Dimethylamine

• Formula: C₂H₇N
• Molecular weight: 45.0837
• IUPAC Standard InChI: InChI=1S/C2H7N/c1-3-2/h3H,1-2H3 Copy

  
• IUPAC Standard InChIKey: ROSDSFDQCJNGOL-UHFFFAOYSA-N Copy
• CAS Registry Number: 124-40-3
• 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: Methanamine, N-methyl-; (CH3)2NH; N-Methylmethanamine; Rcra waste number U092; UN 1032; N,N-Dimethylamine; NSC 8650
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Gas phase ion energetics data
  • Ion clustering data
  • References
  • Notes
• Other data available:
  • Phase change data
  • Reaction thermochemistry data
  • Henry's Law data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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Gas 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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.

Condensed phase thermochemistry data

Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, Ion clustering 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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Constant pressure heat capacity of liquid

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Ion clustering 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
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

View reactions leading to C₂H₇N⁺ (ion structure unspecified)

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

C₂H₆N^- +  =

By formula: C₂H₆N^- + H⁺ = C₂H₇N

Ion clustering data

Go To: Top, Gas phase thermochemistry data, Condensed 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 as indicated in comments:
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
RCD - Robert C. Dunbar

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

C₂H₈N⁺ +  = (C₂H₈N⁺ • )

By formula: C₂H₈N⁺ + C₂H₇N = (C₂H₈N⁺ • C₂H₇N)

(C₂H₈N⁺ • ) +  = (C₂H₈N⁺ • 2)

By formula: (C₂H₈N⁺ • C₂H₇N) + C₂H₇N = (C₂H₈N⁺ • 2C₂H₇N)

(C₂H₈N⁺ • 2) +  = (C₂H₈N⁺ • 3)

By formula: (C₂H₈N⁺ • 2C₂H₇N) + C₂H₇N = (C₂H₈N⁺ • 3C₂H₇N)

(C₂H₈N⁺ • 3) +  = (C₂H₈N⁺ • 4)

By formula: (C₂H₈N⁺ • 3C₂H₇N) + C₂H₇N = (C₂H₈N⁺ • 4C₂H₇N)

(C₂H₈N⁺ • 4) +  = (C₂H₈N⁺ • 5)

By formula: (C₂H₈N⁺ • 4C₂H₇N) + C₂H₇N = (C₂H₈N⁺ • 5C₂H₇N)

C₃H₉Si⁺ +  = (C₃H₉Si⁺ • )

By formula: C₃H₉Si⁺ + C₂H₇N = (C₃H₉Si⁺ • C₂H₇N)

C₃H₉Sn⁺ +  = (C₃H₉Sn⁺ • )

By formula: C₃H₉Sn⁺ + C₂H₇N = (C₃H₉Sn⁺ • C₂H₇N)

Free energy of reaction

C₃H₁₀N⁺ +  = (C₃H₁₀N⁺ • )

By formula: C₃H₁₀N⁺ + C₂H₇N = (C₃H₁₀N⁺ • C₂H₇N)

 +  = ( • )

By formula: K⁺ + C₂H₇N = (K⁺ • C₂H₇N)

 +  = ( • )

By formula: Li⁺ + C₂H₇N = (Li⁺ • C₂H₇N)

 +  = ( • )

By formula: Na⁺ + C₂H₇N = (Na⁺ • C₂H₇N)

Free energy of reaction

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Gas phase ion energetics data, Ion clustering data, Notes

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

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]

Lemoult, 1907
Lemoult, M.P., Recherches theoriques et experimentales sur les chaleurs de combustion et de formation des composes organiques, Ann. Chim. Phys., 1907, 12, 395-432. [all data]

Muller, 1910
Muller, J.-A., Sur les chaleurs de combustion et les poids specifiques des methylamines, Ann. Chim. Phys., 1910, 20, 116-130. [all data]

