Methylamine, N,N-dimethyl-
- Formula: C3H9N
- Molecular weight: 59.1103
- IUPAC Standard InChIKey: GETQZCLCWQTVFV-UHFFFAOYSA-N
- CAS Registry Number: 75-50-3
- 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: Trimethylamine; Methanamine, N,N-dimethyl-; TMA; UN 1083; UN 1297
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Ion clustering data
Go To: Top, Mass spectrum (electron ionization), 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:
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
RCD - Robert C. Dunbar
Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.
Clustering reactions
By formula: C3H9Sn+ + C3H9N = (C3H9Sn+ • C3H9N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 45.6 | kcal/mol | PHPMS | Stone and Splinter, 1984 | gas phase; switching reaction((CH3)3Sn+)CH3OH, Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 32. | cal/mol*K | N/A | Stone and Splinter, 1984 | gas phase; switching reaction((CH3)3Sn+)CH3OH, Entropy change calculated or estimated; M |
Free energy of reaction
ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
28.8 | 525. | PHPMS | Stone and Splinter, 1984 | gas phase; switching reaction((CH3)3Sn+)CH3OH, Entropy change calculated or estimated; M |
By formula: C3H10N+ + C3H9N = (C3H10N+ • C3H9N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 22.0 | kcal/mol | PHPMS | El-Shall, Daly, et al., 1992 | gas phase; M |
ΔrH° | 22.0 | kcal/mol | PHPMS | Meot-Ner (Mautner), 1992 | gas phase; M |
ΔrH° | 22.6 | kcal/mol | MKER | Wei, Tzeng, et al., 1991 | gas phase; from graph; M |
ΔrH° | 22.5 | kcal/mol | PHPMS | Yamdagni and Kebarle, 1973 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 27.2 | cal/mol*K | PHPMS | El-Shall, Daly, et al., 1992 | gas phase; M |
ΔrS° | 27.2 | cal/mol*K | PHPMS | Meot-Ner (Mautner), 1992 | gas phase; M |
ΔrS° | 32.0 | cal/mol*K | PHPMS | Yamdagni and Kebarle, 1973 | gas phase; M |
(C3H10N+ • ) + = (C3H10N+ • 2)
By formula: (C3H10N+ • C3H9N) + C3H9N = (C3H10N+ • 2C3H9N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 6.9 | kcal/mol | MKER | Wei, Tzeng, et al., 1991 | gas phase; from graph; M |
(C3H10N+ • 2) + = (C3H10N+ • 3)
By formula: (C3H10N+ • 2C3H9N) + C3H9N = (C3H10N+ • 3C3H9N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 6.5 | kcal/mol | MKER | Wei, Tzeng, et al., 1991 | gas phase; from graph; M |
(C3H10N+ • 3) + = (C3H10N+ • 4)
By formula: (C3H10N+ • 3C3H9N) + C3H9N = (C3H10N+ • 4C3H9N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 8.3 | kcal/mol | MKER | Wei, Tzeng, et al., 1991 | gas phase; from graph; M |
(C3H10N+ • 4) + = (C3H10N+ • 5)
By formula: (C3H10N+ • 4C3H9N) + C3H9N = (C3H10N+ • 5C3H9N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 8.8 | kcal/mol | MKER | Wei, Tzeng, et al., 1991 | gas phase; from graph; M |
(C3H10N+ • 5) + = (C3H10N+ • 6)
By formula: (C3H10N+ • 5C3H9N) + C3H9N = (C3H10N+ • 6C3H9N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 7.4 | kcal/mol | MKER | Wei, Tzeng, et al., 1991 | gas phase; from graph; M |
(C3H10N+ • • ) + = (C3H10N+ • 2 • )
By formula: (C3H10N+ • C3H9N • H2O) + C3H9N = (C3H10N+ • 2C3H9N • H2O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 11.0 | kcal/mol | PHPMS | El-Shall, Daly, et al., 1992 | gas phase; M |
By formula: K+ + C3H9N = (K+ • C3H9N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 20.0 | kcal/mol | HPMS | Davidson and Kebarle, 1976 | gas phase; switching reaction(K+)H2O; Davidson and Kebarle, 1976, 2; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 23.4 | cal/mol*K | HPMS | Davidson and Kebarle, 1976 | gas phase; switching reaction(K+)H2O; Davidson and Kebarle, 1976, 2; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 13.0 | kcal/mol | HPMS | Davidson and Kebarle, 1976 | gas phase; switching reaction(K+)H2O; Davidson and Kebarle, 1976, 2; M |
By formula: Li+ + C3H9N = (Li+ • C3H9N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 42.1 | kcal/mol | ICR | Woodin and Beauchamp, 1978 | gas phase; switching reaction(Li+)H2O, Entropy change calculated or estimated; Dzidic and Kebarle, 1970 extrapolated; M |
ΔrH° | 40. | kcal/mol | ICR | Staley and Beauchamp, 1975 | gas phase; switching reaction(Li+)H2O, from graph; Dzidic and Kebarle, 1970; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 28. | cal/mol*K | N/A | Woodin and Beauchamp, 1978 | gas phase; switching reaction(Li+)H2O, Entropy change calculated or estimated; Dzidic and Kebarle, 1970 extrapolated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 33. | kcal/mol | ICR | Woodin and Beauchamp, 1978 | gas phase; switching reaction(Li+)H2O, Entropy change calculated or estimated; Dzidic and Kebarle, 1970 extrapolated; M |
By formula: Na+ + C3H9N = (Na+ • C3H9N)
Free energy of reaction
ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
19.0 | 298. | IMRE | McMahon and Ohanessian, 2000 | Anchor alanine=39.89; RCD |
Mass spectrum (electron ionization)
Go To: Top, Ion clustering 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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
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Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | Japan AIST/NIMC Database- Spectrum MS-IW-4392 |
