Cyclobutanone

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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

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Individual Reactions

C4H5O- + Hydrogen cation = Cyclobutanone

By formula: C4H5O- + H+ = C4H6O

Quantity Value Units Method Reference Comment
Δr367.1 ± 4.1kcal/molG+TSBrickhouse and Squires, 1988gas phase; Between Me2C=NOH, EtCHO; B
Quantity Value Units Method Reference Comment
Δr359.0 ± 4.0kcal/molIMRBBrickhouse and Squires, 1988gas phase; Between Me2C=NOH, EtCHO; B

Cyclobutanone + Hydrogen = Cyclobutanol

By formula: C4H6O + H2 = C4H8O

Quantity Value Units Method Reference Comment
Δr-16.23 ± 0.18kcal/molChydWiberg, Crocker, et al., 1991liquid phase; ALS
Δr-12.7 ± 0.3kcal/molChydWiberg, Crocker, et al., 1991gas phase; ALS

1,1-Dimethoxybutane + Water = Cyclobutanone + 2Methyl Alcohol

By formula: C6H12O2 + H2O = C4H6O + 2CH4O

Quantity Value Units Method Reference Comment
Δr6.07 ± 0.07kcal/molCmWiberg, Morgan, et al., 1994liquid phase; ALS

Cyclobutanone + 2Methyl Alcohol = 1,1-Dimethoxybutane + Water

By formula: C4H6O + 2CH4O = C6H12O2 + H2O

Quantity Value Units Method Reference Comment
Δr-12.6 ± 0.41kcal/molCmWiberg, Morgan, et al., 1994gas phase; ALS

References

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Brickhouse and Squires, 1988
Brickhouse, M.D.; Squires, R.R., Gas Phase Bronsted vs. Lewis Acid-Base Reactions of 6,6-Dimethylfulvene. A Sensitive Probe of the Electronic Structures of Organic Anions, J. Am. Chem. Soc., 1988, 110, 9, 2706, https://doi.org/10.1021/ja00217a002 . [all data]

Wiberg, Crocker, et al., 1991
Wiberg, K.B.; Crocker, L.S.; Morgan, K.M., Thermochemical studies of carbonyl compounds. 5. Enthalpies of reduction of carbonyl groups, J. Am. Chem. Soc., 1991, 113, 3447-3450. [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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