Methylamine, N,N-dimethyl-

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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 as indicated in comments:
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
B - John E. Bartmess
RCD - Robert C. Dunbar
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, N,N-dimethyl- = (Lithium ion (1+) • Methylamine, N,N-dimethyl-)

By formula: Li+ + C3H9N = (Li+ • C3H9N)

Quantity Value Units Method Reference Comment
Δr42.1kcal/molICRWoodin and Beauchamp, 1978gas phase; switching reaction(Li+)H2O, Entropy change calculated or estimated; Dzidic and Kebarle, 1970 extrapolated; M
Δr40.kcal/molICRStaley and Beauchamp, 1975gas phase; switching reaction(Li+)H2O, from graph; Dzidic and Kebarle, 1970; M
Quantity Value Units Method Reference Comment
Δr28.cal/mol*KN/AWoodin and Beauchamp, 1978gas phase; switching reaction(Li+)H2O, Entropy change calculated or estimated; Dzidic and Kebarle, 1970 extrapolated; M
Quantity Value Units Method Reference Comment
Δr33.kcal/molICRWoodin and Beauchamp, 1978gas phase; switching reaction(Li+)H2O, Entropy change calculated or estimated; Dzidic and Kebarle, 1970 extrapolated; M

C3H10N+ + Methylamine, N,N-dimethyl- = (C3H10N+ • Methylamine, N,N-dimethyl-)

By formula: C3H10N+ + C3H9N = (C3H10N+ • C3H9N)

Quantity Value Units Method Reference Comment
Δr22.0kcal/molPHPMSEl-Shall, Daly, et al., 1992gas phase; M
Δr22.0kcal/molPHPMSMeot-Ner (Mautner), 1992gas phase; M
Δr22.6kcal/molMKERWei, Tzeng, et al., 1991gas phase; from graph; M
Δr22.5kcal/molPHPMSYamdagni and Kebarle, 1973gas phase; M
Quantity Value Units Method Reference Comment
Δr27.2cal/mol*KPHPMSEl-Shall, Daly, et al., 1992gas phase; M
Δr27.2cal/mol*KPHPMSMeot-Ner (Mautner), 1992gas phase; M
Δr32.0cal/mol*KPHPMSYamdagni and Kebarle, 1973gas phase; M

C3H9Sn+ + Methylamine, N,N-dimethyl- = (C3H9Sn+ • Methylamine, N,N-dimethyl-)

By formula: C3H9Sn+ + C3H9N = (C3H9Sn+ • C3H9N)

Quantity Value Units Method Reference Comment
Δr45.6kcal/molPHPMSStone and Splinter, 1984gas phase; switching reaction((CH3)3Sn+)CH3OH, Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr32.cal/mol*KN/AStone and Splinter, 1984gas phase; switching reaction((CH3)3Sn+)CH3OH, Entropy change calculated or estimated; M

Free energy of reaction

ΔrG° (kcal/mol) T (K) Method Reference Comment
28.8525.PHPMSStone and Splinter, 1984gas phase; switching reaction((CH3)3Sn+)CH3OH, Entropy change calculated or estimated; M

(C3H10N+ • Water • Methylamine, N,N-dimethyl-) + Water = (C3H10N+ • 2Water • Methylamine, N,N-dimethyl-)

By formula: (C3H10N+ • H2O • C3H9N) + H2O = (C3H10N+ • 2H2O • C3H9N)

Quantity Value Units Method Reference Comment
Δr8.1kcal/molPHPMSEl-Shall, Daly, et al., 1992gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr25.cal/mol*KN/AEl-Shall, Daly, et al., 1992gas phase; Entropy change calculated or estimated; M

Free energy of reaction

ΔrG° (kcal/mol) T (K) Method Reference Comment
2.5225.PHPMSEl-Shall, Daly, et al., 1992gas phase; Entropy change calculated or estimated; M

