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, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible 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 | -5.62 | kcal/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 | -2.92 | kcal/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. |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible 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:
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ΔfH°liquid | -11.3 ± 0.11 | kcal/mol | N/A | Cox and Pilcher, 1970 | Review; Unpublished work J. Jaffe; ALS |
ΔfH°liquid | -11.3 ± 0.11 | kcal/mol | Ccb | Aston, Siller, et al., 1937 | Unpublished work J. Jaffe; ALS |
ΔfH°liquid | -8.7 | kcal/mol | Ccb | Lemoult, 1907 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -253.54 ± 0.09 | kcal/mol | N/A | Cox and Pilcher, 1970 | Review; Unpublished work J. Jaffe; ALS |
ΔcH°liquid | -253.54 ± 0.09 | kcal/mol | Ccb | Aston, Siller, et al., 1937 | Unpublished work J. Jaffe; ALS |
ΔcH°liquid | -261.4 | kcal/mol | Ccb | Muller, 1910 | At 288 K; ALS |
ΔcH°liquid | -256.9 | kcal/mol | Ccb | Lemoult, 1907 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 35.90 | cal/mol*K | N/A | Aston, Siller, et al., 1937, 2 | For superheated liquid, using extrapolated heat capacities.; DH |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
24.331 | 259.28 | Aston, Siller, et al., 1937, 2 | T = 14 to 259 K. Value is unsmoothed experimental datum.; DH |
Phase change data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible 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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
DH - Eugene S. Domalski and Elizabeth D. Hearing
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 266.8 ± 0.3 | K | AVG | N/A | Average of 8 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 180.05 | K | N/A | Roberts, Emeleus, et al., 1939 | Uncertainty assigned by TRC = 0.4 K; TRC |
Tfus | 180.05 | K | N/A | Emeleus and Briscoe, 1937 | Uncertainty assigned by TRC = 0.3 K; TRC |
Tfus | 179.7 | K | N/A | McNeight and Smyth, 1936 | Uncertainty assigned by TRC = 0.07 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 179.7 | K | N/A | Aston, Siller, et al., 1937, 3 | Uncertainty assigned by TRC = 0.07 K; T0/K=273.16; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 430.85 | K | N/A | Li and Kiran, 1988 | Uncertainty assigned by TRC = 0.5 K; TRC |
Tc | 430.7 | K | N/A | Kay and Young, 1974 | Uncertainty assigned by TRC = 0.2 K; TRC |
Tc | 430.05 | K | N/A | Berthoud, 1917 | Uncertainty assigned by TRC = 0.7 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 75.50 | atm | N/A | Li and Kiran, 1988 | Uncertainty assigned by TRC = 0.987 atm; TRC |
Pc | 75.14 | atm | N/A | Kay and Young, 1974 | Uncertainty assigned by TRC = 0.04 atm; TRC |
Pc | 73.6000 | atm | N/A | Berthoud, 1917 | Uncertainty assigned by TRC = 0.6000 atm; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Vc | 0.1385 | l/mol | N/A | Li and Kiran, 1988 | Uncertainty assigned by TRC = 0.001 l/mol; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 5.700 | kcal/mol | N/A | Majer and Svoboda, 1985 |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
6.1690 | 266.84 | N/A | Aston, Siller, et al., 1937, 2 | DH |
6.12 | 266.8 | N/A | Majer and Svoboda, 1985 | |
5.93 | 334. | A | Stephenson and Malanowski, 1987 | Based on data from 319. to 381. K.; AC |
5.62 | 388. | A | Stephenson and Malanowski, 1987 | Based on data from 373. to 430. K.; AC |
6.24 | 278. | A | Stephenson and Malanowski, 1987 | Based on data from 263. to 329. K.; AC |
6.50 | 258. | A | Stephenson and Malanowski, 1987 | Based on data from 223. to 273. K. See also Dykyj, 1970.; AC |
6.169 ± 0.030 | 266.84 | V | Aston, Siller, et al., 1937 | ALS |
6.55 | 252. | N/A | Aston, Siller, et al., 1937, 2 | Based on data from 190. to 267. K. See also Boublik, Fried, et al., 1984.; AC |
Entropy of vaporization
ΔvapS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
23.12 | 266.84 | Aston, Siller, et al., 1937, 2 | DH |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
