but-2(E)-enenitrile
- Formula: C4H5N
- Molecular weight: 67.0892
- IUPAC Standard InChI: InChI=1S/C4H5N/c1-2-3-4-5/h2-3H,1H3/b3-2+
- IUPAC Standard InChIKey: NKKMVIVFRUYPLQ-NSCUHMNNSA-N
- CAS Registry Number: 627-26-9
- 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. - Stereoisomers:
- Other names: (E)-2-Butenenitrile
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Gas 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°gas | 140.7 ± 0.92 | kJ/mol | Ccb | Konicek, Prochzka, et al., 1969 |
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°liquid | 100.7 ± 0.92 | kJ/mol | Ccb | Konicek, Prochzka, et al., 1969 | |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -2389.3 ± 0.88 | kJ/mol | Ccb | Konicek, Prochzka, et al., 1969 | |
| ΔcH°liquid | -2393. | kJ/mol | Ccb | Bruylants and Christiaen, 1925 |
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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔvapH° | 40.0 | kJ/mol | V | Konicek, Prochzka, et al., 1969 | ALS |
| ΔvapH° | 40.0 | kJ/mol | N/A | Konicek, Prochzka, et al., 1969 | DRB |
| ΔvapH° | 40.0 | kJ/mol | N/A | Konicek, Prochzka, et al., 1969 | AC |
Enthalpy of vaporization
| ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 39.7 | 307. | A | Stephenson and Malanowski, 1987 | Based on data from 292. to 420. K.; AC |
| 40.5 | 268. | N/A | Stull, 1947 | Based on data from 254. to 395. K.; AC |
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:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 10.23 ± 0.05 | PE | Houk and Munchausen, 1976 | Vertical value; LLK |
Gas Chromatography
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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
Normal alkane RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | HP-1 | 637. | Bendimerad and Bendiab, 2005 | 50. m/0.2 mm/0.5 μm, He, 2. K/min, 250. C @ 60. min; Tstart: 60. C |
Normal alkane RI, polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | Innowax | 1157. | Bendimerad and Bendiab, 2005 | 50. m/0.2 mm/0.5 μm, He, 2. K/min, 250. C @ 60. min; Tstart: 60. C |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Konicek, Prochzka, et al., 1969
Konicek, J.; Prochzka, M.; Krestanov, V.; Smisek, M.,
Thermochemie der nitrile I. Über die bildungswärmen aliphatischer nitrile,
Collect. Czech. Chem. Commun., 1969, 34, 2249-2257. [all data]
Bruylants and Christiaen, 1925
Bruylants, P.; Christiaen, A.,
Thermochimie des Butenes-Nitriles,
Bull. Soc. Chim. Belg., 1925, 34, 144-150. [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]
Stull, 1947
Stull, Daniel R.,
Vapor Pressure of Pure Substances. Organic and Inorganic Compounds,
Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022
. [all data]
Houk and Munchausen, 1976
Houk, K.N.; Munchausen, L.L.,
Ionization potentials, electron affinities, reactivities of cyanoalkenes related electron-deficient alkenes. A frontier molecular orbital treatment of cyanoalkene reactivities in cycloaddition, electrophilic, nucleophilic, and radical reactions.,
J. Am. Chem. Soc., 1976, 98, 937. [all data]
Bendimerad and Bendiab, 2005
Bendimerad, N.; Bendiab, S.A.T.,
Composition and antibacterial activity of Pseudocytisus integrifolius (Salisb.) essential oil from Algeria,
J. Agric. Food Chem., 2005, 53, 8, 2947-2952, https://doi.org/10.1021/jf047937u
. [all data]
Notes
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- Symbols used in this document:
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 ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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