Benzenepropanenitrile, β-oxo-
- Formula: C9H7NO
- Molecular weight: 145.1580
- IUPAC Standard InChI: InChI=1S/C9H7NO/c10-7-6-9(11)8-4-2-1-3-5-8/h1-5H,6H2
- IUPAC Standard InChIKey: ZJRCIQAMTAINCB-UHFFFAOYSA-N
- CAS Registry Number: 614-16-4
- 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: Acetonitrile, benzoyl-; α-Cyanoacetophenone; ω-Cyanoacetophenone; Acetophenone, 2-cyano-; Benzoylacetonitrile; Cyanoacetophenone; Cyanomethyl phenyl ketone; Hydrocinnamonitrile, β-oxo-; Phenacyl cyanide; 2-Cyanoacetophenone; 2-Cyanoacetyl phenone; 3-Phenyl-3-ketopropionitrile; 3-Oxo-3-phenylpropanenitrile; 3-Phenyl-3-oxopropanenitrile; NSC 4713
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | 16.76 | kcal/mol | Ccb | Lebedeva, Dneprovskii, et al., 1969 | See Lebedeva, Rjadnenko, et al., 1969 |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°solid | -5.34 ± 0.10 | kcal/mol | Ccb | Lebedeva, Dneprovskii, et al., 1969 | See Lebedeva, Rjadnenko, et al., 1969 |
| ΔfH°solid | 1.8 | kcal/mol | Ccb | Guinchant, 1918 | Author hf288_condensed[kcal/mol]=-3.6 kcal/mol |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -1080.24 ± 0.10 | kcal/mol | Ccb | Lebedeva, Dneprovskii, et al., 1969 | See Lebedeva, Rjadnenko, et al., 1969 |
| ΔcH°solid | -1087.4 | kcal/mol | Ccb | Guinchant, 1918 | Author hf288_condensed[kcal/mol]=-3.6 kcal/mol |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry 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 as indicated in comments:
B - John E. Bartmess
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 9.56 ± 0.05 | EI | Pignataro, Foffani, et al., 1966 | RDSH |
De-protonation reactions
C9H6NO- + =
By formula: C9H6NO- + H+ = C9H7NO
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrG° | 326.3 ± 2.0 | kcal/mol | IMRE | Taft, Abboud, et al., 1988 | gas phase; Revised 0.9 smaller: 91TAF; B |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry 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.
Lebedeva, Dneprovskii, et al., 1969
Lebedeva, N.D.; Dneprovskii, A.S.; Katin, Yu.A.,
Heats of combustion and enthalpies of formation of benzoyl cyanide, ω-cyanoacetophenone, and β-cyanopropiophenone,
Russ. J. Phys. Chem. (Engl. Transl.), 1969, 43, 770-773. [all data]
Lebedeva, Rjadnenko, et al., 1969
Lebedeva, N.D.; Rjadnenko, B.L.; Gutner, N.M.,
Heats of formation of some N-containing organic compounds,
Int. Conf. Calorim. Therm. (Warsaw, Poland), 1969, 1-8. [all data]
Guinchant, 1918
Guinchant, M.J.,
Etude sur la fonction acide dans les derives metheniques et methiniques,
Ann. Chem., 1918, 10, 30-84. [all data]
Pignataro, Foffani, et al., 1966
Pignataro, S.; Foffani, A.; Innorta, G.; Distefano, G.,
Molecular structural effects on the ionization potentials for metasubstituted aromatic compounds and for compounds of the type X-CH2-R,
Z. Physik. Chem. (Frankfurt), 1966, 49, 291. [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]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔrG° Free energy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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