2-Propenenitrile

Formula: C₃H₃N
Molecular weight: 53.0626
IUPAC Standard InChI: InChI=1S/C3H3N/c1-2-3-4/h2H,1H2
IUPAC Standard InChIKey: NLHHRLWOUZZQLW-UHFFFAOYSA-N
CAS Registry Number: 107-13-1
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: Acrylonitrile; Acrylon; Carbacryl; Cyanoethylene; Fumigrain; Propenenitrile; Ventox; Vinyl cyanide; VCN; CH2CHCN; Acritet; Acrylnitril; Acrylonitrile monomer; Akrylonitryl; Cianuro di vinile; Cyanure de vinyle; ENT 54; Miller's fumigrain; Nitrile acrilico; Nitrile acrylique; TL 314; Akrylonitril; Rcra waste number U009; UN 1093; Vinylkyanid; Cyanoethene; Propenitrile; Propenonitrile; NSC 6362
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Gas phase thermochemistry data

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Data compiled as indicated in comments:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_gas	172.6	kJ/mol	N/A	Baroody and Carpenter, 1972	Value computed using Δ_fH_liquid° value of 140.0 kj/mol from Baroody and Carpenter, 1972 and Δ_vapH° value of 32.6 kj/mol from Hall and Baldt, 1971.; DRB
Δ_fH°_gas	179.7	kJ/mol	Ccr	Hall and Baldt, 1971	ALS

Condensed phase thermochemistry data

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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
Δ_fH°_liquid	140.	kJ/mol	Ccb	Baroody and Carpenter, 1972	ALS
Δ_fH°_liquid	147.1	kJ/mol	Ccr	Hall and Baldt, 1971	ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_liquid	-1756.4 ± 0.42	kJ/mol	Ccr	Hall and Baldt, 1971	ALS
Δ_cH°_liquid	-1759. ± 3.	kJ/mol	Ccb	Davis and Wiedeman, 1945	ALS
Quantity	Value	Units	Method	Reference	Comment
S°_liquid	178.91	J/mol*K	N/A	Finke, Messerly, et al., 1972	DH

Constant pressure heat capacity of liquid

C_p,liquid (J/mol*K)	Temperature (K)	Reference	Comment
98.7	298.15	Mirzaliev, Shakhuradov, et al., 1987	T = 213 to 333 K. Unsmoothed experimental datum given as 1.898 kJ/kgK at 293 K. Cp(liq) = 2.05105 + 0.00465503T/K + 1.34722x10-5T2/K2 kJ/kgK (213 to 333 K). Note, second coefficient should be negative.; DH
108.78	298.15	Finke, Messerly, et al., 1972	T = 12 to 350 K.; DH
106.7	297.	Hall and Baldt, 1971	DH
113.	298.	Davis and Wiedeman, 1945	DH

Phase change data

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Data compiled as indicated in comments:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
BS - Robert L. Brown and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
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
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity	Value	Units	Method	Reference	Comment
T_boil	351. ± 1.	K	AVG	N/A	Average of 11 values; Individual data points
Quantity	Value	Units	Method	Reference	Comment
T_fus	189.47	K	N/A	Witschonke, 1954	Uncertainty assigned by TRC = 0.2 K; TRC
T_fus	189.6	K	N/A	Witschonke, 1954	Uncertainty assigned by TRC = 0.1 K; TRC
T_fus	191.	K	N/A	Timmermans, 1922	Uncertainty assigned by TRC = 2. K; TRC
Quantity	Value	Units	Method	Reference	Comment
T_triple	189.63	K	N/A	Finke, Messerly, et al., 1972, 2	Crystal phase 1 phase; Uncertainty assigned by TRC = 0.01 K; TRC
Quantity	Value	Units	Method	Reference	Comment
T_c	540.	K	N/A	Wilson, Wilson, et al., 1996	Uncertainty assigned by TRC = 2. K; TRC
Quantity	Value	Units	Method	Reference	Comment
P_c	46.60	bar	N/A	Wilson, Wilson, et al., 1996	Uncertainty assigned by TRC = 0.20 bar; TRC
Quantity	Value	Units	Method	Reference	Comment
Δ_vapH°	31.6	kJ/mol	A	Stephenson and Malanowski, 1987	Based on data from 283. to 343. K.; AC
Δ_vapH°	33.	kJ/mol	V	Hall and Baldt, 1971	ALS
Δ_vapH°	32.6	kJ/mol	N/A	Hall and Baldt, 1971	DRB
Δ_vapH°	33.	kJ/mol	E	Davis and Wiedeman, 1945	ALS

