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:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • Henry's Law data
  • References
  • Notes
• Other data available:
  • Phase change data
  • Gas phase ion energetics 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 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, Condensed phase thermochemistry data, Reaction thermochemistry data, Henry's Law 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
DRB - Donald R. Burgess, Jr.

Condensed phase thermochemistry data

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Henry's Law 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

Reaction thermochemistry data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Henry's Law 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

Henry's Law data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, 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 compiled by: Rolf Sander

Henry's Law constant (water solution)

k_H(T) = k°_H exp(d(ln(k_H))/d(1/T) ((1/T) - 1/(298.15 K)))
k°_H = Henry's law constant for solubility in water at 298.15 K (mol/(kg*bar))
d(ln(k_H))/d(1/T) = Temperature dependence constant (K)

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Henry's Law 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, Sagenkahn, et al., 1944
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]

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]

Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Henry's Law data, References

• Symbols used in this document:
  

  Cp,liquid	Constant pressure heat capacity of liquid
  S°liquid	Entropy of liquid at standard conditions
  T	Temperature
  d(ln(kH))/d(1/T)	Temperature dependence parameter for Henry's Law constant
  k°H	Henry's Law constant at 298.15K
  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
• 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.