Methylamine - The NIST WebBook

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 View 3d structure (requires JavaScript / HTML 5)
• 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:
  • Reaction thermochemistry data
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Henry's Law data
  • Gas phase ion energetics data
  • Ion clustering data
  • IR Spectrum
  • Vibrational and/or electronic energy levels
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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Reaction thermochemistry data

Go To: Top, Mass spectrum (electron ionization), UV/Visible spectrum, 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 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)

Quantity	Value	Units	Method	Reference	Comment
ΔrH°	172.	kJ/mol	ICR	Woodin and Beauchamp, 1978	gas phase; switching reaction(Li+)H2O, Entropy change calculated or estimated; Dzidic and Kebarle, 1970 interpolated; M
Quantity	Value	Units	Method	Reference	Comment
ΔrS°	110.	J/mol*K	N/A	Woodin and Beauchamp, 1978	gas phase; switching reaction(Li+)H2O, Entropy change calculated or estimated; Dzidic and Kebarle, 1970 interpolated; M
Quantity	Value	Units	Method	Reference	Comment
ΔrG°	139.	kJ/mol	ICR	Woodin and Beauchamp, 1978	gas phase; switching reaction(Li+)H2O, Entropy change calculated or estimated; Dzidic and Kebarle, 1970 interpolated; M

C3H9Sn+ + = (C3H9Sn+ • )

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

Quantity	Value	Units	Method	Reference	Comment
ΔrH°	176.	kJ/mol	PHPMS	Stone and Splinter, 1984	gas phase; switching reaction((CH3)3Sn+)CH3OH, Entropy change calculated or estimated; M
Quantity	Value	Units	Method	Reference	Comment
ΔrS°	128.	J/mol*K	N/A	Stone and Splinter, 1984	gas phase; switching reaction((CH3)3Sn+)CH3OH, Entropy change calculated or estimated; M

Free energy of reaction

ΔrG° (kJ/mol)	T (K)	Method	Reference	Comment
109.	525.	PHPMS	Stone and Splinter, 1984	gas phase; switching reaction((CH3)3Sn+)CH3OH, Entropy change calculated or estimated; M

+ = ( • )

By formula: K+ + CH5N = (K+ • CH5N)

Quantity	Value	Units	Method	Reference	Comment
ΔrH°	79.9	kJ/mol	HPMS	Davidson and Kebarle, 1976	gas phase; switching reaction(K+)H2O; Davidson and Kebarle, 1976, 2; M
Quantity	Value	Units	Method	Reference	Comment
ΔrS°	91.2	J/mol*K	HPMS	Davidson and Kebarle, 1976	gas phase; switching reaction(K+)H2O; Davidson and Kebarle, 1976, 2; M
Quantity	Value	Units	Method	Reference	Comment
ΔrG°	53.1	kJ/mol	HPMS	Davidson and Kebarle, 1976	gas phase; switching reaction(K+)H2O; Davidson and Kebarle, 1976, 2; M

+ = ( • )

By formula: Na+ + CH5N = (Na+ • CH5N)

Quantity	Value	Units	Method	Reference	Comment
ΔrH°	110. ± 0.8	kJ/mol	HPMS	Hoyau, Norrman, et al., 1999	RCD
ΔrH°	134.	kJ/mol	HPMS	Guo and Castleman, 1990	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
ΔrS°	94600.	J/mol*K	HPMS	Hoyau, Norrman, et al., 1999	RCD
ΔrS°	127.	J/mol*K	HPMS	Guo and Castleman, 1990	gas phase; M

Free energy of reaction

ΔrG° (kJ/mol)	T (K)	Method	Reference	Comment
81.6	298.	IMRE	McMahon and Ohanessian, 2000	Anchor alanine=39.89; RCD

(CH6N+ • 2) + = (CH6N+ • 3)

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

Quantity	Value	Units	Method	Reference	Comment
ΔrH°	56.1	kJ/mol	PHPMS	Meot-Ner (Mautner), 1992	gas phase; M
ΔrH°	71.1	kJ/mol	HPMS	Holland and Castleman, 1982	gas phase; Entropy change is questionable; M
Quantity	Value	Units	Method	Reference	Comment
ΔrS°	105.	J/mol*K	PHPMS	Meot-Ner (Mautner), 1992	gas phase; M
ΔrS°	174.	J/mol*K	HPMS	Holland and Castleman, 1982	gas phase; Entropy change is questionable; M

