Dimethylamine

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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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
RCD - Robert C. Dunbar

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

C3H9Sn+ + Dimethylamine = (C3H9Sn+ • Dimethylamine)

By formula: C3H9Sn+ + C2H7N = (C3H9Sn+ • C2H7N)

Quantity Value Units Method Reference Comment
ΔrH°44.2kcal/molPHPMSStone and Splinter, 1984gas phase; switching reaction((CH3)3Sn+)CH3OH, Entropy change calculated or estimated; M
ΔrH°44.1kcal/molPHPMSStone and Splinter, 1984gas phase; switching reaction((CH3)3Sn+)CH3OH, Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
ΔrS°30.3cal/mol*KN/AStone and Splinter, 1984gas phase; switching reaction((CH3)3Sn+)CH3OH, Entropy change calculated or estimated; M
ΔrS°31.8cal/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
28.3525.PHPMSStone and Splinter, 1984gas phase; switching reaction((CH3)3Sn+)CH3OH, Entropy change calculated or estimated; M
27.4525.PHPMSStone and Splinter, 1984gas phase; switching reaction((CH3)3Sn+)CH3OH, Entropy change calculated or estimated; M

Lithium ion (1+) + Dimethylamine = (Lithium ion (1+) • Dimethylamine)

By formula: Li+ + C2H7N = (Li+ • C2H7N)

Quantity Value Units Method Reference Comment
ΔrH°42.2kcal/molICRWoodin 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
ΔrS°27.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
ΔrG°34.1kcal/molICRWoodin and Beauchamp, 1978gas phase; switching reaction(Li+)H2O, Entropy change calculated or estimated; Dzidic and Kebarle, 1970 extrapolated; M

C2H6N- + Hydrogen cation = Dimethylamine

By formula: C2H6N- + H+ = C2H7N

Quantity Value Units Method Reference Comment
ΔrH°395.1 ± 2.0kcal/molD-EARadisic, Xu, et al., 2002gas phase; BDE supported by 72GOL/SOL, over McMillen and Golden, 1982; B
ΔrH°396.44 ± 0.89kcal/molG+TSMacKay, Hemsworth, et al., 1976gas phase; B
Quantity Value Units Method Reference Comment
ΔrG°387.9 ± 2.1kcal/molH-TSRadisic, Xu, et al., 2002gas phase; BDE supported by 72GOL/SOL, over McMillen and Golden, 1982; B
ΔrG°389.20 ± 0.60kcal/molIMREMacKay, Hemsworth, et al., 1976gas phase; B

C3H9Si+ + Dimethylamine = (C3H9Si+ • Dimethylamine)

By formula: C3H9Si+ + C2H7N = (C3H9Si+ • C2H7N)

Quantity Value Units Method Reference Comment
ΔrH°60.0kcal/molPHPMSLi and Stone, 1990gas phase; switching reaction,Thermochemical ladder((CH3)3Si+)C6H5COOC2H5; Wojtyniak and Stone, 1986; M
Quantity Value Units Method Reference Comment
ΔrS°42.7cal/mol*KPHPMSLi and Stone, 1990gas phase; switching reaction,Thermochemical ladder((CH3)3Si+)C6H5COOC2H5; Wojtyniak and Stone, 1986; M

C2H8N+ + Dimethylamine = (C2H8N+ • Dimethylamine)

By formula: C2H8N+ + C2H7N = (C2H8N+ • C2H7N)

Quantity Value Units Method Reference Comment
ΔrH°24.1kcal/molPHPMSMeot-Ner (Mautner), 1992gas phase; M
ΔrH°20.8kcal/molPHPMSYamdagni and Kebarle, 1973gas phase; M
Quantity Value Units Method Reference Comment
ΔrS°28.1cal/mol*KPHPMSMeot-Ner (Mautner), 1992gas phase; M
ΔrS°25.7cal/mol*KPHPMSYamdagni and Kebarle, 1973gas phase; M

(C2H8N+ • 2Dimethylamine) + Dimethylamine = (C2H8N+ • 3Dimethylamine)

By formula: (C2H8N+ • 2C2H7N) + C2H7N = (C2H8N+ • 3C2H7N)

