2-Butenal
- Formula: C4H6O
- Molecular weight: 70.0898
- 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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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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -109.7 ± 2.4 | kJ/mol | Ccb | Van-chin-syan, Kochubei, et al., 1996 | ALS |
ΔfH°gas | -106.9 | kJ/mol | N/A | Tjebbes, 1960 | Value computed using ΔfHliquid° value of -144.1±0.4 kj/mol from Tjebbes, 1960 and ΔvapH° value of 37.2 kj/mol from Van-chin-syan, Kochubei, et al., 1996.; DRB |
ΔfH°gas | -100.5 ± 1.5 | kJ/mol | Chyd | Dolliver, Gresham, et al., 1938 | Heat of formation derived by Cox and Pilcher, 1970; 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | -146.9 ± 2.4 | kJ/mol | Ccb | Van-chin-syan, Kochubei, et al., 1996 | |
ΔfH°liquid | -144.1 ± 0.4 | kJ/mol | Ccb | Tjebbes, 1960 | |
ΔfH°liquid | -138.6 ± 1.9 | kJ/mol | Chyd | Dolliver, Gresham, et al., 1938 | Heat of formation derived by Cox and Pilcher, 1970 |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -2284.7 ± 2.3 | kJ/mol | Ccb | Van-chin-syan, Kochubei, et al., 1996 | Corresponding ΔfHºliquid = -146.8 kJ/mol (simple calculation by NIST; no Washburn corrections) |
ΔcH°liquid | -2287.4 ± 0.4 | kJ/mol | Ccb | Tjebbes, 1960 | Corresponding ΔfHºliquid = -144.1 kJ/mol (simple calculation by NIST; no Washburn corrections) |
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
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° | 1484. ± 8.8 | kJ/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° | 1456. ± 8.4 | kJ/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° | 253. ± 9.2 | kJ/mol | N/A | Alconcel, Deyerl, et al., 2001 | gas phase; B |
ΔrH° | 256. ± 10. | kJ/mol | Ther | Zimmerman, Reed, et al., 1977 | gas phase; B |
By formula: H2 + C4H6O = C4H8O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -104.2 ± 0.42 | kJ/mol | Chyd | Dolliver, Gresham, et al., 1938 | gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -105.3 ± 0.4 kJ/mol; At 355°K; ALS |
By formula: C6H12O2 + H2O = C4H6O + 2CH4O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 15.3 ± 0.2 | kJ/mol | Cm | Wiberg, Morgan, et al., 1994 | 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.
Van-chin-syan, Kochubei, et al., 1996
Van-chin-syan, Yu.Ya.; Kochubei, V.V.; Sergeev, V.V.; Raevskii, Yu.A.; Gerasimchuk, S.I.; Kotovich, Kh.Z.,
Thermodynamic properties of some acids and aldehydes of the acrylic series,
Sov. J. Chem. Phys. (Engl. Transl.), 1996, 70, 1789-1794, In original 1932. [all data]
Tjebbes, 1960
Tjebbes, J.,
Heats of combustion of butannal and some related compounds,
Acta Chem. Scand., 1960, 14, 180-188. [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]
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]
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, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, References
- 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 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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