Aston, Eidinoff, et al., 1939
Aston, J.G.; Eidinoff, M.L.; Forster, W.S., The heat capacity and entropy, heats of fusion and vaporization and the vapor pressure of dimethylamine, J. Am. Chem. Soc., 1939, 61, 1539-1543. [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, Webb, et al., 1980
Aue, D.H.; Webb, H.M.; Davidson, W.R.; Vidal, M.; Bowers, M.T.; Goldwhite, H.; Vertal, L.E.; Douglas, J.E.; Kollman, P.A.; Kenyon, G.L., Proton affinities photoelectron spectra of three-membered-ring J. Heterocycl. Chem., J. Am. Chem. Soc., 1980, 102, 5151. [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]

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]

Cullen, Frost, et al., 1972
Cullen, W.R.; Frost, D.C.; Leeder, W.R., The ultraviolet and photoelectron spectra of some unsaturated fluorocarbon derivatives, J. Fluorine Chem., 1972, 1, 227. [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]

Al-Joboury and Turner, 1964
Al-Joboury, M.I.; Turner, D.W., Molecular photoelectron spectroscopy. Part II. A summary of ionization potentials, J. Chem. Soc., 1964, 4434. [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]

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]

Gibbins, Lappert, et al., 1975
Gibbins, S.G.; Lappert, M.F.; Pedley, J.B.; Sharp, G.J., Bonding studies of transition-metal complexes. Part II. Helium-I photoelectron spectra of homoleptic d⁰, d¹, and d¹⁰ tetrakis(dialkylamides) of transition group 4B metals tungsten hexakis(dimethylamide), J. Chem. Soc. Dalton Trans., 1975, 72. [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]

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]

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]

Gallegos and Kiser, 1962
Gallegos, E.J.; Kiser, R.W., Electron impact spectroscopy of the four- and five-membered, saturated heterocyclic compounds containing nitrogen, oxygen and sulfur, J. Phys. Chem., 1962, 66, 136. [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]

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]

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]

Haney and Franklin, 1969
Haney, M.A.; Franklin, J.L., Heats of formation of H₃O⁺, H₃S⁺, and NH₄⁺ by electron impact, J. Chem. Phys., 1969, 50, 2028. [all data]

Radisic, Xu, et al., 2002
Radisic, D.; Xu, S.J.; Bowen, K.H., Photoelectron spectroscopy of the anions, CH3NH- and (CH3)(2)N- and the anion complexes, H-(CH3NH2) and (CH3)(2)N-[(CH3)(2)NH), Chem. Phys. Lett., 2002, 354, 1-2, 9-13, https://doi.org/10.1016/S0009-2614(01)01470-1 . [all data]

McMillen and Golden, 1982
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MacKay, Hemsworth, et al., 1976
MacKay, G.J.; Hemsworth, R.S.; Bohme, D.K., Absolute gas-phase acidities of CH₃NH₂, C₂H₅NH₂, (CH₃)₂NH, and (CH₃)₃N, Can. J. Chem., 1976, 54, 1624. [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]

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]

Li and Stone, 1990
Li, X.; Stone, A.J., Gas-Phase (CH3)3Si+ Affinities of Alkylamines and Proton Affinities of Trimethylsilyl Alkylamines, Int. J. Mass Spectrom. Ion Proc., 1990, 101, 2-3, 149, https://doi.org/10.1016/0168-1176(90)87008-5 . [all data]

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Wojtyniak, A.C.M.; Stone, A.J., A High-Pressure Mass Spectrometric Study of the Bonding of Trimethylsilylium to Oxygen and Aromatic Bases, Can. J. Chem., 1986, 74, 59. [all data]

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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]

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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]

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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]

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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]

Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Gas phase ion energetics data, Ion clustering data, References

• Symbols used in this document:
  

  AE	Appearance energy
  Cp,liquid	Constant pressure heat capacity of liquid
  IE (evaluated)	Recommended ionization energy
  S°liquid	Entropy of liquid at standard conditions
  T	Temperature
  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

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