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
View 3d structure (requires JavaScript / HTML 5) - 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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Phase change 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: Robert L. Brown and Stephen E. Stein
Reduced pressure boiling point
| Tboil (K) | Pressure (atm) | Reference |
|---|---|---|
| 381.2 | 0.0003 | Aldrich Chemical Company Inc., 1990 |
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° | 330.3 ± 2.1 | kcal/mol | G+TS | Taft and Topsom, 1987 | gas phase; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 323.7 ± 2.0 | kcal/mol | IMRE | Taft and Topsom, 1987 | gas phase; B |
+
=
+
By formula: C4H5NO2 + H2O = C3H3NO2 + CH4O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -13.0 ± 0.5 | kcal/mol | Eqk | Guthrie and Cullimore, 1980 | liquid phase; ALS |
References
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]
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, Phase change data, Reaction thermochemistry data, References
- Symbols used in this document:
Tboil Boiling point 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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