(CH6N+ • ) + = (CH6N+ • 2)

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

Quantity	Value	Units	Method	Reference	Comment
ΔrH°	66.9	kJ/mol	PHPMS	Meot-Ner (Mautner), 1992	gas phase; M
ΔrH°	80.3	kJ/mol	HPMS	Holland and Castleman, 1982	gas phase; Entropy change is questionable; M
Quantity	Value	Units	Method	Reference	Comment
ΔrS°	95.8	J/mol*K	PHPMS	Meot-Ner (Mautner), 1992	gas phase; M
ΔrS°	167.	J/mol*K	HPMS	Holland and Castleman, 1982	gas phase; Entropy change is questionable; M

CH4N- + =

By formula: CH4N- + H+ = CH5N

Quantity	Value	Units	Method	Reference	Comment
ΔrH°	1682. ± 11.	kJ/mol	D-EA	Radisic, Xu, et al., 2002	gas phase; B
ΔrH°	1687.0 ± 3.4	kJ/mol	G+TS	MacKay, Hemsworth, et al., 1976	gas phase; B
Quantity	Value	Units	Method	Reference	Comment
ΔrG°	1651. ± 11.	kJ/mol	H-TS	Radisic, Xu, et al., 2002	gas phase; B
ΔrG°	1655.6 ± 2.9	kJ/mol	IMRE	MacKay, Hemsworth, et al., 1976	gas phase; B

C3H9Si+ + = (C3H9Si+ • )

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

Quantity	Value	Units	Method	Reference	Comment
ΔrH°	232.	kJ/mol	PHPMS	Li and Stone, 1990	gas phase; switching reaction,Thermochemical ladder((CH3)3Si+)C6H5COOC2H5; Wojtyniak and Stone, 1986; M
Quantity	Value	Units	Method	Reference	Comment
ΔrS°	159.	J/mol*K	PHPMS	Li and Stone, 1990	gas phase; switching reaction,Thermochemical ladder((CH3)3Si+)C6H5COOC2H5; Wojtyniak and Stone, 1986; M

CH6N+ + = (CH6N+ • )

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

Quantity	Value	Units	Method	Reference	Comment
ΔrH°	106.	kJ/mol	PHPMS	Meot-Ner (Mautner), 1992	gas phase; M
ΔrH°	90.8	kJ/mol	PHPMS	Yamdagni and Kebarle, 1973	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
ΔrS°	114.	J/mol*K	PHPMS	Meot-Ner (Mautner), 1992	gas phase; M
ΔrS°	98.7	J/mol*K	PHPMS	Yamdagni and Kebarle, 1973	gas phase; M

C6H12NO3+ + = (C6H12NO3+ • )

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

Bond type: Hydrogen bonds with polydentate bonding in positive ions

Quantity	Value	Units	Method	Reference	Comment
ΔrH°	120.	kJ/mol	PHPMS	Meot-Ner, 1984	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
ΔrS°	83.3	J/mol*K	PHPMS	Meot-Ner, 1984	gas phase; M

( • ) + = ( • 2)

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

Quantity	Value	Units	Method	Reference	Comment
ΔrH°	79.9 ± 0.8	kJ/mol	HPMS	Guo and Castleman, 1990	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
ΔrS°	81.6	J/mol*K	HPMS	Guo and Castleman, 1990	gas phase; M

+ = ( • )

By formula: Pb+ + CH5N = (Pb+ • CH5N)

Quantity	Value	Units	Method	Reference	Comment
ΔrH°	148. ± 1.	kJ/mol	HPMS	Guo and Castleman, 1990	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
ΔrS°	126.	J/mol*K	HPMS	Guo and Castleman, 1990	gas phase; M

(CH6N+ • 3) + = (CH6N+ • 4)

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

Quantity	Value	Units	Method	Reference	Comment
ΔrH°	33.	kJ/mol	PHPMS	Meot-Ner (Mautner), 1992	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
ΔrS°	90.0	J/mol*K	PHPMS	Meot-Ner (Mautner), 1992	gas phase; M

C2H8N+ + = (C2H8N+ • )

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

Quantity	Value	Units	Method	Reference	Comment
ΔrH°	93.7	kJ/mol	PHPMS	Yamdagni and Kebarle, 1973	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
ΔrS°	122.	J/mol*K	PHPMS	Yamdagni and Kebarle, 1973	gas phase; M

