chem. Soc., 1944, 66, 1171-1177. [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]

Day and Felsing, 1950, 2
Day, H.O.; Felsing, W.A., Some Vapor Pressures and the Critical Constants of Trimethylamine, J. Am. Chem. Soc., 1950, 72, 4, 1698-1699, https://doi.org/10.1021/ja01160a077 . [all data]

Swift and Hochanadel, 1945
Swift, Elijah; Hochanadel, Helen Phillips, The Vapor Pressure of Trimethylamine from 0 to 40°, J. Am. Chem. Soc., 1945, 67, 5, 880-881, https://doi.org/10.1021/ja01221a508 . [all data]

Aston, Sagenkahn, et al., 1944, 3
Aston, J.G.; Sagenkahn, M.L.; Szasz, G.J.; Moessen, G.W.; Zuhr, H.F., The heat capacity and entropy, heats of fusion and vaporization and the vapor pressure of trimethylamine. The entropy from spectroscopic and molecular data, J. Am. Chem. Soc., 1944, 66, 1171-11. [all data]

Thompson and Linnett, 1936
Thompson, H.W.; Linnett, J.W., The vapour pressures and association of some metallic and non-metallic alkyls, Trans. Faraday Soc., 1936, 32, 681-685. [all data]

Acree, 1991
Acree, William E., Thermodynamic properties of organic compounds: enthalpy of fusion and melting point temperature compilation, Thermochimica Acta, 1991, 189, 1, 37-56, https://doi.org/10.1016/0040-6031(91)87098-H . [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]

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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
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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]

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]

Notes

Go To: Top, Phase change data, Gas phase ion energetics data, References

• Symbols used in this document:
  

  AE	Appearance energy
  IE (evaluated)	Recommended ionization energy
  Pc	Critical pressure
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  Vc	Critical volume
  ΔfusH	Enthalpy of fusion
  ΔfusS	Entropy of fusion
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions
  ΔvapS	Entropy of vaporization

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