Methanimine

• Formula: CH₃N
• Molecular weight: 29.0412
• IUPAC Standard InChI: InChI=1S/CH3N/c1-2/h2H,1H2 Copy

  
• IUPAC Standard InChIKey: WDWDWGRYHDPSDS-UHFFFAOYSA-N Copy
• CAS Registry Number: 2053-29-4
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
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• Information on this page:
  • Gas phase thermochemistry data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • Vibrational and/or electronic energy levels
  • References
  • Notes
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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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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 by: John E. Bartmess

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

CH₂N^- +  =

By formula: CH₂N^- + H⁺ = CH₃N

(CAS Reg. No. 54448-39-4 • 4294967295) +  = CAS Reg. No. 54448-39-4

By formula: (CAS Reg. No. 54448-39-4 • 4294967295CH₃N) + CH₃N = CAS Reg. No. 54448-39-4

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

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

View reactions leading to CH₃N⁺ (ion structure unspecified)

Ionization energy determinations

De-protonation reactions

CH₂N^- +  =

By formula: CH₂N^- + H⁺ = CH₃N

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: Marilyn E. Jacox

State:   ?

State:   X

Additional references: Jacox, 1994, page 234; Milligan and Jacox, 1963; Johnson and Lovas, 1972; Kirchhoff, Johnson, et al., 1973; Pearson and Lovas, 1977; Margules, Demaison, et al., 2006

Notes

References

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Vibrational and/or electronic energy levels, NIST Free Links, Notes

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

Peerboom, Ingemann, et al., 1990
Peerboom, R.A.L.; Ingemann, S.; Nibbering, N.M.M.; Liebman, J.F., Proton affinities and heats of formation of the imines CH₂=NH, CH₂=NMe and PhCH=NH, J. Chem. Soc. Perkin Trans. 2, 1990, 1825-1828. [all data]

Grela and Colussi, 1988
Grela, M.A.; Colussi, A.J., Decomposition of methylamino and aminomethyl radicals. The heats of formation of methyleneimine (CH₂=NH) and hydrazyl (N₂H₃) radical, Int. J. Chem. Kinet., 1988, 20, 713-718. [all data]

DeFrees and Hehre, 1978
DeFrees, D.J.; Hehre, W.J., Methyleneimine, J. Phys. Chem., 1978, 82, 391-393. [all data]

Kass and DePuy, 1985
Kass, S.R.; DePuy, C.H., Gas phase ion chemistry of azides. The generation of CH=N^- and CH₂=NCH₂^-, J. Org. Chem., 1985, 50, 2874. [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]

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]

Bock and Dammel, 1987
Bock, H.; Dammel, R., Methanimine RR"C=NR": Darstellung und photoelektronen-spektren, J. Am. Chem. Soc., 1987, 120, 1961. [all data]

Tarasenko, Tishenkov, et al., 1986
Tarasenko, N.A.; Tishenkov, A.A.; Zaikin, V.G.; Volkova, V.V.; Gusel'nikov, L.E., Adiabatic ionization energy of methylenimine, Bull. Acad. Sci. USSR, Div. Chem. Sci., 1986, 10, 2196. [all data]

Peel and Willett, 1975
Peel, J.B.; Willett, G.D., Photoelectron spectrum of methylenimine by spectrum stripping, J. Chem. Soc. Faraday Trans. 2, 1975, 71, 1799. [all data]

Teslja, Nizamov, et al., 2004
Teslja, A.; Nizamov, B.; Dagdigian, P.J., The Electronic Spectrum of Methyleneimine, J. Phys. Chem. A, 2004, 108, 20, 4433, https://doi.org/10.1021/jp037938+ . [all data]

Hamada, Hashiguchi, et al., 1984
Hamada, Y.; Hashiguchi, K.; Tsuboi, M.; Koga, Y.; Kondo, S., Pyrolysis of amines: Infrared spectrum of methyleneimine, J. Mol. Spectrosc., 1984, 105, 1, 70, https://doi.org/10.1016/0022-2852(84)90104-8 . [all data]

Halonen and Duxbury, 1985
Halonen, L.; Duxbury, G., Fourier transform infrared spectrum of CH2NH: The ν1 band, Chem. Phys. Lett., 1985, 118, 3, 246, https://doi.org/10.1016/0009-2614(85)85309-4 . [all data]

