Dimethylamine
- Formula: C2H7N
- Molecular weight: 45.0837
- IUPAC Standard InChIKey: ROSDSFDQCJNGOL-UHFFFAOYSA-N
- CAS Registry Number: 124-40-3
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript. - Other names: Methanamine, N-methyl-; (CH3)2NH; N-Methylmethanamine; Rcra waste number U092; UN 1032; N,N-Dimethylamine; NSC 8650
- Permanent link for this species. Use this link for bookmarking this species for future reference.
- Information on this page:
- Other data available:
- Data at other public NIST sites:
- Options:
Data at NIST subscription sites:
NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.
Gas phase thermochemistry data
Go To: Top, Gas phase ion energetics data, Gas Chromatography, 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 | -19. ± 2. | kJ/mol | Eqk | Issoire and Long, 1960 | Heat of formation derived by Cox and Pilcher, 1970; ALS |
ΔfH°gas | -23.8 | kJ/mol | N/A | Lemoult, 1907 | Value 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 |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Gas Chromatography, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias
Data compiled as indicated in comments:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
View reactions leading to C2H7N+ (ion structure unspecified)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 8.24 ± 0.08 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 929.5 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 896.5 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.2 ± 0.1 | PE | Aue, Webb, et al., 1980 | LLK |
8.2 | PE | Aue and Bowers, 1979 | LLK |
8.83 | EI | Baldwin, Loudon, et al., 1977 | LLK |
8.2 ± 0.1 | PE | Aue, Webb, et al., 1976 | LLK |
8.30 | PE | Vovna and Vilesov, 1974 | LLK |
8.25 ± 0.02 | PE | Maier and Turner, 1973 | LLK |
8.07 | PE | Cullen, Frost, et al., 1972 | LLK |
8.25 | PE | Cornford, Frost, et al., 1971 | LLK |
8.36 | PE | Al-Joboury and Turner, 1964 | RDSH |
8.24 ± 0.02 | PI | Watanabe and Mottl, 1957 | RDSH |
8.95 | PE | Daamen and Oskam, 1978 | Vertical value; LLK |
8.97 | PE | Kimura and Osafune, 1975 | Vertical value; LLK |
8.85 | PE | Gibbins, Lappert, et al., 1975 | Vertical value; LLK |
8.929 | PE | Aue, Webb, et al., 1975 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
CH3+ | 14.8 | CH3NH | EI | SenSharma and Franklin, 1973 | LLK |
CH4N+ | 10.80 | ? | EI | Loudon and Webb, 1977 | LLK |
C2H3+ | 16.6 ± 0.5 | ? | EI | Gallegos and Kiser, 1962 | RDSH |
C2H6N+ | 9.65 | H | EI | Lossing, Lam, et al., 1981 | LLK |
C2H6N+ | 10.55 | ? | EI | Loudon and Webb, 1977 | LLK |
C2H6N+ | 10.50 | ? | EI | Loudon and Webb, 1977 | LLK |
C2H6N+ | 9.41 ± 0.06 | H | EI | Solka and Russell, 1974 | LLK |
C2H6N+ | 10.1 ± 0.1 | H | EI | Taft, Martin, et al., 1965 | RDSH |
H4N+ | 14.05 ± 0.05 | ? | EI | Haney and Franklin, 1969 | RDSH |
De-protonation reactions
C2H6N- + =
By formula: C2H6N- + H+ = C2H7N
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1653. ± 8.4 | kJ/mol | D-EA | Radisic, Xu, et al., 2002 | gas phase; BDE supported by 72GOL/SOL, over McMillen and Golden, 1982; B |
ΔrH° | 1658.7 ± 3.7 | kJ/mol | G+TS | MacKay, Hemsworth, et al., 1976 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1623. ± 8.8 | kJ/mol | H-TS | Radisic, Xu, et al., 2002 | gas phase; BDE supported by 72GOL/SOL, over McMillen and Golden, 1982; B |
ΔrG° | 1628.4 ± 2.5 | kJ/mol | IMRE | MacKay, Hemsworth, et al., 1976 | gas phase; B |
Gas Chromatography
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics 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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Kovats' RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Packed | Apiezon L | 100. | 405. | Golovnya, Zhuravleva, et al., 1980 | N2, Chromosorb GAW; Column length: 2.7 m |
Packed | Apiezon L | 100. | 434. | Golovnya and Zhuravleva, 1973 | |