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

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

Quantity	Value	Units	Method	Reference	Comment
ΔrH°	-130.5 ± 2.5	kJ/mol	RSC	Holm, 1983	solvent: Diethyl ether; MS

2 = +

By formula: 2CH5N = C2H7N + H3N

Quantity	Value	Units	Method	Reference	Comment
ΔrH°	-19.7	kJ/mol	Eqk	Issoire and Long, 1960	gas phase; ALS

2 = +

By formula: 2C2H7N = CH5N + C3H9N

Quantity	Value	Units	Method	Reference	Comment
ΔrH°	-13.2	kJ/mol	Eqk	Issoire and Long, 1960	gas phase; ALS

Mass spectrum (electron ionization)

Go To: Top, Reaction thermochemistry data, UV/Visible spectrum, 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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Additional Data

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Owner	NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved.
Origin	Japan AIST/NIMC Database- Spectrum MS-NW- 377
NIST MS number	228024

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UV/Visible spectrum

Go To: Top, Reaction thermochemistry data, Mass spectrum (electron ionization), 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: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.

For Zoom

1.) Enter the desired X axis range (e.g., 100, 200)

2.) Check here for automatic Y scaling

3.) Press here to zoom

• Plot
• Help / Software credits

Help

The interactive spectrum display requires a browser with JavaScript and HTML 5 canvas support.

Select a region with data to zoom. Select a region with no data or click the mouse on the plot to revert to the orginal display.

Credits

The following components were used in generating the plot:

• jQuery
• jQuery UI
• Flot
• Plugins for Flot:
  • Resize (distributed with Flot)
  • Selection (distributed with Flot)
  • Axis labels
  • Labels ( Modified by NIST for use in this application)

Additonal code used was developed at NIST: jcamp-dx.js and jcamp-plot.js.

Use or mention of technologies or programs in this web site is not intended to imply recommendation or endorsement by the National Institute of Standards and Technology, nor is it intended to imply that these items are necessarily the best available for the purpose.

Additional Data

View image of digitized spectrum (can be printed in landscape orientation).

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Source	Tannenbaum, Coffin, et al., 1953
Owner	INEP CP RAS, NIST OSRD Collection (C) 2007 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved.
Origin	INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS
Source reference	RAS UV No. 2772
Instrument	n.i.g.
Sample pressure	0.01-1.8 mm Hg
Melting point	-93.4
Boiling point	-6.3

References

Go To: Top, Reaction thermochemistry data, Mass spectrum (electron ionization), UV/Visible spectrum, Notes

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

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]

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]

Hoyau, Norrman, et al., 1999 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 Guo, B.C.; Castleman, A.W., The Association Reactions of Pb+ Ion with CH3OH and CH3NH2 in the Gas Phase, Int. J. Mass Spectrom. Ion Proc., 1990, 100, 665, https://doi.org/10.1016/0168-1176(90)85101-7 . [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]

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]

Holland and Castleman, 1982 Holland, P.M.; Castleman, A.W., The Thermochemical Properties of Gas - Phase Transition Metal Ion Complexes, J. Chem. Phys., 1982, 76, 8, 4195, https://doi.org/10.1063/1.443497 . [all data]

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 Li, X.; Stone, A.J., Gas-Phase (CH3)3Si+ Affinities of Alkylamines and Proton Affinities of Trimethylsilyl Alkylamines, Int. J. Mass Spectrom. Ion Proc., 1990, 101, 2-3, 149, https://doi.org/10.1016/0168-1176(90)87008-5 . [all data]

Wojtyniak and Stone, 1986 Wojtyniak, A.C.M.; Stone, A.J., A High-Pressure Mass Spectrometric Study of the Bonding of Trimethylsilylium to Oxygen and Aromatic Bases, Can. J. Chem., 1986, 74, 59. [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]

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 Holm, T., Acta Chem. Scand. B, 1983, 37, 797. [all data]

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]

Tannenbaum, Coffin, et al., 1953 Tannenbaum, E.; Coffin, E.M.; Harrison, A.J., The far ultraviolet absorption spectra of simple alkyl amines, J. Chem. Phys., 1953, 21, 2, 311-318. [all data]

Notes

Go To: Top, Reaction thermochemistry data, Mass spectrum (electron ionization), UV/Visible spectrum, References

• Symbols used in this document:

  T	Temperature
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔrS°	Entropy of reaction at standard conditions

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