Propanenitrile
- Formula: C3H5N
- Molecular weight: 55.0785
- IUPAC Standard InChI: InChI=1S/C3H5N/c1-2-3-4/h2H2,1H3
- IUPAC Standard InChIKey: FVSKHRXBFJPNKK-UHFFFAOYSA-N
- CAS Registry Number: 107-12-0
- 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. - Isotopologues:
- Other names: Propionitrile; Cyanoethane; Ether cyanatus; Ethyl cyanide; Hydrocyanic ether; Propionic nitrile; Propiononitrile; Propylnitrile; C2H5CN; Ethylkyanid; Propannitril; Rcra waste number P101; UN 2404; n-Propanenitrile; NSC 7966
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry 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 | 51.46 | kJ/mol | Ccr | Hall and Baldt, 1971 |
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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°liquid | 15.5 | kJ/mol | Ccr | Hall and Baldt, 1971 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -1948.3 ± 0.54 | kJ/mol | Ccr | Hall and Baldt, 1971 | ALS |
| ΔcH°liquid | -1918. | kJ/mol | Ccb | Lemoult and Jungfleisch, 1909 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| S°liquid | 189.33 | J/mol*K | N/A | Weber and Kilpatrick, 1962 | DH |
Constant pressure heat capacity of liquid
| Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 105.3 | 298.15 | Mirzaliev, Shakhuradov, et al., 1987 | T = 193 to 353 K. Unsmoothed experimental datum given as 1.845 kJ/kg*K at 293 K. Cp(liq) = 1.9082 + 0.0027614T/K + 9.3056x10-6T2/K2 kJ/kg*K (193 to 353 K). Note, second term should be negative.; DH |
| 106.0 | 303.15 | Guseinov and Mirzaliev, 1985 | T = 303 to 363 K. p = 0.1 MPa. Unsoothed experimental datum given as 1.9250 kJ/kg*K.; DH |
| 112.9 | 297. | Hall and Baldt, 1971 | DH |
| 119.50 | 298.15 | Weber and Kilpatrick, 1962 | T = 15 to 300 K.; DH |
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
RCD - Robert C. Dunbar
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
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
C3H4N- + =
By formula: C3H4N- + H+ = C3H5N
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1569. ± 8.8 | kJ/mol | G+TS | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1537. ± 8.4 | kJ/mol | IMRE | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale; B |
C3H4N- + =
By formula: C3H4N- + H+ = C3H5N
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1640. ± 21. | kJ/mol | G+TS | Merrill, Dahlke, et al., 1996 | gas phase; comparable to H2O.; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1607. ± 21. | kJ/mol | IMRB | Merrill, Dahlke, et al., 1996 | gas phase; comparable to H2O.; B |
+
= (
•
)
By formula: Na+ + C3H5N = (Na+ • C3H5N)
Free energy of reaction
| ΔrG° (kJ/mol) | T (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 103. | 298. | IMRE | McMahon and Ohanessian, 2000 | Anchor alanine=39.89; RCD |
=
By formula: C3H5N = C3H5N
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -90.0 ± 4.2 | kJ/mol | Cm | Baghal-Vayjooee, Collister, et al., 1977 | gas phase; Heat of isomerization; ALS |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry 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.
Hall and Baldt, 1971
Hall, H.K., Jr.; Baldt, J.H.,
Thermochemistry of strained-ring bridgehead nitriles and esters,
J. Am. Chem. Soc., 1971, 93, 140-145. [all data]
Lemoult and Jungfleisch, 1909
Lemoult, M.P.; Jungfleisch, M.E.,
Thermochimie. - Comparaisons entre les nitriles et les carbylamines,
Compt. Rend., 1909, 148, 1602-1604. [all data]
Weber and Kilpatrick, 1962
Weber, L.A.; Kilpatrick, J.E.,
Entropy and related thermodynamic properties of propionitrile,
J. Chem. Phys., 1962, 36, 829-834. [all data]
Mirzaliev, Shakhuradov, et al., 1987
Mirzaliev, A.A.; Shakhuradov, Sh.G.; Guseinov, S.O.,
Investigation of the isobaric heat capacity of nitriles at different temperatures, Izv. Vyssh. Ucheb. Zaved.,
Neft i Gaz, 1987, 30(4), 55-58. [all data]
Guseinov and Mirzaliev, 1985
Guseinov, S.O.; Mirzaliev, A.A.,
Experimental investigation of volumetric and isobaric heat capacity of saturated nitriles at elevated temperatures and different pressures, Izv. Vyssh. Ucheb. Zaved.,
Neft i Gaz, 1985, 28(5), 58-62. [all data]
Bartmess, Scott, et al., 1979
Bartmess, J.E.; Scott, J.A.; McIver, R.T., Jr.,
The gas phase acidity scale from methanol to phenol,
J. Am. Chem. Soc., 1979, 101, 6047. [all data]
Merrill, Dahlke, et al., 1996
Merrill, G.N.; Dahlke, G.D.; Kass, S.R.,
beta-Cyanoethyl Anion: Lusus Naturae,
J. Am. Chem. Soc., 1996, 118, 18, 4462, https://doi.org/10.1021/ja953796o
. [all data]
McMahon and Ohanessian, 2000
McMahon, T.B.; Ohanessian, G.,
An Experimental and Ab Initio Study of the Nature of the Binding in Gas-Phase Complexes of Sodium Ions,
Chem. Eur. J., 2000, 6, 16, 2931, https://doi.org/10.1002/1521-3765(20000818)6:16<2931::AID-CHEM2931>3.0.CO;2-7
. [all data]
Baghal-Vayjooee, Collister, et al., 1977
Baghal-Vayjooee, M.H.; Collister, J.L.; Pritchard, H.O.,
The enthalpy of isomerisation of methyl isocyanide,
Can. J. Chem., 1977, 55, 2634-2636. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid S°liquid Entropy of liquid at standard conditions T Temperature ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions 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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