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Methyl isocyanide

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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

References

Go To: Top, 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.

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

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