Acetic acid, cyano-, methyl ester
- Formula: C4H5NO2
- Molecular weight: 99.0880
- 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 thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -243.3 ± 1.1 | kJ/mol | Ccb | Verevkin, Beckhaus, et al., 1995 |
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 |
---|---|---|---|---|---|
ΔfH°liquid | -309.53 ± 0.54 | kJ/mol | Ccb | Verevkin, Beckhaus, et al., 1995 | |
ΔfH°liquid | -312. | kJ/mol | Ccb | Guinchant, 1918 | Author hf288_condensed[kcal/mol]=-77.8 kcal/mol |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -1979.1 ± 0.46 | kJ/mol | Ccb | Verevkin, Beckhaus, et al., 1995 | |
ΔcH°liquid | -1977. | kJ/mol | Ccb | Guinchant, 1918 | Author hf288_condensed[kcal/mol]=-77.8 kcal/mol |
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
C4H4NO2- + =
By formula: C4H4NO2- + H+ = C4H5NO2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1426. ± 8.8 | kJ/mol | G+TS | Mishima, Matsuoka, et al., 2004 | gas phase; Calc: keto form of acid more stable.; B |
ΔrH° | 1425. ± 8.8 | kJ/mol | G+TS | Taft, Abboud, et al., 1988 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1400. ± 8.4 | kJ/mol | IMRE | Mishima, Matsuoka, et al., 2004 | gas phase; Calc: keto form of acid more stable.; B |
ΔrG° | 1399. ± 8.4 | kJ/mol | IMRE | Taft, Abboud, et al., 1988 | gas phase; B |
By formula: C6H11NO3 + H2O = C4H5NO2 + 2CH4O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -25.7 ± 1.5 | kJ/mol | Eqk | Guthrie and Cullimore, 1980 | liquid phase; ALS |
By formula: C4H5NO2 + H2O = C3H3NO2 + CH4O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -54. ± 2. | kJ/mol | Eqk | Guthrie and Cullimore, 1980 | liquid phase; ALS |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry 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:
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° | 1426. ± 8.8 | kJ/mol | G+TS | Mishima, Matsuoka, et al., 2004 | gas phase; Calc: keto form of acid more stable.; B |
ΔrH° | 1425. ± 8.8 | kJ/mol | G+TS | Taft, Abboud, et al., 1988 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1400. ± 8.4 | kJ/mol | IMRE | Mishima, Matsuoka, et al., 2004 | gas phase; Calc: keto form of acid more stable.; B |
ΔrG° | 1399. ± 8.4 | kJ/mol | IMRE | Taft, Abboud, et al., 1988 | gas phase; B |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry 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.
Verevkin, Beckhaus, et al., 1995
Verevkin, S.P.; Beckhaus, H.-D.; Ruchardt, C.,
Geminale substituenteneffekte. Teil 6. Standardbildungsenthalpien von alkylsubstituierten-alkoxynitrilen und α-cyano-carbonsaureestern,
Thermochim. Acta, 1995, 249, 1-11. [all data]
Guinchant, 1918
Guinchant, M.J.,
Etude sur la fonction acide dans les derives metheniques et methiniques,
Ann. Chem., 1918, 10, 30-84. [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]
Guthrie and Cullimore, 1980
Guthrie, J.P.; Cullimore, P.A.,
Effect of the acyl substituent on the equilibrium constant for hydration of esters,
Can. J. Chem., 1980, 58, 1281-1294. [all data]
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]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid 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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