Acetic acid, cyano-, methyl ester
- Formula: C4H5NO2
- Molecular weight: 99.0880
- IUPAC Standard InChI: InChI=1S/C4H5NO2/c1-7-4(6)2-3-5/h2H2,1H3
- IUPAC Standard InChIKey: ANGDWNBGPBMQHW-UHFFFAOYSA-N
- CAS Registry Number: 105-34-0
- 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. - Other names: Cyanoacetic acid methyl ester; Methyl cyanoacetate; Methyl cyanoethanoate; Methyl 2-cyanoacetate; USAF kf-22; Methylester kyseliny kyanoctove; Malonic methyl ester nitrile
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Gas phase ion energetics data
Go To: Top, 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:
B - John E. Bartmess
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
LL - Sharon G. Lias and Joel F. Liebman
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 10.87 ± 0.05 | EI | Pignataro, Foffani, et al., 1966 | RDSH |
Appearance energy determinations
| Ion | AE (eV) | Other Products | Method | Reference | Comment |
|---|---|---|---|---|---|
| C2H3O2+ | 10.40 ± 0.02 | C2H2N | EI | Holmes, Lossing, et al., 1993 | LL |
| C2H3O2+ | 11.72 ± 0.03 | ? | EI | Briggs and Shannon, 1969 | RDSH |
De-protonation reactions
C4H4NO2- + =
By formula: C4H4NO2- + H+ = C4H5NO2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 340.8 ± 2.1 | kcal/mol | G+TS | Mishima, Matsuoka, et al., 2004 | gas phase; Calc: keto form of acid more stable.; B |
| ΔrH° | 340.6 ± 2.1 | kcal/mol | G+TS | Taft, Abboud, et al., 1988 | gas phase; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 334.5 ± 2.0 | kcal/mol | IMRE | Mishima, Matsuoka, et al., 2004 | gas phase; Calc: keto form of acid more stable.; B |
| ΔrG° | 334.3 ± 2.0 | kcal/mol | IMRE | Taft, Abboud, et al., 1988 | gas phase; 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.
Pignataro, Foffani, et al., 1966
Pignataro, S.; Foffani, A.; Innorta, G.; Distefano, G.,
Molecular structural effects on the ionization potentials for metasubstituted aromatic compounds and for compounds of the type X-CH2-R,
Z. Physik. Chem. (Frankfurt), 1966, 49, 291. [all data]
Holmes, Lossing, et al., 1993
Holmes, J.L.; Lossing, F.P.; Mayer, P.M.,
The effects of methyl substitution on the structure and thermochemistry of the cyanomethyl radical and cation,
Chem. Phys. Lett., 1993, 212, 134. [all data]
Briggs and Shannon, 1969
Briggs, P.R.; Shannon, T.W.,
The heat of formation of the methoxycarbonyl ion,
J. Am. Chem. Soc., 1969, 91, 4307. [all data]
Mishima, Matsuoka, et al., 2004
Mishima, M.; Matsuoka, M.; Lei, Y.X.; Rappoport, Z.,
Gas-phase acidities of disubstituted methanes and of enols of carboxamides substituted by electron-withdrawing groups,
J. Org. Chem., 2004, 69, 18, 5947-5965, https://doi.org/10.1021/jo040196b
. [all data]
Taft, Abboud, et al., 1988
Taft, R.W.; Abboud, J.L.M.; Anvia, F.; Berthelot, M.; Fujio, M.; Gal, J.-F.; Headley, A.D.; Henderson, W.G.,
Regarding the Inherent Dependence of Resonance Effects of Strongly Conjugated Substituents on Electron Demand,
J. Am. Chem. Soc., 1988, 110, 6, 1797, https://doi.org/10.1021/ja00214a023
. [all data]
Notes
Go To: Top, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy 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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