Methylamine
- Formula: CH5N
- Molecular weight: 31.0571
- IUPAC Standard InChIKey: BAVYZALUXZFZLV-UHFFFAOYSA-N
- CAS Registry Number: 74-89-5
- 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. - Isotopologues:
- Other names: Methanamine; Aminomethane; Carbinamine; Monomethylamine; CH3NH2; Mercurialin; Methylaminen; Metilamine; Metyloamina; UN 1061; MMA
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Gas phase thermochemistry data
Go To: Top, Reaction thermochemistry data, IR Spectrum, 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: Donald R. Burgess, Jr.
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -23.5 | kJ/mol | N/A | Aston, Siller, et al., 1937 | Value computed using ΔfHliquid° value of -47.3±0.46 kj/mol from Aston, Siller, et al., 1937 and ΔvapH° value of 23.85 kj/mol from missing citation. |
ΔfH°gas | -12.2 | kJ/mol | N/A | Lemoult, 1907 | Value computed using ΔfHliquid° value of -36 kj/mol from Lemoult, 1907 and ΔvapH° value of 23.85 kj/mol from missing citation. |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, IR Spectrum, 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
B - John E. Bartmess
MS - José A. Martinho Simões
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
By formula: Li+ + CH5N = (Li+ • CH5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 172. | kJ/mol | ICR | Woodin and Beauchamp, 1978 | gas phase; switching reaction(Li+)H2O, Entropy change calculated or estimated; Dzidic and Kebarle, 1970 interpolated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 110. | J/mol*K | N/A | Woodin and Beauchamp, 1978 | gas phase; switching reaction(Li+)H2O, Entropy change calculated or estimated; Dzidic and Kebarle, 1970 interpolated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 139. | kJ/mol | ICR | Woodin and Beauchamp, 1978 | gas phase; switching reaction(Li+)H2O, Entropy change calculated or estimated; Dzidic and Kebarle, 1970 interpolated; M |
By formula: C3H9Sn+ + CH5N = (C3H9Sn+ • CH5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 176. | kJ/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° | 128. | J/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° (kJ/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
109. | 525. | PHPMS | Stone and Splinter, 1984 | gas phase; switching reaction((CH3)3Sn+)CH3OH, Entropy change calculated or estimated; M |
By formula: K+ + CH5N = (K+ • CH5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 79.9 | kJ/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° | 91.2 | J/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° | 53.1 | kJ/mol | HPMS | Davidson and Kebarle, 1976 | gas phase; switching reaction(K+)H2O; Davidson and Kebarle, 1976, 2; M |
By formula: Na+ + CH5N = (Na+ • CH5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 110. ± 0.8 | kJ/mol | HPMS | Hoyau, Norrman, et al., 1999 | RCD |
ΔrH° | 134. | kJ/mol | HPMS | Guo and Castleman, 1990 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 94600. | J/mol*K | HPMS | Hoyau, Norrman, et al., 1999 | RCD |
ΔrS° | 127. | J/mol*K | HPMS | Guo and Castleman, 1990 | gas phase; M |
Free energy of reaction
ΔrG° (kJ/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
81.6 | 298. | IMRE | McMahon and Ohanessian, 2000 | Anchor alanine=39.89; RCD |
By formula: (CH6N+ • 2CH5N) + CH5N = (CH6N+ • 3CH5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 56.1 | kJ/mol | PHPMS | Meot-Ner (Mautner), 1992 | gas phase; M |
ΔrH° | 71.1 | kJ/mol | HPMS | Holland and Castleman, 1982 | gas phase; Entropy change is questionable; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 105. | J/mol*K | PHPMS | Meot-Ner (Mautner), 1992 | gas phase; M |
ΔrS° | 174. | J/mol*K | HPMS | Holland and Castleman, 1982 | gas phase; Entropy change is questionable; M |
By formula: (CH6N+ • CH5N) + CH5N = (CH6N+ • 2CH5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 66.9 | kJ/mol | PHPMS | Meot-Ner (Mautner), 1992 | gas phase; M |
ΔrH° | 80.3 | kJ/mol | HPMS | Holland and Castleman, 1982 | gas phase; Entropy change is questionable; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 95.8 | J/mol*K | PHPMS | Meot-Ner (Mautner), 1992 | gas phase; M |
ΔrS° | 167. | J/mol*K | HPMS | Holland and Castleman, 1982 | gas phase; Entropy change is questionable; M |
CH4N- + =
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1682. ± 11. | kJ/mol | D-EA | Radisic, Xu, et al., 2002 | gas phase; B |
ΔrH° | 1687.0 ± 3.4 | kJ/mol | G+TS | MacKay, Hemsworth, et al., 1976 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1651. ± 11. | kJ/mol | H-TS | Radisic, Xu, et al., 2002 | gas phase; B |
ΔrG° | 1655.6 ± 2.9 | kJ/mol | IMRE | MacKay, Hemsworth, et al., 1976 | gas phase; B |
By formula: C3H9Si+ + CH5N = (C3H9Si+ • CH5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 232. | kJ/mol | PHPMS | Li and Stone, 1990 | gas phase; switching reaction,Thermochemical ladder((CH3)3Si+)C6H5COOC2H5; Wojtyniak and Stone, 1986; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 159. | J/mol*K | PHPMS | Li and Stone, 1990 | gas phase; switching reaction,Thermochemical ladder((CH3)3Si+)C6H5COOC2H5; Wojtyniak and Stone, 1986; M |
By formula: CH6N+ + CH5N = (CH6N+ • CH5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 106. | kJ/mol | PHPMS | Meot-Ner (Mautner), 1992 | gas phase; M |
ΔrH° | 90.8 | kJ/mol | PHPMS | Yamdagni and Kebarle, 1973 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 114. | J/mol*K | PHPMS | Meot-Ner (Mautner), 1992 | gas phase; M |
ΔrS° | 98.7 | J/mol*K | PHPMS | Yamdagni and Kebarle, 1973 | gas phase; M |
By formula: C6H12NO3+ + CH5N = (C6H12NO3+ • CH5N)