190.06 to 266.92 | 4.514 | 1034.977 | -37.574 | Aston, Siller, et al., 1937, 2 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
1.466 | 179.70 | Aston, Siller, et al., 1937, 2 | DH |
1.47 | 179.7 | Domalski and Hearing, 1996 | AC |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
8.157 | 179.70 | Aston, Siller, et al., 1937, 2 | DH |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible 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° | 41.1 | kcal/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° | 26. | cal/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° | 33.3 | kcal/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° | 42.1 | 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° | 30.7 | 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 |
---|---|---|---|---|
26.0 | 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° | 19.1 | 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° | 21.8 | 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° | 12.7 | kcal/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° | 26.3 ± 0.2 | kcal/mol | HPMS | Hoyau, Norrman, et al., 1999 | RCD |
ΔrH° | 32.1 | kcal/mol | HPMS | Guo and Castleman, 1990 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 22600. | cal/mol*K | HPMS | Hoyau, Norrman, et al., 1999 | RCD |
ΔrS° | 30.3 | cal/mol*K | HPMS | Guo and Castleman, 1990 | gas phase; M |
Free energy of reaction
ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
19.5 | 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° | 13.4 | kcal/mol | PHPMS | Meot-Ner (Mautner), 1992 | gas phase; M |
ΔrH° | 17.0 | kcal/mol | HPMS | Holland and Castleman, 1982 | gas phase; Entropy change is questionable; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 25.1 | cal/mol*K | PHPMS | Meot-Ner (Mautner), 1992 | gas phase; M |
ΔrS° | 41.6 | cal/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° | 16.0 | kcal/mol | PHPMS | Meot-Ner (Mautner), 1992 | gas phase; M |
ΔrH° | 19.2 | kcal/mol | HPMS | Holland and Castleman, 1982 | gas phase; Entropy change is questionable; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 22.9 | cal/mol*K | PHPMS | Meot-Ner (Mautner), 1992 | gas phase; M |
ΔrS° | 39.9 | cal/mol*K | HPMS | Holland and Castleman, 1982 | gas phase; Entropy change is questionable; M |
CH4N- + =
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 402.0 ± 2.6 | kcal/mol | D-EA | Radisic, Xu, et al., 2002 | gas phase; B |
ΔrH° | 403.21 ± 0.82 | kcal/mol | G+TS | MacKay, Hemsworth, et al., 1976 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 394.5 ± 2.7 | kcal/mol | H-TS | Radisic, Xu, et al., 2002 | gas phase; B |
ΔrG° | 395.70 ± 0.70 | kcal/mol | IMRE | MacKay, Hemsworth, et al., 1976 | gas phase; B |
By formula: C3H9Si+ + CH5N = (C3H9Si+ • CH5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 55.4 | kcal/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° | 38.1 | cal/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° | 25.4 | kcal/mol | PHPMS | Meot-Ner (Mautner), 1992 | gas phase; M |
ΔrH° | 21.7 | kcal/mol | PHPMS | Yamdagni and Kebarle, 1973 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 27.3 | cal/mol*K | PHPMS | Meot-Ner (Mautner), 1992 | gas phase; M |
ΔrS° | 23.6 | cal/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° | 28.6 | kcal/mol | PHPMS | Meot-Ner, 1984 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 19.9 | cal/mol*K | PHPMS | Meot-Ner, 1984 | gas phase; M |
By formula: (Pb+ • CH5N) + CH5N = (Pb+ • 2CH5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 19.1 ± 0.2 | kcal/mol | HPMS | Guo and Castleman, 1990 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 19.5 | cal/mol*K | HPMS | Guo and Castleman, 1990 | gas phase; M |
By formula: Pb+ + CH5N = (Pb+ • CH5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 35.4 ± 0.3 | kcal/mol | HPMS | Guo and Castleman, 1990 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 30.0 | cal/mol*K | HPMS | Guo and Castleman, 1990 | gas phase; M |
By formula: (CH6N+ • 3CH5N) + CH5N = (CH6N+ • 4CH5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 7.8 | kcal/mol | PHPMS | Meot-Ner (Mautner), 1992 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 21.5 | cal/mol*K | PHPMS | Meot-Ner (Mautner), 1992 | gas phase; M |
