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, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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 |
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 | kJ/mol | Kin | Samuilov, Nurullina, et al., 1983 | liquid phase; solvent: Dichloroethane; Unpublished results |
Gas phase ion energetics 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:
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
B - John E. Bartmess
Electron affinity determinations
EA (eV) | Method | Reference | Comment |
---|---|---|---|
1.249 ± 0.087 | TDEq | Chowdhury and Kebarle, 1986 | ΔGea(523 K) = -28.4 kcal/mol; ΔSea = -1.0 eu.; B |
0.79 ± 0.10 | SI | Farragher and Page, 1967 | The Magnetron method, lacking mass analysis, is not considered reliable.; B |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
11.16 ± 0.03 | PI | Kotov and Potapov, 1972 | LLK |
11.15 | PE | Bock and Stafast, 1972 | LLK |
11.3 | PE | Bieri, Asbrink, et al., 1982 | Vertical value; LBLHLM |
Mass spectrum (electron ionization)
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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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
Due to licensing restrictions, this spectrum cannot be downloaded.
Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | Japan AIST/NIMC Database- Spectrum MS-NW-4972 |
NIST MS number | 230072 |
References
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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]
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]
Chowdhury and Kebarle, 1986
Chowdhury, S.; Kebarle, P.,
Electron affinities of di- and tetracyanoethylene and cyanobenzenes based on measurements of gas-phase electron transfer equilibria,
J. Am. Chem. Soc., 1986, 108, 5453. [all data]
Farragher and Page, 1967
Farragher, A.L.; Page, F.M.,
Experimental Determination of Electron Affinities. Part 11. - Electron Capture by Some Cyanocarbons and Related Compounds,
Trans. Farad. Soc., 1967, 63, 2369, https://doi.org/10.1039/tf9676302369
. [all data]
Kotov and Potapov, 1972
Kotov, B.V.; Potapov, V.K.,
Ionization potentials of strong organic electron acceptors,
Khim. Vys. Energ., 1972, 6, 375. [all data]
Bock and Stafast, 1972
Bock, H.; Stafast, H.,
Photoelektronenspektren und molekuleigenschaften, IX. Die π-Systeme der cis- und trans-dicyan-athylene,
Chem. Ber., 1972, 105, 1158. [all data]
Bieri, Asbrink, et al., 1982
Bieri, G.; Asbrink, L.; Von Niessen, W.,
30.4-nm He(II) photoelectron spectra of organic molecules,
J. Electron Spectrosc. Relat. Phenom., 1982, 27, 129. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), References
- Symbols used in this document:
EA Electron affinity ΔfH°gas Enthalpy of formation of gas at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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