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Methylamine

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Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry 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 by: Donald R. Burgess, Jr.

Quantity Value Units Method Reference Comment
Deltafgas-5.62kcal/molN/AAston, Siller, et al., 1937Value computed using «DELTA»fHliquid° value of -47.3±0.46 kj/mol from Aston, Siller, et al., 1937 and «DELTA»vapH° value of 23.85 kj/mol from missing citation.
Deltafgas-2.92kcal/molN/ALemoult, 1907Value computed using «DELTA»fHliquid° value of -36 kj/mol from Lemoult, 1907 and «DELTA»vapH° value of 23.85 kj/mol from missing citation.

Condensed phase thermochemistry data

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry 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

Quantity Value Units Method Reference Comment
Deltafliquid-11.3 ± 0.11kcal/molN/ACox and Pilcher, 1970Review; Unpublished work J. Jaffe; ALS
Deltafliquid-11.3 ± 0.11kcal/molCcbAston, Siller, et al., 1937Unpublished work J. Jaffe; ALS
Deltafliquid-8.7kcal/molCcbLemoult, 1907ALS
Quantity Value Units Method Reference Comment
Deltacliquid-253.54 ± 0.09kcal/molN/ACox and Pilcher, 1970Review; Unpublished work J. Jaffe; ALS
Deltacliquid-253.54 ± 0.09kcal/molCcbAston, Siller, et al., 1937Unpublished work J. Jaffe; ALS
Deltacliquid-261.4kcal/molCcbMuller, 1910At 288 K; ALS
Deltacliquid-256.9kcal/molCcbLemoult, 1907ALS
Quantity Value Units Method Reference Comment
liquid35.90cal/mol*KN/AAston, Siller, et al., 1937, 2For superheated liquid, using extrapolated heat capacities.; DH

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference Comment
24.331259.28Aston, Siller, et al., 1937, 2T = 14 to 259 K. Value is unsmoothed experimental datum.; DH

Reaction thermochemistry data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry 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
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

Lithium ion (1+) + Methylamine = (Lithium ion (1+) bullet Methylamine)

By formula: Li+ + CH5N = (Li+ bullet CH5N)

Quantity Value Units Method Reference Comment
Deltar41.1kcal/molICRWoodin and Beauchamp, 1978gas phase; switching reaction(Li+)H2O, Entropy change calculated or estimated; Dzidic and Kebarle, 1970 interpolated; M
Quantity Value Units Method Reference Comment
Deltar26.cal/mol*KN/AWoodin and Beauchamp, 1978gas phase; switching reaction(Li+)H2O, Entropy change calculated or estimated; Dzidic and Kebarle, 1970 interpolated; M
Quantity Value Units Method Reference Comment
Deltar33.3kcal/molICRWoodin and Beauchamp, 1978gas phase; switching reaction(Li+)H2O, Entropy change calculated or estimated; Dzidic and Kebarle, 1970 interpolated; M

C3H9Sn+ + Methylamine = (C3H9Sn+ bullet Methylamine)

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

Quantity Value Units Method Reference Comment
Deltar42.1kcal/molPHPMSStone and Splinter, 1984gas phase; switching reaction((CH3)3Sn+)CH3OH, Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar30.7cal/mol*KN/AStone and Splinter, 1984gas phase; switching reaction((CH3)3Sn+)CH3OH, Entropy change calculated or estimated; M

Free energy of reaction

DeltarG° (kcal/mol) T (K) Method Reference Comment
26.0525.PHPMSStone and Splinter, 1984gas phase; switching reaction((CH3)3Sn+)CH3OH, Entropy change calculated or estimated; M

Potassium ion (1+) + Methylamine = (Potassium ion (1+) bullet Methylamine)

By formula: K+ + CH5N = (K+ bullet CH5N)

Quantity Value Units Method Reference Comment
Deltar19.1kcal/molHPMSDavidson and Kebarle, 1976gas phase; switching reaction(K+)H2O; Davidson and Kebarle, 1976, 2; M
Quantity Value Units Method Reference Comment
Deltar21.8cal/mol*KHPMSDavidson and Kebarle, 1976gas phase; switching reaction(K+)H2O; Davidson and Kebarle, 1976, 2; M
Quantity Value Units Method Reference Comment
Deltar12.7kcal/molHPMSDavidson and Kebarle, 1976gas phase; switching reaction(K+)H2O; Davidson and Kebarle, 1976, 2; M

Sodium ion (1+) + Methylamine = (Sodium ion (1+) bullet Methylamine)

By formula: Na+ + CH5N = (Na+ bullet CH5N)

Quantity Value Units Method Reference Comment
Deltar26.3 ± 0.2kcal/molHPMSHoyau, Norrman, et al., 1999RCD
Deltar32.1kcal/molHPMSGuo and Castleman, 1990gas phase; M
Quantity Value Units Method Reference Comment
Deltar22600.cal/mol*KHPMSHoyau, Norrman, et al., 1999RCD
Deltar30.3cal/mol*KHPMSGuo and Castleman, 1990gas phase; M

Free energy of reaction

DeltarG° (kcal/mol) T (K) Method Reference Comment
19.5298.IMREMcMahon and Ohanessian, 2000Anchor alanine=39.89; RCD

(CH6N+ bullet 2Methylamine) + Methylamine = (CH6N+ bullet 3Methylamine)

