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
- Permanent link for this species. Use this link for bookmarking this species for future reference.
- Information on this page:
- Other data available:
- Data at other public NIST sites:
- Options:
Data at NIST subscription sites:
- NIST / TRC Web Thermo Tables, "lite" edition (thermophysical and thermochemical data)
- NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)
NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.
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 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 |
|---|---|---|---|---|---|
| ΔfH°gas | 172.6 | kJ/mol | N/A | Baroody and Carpenter, 1972 | Value computed using ΔfHliquid° value of 140.0 kj/mol from Baroody and Carpenter, 1972 and ΔvapH° value of 32.6 kj/mol from Hall and Baldt, 1971.; DRB |
| ΔfH°gas | 179.7 | kJ/mol | Ccr | Hall and Baldt, 1971 | ALS |
Condensed phase thermochemistry data
Go To: Top, Gas 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 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 | 140. | kJ/mol | Ccb | Baroody and Carpenter, 1972 | ALS |
| ΔfH°liquid | 147.1 | kJ/mol | Ccr | Hall and Baldt, 1971 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -1756.4 ± 0.42 | kJ/mol | Ccr | Hall and Baldt, 1971 | ALS |
| ΔcH°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
| Cp,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/kg*K at 293 K. Cp(liq) = 2.05105 + 0.00465503T/K + 1.34722x10-5T2/K2 kJ/kg*K (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 |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, Condensed phase 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 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- + =
By formula: C3H2N- + H+ = C3H3N
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1553. ± 9.2 | kJ/mol | G+TS | Bartmess, 1980 | gas phase; value altered from reference due to change in acidity scale; B |
| ΔrH° | 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 |
| ΔrG° | 1528. ± 8.4 | kJ/mol | IMRE | Bartmess, 1980 | gas phase; value altered from reference due to change in acidity scale; B |
+
= C23H17NO
By formula: C3H3N + C20H14O = C23H17NO
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -87. | kJ/mol | Kin | Samuilov, Nurullina, et al., 1983 | liquid phase; solvent: Dichloroethane; Unpublished results; ALS |
| ΔrH° | -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) +
= 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 |
|---|---|---|---|---|---|
| ΔrH° | 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 |
By formula: C3H4N+ + C3H3N = (C3H4N+ • C3H3N)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 128. | kJ/mol | PHPMS | Meot-Ner (Mautner) and Sieck, 1991 | gas phase; M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrS° | 123. | J/mol*K | PHPMS | Meot-Ner (Mautner) and Sieck, 1991 | gas phase; M |
+ 2
= 2
+ ammonium sulphide
By formula: C6H8N2S + 2H3N = 2C3H3N + ammonium sulphide
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 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) +
= 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 |
|---|---|---|---|---|---|
| ΔrH° | 95. ± 10. | kJ/mol | N/A | Bartmess, 1980 | gas phase; B |
2 + ammonium sulphide =
+ 2
By formula: 2C3H3N + ammonium sulphide = C6H8N2S + 2H3N
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -126.4 ± 2.5 | kJ/mol | Cm | Gladstone and Chang, 1966 | liquid phase; 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.
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]
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
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 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 ΔrS° Entropy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
- The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
- Customer support for NIST Standard Reference Data products.