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
  • 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)
  • UV/Visible spectrum
  • Vibrational and/or electronic energy levels
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

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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.

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
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

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

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)

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.

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]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [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, Siller, et al., 1937, 2
Aston, J.G.; Siller, C.W.; Messerly, G.H., Heat capacities and entropies of organic compounds. III. Methylamine from 12K to the boiling point. Heat of vaporization and vapor pressure. The entropy from molecular data, J. Am. Chem. Soc., 1937, 59, 1743-1751. [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]

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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]

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Utsunomiya, C.; Kobayashi, T.; Nagakura, S., Photoelectron angular distribution measurements for some aliphatic alcohols, amines, halides, Bull. Chem. Soc. Jpn., 1980, 53, 1216. [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]

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]

Katsumata, Iwai, et al., 1973
Katsumata, S.; Iwai, T.; Kimura, K., Photoelectron spectra and sum rule consideration. Higher alkyl amines and alcohols, Bull. Chem. Soc. Jpn., 1973, 46, 3391. [all data]

Ogata, Onizuka, et al., 1972
Ogata, H.; Onizuka, H.; Nihei, Y.; Kamada, H., On the first bands of the photoelectron spectra of amines, alcohols, and mercaptans, Chem. Lett., 1972, 895. [all data]

Collin and Franskin, 1966
Collin, J.E.; Franskin, M.J., Ionisation, dissociation et rearrangements intramoleculaires dans les amines aliphatiques par impact electronique. Cas de la methylamine et de la methylamine-Nd₂, Bull. Soc. Roy. Sci. Liege, 1966, 35, 267. [all data]

Burgers, Holmes, et al., 1984
Burgers, P.C.; Holmes, J.L.; Terlouw, J.K., Gaseous [H₂,C,N]⁺ and [H₃,C,N]⁺ ions. Generation of formation, and dissociation characteristics of [H₂CN]⁺, [HCNH]⁺, [CNH₂]⁺, [H₂CNH]⁺, and [HCN]⁺, J. Am. Chem. Soc., 1984, 106, 2762. [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]

Haney and Franklin, 1968
Haney, M.A.; Franklin, J.L., Correlation of excess energies of electron-impact dissociations with the translational energies of the products, J.Chem. Phys., 1968, 48, 4093. [all data]

Lossing, Lam, et al., 1981
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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]

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Cornford, Frost, et al., 1971
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Slifkin, M.A.; Allison, A.C., Measurement of ionization potentials from contact charge transfer spectra, Nature, 1967, 215, 949. [all data]

Watanabe and Mottl, 1957
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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]

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Yamdagni and Kebarle, 1973
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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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Hoyau, S.; Norrman, K.; McMahon, T.B.; Ohanessian, G., A Quantitative Basis for a Scale of Na+ Affinities of Organic and Small Biological Molecules in the Gas Phase, J. Am. Chem. Soc., 1999, 121, 38, 8864, https://doi.org/10.1021/ja9841198 . [all data]

Guo and Castleman, 1990
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McMahon and Ohanessian, 2000
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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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