Enthalpy of vaporization

Δ_vapH (kJ/mol)	Temperature (K)	Method	Reference	Comment
33.6	272.	A	Stephenson and Malanowski, 1987	Based on data from 257. to 352. K.; AC
32.9	308.	N/A	Gubkov, Fermor, et al., 1964	Based on data from 293. to 343. K.; AC
35.5	237.	N/A	Sevrugova, Sokorskii, et al., 1964	Based on data from 222. to 351. K.; AC
32.6	273. to 353.	N/A	Davis and Wiedeman, 1945	AC

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
293. to 343.	2.69607	621.275	-121.929	Gubkov, Fermor, et al., 1964, 2	Coefficents calculated by NIST from author's data.
222. to 351.	4.06661	1255.939	-41.853	Sevrugova, Sokorskii, et al., 1964, 2	Coefficents calculated by NIST from author's data.

Enthalpy of fusion

Δ_fusH (kJ/mol)	Temperature (K)	Reference	Comment
6.23	189.6	Domalski and Hearing, 1996	AC

Entropy of fusion

Δ_fusS (J/mol*K)	Temperature (K)	Reference	Comment
7.32	162.5	Domalski and Hearing, 1996	CAL
32.84	189.6	Domalski and Hearing, 1996	CAL

Enthalpy of phase transition

ΔH_trs (kJ/mol)	Temperature (K)	Initial Phase	Final Phase	Reference	Comment
1.1883	162.5	crystaline, II	crystaline, I	Finke, Messerly, et al., 1972	DH
6.2300	189.63	crystaline, I	liquid	Finke, Messerly, et al., 1972	DH

Entropy of phase transition

ΔS_trs (J/mol*K)	Temperature (K)	Initial Phase	Final Phase	Reference	Comment
7.31	162.5	crystaline, II	crystaline, I	Finke, Messerly, et al., 1972	DH
32.85	189.63	crystaline, I	liquid	Finke, Messerly, et al., 1972	DH

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:

Reaction thermochemistry data

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Data compiled as indicated in comments:
B - John E. Bartmess
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias

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

C₃H₂N^- + = 2-Propenenitrile

By formula: C₃H₂N^- + H⁺ = C₃H₃N

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	1553. ± 9.2	kJ/mol	G+TS	Bartmess, 1980	gas phase; value altered from reference due to change in acidity scale; B
Δ_rH°	1524. ± 19.	kJ/mol	EIAE	Heni and Illenberger, 1986	gas phase; From CH2=CHCN. G3MP2B3 calculations indicate a dHacdi ca. 374 kcal/mol; B
Quantity	Value	Units	Method	Reference	Comment
Δ_rG°	1528. ± 8.4	kJ/mol	IMRE	Bartmess, 1980	gas phase; value altered from reference due to change in acidity scale; B

2-Propenenitrile + = C₂₃H₁₇NO

By formula: C₃H₃N + C₂₀H₁₄O = C₂₃H₁₇NO

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-87.	kJ/mol	Kin	Samuilov, Nurullina, et al., 1983	liquid phase; solvent: Dichloroethane; Unpublished results; ALS
Δ_rH°	-87.4 ± 0.8	kJ/mol	Cm	Kiselev, Ustyugov, et al., 1977	liquid phase; solvent: 1,2-Dichloroethane; ALS

(CAS Reg. No. 42117-12-4 • 4294967295 2-Propenenitrile ) + = CAS Reg. No. 42117-12-4

By formula: (CAS Reg. No. 42117-12-4 • 4294967295C₃H₃N) + C₃H₃N = CAS Reg. No. 42117-12-4

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	239. ± 9.2	kJ/mol	N/A	Bartmess, Scott, et al., 1979	gas phase; value altered from reference due to change in acidity scale; B

