Acetic acid, cyano-
- Formula: C3H3NO2
- Molecular weight: 85.0614
- IUPAC Standard InChI: InChI=1S/C3H3NO2/c4-2-1-3(5)6/h1H2,(H,5,6)
- IUPAC Standard InChIKey: MLIREBYILWEBDM-UHFFFAOYSA-N
- CAS Registry Number: 372-09-8
- 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; Malonic mononitrile; Monocyanoacetic acid; NCCH2COOH; 2-Cyanoacetic acid; Acide cyanacetique; USAF KF-17; Cyanessigsaeure; Kyselina kyanoctova; Cyanoethanoic acid; NSC 5571
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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
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Individual Reactions
C3H2NO2- + =
By formula: C3H2NO2- + H+ = C3H3NO2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1382. ± 8.8 | kJ/mol | G+TS | Taft and Topsom, 1987 | gas phase; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1354. ± 8.4 | kJ/mol | IMRE | Taft and Topsom, 1987 | gas phase; B |
+
=
+
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.
Taft and Topsom, 1987
Taft, R.W.; Topsom, R.D.,
The Nature and Analysis of Substituent Effects,
Prog. Phys. Org. Chem., 1987, 16, 1. [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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