Propanenitrile
- Formula: C3H5N
- Molecular weight: 55.0785
- 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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Condensed phase thermochemistry data
Go To: Top, Phase change data, Henry's Law 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 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 |
Phase change data
Go To: Top, Condensed phase thermochemistry data, Henry's Law 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 as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
DH - Eugene S. Domalski and Elizabeth D. Hearing
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 370. ± 1. | K | AVG | N/A | Average of 31 out of 35 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 180. ± 7. | K | AVG | N/A | Average of 8 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 180.37 | K | N/A | Weber and Kilpatrick, 1962, 2 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.02 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 561.3 | K | N/A | Castillo-Lopez and Trejo Rodriguez, 1987 | Uncertainty assigned by TRC = 0.2 K; Visual, TE with digital voltmeter calibr. by meas. on alkanes.; TRC |
Tc | 558.7 | K | N/A | Guye and Mallet, 1902 | Uncertainty assigned by TRC = 2. K; TRC |
Tc | 558.85 | K | N/A | Guye and Mallet, 1902, 2 | Uncertainty assigned by TRC = 1. K; TRC |
Tc | 558.85 | K | N/A | Guye and Mallet, 1902, 2 | Uncertainty assigned by TRC = 1. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 42.60 | bar | N/A | Castillo-Lopez and Trejo Rodriguez, 1987 | Uncertainty assigned by TRC = 0.10 bar; Visual; TRC |
Pc | 41.80 | bar | N/A | Guye and Mallet, 1902 | Uncertainty assigned by TRC = 0.9119 bar; TRC |
Pc | 41.7459 | bar | N/A | Guye and Mallet, 1902, 2 | Uncertainty assigned by TRC = 0.8106 bar; TRC |
Pc | 41.9485 | bar | N/A | Guye and Mallet, 1902, 2 | Uncertainty assigned by TRC = 0.8106 bar; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 36.3 ± 0.8 | kJ/mol | AVG | N/A | Average of 6 values; Individual data points |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
36.116 | 298.15 | N/A | Weber and Kilpatrick, 1962 | P = 6.29 kPa; DH |
31.81 | 371. | N/A | Majer and Svoboda, 1985 | |
36.1 | 303. | A | Stephenson and Malanowski, 1987 | Based on data from 288. to 371. K.; AC |
36.7 | 326. | BG | Baldt and Hall, 1971 | Based on data from 308. to 363. K.; AC |
36.5 | 280. | N/A | Milazzo, 1956 | Based on data from 189. to 295. K. See also Boublik, Fried, et al., 1984.; AC |
35.9 | 323. | N/A | Dreisbach and Shrader, 1949 | Based on data from 308. to 370. K. See also Dreisbach and Martin, 1949 and Boublik, Fried, et al., 1984.; AC |
Entropy of vaporization
ΔvapS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
121.1 | 298.15 | Weber and Kilpatrick, 1962 | P; DH |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
308.7 to 370.50 | 3.61732 | 1036.424 | -83.76 | Dreisbach and Shrader, 1949 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
5.03 | 180.4 | Domalski and Hearing, 1996 | AC |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
9.67 | 177.0 | Domalski and Hearing, 1996 | CAL |
27.91 | 180.4 |
Enthalpy of phase transition
ΔHtrs (kJ/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
1.7067 | 176.96 | crystaline, II | crystaline, I | Weber and Kilpatrick, 1962 | DH |
5.0300 | 180.37 | crystaline, I | liquid | Weber and Kilpatrick, 1962 | DH |
Entropy of phase transition
ΔStrs (J/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
9.64 | 176.96 | crystaline, II | crystaline, I | Weber and Kilpatrick, 1962 | DH |
27.89 | 180.37 | crystaline, I | liquid | Weber and Kilpatrick, 1962 | DH |
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 |
Gas phase ion energetics data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Henry's Law 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
L - Sharon G. Lias
Data compiled as indicated in comments:
B - John E. Bartmess
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
View reactions leading to C3H5N+ (ion structure unspecified)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 11.85 ± 0.02 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 794.1 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 763.0 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Electron affinity determinations
EA (eV) | Reference | Comment |
---|---|---|
0.015092 ± 0.000087 | Hammer, Diri, et al., 2003 | B |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
11.5 ± 0.25 | EI | Chess, Lapp, et al., 1982 | LBLHLM |
11.90 | PE | Kimura, Katsumata, et al., 1981 | LLK |
11.85 ± 0.01 | PE | Staley, Kleckner, et al., 1976 | LLK |
11.85 | PE | Lake and Thompson, 1970 | RDSH |
11.84 ± 0.02 | PI | Watanabe, Nakayama, et al., 1962 | RDSH |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
CH2N+ | 14.88 | ? | EI | Heerma, deRidder, et al., 1969 | RDSH |
C2H2+ | 14.70 | ? | EI | Heerma, deRidder, et al., 1969 | RDSH |
C2H3+ | 15.40 | ? | EI | Heerma, deRidder, et al., 1969 | RDSH |
C2H4+ | 12.40 ± 0.05 | HCN | EI | Franklin, Wada, et al., 1966 | RDSH |
C3H4N+ | 13.00 | H | EI | Heerma, deRidder, et al., 1969 | RDSH |
C3H4N+ | 12.55 ± 0.05 | H | EI | Franklin, Wada, et al., 1966 | RDSH |
De-protonation 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 |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Henry's Law 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.