C₃H₄N⁺ + 2-Propenenitrile = (C₃H₄N⁺ • )

By formula: C₃H₄N⁺ + C₃H₃N = (C₃H₄N⁺ • C₃H₃N)

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	128.	kJ/mol	PHPMS	Meot-Ner (Mautner) and Sieck, 1991	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
Δ_rS°	123.	J/mol*K	PHPMS	Meot-Ner (Mautner) and Sieck, 1991	gas phase; M

+ 2 = 2 2-Propenenitrile + ammonium sulphide

By formula: C₆H₈N₂S + 2H₃N = 2C₃H₃N + ammonium sulphide

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	126.4 ± 2.5	kJ/mol	Cm	Gladstone and Chang, 1966	liquid phase; Heat of formation derived by Cox and Pilcher, 1970; ALS

(CAS Reg. No. 180058-39-3 • 4294967295 2-Propenenitrile ) + = CAS Reg. No. 180058-39-3

By formula: (CAS Reg. No. 180058-39-3 • 4294967295C₃H₃N) + C₃H₃N = CAS Reg. No. 180058-39-3

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	95. ± 10.	kJ/mol	N/A	Bartmess, 1980	gas phase; B

2 2-Propenenitrile + ammonium sulphide = + 2

By formula: 2C₃H₃N + ammonium sulphide = C₆H₈N₂S + 2H₃N

Quantity	Value	Units	Method	Reference	Comment
Δ_rH°	-126.4 ± 2.5	kJ/mol	Cm	Gladstone and Chang, 1966	liquid phase; ALS

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

SOLUTION (10% IN CCl4 FOR 3800-1300, 10% IN CS2 FOR 1300-650, 10% IN CCl4 FOR 650-240 CM^-1) VERSUS SOLVENT; PERKIN-ELMER 521 (GRATING); DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm^-1 resolution

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Data compiled by: Pamela M. Chu, Franklin R. Guenther, George C. Rhoderick, and Walter J. Lafferty

gas; IFS66V (Bruker); 3-Term B-H Apodization
0.1250, 0.2410, 0.4820, 0.9640, 1.9290 cm^-1 resolution
gas; IFS66V (Bruker); Boxcar Apodization
0.1250, 0.2410, 0.4820, 0.9640, 1.9290 cm^-1 resolution
gas; IFS66V (Bruker); Happ Genzel Apodization
0.1250, 0.2410, 0.4820, 0.9640, 1.9290 cm^-1 resolution
gas; IFS66V (Bruker); NB Strong Apodization
0.1250, 0.2410, 0.4820, 0.9640, 1.9290 cm^-1 resolution
gas; IFS66V (Bruker); Triangular Apodization
0.1250, 0.2410, 0.4820, 0.9640, 1.9290 cm^-1 resolution

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Notes

Baroody and Carpenter, 1972
Baroody, E.E.; Carpenter, G.A., Heats of formation of propellant compounds (U), Rpt. Naval Ordnance Systems Command Task No. 331-003/067-1/UR2402-001 for Naval Ordance Station, Indian Head, MD, 1972, 1-9. [all data]

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]

Davis and Wiedeman, 1945
Davis, H.S.; Wiedeman, O.F., Physical properties of acrylonitrile, Ind. Chim. Belge, 1945, 37, 482-485. [all data]

Finke, Messerly, et al., 1972
Finke, H.L.; Messerly, J.F.; Todd, S.S., Thermodynamic properties of acrylonitrile, 1-aminopropane, 2-aminopropane, and 2-methyl-2-aminopropane, J. Chem. Thermodynam., 1972, 4, 359-374. [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]

Witschonke, 1954
Witschonke, C.R., Freezing point and purity data for some organic compounds, Anal. Chem., 1954, 26, 562-4. [all data]

Timmermans, 1922
Timmermans, J., Investigation of the Freezing Point of Organic Substances VII, Bull. Soc. Chim. Belg., 1922, 31, 389. [all data]

Finke, Messerly, et al., 1972, 2
Finke, H.L.; Messerly, J.F.; Todd, S.S., Thermodynamic properties of acrylonitrile, 1-aminopropane, 2-aminopropane, and 2-methyl-2-aminopropane, J. Chem. Thermodyn., 1972, 4, 359. [all data]

