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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Phase change data
Go To: Top, 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: Robert L. Brown and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Tboil | 365.5 | K | N/A | Weast and Grasselli, 1989 |
Gas phase ion energetics data
Go To: Top, Phase change data, References, Notes
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) | 178.5 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
| Quantity | Value | Units | Method | Reference | Comment |
| Gas basicity | 171.2 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
De-protonation reactions
C3H2NO- + =
By formula: C3H2NO- + H+ = C3H3NO
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 344.5 ± 2.1 | kcal/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° | 337.7 ± 2.0 | kcal/mol | IMRE | Taft, 1987 | gas phase; value altered from reference due to change in acidity scale; B |
| ΔrG° | 342.2 ± 5.0 | kcal/mol | IMRB | Brauman and Blair, 1968 | gas phase; B |
References
Go To: Top, Phase change 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.
Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]
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, Phase change data, Gas phase ion energetics 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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