Methylamine

• Formula: CH₅N
• Molecular weight: 31.0571
• IUPAC Standard InChI: InChI=1S/CH5N/c1-2/h2H2,1H3 Copy

  
• IUPAC Standard InChIKey: BAVYZALUXZFZLV-UHFFFAOYSA-N Copy
• CAS Registry Number: 74-89-5
• 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.
• Isotopologues:
  • methan-d3-amine
• Other names: Methanamine; Aminomethane; Carbinamine; Monomethylamine; CH3NH2; Mercurialin; Methylaminen; Metilamine; Metyloamina; UN 1061; MMA
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Vibrational and/or electronic energy levels
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Phase change data
  • Henry's Law data
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
• Options:
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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 by: Donald R. Burgess, Jr.

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
RCD - Robert C. Dunbar
B - John E. Bartmess
MS - José A. Martinho Simões
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⁺ + CH₅N = (Li⁺ • CH₅N)

C₃H₉Sn⁺ +  = (C₃H₉Sn⁺ • )

By formula: C₃H₉Sn⁺ + CH₅N = (C₃H₉Sn⁺ • CH₅N)

Free energy of reaction

 +  = ( • )

By formula: K⁺ + CH₅N = (K⁺ • CH₅N)

 +  = ( • )

By formula: Na⁺ + CH₅N = (Na⁺ • CH₅N)

Free energy of reaction

(CH₆N⁺ • 2) +  = (CH₆N⁺ • 3)

By formula: (CH₆N⁺ • 2CH₅N) + CH₅N = (CH₆N⁺ • 3CH₅N)

(CH₆N⁺ • ) +  = (CH₆N⁺ • 2)

By formula: (CH₆N⁺ • CH₅N) + CH₅N = (CH₆N⁺ • 2CH₅N)

CH₄N^- +  =

By formula: CH₄N^- + H⁺ = CH₅N

C₃H₉Si⁺ +  = (C₃H₉Si⁺ • )

By formula: C₃H₉Si⁺ + CH₅N = (C₃H₉Si⁺ • CH₅N)

CH₆N⁺ +  = (CH₆N⁺ • )

By formula: CH₆N⁺ + CH₅N = (CH₆N⁺ • CH₅N)

C₆H₁₂NO₃⁺ +  = (C₆H₁₂NO₃⁺ • )

By formula: C₆H₁₂NO₃⁺ + CH₅N = (C₆H₁₂NO₃⁺ • CH₅N)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

( • ) +  = ( • 2)

By formula: (Pb⁺ • CH₅N) + CH₅N = (Pb⁺ • 2CH₅N)

 +  = ( • )

By formula: Pb⁺ + CH₅N = (Pb⁺ • CH₅N)

(CH₆N⁺ • 3) +  = (CH₆N⁺ • 4)

By formula: (CH₆N⁺ • 3CH₅N) + CH₅N = (CH₆N⁺ • 4CH₅N)

C₂H₈N⁺ +  = (C₂H₈N⁺ • )

By formula: C₂H₈N⁺ + CH₅N = (C₂H₈N⁺ • CH₅N)

C₅H₁₁BrMg (solution) +  (solution) = CH₄BrMgN (solution) +  (solution)

By formula: C₅H₁₁BrMg (solution) + CH₅N (solution) = CH₄BrMgN (solution) + C₅H₁₂ (solution)

2 =  + 

By formula: 2CH₅N = C₂H₇N + H₃N

2 =  + 

By formula: 2C₂H₇N = CH₅N + C₃H₉N

Gas phase ion energetics 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 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

View reactions leading to CH₅N⁺ (ion structure unspecified)

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

CH₄N^- +  =

By formula: CH₄N^- + H⁺ = CH₅N

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

CH₆N⁺ +  = (CH₆N⁺ • )

By formula: CH₆N⁺ + CH₅N = (CH₆N⁺ • CH₅N)

(CH₆N⁺ • ) +  = (CH₆N⁺ • 2)

By formula: (CH₆N⁺ • CH₅N) + CH₅N = (CH₆N⁺ • 2CH₅N)

(CH₆N⁺ • 2) +  = (CH₆N⁺ • 3)

By formula: (CH₆N⁺ • 2CH₅N) + CH₅N = (CH₆N⁺ • 3CH₅N)

