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
  • Phase change data
  • Reaction thermochemistry data
  • Ion clustering data
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Henry's Law data
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
• 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

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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
DH - Eugene S. Domalski and Elizabeth D. Hearing

Constant pressure heat capacity of liquid

Phase change 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:
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

Entropy of vaporization

Antoine Equation Parameters

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

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Enthalpy of fusion

Entropy of fusion

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
RCD - Robert C. Dunbar

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

C₃H₉Sn⁺ +  = (C₃H₉Sn⁺ • )

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

Free energy of reaction

 +  = ( • )

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

C₂H₆N^- +  =

By formula: C₂H₆N^- + H⁺ = C₂H₇N

C₃H₉Si⁺ +  = (C₃H₉Si⁺ • )

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

C₂H₈N⁺ +  = (C₂H₈N⁺ • )

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

(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)

(C₂H₈N⁺ • ) +  = (C₂H₈N⁺ • 2)

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

C₃H₁₀N⁺ +  = (C₃H₁₀N⁺ • )

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

 +  = ( • )

By formula: K⁺ + C₂H₇N = (K⁺ • C₂H₇N)

=  + 

By formula: C₃H₉NO = C₂H₇N + CH₂O

 +  = ( • )

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

Free energy of reaction

=  + 

By formula: C₉H₁₁ClN₂O = C₇H₄ClNO + C₂H₇N

=  + 

By formula: C₁₀H₁₄N₂O = C₂H₇N + C₈H₇NO

=  + 

By formula: C₁₀H₁₄N₂O₂ = C₂H₇N + C₈H₇NO₂

=  + 

By formula: C₉H₁₁ClN₂O = C₂H₇N + C₇H₄ClNO

=  + 

By formula: C₁₀H₁₁F₃N₂O = C₂H₇N + C₈H₄F₃NO

=  + 

By formula: C₉H₁₀Cl₂N₂O = C₇H₃Cl₂NO + C₂H₇N

 + 2 =  + 

By formula: C₃H₅Cl + 2C₂H₇N = C₅H₁₁N + C₂H₈ClN

=  + 

By formula: C₁₀H₁₄N₂O = C₂H₇N + C₈H₇NO

2 +  =  + 

By formula: 2C₂H₇N + CH₂O = C₅H₁₄N₂ + H₂O

=  + 

By formula: C₉H₁₂N₂O = C₇H₅NO + C₂H₇N

 +  =

By formula: C₂H₇N + CH₂O = C₃H₉NO

2 =  + 

By formula: 2CH₅N = C₂H₇N + H₃N

Ion clustering 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
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

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, non-polar column, isothermal

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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, temperature ramp

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

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References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Ion clustering data, Gas Chromatography, 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]

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]

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

Aston, Eidinoff, et al., 1939, 2
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. [all data]

Kay and Young, 1974
Kay, W.B.; Young, C.L., Int. DATA Ser., Sel. Data Mixtures, Ser. A, 1974, No. 2, 156. [all data]

Berthoud, 1917
Berthoud, A., Determination of Critical Temperatures and Pressures of Amines and Alkyl Chlorides, J. Chim. Phys. Phys.-Chim. Biol., 1917, 15, 3. [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]

Aston, Eidinoff, et al., 1939, 3
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, 1539-15. [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]

Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E., The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [all data]

Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [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]

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]

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
McMillen, D.F.; Golden, D.M., Hydrocarbon bond dissociation energies, Ann. Rev. Phys. Chem., 1982, 33, 493. [all data]

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]

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]

Wojtyniak and Stone, 1986
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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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]

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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Rogers, F.E.; Rapiejko, R.J., Thermochemistry of carbonyl addition reactions. II. Enthalpy of addition of dimethylamine to formaldehyde, J. Phys. Chem., 1974, 78, 599-603. [all data]

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Golovnya, R.V.; Zhuravleva, N.L.; Svetlova, N.I.; Grigor'eva, D.N., Gas-chromatographic separation of secondary normal alphatic amines, J. Anal. Chem. USSR (Engl. Transl.), 1980, 35, 10, 1280-1285. [all data]

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Golovnya, R.V.; Zhuravleva, I.L., Gas Chromatographic Method of Identification of n-Aliphatic Amines Through the Use of Donor-Acceptor Interaction with Phosphate, Chromatographia, 1973, 6, 12, 508-513, https://doi.org/10.1007/BF02269131 . [all data]

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Zenkevich, I.G., Experimentally measured retention indices., 2005. [all data]

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Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Ion clustering data, Gas Chromatography, References

• Symbols used in this document:
  

  Cp,liquid	Constant pressure heat capacity of liquid
  Pc	Critical pressure
  S°liquid	Entropy of liquid at standard conditions
  T	Temperature
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  Ttriple	Triple point 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
  ΔfusH	Enthalpy of fusion
  ΔfusS	Entropy of fusion
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔrS°	Entropy of reaction at standard conditions
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions
  ΔvapS	Entropy of vaporization

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