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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Reaction thermochemistry 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
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 |
+
=
+ 2
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 |
References
Go To: Top, Reaction thermochemistry data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
Notes
Go To: Top, Reaction thermochemistry data, References
- Symbols used in this document:
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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