Quantity Value Units Method Reference Comment
ΔrH°9.9kcal/molPHPMSMeot-Ner (Mautner), 1992gas phase; M
Quantity Value Units Method Reference Comment
ΔrS°26.1cal/mol*KPHPMSMeot-Ner (Mautner), 1992gas phase; M

(C2H8N+ • 3Dimethylamine) + Dimethylamine = (C2H8N+ • 4Dimethylamine)

By formula: (C2H8N+ • 3C2H7N) + C2H7N = (C2H8N+ • 4C2H7N)

Quantity Value Units Method Reference Comment
ΔrH°7.9kcal/molPHPMSMeot-Ner (Mautner), 1992gas phase; M
Quantity Value Units Method Reference Comment
ΔrS°22.5cal/mol*KPHPMSMeot-Ner (Mautner), 1992gas phase; M

(C2H8N+ • 4Dimethylamine) + Dimethylamine = (C2H8N+ • 5Dimethylamine)

By formula: (C2H8N+ • 4C2H7N) + C2H7N = (C2H8N+ • 5C2H7N)

Quantity Value Units Method Reference Comment
ΔrH°6.3kcal/molPHPMSMeot-Ner (Mautner), 1992gas phase; M
Quantity Value Units Method Reference Comment
ΔrS°22.5cal/mol*KPHPMSMeot-Ner (Mautner), 1992gas phase; M

(C2H8N+ • Dimethylamine) + Dimethylamine = (C2H8N+ • 2Dimethylamine)

By formula: (C2H8N+ • C2H7N) + C2H7N = (C2H8N+ • 2C2H7N)

Quantity Value Units Method Reference Comment
ΔrH°16.4kcal/molPHPMSMeot-Ner (Mautner), 1992gas phase; M
Quantity Value Units Method Reference Comment
ΔrS°27.2cal/mol*KPHPMSMeot-Ner (Mautner), 1992gas phase; M

C3H10N+ + Dimethylamine = (C3H10N+ • Dimethylamine)

By formula: C3H10N+ + C2H7N = (C3H10N+ • C2H7N)

Quantity Value Units Method Reference Comment
ΔrH°20.5kcal/molPHPMSYamdagni and Kebarle, 1973gas phase; M
Quantity Value Units Method Reference Comment
ΔrS°28.5cal/mol*KPHPMSYamdagni and Kebarle, 1973gas phase; M

Potassium ion (1+) + Dimethylamine = (Potassium ion (1+) • Dimethylamine)

By formula: K+ + C2H7N = (K+ • C2H7N)

Quantity Value Units Method Reference Comment
ΔrH°19.5kcal/molHPMSDavidson and Kebarle, 1976gas phase; M
Quantity Value Units Method Reference Comment
ΔrS°21.4cal/mol*KHPMSDavidson and Kebarle, 1976gas phase; M

(dimethylamino)methanol = Dimethylamine + Formaldehyde

By formula: C3H9NO = C2H7N + CH2O

Quantity Value Units Method Reference Comment
ΔrH°30.2 ± 0.2kcal/molCmRogers and Rapiejko, 1974liquid phase; Heat of formation derived by 77PED/RYL; ALS

Sodium ion (1+) + Dimethylamine = (Sodium ion (1+) • Dimethylamine)

By formula: Na+ + C2H7N = (Na+ • C2H7N)

Free energy of reaction

ΔrG° (kcal/mol) T (K) Method Reference Comment
19.6298.IMREMcMahon and Ohanessian, 2000Anchor alanine=39.89; RCD

1-(4-chlorophenyl)-1,3-dimethylurea = Benzene, 1-chloro-4-isocyanato- + Dimethylamine

By formula: C9H11ClN2O = C7H4ClNO + C2H7N

Quantity Value Units Method Reference Comment
ΔrH°37.05 ± 0.60kcal/molEqkChimishkyan, Svetlova, et al., 1984solid phase; Dissociation; ALS

N,N-Dimethyl-N'-p-methylphenylurea = Dimethylamine + Benzene, 1-isocyanato-4-methyl-

By formula: C10H14N2O = C2H7N + C8H7NO

Quantity Value Units Method Reference Comment
ΔrH°30.7 ± 0.1kcal/molEqkChimishkyan, Svetlova, et al., 1984solid phase; Dissociation; ALS

3-(4-Methoxyphenyl)-1,1-dimethylurea = Dimethylamine + Benzene, 1-isocyanato-4-methoxy-

