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2-Butenal

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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 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- + Hydrogen cation = 2-Butenal

By formula: C4H5O- + H+ = C4H6O

Quantity Value Units Method Reference Comment
Deltar354.7 ± 2.1kcal/molG+TSBartmess and Kiplinger, 1986gas phase; Acid: CH3CH=CHCHO; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Deltar348.1 ± 2.0kcal/molIMREBartmess and Kiplinger, 1986gas phase; Acid: CH3CH=CHCHO; value altered from reference due to change in acidity scale; B

(CAS Reg. No. 64724-02-3 bullet 42949672952-Butenal) + 2-Butenal = CAS Reg. No. 64724-02-3

By formula: (CAS Reg. No. 64724-02-3 bullet 4294967295C4H6O) + C4H6O = CAS Reg. No. 64724-02-3

Quantity Value Units Method Reference Comment
Deltar60.5 ± 2.2kcal/molN/AAlconcel, Deyerl, et al., 2001gas phase; B
Deltar61.1 ± 2.4kcal/molTherZimmerman, Reed, et al., 1977gas phase; B

Hydrogen + 2-Butenal = Butanal

By formula: H2 + C4H6O = C4H8O

Quantity Value Units Method Reference Comment
Deltar-24.91 ± 0.10kcal/molChydDolliver, Gresham, et al., 1938gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -25.2 ± 0.1 kcal/mol; At 355°K; ALS

2-Butene, 1,1-dimethoxy- + Water = 2-Butenal + 2Methyl Alcohol

By formula: C6H12O2 + H2O = C4H6O + 2CH4O

Quantity Value Units Method Reference Comment
Deltar3.66 ± 0.04kcal/molCmWiberg, Morgan, et al., 1994liquid 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

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