- Formula: C4H6O
- Molecular weight: 70.0898
- IUPAC Standard InChI:
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- 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
- Other names: Crotonaldehyde; Crotonal; Crotonic aldehyde; Crotylaldehyde; «beta»-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
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C4H5O- + =
By formula: C4H5O- + H+ = C4H6O
|rH°||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|
|rG°||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
|rH°||60.5 ± 2.2||kcal/mol||N/A||Alconcel, Deyerl, et al., 2001||gas phase; B|
|rH°||61.1 ± 2.4||kcal/mol||Ther||Zimmerman, Reed, et al., 1977||gas phase; B|
By formula: H2 + C4H6O = C4H8O
|rH°||-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
|rH°||3.66 ± 0.04||kcal/mol||Cm||Wiberg, Morgan, et al., 1994||liquid phase; ALS|
Go To: Top, Reaction thermochemistry data, Notes
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]
Go To: Top, Reaction thermochemistry data, References
- Symbols used in this document:
rG° Free energy of reaction at standard conditions rH° Enthalpy of reaction at standard conditions
- Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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