Potassium ion (1+) + Methylamine, N,N-dimethyl- = (Potassium ion (1+) • Methylamine, N,N-dimethyl-)

By formula: K+ + C3H9N = (K+ • C3H9N)

Quantity Value Units Method Reference Comment
Δr20.0kcal/molHPMSDavidson and Kebarle, 1976gas phase; switching reaction(K+)H2O; Davidson and Kebarle, 1976, 2; M
Quantity Value Units Method Reference Comment
Δr23.4cal/mol*KHPMSDavidson and Kebarle, 1976gas phase; switching reaction(K+)H2O; Davidson and Kebarle, 1976, 2; M
Quantity Value Units Method Reference Comment
Δr13.0kcal/molHPMSDavidson and Kebarle, 1976gas phase; switching reaction(K+)H2O; Davidson and Kebarle, 1976, 2; M

C3H8N- + Hydrogen cation = Methylamine, N,N-dimethyl-

By formula: C3H8N- + H+ = C3H9N

Quantity Value Units Method Reference Comment
Δr>406.22 ± 0.60kcal/molG+TSMacKay and Bohme, 1978gas phase; Computations put dHacid ca. 412 kcal/mol; B
Quantity Value Units Method Reference Comment
Δr>398.00kcal/molIMRBMacKay and Bohme, 1978gas phase; Computations put dHacid ca. 412 kcal/mol; B

(C3H10N+ • Methylamine, N,N-dimethyl-) + Methyl Alcohol = (C3H10N+ • Methyl Alcohol • Methylamine, N,N-dimethyl-)

By formula: (C3H10N+ • C3H9N) + CH4O = (C3H10N+ • CH4O • C3H9N)

Bond type: Hydrogen bonds of the type NH+-O between organics

Quantity Value Units Method Reference Comment
Δr10.6kcal/molPHPMSEl-Shall, Daly, et al., 1992gas phase; M
Quantity Value Units Method Reference Comment
Δr25.2cal/mol*KPHPMSEl-Shall, Daly, et al., 1992gas phase; M

(C3H10N+ • 2Methylamine, N,N-dimethyl-) + Water = (C3H10N+ • Water • 2Methylamine, N,N-dimethyl-)

By formula: (C3H10N+ • 2C3H9N) + H2O = (C3H10N+ • H2O • 2C3H9N)

Bond type: Hydrogen bond (positive ion to hydride)

Quantity Value Units Method Reference Comment
Δr8.9kcal/molPHPMSEl-Shall, Daly, et al., 1992gas phase; M
Quantity Value Units Method Reference Comment
Δr24.3cal/mol*KPHPMSEl-Shall, Daly, et al., 1992gas phase; M

(C3H10N+ • Methyl Alcohol • Methylamine, N,N-dimethyl-) + Methyl Alcohol = (C3H10N+ • 2Methyl Alcohol • Methylamine, N,N-dimethyl-)

By formula: (C3H10N+ • CH4O • C3H9N) + CH4O = (C3H10N+ • 2CH4O • C3H9N)

Bond type: Hydrogen bonds of the type NH+-O between organics

Quantity Value Units Method Reference Comment
Δr9.5kcal/molPHPMSEl-Shall, Daly, et al., 1992gas phase; M

(C3H10N+ • Methylamine, N,N-dimethyl- • Water) + Methylamine, N,N-dimethyl- = (C3H10N+ • 2Methylamine, N,N-dimethyl- • Water)

By formula: (C3H10N+ • C3H9N • H2O) + C3H9N = (C3H10N+ • 2C3H9N • H2O)

Quantity Value Units Method Reference Comment
Δr11.0kcal/molPHPMSEl-Shall, Daly, et al., 1992gas phase; M

(C3H10N+ • 2Methylamine, N,N-dimethyl-) + Methylamine, N,N-dimethyl- = (C3H10N+ • 3Methylamine, N,N-dimethyl-)

By formula: (C3H10N+ • 2C3H9N) + C3H9N = (C3H10N+ • 3C3H9N)