By formula: C2H8N+ + CH5N = (C2H8N+ • CH5N)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 22.4 | kcal/mol | PHPMS | Yamdagni and Kebarle, 1973 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 29.2 | cal/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° | -31.19 ± 0.60 | kcal/mol | RSC | Holm, 1983 | solvent: Diethyl ether; MS |
By formula: 2CH5N = C2H7N + H3N
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -4.70 | kcal/mol | Eqk | Issoire and Long, 1960 | gas phase; ALS |
By formula: 2C2H7N = CH5N + C3H9N
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -3.15 | kcal/mol | Eqk | Issoire and Long, 1960 | gas phase; ALS |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible 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 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
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
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 CH5N+ (ion structure unspecified)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 8.9 ± 0.1 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 214.9 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 206.6 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.9 | PE | Aue and Bowers, 1979 | LLK |
9.45 | EI | Baldwin, Loudon, et al., 1977 | LLK |
8.9 ± 0.1 | PE | Aue, Webb, et al., 1976 | LLK |
9.08 | PE | Vovna and Vilesov, 1974 | LLK |
8.80 ± 0.02 | PE | Maier and Turner, 1973 | LLK |
9.65 | PE | Elbel, Dieck, et al., 1982 | Vertical value; LBLHLM |
9.0 | PE | Bieri, Asbrink, et al., 1982 | Vertical value; LBLHLM |
9.58 | PE | Utsunomiya, Kobayashi, et al., 1980 | Vertical value; LLK |
9.58 | PE | Kobayashi, 1978 | Vertical value; LLK |
9.64 | PE | Kimura and Osafune, 1975 | Vertical value; LLK |
9.64 | PE | Katsumata, Iwai, et al., 1973 | Vertical value; LLK |
9.65 | PE | Ogata, Onizuka, et al., 1972 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
CH2N+ | 15.2 ± 0.3 | H2+H | EI | Collin and Franskin, 1966 | RDSH |
CH2N+[CNH2+] | 14.0 ± 0.4 | ? | EI | Burgers, Holmes, et al., 1984 | LBLHLM |
CH3+ | 14.5 | NH2 | EI | SenSharma and Franklin, 1973 | LLK |
CH3+ | 14.7 | NH2 | EI | Haney and Franklin, 1968 | RDSH |
CH3N+ | 13.3 ± 0.2 | H2 | EI | Collin and Franskin, 1966 | RDSH |
CH4N+ | 10.18 | H | EI | Lossing, Lam, et al., 1981 | LLK |
CH4N+ | 10.70 | H | EI | Loudon and Webb, 1977 | LLK |
CH4N+ | 10.55 | H | EI | Loudon and Webb, 1977 | LLK |
CH4N+ | 10.82 ± 0.15 | H | EI | Collin and Franskin, 1966 | RDSH |
CH4N+ | 10.3 ± 0.1 | H | EI | Taft, Martin, et al., 1965 | RDSH |
CH5N+ | 8.99 | ? | PI | Cornford, Frost, et al., 1971 | LLK |
CH5N+ | 9.29 | ? | CTS | Slifkin and Allison, 1967 | RDSH |
CH5N+ | 9.36 ± 0.02 | ? | EI | Collin and Franskin, 1966 | RDSH |
CH5N+ | 8.97 ± 0.02 | ? | PI | Watanabe and Mottl, 1957 | RDSH |
H2N+ | 15.9 | CH3 | EI | SenSharma and Franklin, 1973 | LLK |
NH2+ | 15.7 | CH3 | EI | Haney and Franklin, 1968 | RDSH |
De-protonation reactions
CH4N- + =
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 402.0 ± 2.6 | kcal/mol | D-EA | Radisic, Xu, et al., 2002 | gas phase; B |
ΔrH° | 403.21 ± 0.82 | kcal/mol | G+TS | MacKay, Hemsworth, et al., 1976 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 394.5 ± 2.7 | kcal/mol | H-TS | Radisic, Xu, et al., 2002 | gas phase; B |
ΔrG° | 395.70 ± 0.70 | kcal/mol | IMRE | MacKay, Hemsworth, et al., 1976 | gas phase; B |
IR Spectrum
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible 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: 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 |
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, UV/Visible 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: 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-NW- 377 |
NIST MS number | 228024 |
UV/Visible spectrum
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, 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 by: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina
Spectrum
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Additional Data
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Download spectrum in JCAMP-DX format.