NIST MS number | 233394 |
Gas Chromatography
Go To: Top, Ion clustering data, Mass spectrum (electron ionization), 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, polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Packed | PEG-2000 | 152. | 576. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Packed | PEG-2000 | 179. | 570. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Van Den Dool and Kratz RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | HP-5MS | 479. | Bonaiti, Irlinger, et al., 2005 | 30. m/0.25 mm/0.25 μm, He; Program: 5C(8min) => 3C/min => 20C => 10C/min => 150C(10min) |
Van Den Dool and Kratz RI, polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-Wax | 609. | Lee, Suriyaphan, et al., 2001 | 60. m/0.25 mm/0.25 μm, He, 2. K/min; Tstart: 40. C; Tend: 200. C |
Capillary | DB-Wax | 609. | Lee, Suriyaphan, et al., 2001 | 60. m/0.25 mm/0.25 μm, He, 2. K/min; Tstart: 40. C; Tend: 200. C |
Capillary | DB-Wax | 570. | Shimoda, Peralta, et al., 1996 | 60. m/0.25 mm/0.25 μm, He, 3. K/min; Tstart: 50. C; Tend: 230. C |
Van Den Dool and Kratz RI, polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | FFAP | 553. | Ranau and Steinhart, 2005 | 60. m/0.25 mm/0.5 μm, He; Program: 50C(3min) => 3C/min => 100C => 10C/min => 220C (13.5min) |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | OV-101 | 518. | 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 | HP-5 MS | 503. | Kotowska, Zalikowski, et al., 2012 | 30. m/0.25 mm/0.25 μm, Helium; Program: not specified |
Normal alkane RI, polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-Wax | 546. | Rochat, Egger, et al., 2009 | 30. m/0.25 mm/0.25 μm, Helium, 60. C @ 3. min, 8. K/min, 200. C @ 9.5 min |
Capillary | DB-Wax | 554. | Rochat, Egger, et al., 2009 | 30. m/0.25 mm/0.25 μm, Helium, 60. C @ 3. min, 8. K/min, 200. C @ 9.5 min |
Capillary | DB-Wax | 570. | Rochat, Egger, et al., 2009 | 30. m/0.25 mm/0.25 μm, Helium, 60. C @ 3. min, 8. K/min, 200. C @ 9.5 min |
Normal alkane RI, polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-Wax | 561. | Rochat, Egger, et al., 2009 | 30. m/0.25 mm/0.25 μm, Helium; Program: not specified |
Capillary | CP-Wax 52CB | 610. | Muresan, Eillebrecht, et al., 2000 | 50. m/0.32 mm/1.2 μm; Program: 40C(10min) => 3C/min => 190C => 10C/min => 250C(5min) |
References
Go To: Top, Ion clustering data, Mass spectrum (electron ionization), Gas Chromatography, Notes
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]
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]
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]
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]
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]
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]
Bonaiti, Irlinger, et al., 2005
Bonaiti, C.; Irlinger, F.; Spinnler, H.E.; Engel, E.,
An iterative sensory procedure to select odor-active associations in complex consortia of microorganisms: application to the construction of a cheese model,
J. Dairy Sci., 2005, 88, 5, 1671-1684, https://doi.org/10.3168/jds.S0022-0302(05)72839-3
. [all data]
Lee, Suriyaphan, et al., 2001
Lee, G.-H.; Suriyaphan, O.; Cadwallader, K.R.,
Aroma components of cooked tail meat of American lobster (Homarus americanus),
J. Agric. Food Chem., 2001, 49, 9, 4324-4332, https://doi.org/10.1021/jf001523t
. [all data]
Shimoda, Peralta, et al., 1996
Shimoda, M.; Peralta, R.R.; Osajima, Y.,
Headspace gas analysis of fish sauce,
J. Agric. Food Chem., 1996, 44, 11, 3601-3605, https://doi.org/10.1021/jf960345u
. [all data]
Ranau and Steinhart, 2005
Ranau, R.; Steinhart, H.,
Identification and evaluation of volatile odor-active pollutants from different odor emission sources in the food industry,
Eur. Food Res. Technol., 2005, 220, 2, 226-231, https://doi.org/10.1007/s00217-004-1073-4
. [all data]
Zenkevich, 2005
Zenkevich, I.G.,
Experimentally measured retention indices., 2005. [all data]
Kotowska, Zalikowski, et al., 2012
Kotowska, U.; Zalikowski, M.; Isidorov, V.A.,
HS-SPME/GC-MS analysis of volatile and semi-volatile organic compounds emitted from municipal sewage sludge,
Environ. Monit. Asses., 2012, 184, 5, 2893-2907, https://doi.org/10.1007/s10661-011-2158-8
. [all data]
Rochat, Egger, et al., 2009
Rochat, S.; Egger, J.; Chaintreau, A.,
Strategy for the identification of key odorants: application to shrimp aroma,
J. Chromatogr. A, 2009, 1216, 36, 6424-6432, https://doi.org/10.1016/j.chroma.2009.07.014
. [all data]
Muresan, Eillebrecht, et al., 2000
Muresan, S.; Eillebrecht, M.A.J.L.; de Rijk, T.C.; de Jonge, H.G.; Leguijt, T.; Nijhuis, H.H.,
Aroma profile development of intermediate chocolate products. I. Volatile constituents of block-milk,
Food Chem., 2000, 68, 2, 167-174, https://doi.org/10.1016/S0308-8146(99)00171-5
. [all data]
Notes
Go To: Top, Ion clustering data, Mass spectrum (electron ionization), Gas Chromatography, References
- Symbols used in this document:
T Temperature ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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