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
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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°gas | 12.30 | kcal/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 | 3.70 | kcal/mol | Ccr | Hall and Baldt, 1971 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -465.65 ± 0.13 | kcal/mol | Ccr | Hall and Baldt, 1971 | ALS |
| ΔcH°liquid | -458.5 | kcal/mol | Ccb | Lemoult and Jungfleisch, 1909 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| S°liquid | 45.251 | cal/mol*K | N/A | Weber and Kilpatrick, 1962 | DH |
Constant pressure heat capacity of liquid
| Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 25.17 | 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 |
| 25.33 | 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 |
| 26.98 | 297. | Hall and Baldt, 1971 | DH |
| 28.561 | 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° | 375.0 ± 2.1 | kcal/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° | 367.4 ± 2.0 | kcal/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° | 392.0 ± 5.1 | kcal/mol | G+TS | Merrill, Dahlke, et al., 1996 | gas phase; comparable to H2O.; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 384.0 ± 5.0 | kcal/mol | IMRB | Merrill, Dahlke, et al., 1996 | gas phase; comparable to H2O.; B |
+
= (
•
)
By formula: Na+ + C3H5N = (Na+ • C3H5N)
Free energy of reaction
| ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 24.6 | 298. | IMRE | McMahon and Ohanessian, 2000 | Anchor alanine=39.89; RCD |
=
By formula: C3H5N = C3H5N
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -21.5 ± 1.0 | kcal/mol | Cm | Baghal-Vayjooee, Collister, et al., 1977 | gas phase; Heat of isomerization; ALS |
Henry's Law 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: Rolf Sander
Henry's Law constant (water solution)
kH(T) = k°H exp(d(ln(kH))/d(1/T) ((1/T) - 1/(298.15 K)))
k°H = Henry's law constant for solubility in water at 298.15 K (mol/(kg*bar))
d(ln(kH))/d(1/T) = Temperature dependence constant (K)
| k°H (mol/(kg*bar)) | d(ln(kH))/d(1/T) (K) | Method | Reference |
|---|---|---|---|
| 27. | M | N/A |
Vibrational and/or electronic energy levels
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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: Takehiko Shimanouchi
Symmetry: Cs Symmetry Number σ = 1
| Sym. | No | Approximate | Selected Freq. | Infrared | Raman | Comments | ||||
|---|---|---|---|---|---|---|---|---|---|---|
| Species | type of mode | Value | Rating | Value | Phase | Value | Phase | |||
| a' | 1 | CH3 d-str | 3001 | C | 3001 VS | liq. | 2999 S | liq. | OV(ν14) | |
| a' | 2 | CH2 s-str | 2955 | C | 2955 VS | liq. | 2949 VS p | liq. | ||
| a' | 3 | CH3 s-str | 2900 | C | 2900 S | liq. | 2898 S p | liq. | ||
| a' | 4 | CN str | 2254 | C | 2254 VS | liq. | 2251 VS p | liq. | ||
| a' | 5 | CH3 d-deform | 1465 | C | 1465 S | liq. | 1466 VS p | liq. | SF(ν16) | |
| a' | 6 | CH2 scis | 1433 | C | 1433 S | liq. | 1436 M p | liq. | ||
| a' | 7 | CH3 s-deform | 1387 | C | 1387 M | liq. | 1374 VW p | liq. | ||
| a' | 8 | CH2 wag | 1319 | C | 1319 M | liq. | 1322 W p | liq. | ||
| a' | 9 | C-CN str | 1077 | C | 1077 S | liq. | 1078 M p | liq. | ||
| a' | 10 | CC str | 1005 | C | 1005 M | liq. | 1010 S p | liq. | ||
| a' | 11 | CH3 rock | 836 | C | 836 W | liq. | 838 S p | liq. | ||
| a' | 12 | CCC deform | 545 | C | 545 M | liq. | 548 M p | liq. | ||
| a' | 13 | CCN bend | 226 | C | 226 M | liq. | 226 M p | liq. | ||
| a | 14 | CH3 d-str | 3001 | C | 3001 VS | liq. | 2999 S | liq. | OV(ν1) | |
| a | 15 | CH2 a-str | 2849 | C | 2849 S | liq. | 2850 M | liq. | ||
| a | 16 | CH3 d-deform | 1465 | C | 1465 S | liq. | 1466 VS dp | liq. | SF(ν5) | |
| a | 17 | CH2 twist | 1256 | C | 1256 VW | liq. | 1270 VW dp | liq. | ||
| a | 18 | CH3 rock | 1022 | E | CF | |||||
| a | 19 | CH2 rock | 786 | C | 786 M | liq. | 784 VW dp | liq. | ||
| a | 20 | CCN bend | 378 | C | 378 M | liq. | 378 M dp | liq. | ||
| a | 21 | Torsion | 222 | C | MW | |||||
Source: Shimanouchi, 1972
Notes
| VS | Very strong |
| S | Strong |
| M | Medium |
| W | Weak |
| VW | Very weak |
| p | Polarized |
| dp | Depolarized |
| CF | Calculated frequency |
| SF | Calculation shows that the frequency approximately equals that of the vibration indicated in the parentheses. |
| OV | Overlapped by band indicated in parentheses. |
| MW | Torsional Frequency calculated from microwave spectroscopic data. |
| C | 3~6 cm-1 uncertainty |
| E | 15~30 cm-1 uncertainty |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Henry's Law data, Vibrational and/or electronic energy levels, 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]
Shimanouchi, 1972
Shimanouchi, T.,
Tables of Molecular Vibrational Frequencies Consolidated Volume I, National Bureau of Standards, 1972, 1-160. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Henry's Law data, Vibrational and/or electronic energy levels, References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid S°liquid Entropy of liquid at standard conditions T Temperature d(ln(kH))/d(1/T) Temperature dependence parameter for Henry's Law constant k°H Henry's Law constant at 298.15K 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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