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

Quantity Value Units Method Reference Comment
Deltar13.4kcal/molPHPMSMeot-Ner (Mautner), 1992gas phase; M
Deltar17.0kcal/molHPMSHolland and Castleman, 1982gas phase; Entropy change is questionable; M
Quantity Value Units Method Reference Comment
Deltar25.1cal/mol*KPHPMSMeot-Ner (Mautner), 1992gas phase; M
Deltar41.6cal/mol*KHPMSHolland and Castleman, 1982gas phase; Entropy change is questionable; M

(CH6N+ bullet Methylamine) + Methylamine = (CH6N+ bullet 2Methylamine)

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

Quantity Value Units Method Reference Comment
Deltar16.0kcal/molPHPMSMeot-Ner (Mautner), 1992gas phase; M
Deltar19.2kcal/molHPMSHolland and Castleman, 1982gas phase; Entropy change is questionable; M
Quantity Value Units Method Reference Comment
Deltar22.9cal/mol*KPHPMSMeot-Ner (Mautner), 1992gas phase; M
Deltar39.9cal/mol*KHPMSHolland and Castleman, 1982gas phase; Entropy change is questionable; M

CH4N- + Hydrogen cation = Methylamine

By formula: CH4N- + H+ = CH5N

Quantity Value Units Method Reference Comment
Deltar402.0 ± 2.6kcal/molD-EARadisic, Xu, et al., 2002gas phase; B
Deltar403.21 ± 0.82kcal/molG+TSMacKay, Hemsworth, et al., 1976gas phase; B
Quantity Value Units Method Reference Comment
Deltar394.5 ± 2.7kcal/molH-TSRadisic, Xu, et al., 2002gas phase; B
Deltar395.70 ± 0.70kcal/molIMREMacKay, Hemsworth, et al., 1976gas phase; B

C3H9Si+ + Methylamine = (C3H9Si+ bullet Methylamine)

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

Quantity Value Units Method Reference Comment
Deltar55.4kcal/molPHPMSLi and Stone, 1990gas phase; switching reaction,Thermochemical ladder((CH3)3Si+)C6H5COOC2H5; Wojtyniak and Stone, 1986; M
Quantity Value Units Method Reference Comment
Deltar38.1cal/mol*KPHPMSLi and Stone, 1990gas phase; switching reaction,Thermochemical ladder((CH3)3Si+)C6H5COOC2H5; Wojtyniak and Stone, 1986; M

CH6N+ + Methylamine = (CH6N+ bullet Methylamine)

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

Quantity Value Units Method Reference Comment
Deltar25.4kcal/molPHPMSMeot-Ner (Mautner), 1992gas phase; M
Deltar21.7kcal/molPHPMSYamdagni and Kebarle, 1973gas phase; M
Quantity Value Units Method Reference Comment
Deltar27.3cal/mol*KPHPMSMeot-Ner (Mautner), 1992gas phase; M
Deltar23.6cal/mol*KPHPMSYamdagni and Kebarle, 1973gas phase; M

C6H12NO3+ + Methylamine = (C6H12NO3+ bullet Methylamine)

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

Bond type: Hydrogen bonds with polydentate bonding in positive ions

Quantity Value Units Method Reference Comment
Deltar28.6kcal/molPHPMSMeot-Ner, 1984gas phase; M
Quantity Value Units Method Reference Comment
Deltar19.9cal/mol*KPHPMSMeot-Ner, 1984gas phase; M

(Lead ion (1+) bullet Methylamine) + Methylamine = (Lead ion (1+) bullet 2Methylamine)

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

Quantity Value Units Method Reference Comment
Deltar19.1 ± 0.2kcal/molHPMSGuo and Castleman, 1990gas phase; M
Quantity Value Units Method Reference Comment
Deltar19.5cal/mol*KHPMSGuo and Castleman, 1990gas phase; M

Lead ion (1+) + Methylamine = (Lead ion (1+) bullet Methylamine)

By formula: Pb+ + CH5N = (Pb+ bullet CH5N)

Quantity Value Units Method Reference Comment
Deltar35.4 ± 0.3kcal/molHPMSGuo and Castleman, 1990gas phase; M
Quantity Value Units Method Reference Comment
Deltar30.0cal/mol*KHPMSGuo and Castleman, 1990gas phase; M

(CH6N+ bullet 3Methylamine) + Methylamine = (CH6N+ bullet 4Methylamine)

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

Quantity Value Units Method Reference Comment
Deltar7.8kcal/molPHPMSMeot-Ner (Mautner), 1992gas phase; M
Quantity Value Units Method Reference Comment
Deltar21.5cal/mol*KPHPMSMeot-Ner (Mautner), 1992gas phase; M

C2H8N+ + Methylamine = (C2H8N+ bullet Methylamine)

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

Quantity Value Units Method Reference Comment
Deltar22.4kcal/molPHPMSYamdagni and Kebarle, 1973gas phase; M
Quantity Value Units Method Reference Comment
Deltar29.2cal/mol*KPHPMSYamdagni and Kebarle, 1973gas phase; M

C5H11BrMg (solution) + Methylamine (solution) = CH4BrMgN (solution) + Pentane (solution)

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

Quantity Value Units Method Reference Comment
Deltar-31.19 ± 0.60kcal/molRSCHolm, 1983solvent: Diethyl ether; MS

2Methylamine = Dimethylamine + Ammonia

By formula: 2CH5N = C2H7N + H3N

Quantity Value Units Method Reference Comment
Deltar-4.70kcal/molEqkIssoire and Long, 1960gas phase; ALS

2Ethylamine = Methylamine + Methylamine, N,N-dimethyl-

By formula: 2C2H7N = CH5N + C3H9N

Quantity Value Units Method Reference Comment
Deltar-3.15kcal/molEqkIssoire and Long, 1960gas phase; ALS

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry 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]

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]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, References