Methyl isocyanide
- Formula: C2H3N
- Molecular weight: 41.0519
- IUPAC Standard InChI: InChI=1S/C2H3N/c1-3-2/h1H3
- IUPAC Standard InChIKey: ZRKSVHFXTRFQFL-UHFFFAOYSA-N
- CAS Registry Number: 593-75-9
- Chemical structure:
This structure is also available as a 2d Mol file - Other names: Methane, isocyano-; Isocyanomethane; Methyl isonitrile; CH3NC
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Gas phase thermochemistry data
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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 | 163.5 ± 7.2 | kJ/mol | Cm | Baghal-Vayjooee, Collister, et al., 1977 | Reanalyzed by Pedley, Naylor, et al., 1986, Original value = 172.9 ± 1.0 kJ/mol; Heat of isomerization; ALS |
| ΔfH°gas | 142.8 | kJ/mol | N/A | Lemoult, 1906 | Value computed using ΔfHliquid° value of 112.0 kj/mol from Lemoult, 1906 and ΔvapH° value of 30.8 kj/mol from Baghal-Vayjooee, Collister, et al., 1977.; DRB |
Reaction thermochemistry data
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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:
B - John E. Bartmess
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
C2H2N- + =
By formula: C2H2N- + H+ = C2H3N
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1592. ± 8.8 | kJ/mol | G+TS | Matimba, Crabbendam, et al., 1992 | gas phase; B |
| ΔrH° | 1567. ± 8.8 | kJ/mol | G+TS | Filley, DePuy, et al., 1987 | gas phase; Matimba, Crabbendam, et al., 1992 indicate that CN- loss interfered with equilibrium here.; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1561. ± 8.4 | kJ/mol | IMRE | Matimba, Crabbendam, et al., 1992 | gas phase; B |
| ΔrG° | 1536. ± 8.4 | kJ/mol | IMRE | Filley, DePuy, et al., 1987 | gas phase; Matimba, Crabbendam, et al., 1992 indicate that CN- loss interfered with equilibrium here.; B |
=
By formula: C2H3N = C2H3N
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -99.16 ± 0.59 | kJ/mol | Cm | Baghal-Vayjooee, Collister, et al., 1977 | gas phase; Heat of isomerization; ALS |
Vibrational and/or electronic energy levels
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: Takehiko Shimanouchi
Symmetry: C3ν Symmetry Number σ = 3
| Sym. | No | Approximate | Selected Freq. | Infrared | Raman | Comments | ||||
|---|---|---|---|---|---|---|---|---|---|---|
| Species | type of mode | Value | Rating | Value | Phase | Value | Phase | |||
| a1 | 1 | CH3 s-str | 2966 | B | 2965.8 M | gas | 2951 S | liq. | ||
| a1 | 2 | NC str | 2166 | B | 2166.0 M | gas | 2161 S | liq. | ||
| a1 | 3 | CH3 s-deform | 1429 | D | 1429 | gas | 1414 M | liq. | ||
| a1 | 4 | CN str | 945 | B | 944.6 M | gas | 928 M | liq. | ||
| e | 5 | CH3 d-str | 3014 | B | 3014.3 S | gas | 3002 W | liq. | ||
| e | 6 | CH3 d-deform | 1467 | B | 1466.9 S | gas | 1456 W | liq. | ||
| e | 7 | CH3 rock | 1129 | B | 1129.3 S | gas | ||||
| e | 8 | CNC bend | 263 | C | 263 W | gas | 290 S | liq. | ||
Source: Shimanouchi, 1972
Notes
| S | Strong |
| M | Medium |
| W | Weak |
| B | 1~3 cm-1 uncertainty |
| C | 3~6 cm-1 uncertainty |
| D | 6~15 cm-1 uncertainty |
References
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Vibrational and/or electronic energy levels, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Baghal-Vayjooee, Collister, et al., 1977
Baghal-Vayjooee, M.H.; Collister, J.L.; Pritchard, H.O.,
The enthalpy of isomerisation of methyl isocyanide,
Can. J. Chem., 1977, 55, 2634-2636. [all data]
Pedley, Naylor, et al., 1986
Pedley, J.B.; Naylor, R.D.; Kirby, S.P.,
Thermochemical Data of Organic Compounds, Chapman and Hall, New York, 1986, 1-792. [all data]
Lemoult, 1906
Lemoult, P.,
Carbylamines et nitriles.,
Compt. Rend., 1906, 143, 902-904. [all data]
Matimba, Crabbendam, et al., 1992
Matimba, H.E.K.; Crabbendam, A.M.; Ingemann, S.; Nibbering, N.M.M.,
Gas-phase Bimolecular Chemistry of the .-CHNC and .-CHCN Radical Anions,
Int. J. Mass Spectrom. Ion Proc., 1992, 114, 1-2, 85, https://doi.org/10.1016/0168-1176(92)85024-T
. [all data]
Filley, DePuy, et al., 1987
Filley, J.; DePuy, C.H.; Bierbaum, V.M.,
Gas-Phase Negative Ion Chemistry of Methyl Isocyanide,
J. Am. Chem. Soc., 1987, 109, 20, 5992, https://doi.org/10.1021/ja00254a017
. [all data]
Shimanouchi, 1972
Shimanouchi, T.,
Tables of Molecular Vibrational Frequencies Consolidated Volume I, National Bureau of Standards, 1972, 1-160. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Vibrational and/or electronic energy levels, References
- Symbols used in this document:
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
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