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Methyl isocyanide

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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
Deltafgas163.5 ± 7.2kJ/molCmBaghal-Vayjooee, Collister, et al., 1977Reanalyzed by Pedley, Naylor, et al., 1986, Original value = 172.9 ± 1.0 kJ/mol; Heat of isomerization; ALS
Deltafgas142.8kJ/molN/ALemoult, 1906Value computed using «DELTA»fHliquid° value of 112.0 kj/mol from Lemoult, 1906 and «DELTA»vapH° value of 30.8 kj/mol from Baghal-Vayjooee, Collister, et al., 1977.; DRB

Condensed 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Deltafliquid132.7 ± 7.3kJ/molCmBaghal-Vayjooee, Collister, et al., 1977Reanalyzed by Pedley, Naylor, et al., 1986, Original value = 142.0 ± 1.5 kJ/mol; Heat of isomerization
Deltafliquid112.kJ/molCcbLemoult, 1906 
Quantity Value Units Method Reference Comment
Deltacliquid-1333.kJ/molCcbLemoult and Jungfleisch, 1909 
Deltacliquid-1333.kJ/molCcbLemoult, 1906 

Phase change 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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Kenneth Kroenlein director
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.

Quantity Value Units Method Reference Comment
Tfus228.15KN/AGautier, 1869Uncertainty assigned by TRC = 3. K; TRC
Quantity Value Units Method Reference Comment
Deltavap30.8 ± 1.0kJ/molVBaghal-Vayjooee, Collister, et al., 1977Heat of isomerization; ALS
Deltavap30.8kJ/molN/ABaghal-Vayjooee, Collister, et al., 1977DRB

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


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- + Hydrogen cation = Methyl isocyanide

By formula: C2H2N- + H+ = C2H3N

Quantity Value Units Method Reference Comment
Deltar1592. ± 8.8kJ/molG+TSMatimba, Crabbendam, et al., 1992gas phase; B
Deltar1567. ± 8.8kJ/molG+TSFilley, DePuy, et al., 1987gas phase; Matimba, Crabbendam, et al., 1992 indicate that CN- loss interfered with equilibrium here.; B
Quantity Value Units Method Reference Comment
Deltar1561. ± 8.4kJ/molIMREMatimba, Crabbendam, et al., 1992gas phase; B
Deltar1536. ± 8.4kJ/molIMREFilley, DePuy, et al., 1987gas phase; Matimba, Crabbendam, et al., 1992 indicate that CN- loss interfered with equilibrium here.; B

Methyl isocyanide = Acetonitrile

By formula: C2H3N = C2H3N

Quantity Value Units Method Reference Comment
Deltar-99.16 ± 0.59kJ/molCmBaghal-Vayjooee, Collister, et al., 1977gas phase; Heat of isomerization; ALS

Gas phase ion energetics 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 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)839.1kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity806.6kJ/molN/AHunter and Lias, 1998HL

Gas basicity at 298K

Gas basicity (review) (kJ/mol) Reference Comment
848.6 ± 5.3Witt and Grutzmacher, 1997T = 298K; Equilibrium constant measured directly. Data readjusted to 98 HUN/LIA; MM

Ionization energy determinations

IE (eV) Method Reference Comment
11.53 ± 0.04EIHarland and McIntosh, 1985LBLHLM
11.5 ± 0.25EIChess, Lapp, et al., 1982LBLHLM
11.24PEBevan, Sandorfy, et al., 1981LLK
11.24PELake and Thompson, 1971LLK
11.83EIHeerma and deRidder, 1970RDSH
11.27PEBevan, Sandorfy, et al., 1981Vertical value; LLK
11.32PEAsbrink, Von Niessen, et al., 1980Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
CH3+14.76CNEIHeerma and deRidder, 1970RDSH
C2HN+14.56 ± 0.08?EIHarland and McIntosh, 1985LBLHLM
C2HN+14.46H2EIHeerma and deRidder, 1970RDSH
C2H2N+13.21 ± 0.04HEIHarland and McIntosh, 1985LBLHLM
C2H2N+13.21HEIHeerma and deRidder, 1970RDSH
C2N+18.33 ± 0.06?EIHarland and McIntosh, 1985LBLHLM
C2N+18.28?EIHeerma and deRidder, 1970RDSH

