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, Phase change data, Reaction 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | 70.12 | kJ/mol | Ccb | Lebedeva, Dneprovskii, et al., 1969 | See Lebedeva, Rjadnenko, et al., 1969 |
Condensed phase 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°solid | -22.3 ± 0.42 | kJ/mol | Ccb | Lebedeva, Dneprovskii, et al., 1969 | See Lebedeva, Rjadnenko, et al., 1969 |
| ΔfH°solid | 7.5 | kJ/mol | Ccb | Guinchant, 1918 | Author hf288_condensed[kcal/mol]=-3.6 kcal/mol |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -4519.72 ± 0.42 | kJ/mol | Ccb | Lebedeva, Dneprovskii, et al., 1969 | See Lebedeva, Rjadnenko, et al., 1969 |
| ΔcH°solid | -4549.7 | kJ/mol | Ccb | Guinchant, 1918 | Author hf288_condensed[kcal/mol]=-3.6 kcal/mol |
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 as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔsubH° | 92.5 | kJ/mol | V | Lebedeva, Dneprovskii, et al., 1969 | See Lebedeva, Rjadnenko, et al., 1969; ALS |
Reduced pressure boiling point
| Tboil (K) | Pressure (bar) | Reference | Comment |
|---|---|---|---|
| 433.2 | 0.013 | Weast and Grasselli, 1989 | BS |
Enthalpy of sublimation
| ΔsubH (kJ/mol) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 99.8 | 325.5 | Stephenson and Malanowski, 1987 | Based on data from 318. to 333. K.; AC |
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 by: John E. Bartmess
Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.
Individual Reactions
C9H6NO- + =
By formula: C9H6NO- + H+ = C9H7NO
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrG° | 1365. ± 8.4 | kJ/mol | IMRE | Taft, Abboud, et al., 1988 | gas phase; Revised 0.9 smaller: 91TAF |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry 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]
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]
Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw,
Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2
. [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, Phase change data, Reaction thermochemistry data, References
- Symbols used in this document:
Tboil Boiling point 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 ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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