Dimethylamine

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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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.

Quantity Value Units Method Reference Comment
ΔfH°gas-4.7 ± 0.5kcal/molEqkIssoire and Long, 1960Heat of formation derived by Cox and Pilcher, 1970; ALS
ΔfH°gas-5.69kcal/molN/ALemoult, 1907Value computed using ΔfHliquid° value of -49.8 kj/mol from Lemoult, 1907 and ΔvapH° value of 26.0 kj/mol from Issoire and Long, 1960.; DRB

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
ΔfH°liquid-10.7 ± 0.5kcal/molEqkIssoire and Long, 1960Heat of formation derived by Cox and Pilcher, 1970; ALS
ΔfH°liquid-11.9kcal/molCcbLemoult, 1907ALS
Quantity Value Units Method Reference Comment
ΔcH°liquid-428.2kcal/molCcbMuller, 1910At 288 K; ALS
ΔcH°liquid-418.2kcal/molCcbLemoult, 1907ALS
Quantity Value Units Method Reference Comment
S°liquid41.551cal/mol*KN/AAston, Eidinoff, et al., 1939Saturated liquid at boiling point.; DH

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference Comment
32.689280.44Aston, Eidinoff, et al., 1939T = 14 to 280 K. Value for saturated liquid.; 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
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

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.

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]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [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]

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, Eidinoff, et al., 1939
Aston, J.G.; Eidinoff, M.L.; Forster, W.S., The heat capacity and entropy, heats of fusion and vaporization and the vapor pressure of dimethylamine, J. Am. Chem. Soc., 1939, 61, 1539-1543. [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]

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]

Notes

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