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N-Methyl methanimine


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

Quantity Value Units Method Reference Comment
Deltafgas11. ± 2.kcal/molIonPeerboom, Ingemann, et al., 1990Appearance potentials

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

C2H4N- + Hydrogen cation = C2H5N

By formula: C2H4N- + H+ = C2H5N

Quantity Value Units Method Reference Comment
Deltar384.6 ± 5.1kcal/molG+TSKass and DePuy, 1985gas phase
Quantity Value Units Method Reference Comment
Deltar378.0 ± 5.0kcal/molIMRBKass and DePuy, 1985gas phase

(CAS Reg. No. 34285-60-4 bullet 4294967295C2H5N) + C2H5N = CAS Reg. No. 34285-60-4

By formula: (CAS Reg. No. 34285-60-4 bullet 4294967295C2H5N) + C2H5N = CAS Reg. No. 34285-60-4

Quantity Value Units Method Reference Comment
Deltar18.9 ± 2.2kcal/molN/AMacKay, Hemsworth, et al., 1976gas phase

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
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

View reactions leading to C2H5N+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
Proton affinity (review)211.4kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity203.7kcal/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
9.3PEBock and Dammel, 1987LBLHLM
9.4PEFrost, MacDonald, et al., 1978LLK
9.8 ± 0.1EIFisher and Henderson, 1967RDSH
10.0PEBock and Dammel, 1987Vertical value; LBLHLM
9.90 ± 0.02PEFrost, MacDonald, et al., 1978Vertical value; LLK

De-protonation reactions

C2H4N- + Hydrogen cation = C2H5N

By formula: C2H4N- + H+ = C2H5N

Quantity Value Units Method Reference Comment
Deltar384.6 ± 5.1kcal/molG+TSKass and DePuy, 1985gas phase; B
Quantity Value Units Method Reference Comment
Deltar378.0 ± 5.0kcal/molIMRBKass and DePuy, 1985gas phase; B

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:   X


Vib. 
sym. 
 No.   Approximate 
 type of mode 
 cm-1   Med.   Method   References

a' 1 CH2 a-stretch 3024 s gas IR Stolkin, Ha, et al., 1977
1 CH2 a-stretch 3012 s Ar IR Hinze and Curl, 1964
Stolkin, Ha, et al., 1977
Machara and Ault, 1987
2 CH3 a-stretch 2962 s gas IR Stolkin, Ha, et al., 1977
2 CH3 a-stretch 2953 s Ar IR Stolkin, Ha, et al., 1977
3 CH2 s-stretch 2897 w gas IR Stolkin, Ha, et al., 1977
3 CH2 s-stretch 2900 s Ar IR Hinze and Curl, 1964
Stolkin, Ha, et al., 1977
Machara and Ault, 1987
4 CH3 s-stretch 2854 s Ar IR Stolkin, Ha, et al., 1977
Machara and Ault, 1987
4 CH3 s-stretch 2849 s Ar IR Sastry and Curl, 1964
5 C=N stretch 1661 s gas IR Stolkin, Ha, et al., 1977
5 C=N stretch 1659 m Ar IR Hinze and Curl, 1964
Stolkin, Ha, et al., 1977
6 CH2 scissors 1475 vs gas IR Stolkin, Ha, et al., 1977
6 CH2 scissors 1470 vs Ar IR Hinze and Curl, 1964
Stolkin, Ha, et al., 1977
7 CH3 a-deform. 1425 w T gas IR Stolkin, Ha, et al., 1977
8 CH3 s-deform. 1405 w gas IR Stolkin, Ha, et al., 1977
8 CH3 s-deform. 1402 m Ar IR Hinze and Curl, 1964
Stolkin, Ha, et al., 1977
9 CH3 rock 1220 s gas IR Stolkin, Ha, et al., 1977
9 CH3 rock 1221 s Ar IR Hinze and Curl, 1964
Stolkin, Ha, et al., 1977
Machara and Ault, 1987
9 CH3 rock 1221 N2 IR Machara and Ault, 1987
10 C-N stretch 952 m gas IR Stolkin, Ha, et al., 1977
10 C-N stretch 950 m s Ar IR Hinze and Curl, 1964
Stolkin, Ha, et al., 1977
Machara and Ault, 1987
10 C-N stretch 949 N2 IR Machara and Ault, 1987
12 CNC bend 484 m s gas IR Stolkin, Ha, et al., 1977
12 CNC bend 479 m s Ar IR Hinze and Curl, 1964
Stolkin, Ha, et al., 1977
Machara and Ault, 1987
12 CNC bend 484 N2 IR Machara and Ault, 1987
a 13 CH3 a-stretch 2975 s gas IR Stolkin, Ha, et al., 1977
13 CH3 a-stretch 2962 m s Ar IR Hinze and Curl, 1964
Stolkin, Ha, et al., 1977
Machara and Ault, 1987
14 CH3 a-deform. 1444 s gas IR Stolkin, Ha, et al., 1977
14 CH3 a-deform. 1441 m Ar IR Hinze and Curl, 1964
Stolkin, Ha, et al., 1977
15 CH3 wag 1100 w Ar IR Hinze and Curl, 1964
Stolkin, Ha, et al., 1977
16 CH2 OPLA 1026.14 vs gas IR Stolkin, Ha, et al., 1977
Yu and Duxbury, 1992
16 CH2 OPLA 1026 vs Ar IR Hinze and Curl, 1964
Stolkin, Ha, et al., 1977
Machara and Ault, 1987
16 CH2 OPLA 1030 N2 IR Machara and Ault, 1987
17 C=N torsion 686 w gas IR Stolkin, Ha, et al., 1977
18 CH3 twist 220 w T Ar IR Stolkin, Ha, et al., 1977

