Acetyl cyanide
- Formula: C3H3NO
- Molecular weight: 69.0620
- IUPAC Standard InChI: InChI=1S/C3H3NO/c1-3(5)2-4/h1H3
- IUPAC Standard InChIKey: QLDHWVVRQCGZLE-UHFFFAOYSA-N
- CAS Registry Number: 631-57-2
- 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: Pyruvonitrile; Propanenitrile, 2-oxo-; α-Oxopropionitrile; Oxopropionitrile; Oxypropionitrile; Pyruvic acid nitrile; 2-Oxopropionitrile; CH3C(O)CN; 2-Oxopropanenitrile; 2-Oxopropiononitrile
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Gas phase ion energetics 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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
Data compiled as indicated in comments:
B - John E. Bartmess
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Proton affinity (review) | 746.9 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
| Quantity | Value | Units | Method | Reference | Comment |
| Gas basicity | 716.2 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
De-protonation reactions
C3H2NO- + =
By formula: C3H2NO- + H+ = C3H3NO
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1441. ± 8.8 | kJ/mol | G+TS | Taft, 1987 | gas phase; value altered from reference due to change in acidity scale; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1413. ± 8.4 | kJ/mol | IMRE | Taft, 1987 | gas phase; value altered from reference due to change in acidity scale; B |
| ΔrG° | 1432. ± 21. | kJ/mol | IMRB | Brauman and Blair, 1968 | 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.
Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G.,
Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update,
J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018
. [all data]
Taft, 1987
Taft, R.W.,
The Nature and Analysis of Substitutent Electronic Effects,
Personal communication. See also Prog. Phys. Org. Chem., 1987, 16, 1. [all data]
Brauman and Blair, 1968
Brauman, J.I.; Blair, L.K.,
Gas Phase Acidities of Carbon Acids,
J. Am. Chem. Soc., 1968, 90, 20, 5636, https://doi.org/10.1021/ja01022a073
. [all data]
Notes
Go To: Top, Gas phase ion energetics 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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