Bond type: Hydrogen bonds with polydentate bonding in positive ions
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 120. | kJ/mol | PHPMS | Meot-Ner, 1984 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 83.3 | J/mol*K | PHPMS | Meot-Ner, 1984 | gas phase; M |
By formula: (Pb+ • CH5N) + CH5N = (Pb+ • 2CH5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 79.9 ± 0.8 | kJ/mol | HPMS | Guo and Castleman, 1990 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 81.6 | J/mol*K | HPMS | Guo and Castleman, 1990 | gas phase; M |
By formula: Pb+ + CH5N = (Pb+ • CH5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 148. ± 1. | kJ/mol | HPMS | Guo and Castleman, 1990 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 126. | J/mol*K | HPMS | Guo and Castleman, 1990 | gas phase; M |
By formula: (CH6N+ • 3CH5N) + CH5N = (CH6N+ • 4CH5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 33. | kJ/mol | PHPMS | Meot-Ner (Mautner), 1992 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 90.0 | J/mol*K | PHPMS | Meot-Ner (Mautner), 1992 | gas phase; M |
By formula: C2H8N+ + CH5N = (C2H8N+ • CH5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 93.7 | kJ/mol | PHPMS | Yamdagni and Kebarle, 1973 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 122. | J/mol*K | PHPMS | Yamdagni and Kebarle, 1973 | gas phase; M |
C5H11BrMg (solution) + (solution) = CH4BrMgN (solution) + (solution)
By formula: C5H11BrMg (solution) + CH5N (solution) = CH4BrMgN (solution) + C5H12 (solution)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -130.5 ± 2.5 | kJ/mol | RSC | Holm, 1983 | solvent: Diethyl ether; MS |
By formula: 2CH5N = C2H7N + H3N
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -19.7 | kJ/mol | Eqk | Issoire and Long, 1960 | gas phase; ALS |
By formula: 2C2H7N = CH5N + C3H9N
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -13.2 | kJ/mol | Eqk | Issoire and Long, 1960 | gas phase; ALS |
IR Spectrum
Go To: Top, Gas phase thermochemistry data, Reaction 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 compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Gas Phase Spectrum
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Additional Data
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Owner | NIST Standard Reference Data Program Collection (C) 2018 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | Sadtler Research Labs Under US-EPA Contract |
State | gas |
Gas Chromatography
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, IR Spectrum, 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 | PMS-100 | 180. | 305. | Anderson, Jurel, et al., 1973 | He, Celite 545 (44-60 mesh); Column length: 3. m |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Methyl Silicone | 380. | Chen and Feng, 2007 | Program: not specified |
Capillary | Polydimethyl siloxanes | 328. | Zenkevich and Chupalov, 1996 | Program: not specified |
References
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, IR Spectrum, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Aston, Siller, et al., 1937
Aston, J.G.; Siller, C.W.; Messerly, G.H.,
Heat capacities and entropies of organic compounds. III. Methylamine from 11.5°K. to the boiling point. Heat of vaporization and vapor pressure. The entropy from molecular data,
J. Am. Chem. Soc., 1937, 59, 1743-17. [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]
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]
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]
Hoyau, Norrman, et al., 1999
Hoyau, S.; Norrman, K.; McMahon, T.B.; Ohanessian, G.,
A Quantitative Basis for a Scale of Na+ Affinities of Organic and Small Biological Molecules in the Gas Phase,
J. Am. Chem. Soc., 1999, 121, 38, 8864, https://doi.org/10.1021/ja9841198
. [all data]
Guo and Castleman, 1990
Guo, B.C.; Castleman, A.W.,
The Association Reactions of Pb+ Ion with CH3OH and CH3NH2 in the Gas Phase,
Int. J. Mass Spectrom. Ion Proc., 1990, 100, 665, https://doi.org/10.1016/0168-1176(90)85101-7
. [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]
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]
Holland and Castleman, 1982
Holland, P.M.; Castleman, A.W.,
The Thermochemical Properties of Gas - Phase Transition Metal Ion Complexes,
J. Chem. Phys., 1982, 76, 8, 4195, https://doi.org/10.1063/1.443497
. [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]
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]
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]
Meot-Ner, 1984
Meot-Ner, (Mautner),
The Ionic Hydrogen Bond. 4. Intramolecular and Multiple Bonds. Proton Affinities, Hydration and Complexes of Amides and Amino Acid Derivatives,
J. Am. Chem. Soc., 1984, 106, 2, 278, https://doi.org/10.1021/ja00314a003
. [all data]
Holm, 1983
Holm, T.,
Acta Chem. Scand. B, 1983, 37, 797. [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]
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]
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]
Zenkevich and Chupalov, 1996
Zenkevich, I.G.; Chupalov, A.A.,
New Possibilities of Chromato Mass Pectrometric Identification of Organic Compounds Using Increments of Gas Chromatographic Retention Indices of Molecular Structural Fragments,
Zh. Org. Khim. (Rus.), 1996, 32, 5, 656-666. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, IR Spectrum, Gas Chromatography, References
- Symbols used in this document:
T Temperature 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 ΔrS° Entropy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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