2-Butenal
- Formula: C4H6O
- Molecular weight: 70.0898
- IUPAC Standard InChI: InChI=1S/C4H6O/c1-2-3-4-5/h2-4H,1H3
- IUPAC Standard InChIKey: MLUCVPSAIODCQM-UHFFFAOYSA-N
- CAS Registry Number: 4170-30-3
- 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: Crotonaldehyde; Crotonal; Crotonic aldehyde; Crotylaldehyde; β-Methylacrolein; Propylene aldehyde; Krotonaldehyd; Rcra waste number U053; UN 1143; But-2-enal; 1-Formylpropene; 2-Butenaldehyde; NSC 56354
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Reaction thermochemistry data
Go To: Top, 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
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
C4H5O- + =
By formula: C4H5O- + H+ = C4H6O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 354.7 ± 2.1 | kcal/mol | G+TS | Bartmess and Kiplinger, 1986 | gas phase; Acid: CH3CH=CHCHO; value altered from reference due to change in acidity scale; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 348.1 ± 2.0 | kcal/mol | IMRE | Bartmess and Kiplinger, 1986 | gas phase; Acid: CH3CH=CHCHO; value altered from reference due to change in acidity scale; B |
(CAS Reg. No. 64724-02-3 • 4294967295) +
= CAS Reg. No. 64724-02-3
By formula: (CAS Reg. No. 64724-02-3 • 4294967295C4H6O) + C4H6O = CAS Reg. No. 64724-02-3
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 60.5 ± 2.2 | kcal/mol | N/A | Alconcel, Deyerl, et al., 2001 | gas phase; B |
| ΔrH° | 61.1 ± 2.4 | kcal/mol | Ther | Zimmerman, Reed, et al., 1977 | gas phase; B |
+
=
By formula: H2 + C4H6O = C4H8O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -24.91 ± 0.10 | kcal/mol | Chyd | Dolliver, Gresham, et al., 1938 | gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -25.2 ± 0.1 kcal/mol; At 355°K; ALS |
+
=
+ 2
By formula: C6H12O2 + H2O = C4H6O + 2CH4O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 3.66 ± 0.04 | kcal/mol | Cm | Wiberg, Morgan, et al., 1994 | liquid phase; ALS |
References
Go To: Top, Reaction thermochemistry data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Bartmess and Kiplinger, 1986
Bartmess, J.E.; Kiplinger, J.P.,
'Kinetic' vs. thermodynamic acidities of enones in the gas phase,
J. Org. Chem., 1986, 51, 2173. [all data]
Alconcel, Deyerl, et al., 2001
Alconcel, L.S.; Deyerl, H.J.; Continetti, R.E.,
Effects of alkyl substitution on the energetics of enolate anions and radicals,
J. Am. Chem. Soc., 2001, 123, 50, 12675-12681, https://doi.org/10.1021/ja0120431
. [all data]
Zimmerman, Reed, et al., 1977
Zimmerman, A.H.; Reed, K.J.; Brauman, J.I.,
Photodetachment of electrons from enolate anions. Gas phase electron affinities of enolate radicals,
J. Am. Chem. Soc., 1977, 99, 7203. [all data]
Dolliver, Gresham, et al., 1938
Dolliver, M.A.; Gresham, T.L.; Kistiakowsky, G.B.; Smith, E.A.; Vaughan, W.E.,
Heats of organic reactions. VI. Heats of hydrogenation of some oxygen-containing compounds,
J. Am. Chem. Soc., 1938, 60, 440-450. [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]
Wiberg, Morgan, et al., 1994
Wiberg, K.B.; Morgan, K.M.; Maltz, H.,
Thermochemistry of carbonyl reactions. 6. A study of hydration equilibria,
J. Am. Chem. Soc., 1994, 116, 11067-11077. [all data]
Notes
Go To: Top, Reaction thermochemistry data, References
- Symbols used in this document:
ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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