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]
Weber and Kilpatrick, 1962, 2
Weber, L.A.; Kilpatrick, J.E.,
Entropy and related thermodynamic properties of propionitrile,
J. Chem. Phys., 1962, 36, 829. [all data]
Castillo-Lopez and Trejo Rodriguez, 1987
Castillo-Lopez, N.; Trejo Rodriguez, A.,
The critical temperatures and pressures of several n-alkanenitriles,
J. Chem. Thermodyn., 1987, 19, 671. [all data]
Guye and Mallet, 1902
Guye, P.A.; Mallet, E.,
Critical Constant and Molecular Complexity of Several Organic Compds.,
C. R. Hebd. Seances Acad. Sci., 1902, 133, 168. [all data]
Guye and Mallet, 1902, 2
Guye, P.A.; Mallet, E.,
Measurement of Critical Constants,
Arch. Sci. Phys. Nat., 1902, 13, 274-296. [all data]
Majer and Svoboda, 1985
Majer, V.; Svoboda, V.,
Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [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]
Baldt and Hall, 1971
Baldt, J.H.; Hall, H.K.K., Jr.,
Thermochemistry of strained-ring bridgehead nitriles and esters,
J. Am. Chem. Soc., 1971, 93, 140-145. [all data]
Milazzo, 1956
Milazzo, G.,
Ann. Chim. (Rome), 1956, 46, 1105. [all data]
Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E.,
The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [all data]
Dreisbach and Shrader, 1949
Dreisbach, R.R.; Shrader, S.A.,
Vapor Pressure--Temperature Data on Some Organic Compounds,
Ind. Eng. Chem., 1949, 41, 12, 2879-2880, https://doi.org/10.1021/ie50480a054
. [all data]
Dreisbach and Martin, 1949
Dreisbach, R.R.; Martin, R.A.,
Physical Data on Some Organic Compounds,
Ind. Eng. Chem., 1949, 41, 12, 2875-2878, https://doi.org/10.1021/ie50480a053
. [all data]
Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D.,
Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III,
J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985
. [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]
Hammer, Diri, et al., 2003
Hammer, N.I.; Diri, K.; Jordan, K.D.; Desfrancois, C.; Compton, R.N.,
Dipole-bound anions of carbonyl, nitrile, and sulfoxide containing molecules,
J. Chem. Phys., 2003, 119, 7, 3650-3660, https://doi.org/10.1063/1.1590959
. [all data]
Chess, Lapp, et al., 1982
Chess, E.K.; Lapp, R.L.; Gross, M.L.,
The question of tautomerism of alkylnitrile and isonitrile radical cations,
Org. Mass Spectrom., 1982, 17, 475. [all data]
Kimura, Katsumata, et al., 1981
Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki, T.; Iwata, S.,
Ionization energies, Ab initio assignments, and valence electronic structure for 200 molecules
in Handbook of HeI Photoelectron Spectra of Fundamental Organic Compounds, Japan Scientific Soc. Press, Tokyo, 1981. [all data]
Staley, Kleckner, et al., 1976
Staley, R.H.; Kleckner, J.E.; Beauchamp, J.L.,
Relationship between orbital ionization energies and molecular properties. Proton affinities and photoelectron spectra of nitriles,
J. Am. Chem. Soc., 1976, 98, 2081. [all data]
Lake and Thompson, 1970
Lake, R.F.; Thompson, H.,
The photoelectron spectra of some molecules containing the C N group,
Proc. Roy. Soc. (London), 1970, A317, 187. [all data]
Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J.,
Ionization potentials of some molecules,
J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [all data]
Heerma, deRidder, et al., 1969
Heerma, W.; deRidder, J.J.; Dijkstra, G.,
The electron-impact-induced fragmentation of n-alkyl cyanides,
Org. Mass Spectrom., 1969, 2, 1103. [all data]
Franklin, Wada, et al., 1966
Franklin, J.L.; Wada, Y.; Natalis, P.; Hierl, P.M.,
Ion-molecule reactions in acetonitrile and propionitrile,
J. Phys. Chem., 1966, 70, 2353. [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]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Henry's Law data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy Cp,liquid Constant pressure heat capacity of liquid EA Electron affinity IE (evaluated) Recommended ionization energy Pc Critical pressure S°liquid Entropy of liquid at standard conditions Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point Ttriple Triple point temperature d(ln(kH))/d(1/T) Temperature dependence parameter for Henry's Law constant k°H Henry's Law constant at 298.15K ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions ΔvapS Entropy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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