Packed | Apiezon L | 130. | 458. | Landault and Guiochon, 1964 | Teflon-Haloport; Column length: 2.26 m |
Kovats' RI, polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Packed | PEG-2000 | 152. | 650. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Packed | PEG-2000 | 179. | 646. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-5 | 426. | Flamini, Luigi Cioni, et al., 2003 | 30. m/0.25 mm/0.25 μm, He, 3. K/min; Tstart: 60. C; Tend: 240. C |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | OV-101 | 425. | Zenkevich, 2005 | 25. m/0.20 mm/0.10 μm, N2/He, 6. K/min; Tstart: 50. C; Tend: 250. C |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Methyl Silicone | 434. | Chen and Feng, 2007 | Program: not specified |
References
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, Gas Chromatography, 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]
Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G.,
Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update,
J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018
. [all data]
Aue, Webb, et al., 1980
Aue, D.H.; Webb, H.M.; Davidson, W.R.; Vidal, M.; Bowers, M.T.; Goldwhite, H.; Vertal, L.E.; Douglas, J.E.; Kollman, P.A.; Kenyon, G.L.,
Proton affinities photoelectron spectra of three-membered-ring J. Heterocycl. Chem.,
J. Am. Chem. Soc., 1980, 102, 5151. [all data]
Aue and Bowers, 1979
Aue, D.H.; Bowers, M.T.,
Chapter 9. Stabilities of positive ions from equilibrium gas phase basicity measurements
in Ions Chemistry,, ed. M.T. Bowers, 1979. [all data]
Baldwin, Loudon, et al., 1977
Baldwin, M.A.; Loudon, A.G.; Webb, K.S.; Cardnell, P.C.,
Charge location and fragmentation under electron impact. V-The ionization potentials of (methylated) phosphoramides, guanidines, formamides, acetamides, ureas and thioureas,
Org. Mass Spectrom., 1977, 12, 279. [all data]
Aue, Webb, et al., 1976
Aue, D.H.; Webb, H.M.; Bowers, M.T.,
Quantitative proton affinities, ionization potentials, and hydrogen affinities of alkylamines,
J. Am. Chem. Soc., 1976, 98, 311. [all data]
Vovna and Vilesov, 1974
Vovna, V.I.; Vilesov, F.I.,
Photoelectron spectra the structure of molecular orbitals of methyl amines,
Opt. Spectrosc., 1974, 36, 251. [all data]
Maier and Turner, 1973
Maier, J.P.; Turner, D.W.,
Steric inhibition of resonance studied by molecular photoelectron spectroscopy Part 3. Anilines, Phenols and Related Compounds,
J. Chem. Soc. Faraday Trans. 2, 1973, 69, 521. [all data]
Cullen, Frost, et al., 1972
Cullen, W.R.; Frost, D.C.; Leeder, W.R.,
The ultraviolet and photoelectron spectra of some unsaturated fluorocarbon derivatives,
J. Fluorine Chem., 1972, 1, 227. [all data]
Cornford, Frost, et al., 1971
Cornford, A.B.; Frost, D.C.; Herring, F.G.; McDowell, C.A.,
Electronic levels of methyl amines by photoelectron spectroscopy and an i.n.d.o. calculation,
Can. J. Chem., 1971, 49, 1135. [all data]
Al-Joboury and Turner, 1964
Al-Joboury, M.I.; Turner, D.W.,
Molecular photoelectron spectroscopy. Part II. A summary of ionization potentials,
J. Chem. Soc., 1964, 4434. [all data]
Watanabe and Mottl, 1957
Watanabe, K.; Mottl, J.R.,
Ionization potentials of ammonia and some amines,
J. Chem. Phys., 1957, 26, 1773. [all data]
Daamen and Oskam, 1978
Daamen, H.; Oskam, A.,
Bonding properties of some monosubstituted chromium and tungsten hexacarbonyls M(CO)5L (L=amine, substituted pyridine, azine),
Inorg. Chim. Acta, 1978, 26, 81. [all data]
Kimura and Osafune, 1975
Kimura, K.; Osafune, K.,
Sum rule consideration on valence orbital ionization energies in methyl amines,
Mol. Phys., 1975, 29, 1073. [all data]
Gibbins, Lappert, et al., 1975
Gibbins, S.G.; Lappert, M.F.; Pedley, J.B.; Sharp, G.J.,
Bonding studies of transition-metal complexes. Part II. Helium-I photoelectron spectra of homoleptic d0, d1, and d10 tetrakis(dialkylamides) of transition group 4B metals tungsten hexakis(dimethylamide),