Quantity Value Units Method Reference Comment
Δr6.5kcal/molMKERWei, Tzeng, et al., 1991gas phase; from graph; M

(C3H10N+ • 3Methylamine, N,N-dimethyl-) + Methylamine, N,N-dimethyl- = (C3H10N+ • 4Methylamine, N,N-dimethyl-)

By formula: (C3H10N+ • 3C3H9N) + C3H9N = (C3H10N+ • 4C3H9N)

Quantity Value Units Method Reference Comment
Δr8.3kcal/molMKERWei, Tzeng, et al., 1991gas phase; from graph; M

(C3H10N+ • 4Methylamine, N,N-dimethyl-) + Methylamine, N,N-dimethyl- = (C3H10N+ • 5Methylamine, N,N-dimethyl-)

By formula: (C3H10N+ • 4C3H9N) + C3H9N = (C3H10N+ • 5C3H9N)

Quantity Value Units Method Reference Comment
Δr8.8kcal/molMKERWei, Tzeng, et al., 1991gas phase; from graph; M

(C3H10N+ • 5Methylamine, N,N-dimethyl-) + Methylamine, N,N-dimethyl- = (C3H10N+ • 6Methylamine, N,N-dimethyl-)

By formula: (C3H10N+ • 5C3H9N) + C3H9N = (C3H10N+ • 6C3H9N)

Quantity Value Units Method Reference Comment
Δr7.4kcal/molMKERWei, Tzeng, et al., 1991gas phase; from graph; M

Sodium ion (1+) + Methylamine, N,N-dimethyl- = (Sodium ion (1+) • Methylamine, N,N-dimethyl-)

By formula: Na+ + C3H9N = (Na+ • C3H9N)

Free energy of reaction

ΔrG° (kcal/mol) T (K) Method Reference Comment
19.0298.IMREMcMahon and Ohanessian, 2000Anchor alanine=39.89; RCD

(C3H10N+ • Methylamine, N,N-dimethyl-) + Methylamine, N,N-dimethyl- = (C3H10N+ • 2Methylamine, N,N-dimethyl-)

By formula: (C3H10N+ • C3H9N) + C3H9N = (C3H10N+ • 2C3H9N)

Quantity Value Units Method Reference Comment
Δr6.9kcal/molMKERWei, Tzeng, et al., 1991gas phase; from graph; M

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

By formula: 2C2H7N = CH5N + C3H9N

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

References

Go To: Top, Reaction thermochemistry data, 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]

Staley and Beauchamp, 1975
Staley, R.H.; Beauchamp, J.L., Intrinsic Acid - Base Properties of Molecules. Binding Energies of Li+ to pi - and n - Donor Bases, J. Am. Chem. Soc., 1975, 97, 20, 5920, https://doi.org/10.1021/ja00853a050 . [all data]

El-Shall, Daly, et al., 1992
El-Shall, M.S.; Daly, G.M.; Gao, J.; Meot-Ner (Mautner), M.; Sieck, L.W., How Sensitive are Cluster Compositions to Energetics? A Joint Beam Expansion/ Thermochemical Study of Water - Methanol - Trimethylamine Clusters, J. Phys. Chem., 1992, 96, 2, 507, https://doi.org/10.1021/j100181a002 . [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]

Wei, Tzeng, et al., 1991
Wei, S.; Tzeng, W.B.; Castleman, A.W., Structure of protonated solvation complexes - ammonia trimethylamine cluster ions and their metastable decompositions, J. Phys. Chem., 1991, 95, 2, 585, https://doi.org/10.1021/j100155a019 . [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]

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]

MacKay and Bohme, 1978
MacKay, G.I.; Bohme, D.K., Proton-Transfer Reactions in Nitromethane at 297K, Int. J. Mass Spectrom. Ion Phys., 1978, 26, 4, 327, https://doi.org/10.1016/0020-7381(78)80052-7 . [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]

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

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