Wilson, Wilson, et al., 1996
Wilson, L.C.; Wilson, H.L.; Wilding, W.V.; Wilson, G.M., Critical Point Measurements for Fourteen Compounds by a Static Method and a Flow Method, J. Chem. Eng. Data, 1996, 41, 1252-4. [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]

Gubkov, Fermor, et al., 1964
Gubkov, A.N.; Fermor, N.A.; Smirnov, N.I., Zh. Prikl. Khim. (S.-Peterburg), 1964, 37, 2204. [all data]

Sevrugova, Sokorskii, et al., 1964
Sevrugova, N.N.; Sokorskii, V.A.; Zhavoronkov, N.M., Zh. Prikl. Khim. (Leningrad), 1964, 37, 1989. [all data]

Gubkov, Fermor, et al., 1964, 2
Gubkov, A.N.; Fermor, N.A.; Smirnov, N.I., Vapor Pressure of Mono-Poly Systems, Zh. Prikl. Khim. (Leningrad), 1964, 37, 2204-2210. [all data]

Sevrugova, Sokorskii, et al., 1964, 2
Sevrugova, N.N.; Sokorskii, V.A.; Zhavoronkov, N.M., Phase of Equilibrium for Mixtures Acrylonitrile-Acetonitrile, Zh. Prikl. Khim. (Leningrad), 1964, 37, 9, 1989-1993. [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]

Bartmess, 1980
Bartmess, J.E., Solvent effects on ion-molecule reactions. Vinyl anions vs. conjugate addition, J. Am. Chem. Soc., 1980, 102, 2483. [all data]

Heni and Illenberger, 1986
Heni, M.; Illenberger, E., Electron attachment by saturated nitriles. Acrylonitrile (CH₂H₃CN), and benzonitrile (C₆H₅CN), Int. J. Mass Spectrom. Ion Phys., 1986, 73, 127. [all data]

Samuilov, Nurullina, et al., 1983
Samuilov, Ya.D.; Nurullina, R.L.; Konovalov, A.I., Thermochemical and kinetic study of the Diels-Alder reaction with ethylene and acetylene dienophiles, Zh. Org. Khim., 1983, 19, 1431-1435. [all data]

Kiselev, Ustyugov, et al., 1977
Kiselev, V.D.; Ustyugov, A.N.; Breus, I.P.; Konovalov, A.I., Kinetic and thermochemical study of the Diels-Alder reaction, Dokl. Phys. Chem. (Engl. Transl.), 1977, 234, 320-322, In original 1089. [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]

Meot-Ner (Mautner) and Sieck, 1991
Meot-Ner (Mautner), M.; Sieck, L.W., Proton affinity ladders from variable-temperature equilibrium measurements. 1. A reevaluation of the upper proton affinity range, J. Am. Chem. Soc., 1991, 113, 12, 4448, https://doi.org/10.1021/ja00012a012 . [all data]

Gladstone and Chang, 1966
Gladstone, S.; Chang, H.Y., Determination of the standard heat of formation of 3,3'-thiodipropionitrile, J. Chem. Eng. Data, 1966, 11, 238-239. [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

Notes

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Symbols used in this document:

C_p,liquid	Constant pressure heat capacity of liquid
P_c	Critical pressure
S°_liquid	Entropy of liquid at standard conditions
T_boil	Boiling point
T_c	Critical temperature
T_fus	Fusion (melting) point
T_triple	Triple point temperature
ΔH_trs	Enthalpy of phase transition
ΔS_trs	Entropy of phase transition
Δ_cH°_liquid	Enthalpy of combustion of liquid at standard conditions
Δ_fH°_gas	Enthalpy of formation of gas at standard conditions
Δ_fH°_liquid	Enthalpy of formation of liquid at standard conditions
Δ_fusH	Enthalpy of fusion
Δ_fusS	Entropy of fusion
Δ_rG°	Free energy of reaction at standard conditions
Δ_rH°	Enthalpy of reaction at standard conditions
Δ_rS°	Entropy of reaction at standard conditions
Δ_vapH	Enthalpy of vaporization
Δ_vapH°	Enthalpy of vaporization at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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