De-protonation reactions

C2H2N- + Hydrogen cation = Methyl isocyanide

By formula: C2H2N- + H+ = C2H3N

Quantity Value Units Method Reference Comment
Deltar1592. ± 8.8kJ/molG+TSMatimba, Crabbendam, et al., 1992gas phase; B
Deltar1567. ± 8.8kJ/molG+TSFilley, DePuy, et al., 1987gas phase; Matimba, Crabbendam, et al., 1992 indicate that CN- loss interfered with equilibrium here.; B
Quantity Value Units Method Reference Comment
Deltar1561. ± 8.4kJ/molIMREMatimba, Crabbendam, et al., 1992gas phase; B
Deltar1536. ± 8.4kJ/molIMREFilley, DePuy, et al., 1987gas phase; Matimba, Crabbendam, et al., 1992 indicate that CN- loss interfered with equilibrium here.; B

Mass spectrum (electron ionization)

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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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Mass 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 R.G.GILLIS AUST SCI SERVICE, ASCOT VALE, VIC., AUSTRALIA
NIST MS number 47

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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:   C3nu     Symmetry Number sigma = 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

SStrong
MMedium
WWeak
B1~3 cm-1 uncertainty
C3~6 cm-1 uncertainty
D6~15 cm-1 uncertainty

Gas Chromatography

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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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Normal alkane RI, polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryDB-Wax1010.Duque, Bonilla, et al., 200130. m/0.25 mm/0.25 «mu»m, Helium, 4. K/min, 220. C @ 30. min; Tstart: 25. C

Normal alkane RI, polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
CapillarySOLGel-Wax1002.Johanningsmeier and McFeeters, 201130. m/0.25 mm/0.25 «mu»m, Helium; Program: 40 0C (2 min) 5 0C/min -> 140 0C 10 0C/min -> 250 0C (3 min)

References

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), Vibrational and/or electronic energy levels, Gas Chromatography, NIST Free Links, 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]

Lemoult and Jungfleisch, 1909
Lemoult, M.P.; Jungfleisch, M.E., Thermochimie. - Comparaisons entre les nitriles et les carbylamines, Compt. Rend., 1909, 148, 1602-1604. [all data]

Gautier, 1869
Gautier, A., Ann. Chim. Phys., 1869, 17, 103. [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]

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]

Shimanouchi, 1972
Shimanouchi, T., Tables of Molecular Vibrational Frequencies Consolidated Volume I, National Bureau of Standards, 1972, 1-160. [all data]

Duque, Bonilla, et al., 2001
Duque, C.; Bonilla, A.; Bautista, E.; Zea, S., Exudation of low molecular wight compounds (thiobismethane, methyl isocyanide, amd methyl isothiocyanate) as a possible chemical defense mechanism in the marine sponge Ircinia felix, Biochem. Systematics Ecol., 2001, 29, 5, 459-467, https://doi.org/10.1016/S0305-1978(00)00081-8 . [all data]

Johanningsmeier and McFeeters, 2011
Johanningsmeier, S.D.; McFeeters, R.F., Detection of volatile spoilage metabolites in fermented cucumbers using nontargeted, comprehensive 2-dimensional gas chromatography-time-of-flight mass spectrometry (GCxGCxTOFMS), J. Food Sci., 2011, 76, 1, c168-c177, https://doi.org/10.1111/j.1750-3841.2010.01918.x . [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, Mass spectrum (electron ionization), Vibrational and/or electronic energy levels, Gas Chromatography, NIST Free Links, References