Fumaronitrile
- Formula: C4H2N2
- Molecular weight: 78.0721
- IUPAC Standard InChIKey: KYPOHTVBFVELTG-OWOJBTEDSA-N
- CAS Registry Number: 764-42-1
- 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: 2-Butenedinitrile, (E)-; trans-1,2-Dicyanoethylene; Fumaric nitrile; Fumarodinitrile; Furmaronitrile; (E)-Butenedinitrile; (E)-CH(CN)CH(CN); But-2-enedinitrile, (E)-; (2E)-2-Butenedinitrile; (E)-1,2-Dicyanoethylene; 2-Butenedinitrile, (2E)-; NSC 17555; trans-1,2-Dicyanoethene
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change 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 | 340. ± 3. | kJ/mol | Ccb | Boyd, Guha, et al., 1967 |
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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°solid | 268. ± 2. | kJ/mol | Ccb | Boyd, Guha, et al., 1967 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -2128. ± 2. | kJ/mol | Ccb | Boyd, Guha, et al., 1967 |
Phase change 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:
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.
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 459.2 | K | N/A | Weast and Grasselli, 1989 | BS |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 369. | K | N/A | Bader, Buckley, et al., 1957 | Uncertainty assigned by TRC = 3. K; TRC |
Tfus | 369.2 | K | N/A | de Wolf and Van de Straete, 1935 | Uncertainty assigned by TRC = 0.8 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 68.6 | kJ/mol | N/A | De Wit, Van Miltenburg, et al., 1983 | AC |
ΔsubH° | 72.0 ± 0.8 | kJ/mol | V | Boyd, Guha, et al., 1967 | ALS |
ΔsubH° | 72.0 | kJ/mol | N/A | Boyd, Guha, et al., 1967 | DRB |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
69.6 | 260. | TE,ME | De Wit, Van Miltenburg, et al., 1983 | Based on data from 250. to 269. K.; AC |
72. ± 0.8 | 263. | ME | Boyd, Guha, et al., 1967 | Based on data from 245. to 281. K. See also Cox and Pilcher, 1970.; AC |
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 by: 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
+
= C24H16N2O
By formula: C20H14O + C4H2N2 = C24H16N2O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -82. | kJ/mol | Kin | Samuilov, Nurullina, et al., 1983 | liquid phase; solvent: Dichloroethane; Unpublished results |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change 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.
Boyd, Guha, et al., 1967
Boyd, R.H.; Guha, K.R.; Wuthrich, R.,
Thermochemistry of cyanocarbons. II. The heats of combustion of pyridinium dicyanomethylide, malononitrile, and fumaronitrile,
J. Phys. Chem., 1967, 71, 2187-2191. [all data]
Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]
Bader, Buckley, et al., 1957
Bader, A.R.; Buckley, R.P.; Leavitt, F.; Szwarc, M.,
J. Am. Chem. Soc., 1957, 79, 5621. [all data]
de Wolf and Van de Straete, 1935
de Wolf, J.; Van de Straete, L.,
Maleonitrile and Fumaronitrole,
Bull. Cl. Sci., Acad. R. Belg., 1935, 21, 216. [all data]
De Wit, Van Miltenburg, et al., 1983
De Wit, H.G.M.; Van Miltenburg, J.C.; De Kruif, C.G.,
Thermodynamic properties of molecular organic crystals containing nitrogen, oxygen, and sulphur 1. Vapour pressures and enthalpies of sublimation,
The Journal of Chemical Thermodynamics, 1983, 15, 7, 651-663, https://doi.org/10.1016/0021-9614(83)90079-4
. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press Inc., London, 1970, 643. [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]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, References
- Symbols used in this document:
Tboil Boiling point Tfus Fusion (melting) point ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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