Methyl isocyanide
- Formula: C2H3N
- Molecular weight: 41.0519
- 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
- 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.
Phase change data
Go To: Top, 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 as indicated in comments:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tfus | 228.15 | K | N/A | Gautier, 1869 | Uncertainty assigned by TRC = 3. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 30.8 ± 1.0 | kJ/mol | V | Baghal-Vayjooee, Collister, et al., 1977 | Heat of isomerization; ALS |
ΔvapH° | 30.8 | kJ/mol | N/A | Baghal-Vayjooee, Collister, et al., 1977 | DRB |
Gas phase ion energetics data
Go To: Top, Phase change data, 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
Data compiled as indicated in comments:
B - John E. Bartmess
MM - Michael M. Meot-Ner (Mautner)
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 C2H3N+ (ion structure unspecified)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 839.1 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 806.6 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Gas basicity at 298K
Gas basicity (review) (kJ/mol) | Reference | Comment |
---|---|---|
848.6 ± 5.3 | Witt and Grutzmacher, 1997 | T = 298K; Equilibrium constant measured directly. Data readjusted to 98 HUN/LIA; MM |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
11.53 ± 0.04 | EI | Harland and McIntosh, 1985 | LBLHLM |
11.5 ± 0.25 | EI | Chess, Lapp, et al., 1982 | LBLHLM |
11.24 | PE | Bevan, Sandorfy, et al., 1981 | LLK |
11.24 | PE | Lake and Thompson, 1971 | LLK |
11.83 | EI | Heerma and deRidder, 1970 | RDSH |
11.27 | PE | Bevan, Sandorfy, et al., 1981 | Vertical value; LLK |
11.32 | PE | Asbrink, Von Niessen, et al., 1980 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
CH3+ | 14.76 | CN | EI | Heerma and deRidder, 1970 | RDSH |
C2HN+ | 14.56 ± 0.08 | ? | EI | Harland and McIntosh, 1985 | LBLHLM |
C2HN+ | 14.46 | H2 | EI | Heerma and deRidder, 1970 | RDSH |
C2H2N+ | 13.21 ± 0.04 | H | EI | Harland and McIntosh, 1985 | LBLHLM |
C2H2N+ | 13.21 | H | EI | Heerma and deRidder, 1970 | RDSH |
C2N+ | 18.33 ± 0.06 | ? | EI | Harland and McIntosh, 1985 | LBLHLM |
C2N+ | 18.28 | ? | EI | Heerma and deRidder, 1970 | RDSH |
De-protonation 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 |
References
Go To: Top, Phase change data, Gas phase ion energetics data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Gautier, 1869
Gautier, A.,
Ann. Chim. Phys., 1869, 17, 103. [all data]
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]
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]
Witt and Grutzmacher, 1997
Witt, M.; Grutzmacher, H.F.,
The gas phase basicity and proton affinity of propionamide: a comparison of methods,
Int. J. Mass Spectrom. Ion. Processes, 1997, 164, 93. [all data]
Harland and McIntosh, 1985
Harland, P.W.; McIntosh, B.J.,
Enthalpies of formation for the isomeric ions HxCCN+ and HxCNC+ (x = 0-3) by monochromatic electron impact on C2N2, CH3CN and CH3NC.,
Int. J. Mass Spectrom. Ion Processes, 1985, 67, 29. [all data]
Chess, Lapp, et al., 1982
Chess, E.K.; Lapp, R.L.; Gross, M.L.,
The question of tautomerism of alkylnitrile and isonitrile radical cations,
Org. Mass Spectrom., 1982, 17, 475. [all data]
Bevan, Sandorfy, et al., 1981
Bevan, J.W.; Sandorfy, C.; Pang, F.; Bogg, J.E.,
The photoelectron spectrum of methylisocyanide-borane,
Spectrochim. Acta A:, 1981, 37, 601. [all data]
Lake and Thompson, 1971
Lake, R.F.; Thompson, H.W.,
The photoelectron spectra of methyl isocyanide and trideuteromethyl isocyanide,
Spectrochim. Acta, 1971, 27A, 783. [all data]
Heerma and deRidder, 1970
Heerma, W.; deRidder, J.J.,
The electron-impact induced fragmentation of some alkyl isocyanides and alpha-branched alkyl cyanides,
Org. Mass Spectrom., 1970, 3, 1439. [all data]
Asbrink, Von Niessen, et al., 1980
Asbrink, L.; Von Niessen, W.; Bieri, G.,
30.4-nm He(II) photoelectron spectra of organic molecules,
J. Electron Spectrosc. Relat. Phenom., 1980, 21, 93. [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]
Notes
Go To: Top, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy Tfus Fusion (melting) point ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔvapH° Enthalpy of vaporization 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.