Source | Tannenbaum, Coffin, et al., 1953 |
---|---|
Owner | INEP CP RAS, NIST OSRD Collection (C) 2007 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
Origin | INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS |
Source reference | RAS UV No. 2772 |
Instrument | n.i.g. |
Sample pressure | 0.01-1.8 mm Hg |
Melting point | -93.4 |
Boiling point | -6.3 |
Gas Chromatography
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible 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, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible 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]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [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, Siller, et al., 1937, 2
Aston, J.G.; Siller, C.W.; Messerly, G.H.,
Heat capacities and entropies of organic compounds. III. Methylamine from 12K to the boiling point. Heat of vaporization and vapor pressure. The entropy from molecular data,
J. Am. Chem. Soc., 1937, 59, 1743-1751. [all data]
Roberts, Emeleus, et al., 1939
Roberts, E.R.; Emeleus, H.J.; Briscoe, H.V.A.,
Preparation and Prop. of Ethyldideuteramine and Dimethyldeuteramine,
J. Chem. Soc., 1939, 1939, 41. [all data]
Emeleus and Briscoe, 1937
Emeleus, H.J.; Briscoe, H.V.A.,
Preparation and Properties of Methyldideuteramine,
J. Chem. Soc., 1937, 1937, 127. [all data]
McNeight and Smyth, 1936
McNeight, S.A.; Smyth, C.P.,
Non-Rotation of Molecules in a Number of Solids,
J. Am. Chem. Soc., 1936, 58, 1718. [all data]
Aston, Siller, et al., 1937, 3
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. [all data]
Li and Kiran, 1988
Li, L.; Kiran, E.,
Gas-Liquid Critical Properties of Methylamine + Nitrous Oxide and Methylamine + Ethylene Binary Mixtures,
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Kay and Young, 1974
Kay, W.B.; Young, C.L.,
Int. DATA Ser., Sel. Data Mixtures, Ser. A, 1974, No. 2, 158. [all data]
Berthoud, 1917
Berthoud, A.,
Determination of Critical Temperatures and Pressures of Amines and Alkyl Chlorides,
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Majer and Svoboda, 1985
Majer, V.; Svoboda, V.,
Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]
Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw,
Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2
. [all data]
Dykyj, 1970
Dykyj, J.,
Petrochemica, 1970, 10, 2, 51. [all data]
Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E.,
The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [all data]
Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D.,
Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III,
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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]
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 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]
Elbel, Dieck, et al., 1982
Elbel, S.; Dieck, H.T.; Demuth, R.,
Photoelectron sSpectra of group V compounds. IX. The relative perfluoroalkyl substituent effect,
J. Fluorine Chem., 1982, 19, 349. [all data]
Bieri, Asbrink, et al., 1982
Bieri, G.; Asbrink, L.; Von Niessen, W.,
30.4-nm He(II) photoelectron spectra of organic molecules,
J. Electron Spectrosc. Relat. Phenom., 1982, 27, 129. [all data]
Utsunomiya, Kobayashi, et al., 1980
Utsunomiya, C.; Kobayashi, T.; Nagakura, S.,
Photoelectron angular distribution measurements for some aliphatic alcohols, amines, halides,
Bull. Chem. Soc. Jpn., 1980, 53, 1216. [all data]
Kobayashi, 1978
Kobayashi, T.,
A simple general tendency in photoelectron angular distributions of some monosubstituted benzenes,
Phys. Lett., 1978, 69, 105. [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]
Katsumata, Iwai, et al., 1973
Katsumata, S.; Iwai, T.; Kimura, K.,
Photoelectron spectra and sum rule consideration. Higher alkyl amines and alcohols,
Bull. Chem. Soc. Jpn., 1973, 46, 3391. [all data]
Ogata, Onizuka, et al., 1972
Ogata, H.; Onizuka, H.; Nihei, Y.; Kamada, H.,
On the first bands of the photoelectron spectra of amines, alcohols, and mercaptans,
Chem. Lett., 1972, 895. [all data]
Collin and Franskin, 1966
Collin, J.E.; Franskin, M.J.,
Ionisation, dissociation et rearrangements intramoleculaires dans les amines aliphatiques par impact electronique. Cas de la methylamine et de la methylamine-Nd2,
Bull. Soc. Roy. Sci. Liege, 1966, 35, 267. [all data]
Burgers, Holmes, et al., 1984
Burgers, P.C.; Holmes, J.L.; Terlouw, J.K.,
Gaseous [H2,C,N]+ and [H3,C,N]+ ions. Generation of formation, and dissociation characteristics of [H2CN]+, [HCNH]+, [CNH2]+, [H2CNH]+, and [HCN]+,
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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]
Haney and Franklin, 1968
Haney, M.A.; Franklin, J.L.,
Correlation of excess energies of electron-impact dissociations with the translational energies of the products,
J.Chem. Phys., 1968, 48, 4093. [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]
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]
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]
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]
Slifkin and Allison, 1967
Slifkin, M.A.; Allison, A.C.,
Measurement of ionization potentials from contact charge transfer spectra,
Nature, 1967, 215, 949. [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]
Tannenbaum, Coffin, et al., 1953
Tannenbaum, E.; Coffin, E.M.; Harrison, A.J.,
The far ultraviolet absorption spectra of simple alkyl amines,
J. Chem. Phys., 1953, 21, 2, 311-318. [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, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, References
- Symbols used in this document:
AE Appearance energy Cp,liquid Constant pressure heat capacity of liquid IE (evaluated) Recommended ionization energy Pc Critical pressure S°liquid Entropy of liquid at standard conditions T Temperature Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point Ttriple Triple point temperature Vc Critical volume ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy of reaction at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions ΔvapS Entropy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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