Halonen and Duxbury, 1985, 2
Halonen, L.; Duxbury, G., High resolution infrared spectrum of methyleneimine, CH2NH,in the 3 μm region, J. Chem. Phys., 1985, 83, 5, 2091, https://doi.org/10.1063/1.449351 . [all data]

Milligan, 1961
Milligan, D.E., Infrared Spectroscopic Study of the Photolysis of Methyl Azide and Methyl-d3 Azide in Solid Argon and Carbon Dioxide, J. Chem. Phys., 1961, 35, 4, 1491, https://doi.org/10.1063/1.1732070 . [all data]

Jacox and Milligan, 1975
Jacox, M.E.; Milligan, D.E., The infrared spectrum of methylenimine, J. Mol. Spectrosc., 1975, 56, 3, 333, https://doi.org/10.1016/0022-2852(75)90122-8 . [all data]

Allegrini, Johns, et al., 1979
Allegrini, M.; Johns, J.W.C.; McKellar, A.R.W., Laser Stark spectroscopy of the ν4 fundamental band of CH2NH at 6.1 μm, J. Chem. Phys., 1979, 70, 6, 2829, https://doi.org/10.1063/1.437815 . [all data]

Duxbury, Kato, et al., 1981
Duxbury, G.; Kato, H.; Le Lerre, M.L., Laser Stark and interferometric studies of thioformaldehyde and methyleneimine, Discuss. Faraday Soc., 1981, 71, 97, https://doi.org/10.1039/dc9817100097 . [all data]

Duxbury and Le Lerre, 1982
Duxbury, G.; Le Lerre, M.L., Fourier transform infrared spectra of CH2NH: The ν5 and ν6 bands, J. Mol. Spectrosc., 1982, 92, 2, 326, https://doi.org/10.1016/0022-2852(82)90106-0 . [all data]

Halonen and Duxbury, 1985, 3
Halonen, L.; Duxbury, G., The Fourier transform infrared spectrum of methyleneimine in the 10 μm region, J. Chem. Phys., 1985, 83, 5, 2078, https://doi.org/10.1063/1.449350 . [all data]

Halonen, Deeley, et al., 1986
Halonen, L.; Deeley, C.M.; Mills, I.M., Intensities in the ν7, ν8, and ν9 bands of CH2NH and the harmonic force field of methyleneimine, J. Chem. Phys., 1986, 85, 2, 692, https://doi.org/10.1063/1.451274 . [all data]

Duxbury and Le Lerre, 1984
Duxbury, G.; Le Lerre, M.L., High-resolution IR spectra of methyleneimine (CH2NH) in the 10 μm region, the ν8 band, Infrared Phys., 1984, 24, 2-3, 261, https://doi.org/10.1016/0020-0891(84)90080-0 . [all data]

Jacox, 1994
Jacox, M.E., Vibrational and electronic energy levels of polyatomic transient molecules, American Chemical Society, Washington, DC, 1994, 464. [all data]

Milligan and Jacox, 1963
Milligan, D.E.; Jacox, M.E., Infrared Spectroscopic Evidence for the Species HNC, J. Chem. Phys., 1963, 39, 3, 712, https://doi.org/10.1063/1.1734312 . [all data]

Johnson and Lovas, 1972
Johnson, D.R.; Lovas, F.J., Microwave detection of the molecular transient methyleneimine (CH2=NH), Chem. Phys. Lett., 1972, 15, 1, 65, https://doi.org/10.1016/0009-2614(72)87017-9 . [all data]

Kirchhoff, Johnson, et al., 1973
Kirchhoff, W.H.; Johnson, D.R.; Lovas, F.J., Microwave Spectra of Molecules of Astrophysical Interest: II Methylenimine, J. Phys. Chem. Ref. Data, 1973, 2, 1, 1, https://doi.org/10.1063/1.3253110 . [all data]

Pearson and Lovas, 1977
Pearson, R., Jr.; Lovas, F.J., Microwave spectrum and molecular structure of methylenimine (CH2NH), J. Chem. Phys., 1977, 66, 9, 4149, https://doi.org/10.1063/1.434490 . [all data]

Margules, Demaison, et al., 2006
Margules, L.; Demaison, J.; Streeja, P.B.; Guillemin, J.-C., Submillimeterwave spectrum of CH2PH and equilibrium structures of CH2PH and CH2NH, J. Mol. Spectrosc., 2006, 238, 2, 234, https://doi.org/10.1016/j.jms.2006.05.008 . [all data]

Notes

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• Symbols used in this document:
  

  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

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