By formula: C10H14N2O2 = C2H7N + C8H7NO2

Quantity Value Units Method Reference Comment
ΔrH°22.8 ± 0.2kcal/molEqkChimishkyan, Svetlova, et al., 1984solid phase; Dissociation; ALS

Urea, N'-(3-chlorophenyl)-N,N-dimethyl- = Dimethylamine + Benzene, 1-chloro-3-isocyanato-

By formula: C9H11ClN2O = C2H7N + C7H4ClNO

Quantity Value Units Method Reference Comment
ΔrH°35.37 ± 0.43kcal/molEqkChimishkyan, Svetlova, et al., 1984solid phase; Dissociation; ALS

Fluometuron = Dimethylamine + Benzene, 1-isocyanato-3-(trifluoromethyl)-

By formula: C10H11F3N2O = C2H7N + C8H4F3NO

Quantity Value Units Method Reference Comment
ΔrH°36.35 ± 0.67kcal/molEqkChimishkyan, Svetlova, et al., 1984solid phase; Dissociation; ALS

Diuron = Benzene, 1,2-dichloro-4-isocyanato- + Dimethylamine

By formula: C9H10Cl2N2O = C7H3Cl2NO + C2H7N

Quantity Value Units Method Reference Comment
ΔrH°28.32 ± 0.55kcal/molEqkChimishkyan, Svetlova, et al., 1984solid phase; Dissociation; ALS

Allyl chloride + 2Dimethylamine = N-Allyl-N,N-dimethylamine + Dimethylamine hydrochloride

By formula: C3H5Cl + 2C2H7N = C5H11N + C2H8ClN

Quantity Value Units Method Reference Comment
ΔrH°-19.74 ± 0.09kcal/molCmBeldie, Aelenei, et al., 1982liquid phase; ALS

N,N-Dimethyl-N'-m-methylphenylurea = Dimethylamine + Benzene, 1-isocyanato-3-methyl-

By formula: C10H14N2O = C2H7N + C8H7NO

Quantity Value Units Method Reference Comment
ΔrH°26.27kcal/molEqkChimishkyan, Svetlova, et al., 1984solid phase; Dissociation; ALS

2Dimethylamine + Formaldehyde = Methanediamine, N,N,N',N'-tetramethyl- + Water

By formula: 2C2H7N + CH2O = C5H14N2 + H2O

Quantity Value Units Method Reference Comment
ΔrH°-45.6 ± 0.6kcal/molCmRogers and Rapiejko, 1974gas phase; ALS

Fenuron = Benzene, isocyanato- + Dimethylamine

By formula: C9H12N2O = C7H5NO + C2H7N

Quantity Value Units Method Reference Comment
ΔrH°32.07 ± 0.69kcal/molEqkChimishkyan, Svetlova, et al., 1984solid phase; ALS

Dimethylamine + Formaldehyde = (dimethylamino)methanol

By formula: C2H7N + CH2O = C3H9NO

Quantity Value Units Method Reference Comment
ΔrH°-30.2 ± 0.2kcal/molCmRogers and Rapiejko, 1974gas phase; ALS

2Methylamine = Dimethylamine + Ammonia

By formula: 2CH5N = C2H7N + H3N

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

References

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

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]

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]

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]

McMillen and Golden, 1982
McMillen, D.F.; Golden, D.M., Hydrocarbon bond dissociation energies, Ann. Rev. Phys. Chem., 1982, 33, 493. [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]

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]

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]

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]

Rogers and Rapiejko, 1974
Rogers, F.E.; Rapiejko, R.J., Thermochemistry of carbonyl addition reactions. II. Enthalpy of addition of dimethylamine to formaldehyde, J. Phys. Chem., 1974, 78, 599-603. [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]

Chimishkyan, Svetlova, et al., 1984
Chimishkyan, A.L.; Svetlova, L.P.; Leonova, T.V.; Gluyaev, N.D., Thermal decomposition of substituted ureas, J. Gen. Chem. USSR, 1984, 54, 1317-1320. [all data]

Beldie, Aelenei, et al., 1982
Beldie, C.; Aelenei, N.; Onu, A.; Nemtoi, G., Thermochemical characterization of the reactions involved in the allyldimethylamine synthesis, Rev. Chim. (Bucharest), 1982, 33, 917-919. [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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