Additional references: Jacox, 1994, page 375

Notes

wWeak
mMedium
sStrong
vsVery strong
TTentative assignment or approximate value

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]

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]

Frost, MacDonald, et al., 1978
Frost, D.C.; MacDonald, B.; McDowell, C.A.; Westwood, N.P.C., Pyrolysis of trimethyl hexahydro-s-triazines. The photoelectron spectra of N-methylmethylenimine, CH2=NCH3, and C-methyl- methylenimine, CH3CH=NH, J. Electron Spectrosc. Relat. Phenom., 1978, 14, 379. [all data]

Fisher and Henderson, 1967
Fisher, I.P.; Henderson, E., Mass spectrometry of free radicals, J. Chem. Soc. Faraday Trans., 1967, 63, 1342. [all data]

Stolkin, Ha, et al., 1977
Stolkin, I.; Ha, T.-K.; Gunthard, H.H., N-methylmethyleneimine and ethylideneimine: Gas- and matrix-infrared spectra, AB initio calculations and thermodynamic properties, Chem. Phys., 1977, 21, 3, 327, https://doi.org/10.1016/0301-0104(77)85189-6 . [all data]

Hinze and Curl, 1964
Hinze, J.; Curl, R.F., Jr., None, J. Am. Chem. Soc., 1964, 86, 23, 5068, https://doi.org/10.1021/ja01077a004 . [all data]

Machara and Ault, 1987
Machara, N.P.; Ault, B.S., 193 nm Excimer laser photochemistry in cryogenic matrices: synthesis of N-methylmethyleneimine, Chem. Phys. Lett., 1987, 140, 4, 411, https://doi.org/10.1016/0009-2614(87)80757-1 . [all data]

Sastry and Curl, 1964
Sastry, K.V.L.N.; Curl, R.F., Jr., Microwave Spectrum of N-Methyl Methylenimine, J. Chem. Phys., 1964, 41, 1, 77, https://doi.org/10.1063/1.1725653 . [all data]

Yu and Duxbury, 1992
Yu, G.; Duxbury, G., High-resolution diode laser spectroscopy of the «nu»16 band of N-methylmethylenimine, J. Mol. Spectrosc., 1992, 155, 1, 105, https://doi.org/10.1016/0022-2852(92)90551-X . [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]


Notes

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