J. Chem. Soc. Dalton Trans., 1975, 72. [all data]
Aue, Webb, et al., 1975
Aue, D.H.; Webb, H.M.; Bowers, M.T.,
Proton affinities, ionization potentials, and hydrogen affinities of nitrogen and oxygen bases. Hybridization effects,
J. Am. Chem. Soc., 1975, 97, 4137. [all data]
SenSharma and Franklin, 1973
SenSharma, D.K.; Franklin, J.L.,
Heat of formation of free radicals by mass spectrometry,
J. Am. Chem. Soc., 1973, 95, 6562. [all data]
Loudon and Webb, 1977
Loudon, A.G.; Webb, K.S.,
The nature of the [C2H6N]+ and [CH4N]+ ions formed by electron impact on methylated formamides, acetamides, ureas, thioureas and hexamethylphosphoramide,
Org. Mass Spectrom., 1977, 12, 283. [all data]
Gallegos and Kiser, 1962
Gallegos, E.J.; Kiser, R.W.,
Electron impact spectroscopy of the four- and five-membered, saturated heterocyclic compounds containing nitrogen, oxygen and sulfur,
J. Phys. Chem., 1962, 66, 136. [all data]
Lossing, Lam, et al., 1981
Lossing, F.P.; Lam, Y.-T.; Maccoll, A.,
Gas phase heats of formation of alkyl immonium ions,
Can. J. Chem., 1981, 59, 2228. [all data]
Solka and Russell, 1974
Solka, B.H.; Russell, M.E.,
Energetics of formation of some structural isomers of gaseous C2H5O+ C2H6N+ ions,
J. Phys. Chem., 1974, 78, 1268. [all data]
Taft, Martin, et al., 1965
Taft, R.W.; Martin, R.H.; Lampe, F.W.,
Stabilization energies of substituted methyl cations. The effect of strong demand on the resonance order,
J. Am. Chem. Soc., 1965, 87, 2490. [all data]
Haney and Franklin, 1969
Haney, M.A.; Franklin, J.L.,
Heats of formation of H3O+, H3S+, and NH4+ by electron impact,
J. Chem. Phys., 1969, 50, 2028. [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]
Golovnya, Zhuravleva, et al., 1980
Golovnya, R.V.; Zhuravleva, N.L.; Svetlova, N.I.; Grigor'eva, D.N.,
Gas-chromatographic separation of secondary normal alphatic amines,
J. Anal. Chem. USSR (Engl. Transl.), 1980, 35, 10, 1280-1285. [all data]
Golovnya and Zhuravleva, 1973
Golovnya, R.V.; Zhuravleva, I.L.,
Gas Chromatographic Method of Identification of n-Aliphatic Amines Through the Use of Donor-Acceptor Interaction with Phosphate,
Chromatographia, 1973, 6, 12, 508-513, https://doi.org/10.1007/BF02269131
. [all data]
Landault and Guiochon, 1964
Landault, C.; Guiochon, G.,
Separation des amines par chromatographie gaz-liquide en utilisant le teflon comme support,
J. Chromatogr., 1964, 13, 327-336, https://doi.org/10.1016/S0021-9673(01)95126-X
. [all data]
Anderson, Jurel, et al., 1973
Anderson, A.; Jurel, S.; Shymanska, M.; Golender, L.,
Gas-liquid chromatography of some aliphatic and heterocyclic mono- and pollyfunctional amines. VII. Retention indices of amines in some polar and unpolar stationary phases,
Latv. PSR Zinat. Akad. Vestis Kim. Ser., 1973, 1, 51-63. [all data]
Flamini, Luigi Cioni, et al., 2003
Flamini, G.; Luigi Cioni, P.; Morelli, I.,
Volatiles from leaves, fruits, and virgin oil from Olea europaea Cv. Olivastra Seggianese from Italy,
J. Agric. Food Chem., 2003, 51, 5, 1382-1386, https://doi.org/10.1021/jf020854y
. [all data]
Zenkevich, 2005
Zenkevich, I.G.,
Experimentally measured retention indices., 2005. [all data]
Chen and Feng, 2007
Chen, Y.; Feng, C.,
QSPR study on gas chromatography retention index of some organic pollutants,
Comput. Appl. Chem. (China), 2007, 24, 10, 1404-1408. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, Gas Chromatography, References
- Symbols used in this document:
AE Appearance energy IE (evaluated) Recommended ionization energy ΔfH°gas Enthalpy of formation of gas at standard conditions ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
- The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
- Customer support for NIST Standard Reference Data products.