(CH₆N⁺ • 3) +  = (CH₆N⁺ • 4)

By formula: (CH₆N⁺ • 3CH₅N) + CH₅N = (CH₆N⁺ • 4CH₅N)

C₂H₈N⁺ +  = (C₂H₈N⁺ • )

By formula: C₂H₈N⁺ + CH₅N = (C₂H₈N⁺ • CH₅N)

C₃H₉Si⁺ +  = (C₃H₉Si⁺ • )

By formula: C₃H₉Si⁺ + CH₅N = (C₃H₉Si⁺ • CH₅N)

C₃H₉Sn⁺ +  = (C₃H₉Sn⁺ • )

By formula: C₃H₉Sn⁺ + CH₅N = (C₃H₉Sn⁺ • CH₅N)

Free energy of reaction

C₆H₁₂NO₃⁺ +  = (C₆H₁₂NO₃⁺ • )

By formula: C₆H₁₂NO₃⁺ + CH₅N = (C₆H₁₂NO₃⁺ • CH₅N)

Bond type: Hydrogen bonds with polydentate bonding in positive ions

 +  = ( • )

By formula: K⁺ + CH₅N = (K⁺ • CH₅N)

 +  = ( • )

By formula: Li⁺ + CH₅N = (Li⁺ • CH₅N)

 +  = ( • )

By formula: Na⁺ + CH₅N = (Na⁺ • CH₅N)

Free energy of reaction

 +  = ( • )

By formula: Pb⁺ + CH₅N = (Pb⁺ • CH₅N)

( • ) +  = ( • 2)

By formula: (Pb⁺ • CH₅N) + CH₅N = (Pb⁺ • 2CH₅N)

IR Spectrum

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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

Gas Phase Spectrum

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Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.

Additional Data

Mass spectrum (electron ionization)

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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

Spectrum

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Additional Data

UV/Visible spectrum

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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: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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Additional Data

Vibrational and/or electronic energy levels

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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: Takehiko Shimanouchi

Symmetry:   C_s     Symmetry Number σ = 1

Source: Shimanouchi, 1972

Notes

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

View large format table.

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

View large format table.

References

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Vibrational and/or electronic energy levels, Gas Chromatography, Notes

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

Aston, Siller, et al., 1937
Aston, J.G.; Siller, C.W.; Messerly, G.H., Heat capacities and entropies of organic compounds. III. Methylamine from 11.5°K. to the boiling point. Heat of vaporization and vapor pressure. The entropy from molecular data, J. Am. Chem. Soc., 1937, 59, 1743-17. [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]

Woodin and Beauchamp, 1978
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Dzidic and Kebarle, 1970
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Stone and Splinter, 1984
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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]

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]

Hoyau, Norrman, et al., 1999
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Guo and Castleman, 1990
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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]

Meot-Ner (Mautner), 1992
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Holland and Castleman, 1982
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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]

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
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Wojtyniak and Stone, 1986
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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]

Meot-Ner, 1984
Meot-Ner, (Mautner), The Ionic Hydrogen Bond. 4. Intramolecular and Multiple Bonds. Proton Affinities, Hydration and Complexes of Amides and Amino Acid Derivatives, J. Am. Chem. Soc., 1984, 106, 2, 278, https://doi.org/10.1021/ja00314a003 . [all data]

Holm, 1983
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Issoire and Long, 1960
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Hunter and Lias, 1998
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Aue and Bowers, 1979
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Baldwin, Loudon, et al., 1977
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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
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Ogata, Onizuka, et al., 1972
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Cornford, Frost, et al., 1971
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Zenkevich and Chupalov, 1996
Zenkevich, I.G.; Chupalov, A.A., New Possibilities of Chromato Mass Pectrometric Identification of Organic Compounds Using Increments of Gas Chromatographic Retention Indices of Molecular Structural Fragments, Zh. Org. Khim. (Rus.), 1996, 32, 5, 656-666. [all data]

Notes

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Vibrational and/or electronic energy levels, Gas Chromatography, References

• Symbols used in this document:
  

  AE	Appearance energy
  IE (evaluated)	Recommended ionization energy
  T	Temperature
  ΔfH°gas	Enthalpy of formation of gas 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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