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Acetylacetone

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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
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias

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Individual Reactions

C5H7O2- + Hydrogen cation = Acetylacetone

By formula: C5H7O2- + H+ = C5H8O2

Quantity Value Units Method Reference Comment
Deltar1438. ± 8.8kJ/molG+TSTaft and Bordwell, 1988gas phase; at 330K: neutral enol/keto ratio should be 8:1 ( Strohmeier and Höhne, 1952); B
Deltar1438. ± 9.6kJ/molG+TSCumming and Kebarle, 1978gas phase; At 500K: neutral enol/keto ratio is 1.7:1, Folkendt, Weiss-Lopez, et al., 1989. «DELTA»H=-4.7 kcal/mol, enol favored. Carbonyls anti in anion, via calc: Irikura, 1999; B
Quantity Value Units Method Reference Comment
Deltar1409. ± 8.4kJ/molIMRETaft and Bordwell, 1988gas phase; at 330K: neutral enol/keto ratio should be 8:1 ( Strohmeier and Höhne, 1952); B
Deltar1408. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase; At 500K: neutral enol/keto ratio is 1.7:1, Folkendt, Weiss-Lopez, et al., 1989. «DELTA»H=-4.7 kcal/mol, enol favored. Carbonyls anti in anion, via calc: Irikura, 1999; B

Acetylacetone = 3-Penten-2-one, 4-hydroxy-

By formula: C5H8O2 = C5H8O2

Quantity Value Units Method Reference Comment
Deltar-7.9 ± 0.4kJ/molKinSchweig, Vermeer, et al., 1974liquid phase; Photoelectron spectroscopy; ALS
Deltar-10. ± 0.8kJ/molEqkThompson and Allred, 1971liquid phase; solvent: Cyclohexane; NMR, UV; ALS
Deltar-12. ± 0.8kJ/molEqkCalmon, 1969liquid phase; ALS

Chlorine anion + Acetylacetone = (Chlorine anion bullet Acetylacetone)

By formula: Cl- + C5H8O2 = (Cl- bullet C5H8O2)

Quantity Value Units Method Reference Comment
Deltar56.07kJ/molTDEqFrench, Ikuta, et al., 1982gas phase; B

Free energy of reaction

DeltarG° (kJ/mol) T (K) Method Reference Comment
46.0421.PHPMSFrench, Ikuta, et al., 1982gas phase; M

Iodide + Acetylacetone = (Iodide bullet Acetylacetone)

By formula: I- + C5H8O2 = (I- bullet C5H8O2)

Quantity Value Units Method Reference Comment
Deltar63.2 ± 4.2kJ/molTDAsCaldwell, Masucci, et al., 1989gas phase; B,M

Acetylacetone = 2-Propenoic acid, 3-hydroxy-2-methyl-, ethyl ester

By formula: C5H8O2 = C6H10O3

Quantity Value Units Method Reference Comment
Deltar-19.5 ± 0.75kJ/molEqkFolkendt, Weiss-Lopez, et al., 1985gas phase; NMR; ALS

3-Penten-2-one, 4-hydroxy- = Acetylacetone

By formula: C5H8O2 = C5H8O2

Quantity Value Units Method Reference Comment
Deltar16.8kJ/molEqkMines and Thompson, 1975gas 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.

Taft and Bordwell, 1988
Taft, R.W.; Bordwell, F.G., Structural and Solvent Effects Evaluated from Acidities Measured in Dimethyl Sulfoxide and in the Gas Phase, Acc. Chem. Res., 1988, 21, 12, 463, https://doi.org/10.1021/ar00156a005 . [all data]

Strohmeier and Höhne, 1952
Strohmeier, W.; Höhne, I., Keto-Enol-Umwandlung des Acetylacteons in Gaszustand, Z. Naturfor., 1952, 7B, 184. [all data]

Cumming and Kebarle, 1978
Cumming, J.B.; Kebarle, P., Summary of gas phase measurements involving acids AH. Entropy changes in proton transfer reactions involving negative ions. Bond dissociation energies D(A-H) and electron affinities EA(A), Can. J. Chem., 1978, 56, 1. [all data]

Folkendt, Weiss-Lopez, et al., 1989
Folkendt, M.M.; Weiss-Lopez, B.E.; Chauvel, J.P., Jr.; True, N.S., Gas-Phase 1H NMR Studies of Keto-Enol Tautomerization of Acetylacetone, Methyl Acetoacetate, and Ethyl Acetoacetate, J. Phys. Chem., 1989, 89, 15, 3347, https://doi.org/10.1021/j100261a038 . [all data]

Irikura, 1999
Irikura, K.K., Acetylacetonate (acac) anion in the gas phase: predicted structures, vibrational spectra, and photodetachment energies, Int. J. Mass Spectrom., 1999, 187, 577-587, https://doi.org/10.1016/S1387-3806(98)14192-1 . [all data]

Schweig, Vermeer, et al., 1974
Schweig, A.; Vermeer, H.; Weidner, U., A photoelectron spectroscopic study of keto-enol tautomerism in acetylacetones - a new application of photoelectron spectroscopy, Chem. Phys. Lett., 1974, 26, 229-233. [all data]

Thompson and Allred, 1971
Thompson, D.W.; Allred, A.L., Keto-enol equilibria in 2,4-Pentanedione and 3,3-dideuterio-2,4-pentanedione, J. Phys. Chem., 1971, 75, 433-435. [all data]

Calmon, 1969
Calmon, J.P., Thermodynamic functions of enolization of aliphatic «beta»-diketones, C. R. Acad. Sci. Paris, 1969, 268, 1435-1438. [all data]

French, Ikuta, et al., 1982
French, M.A.; Ikuta, S.; Kebarle, P., Hydrogen bonding of O-H and C-H hydrogen donors to Cl-. Results from mass spectrometric measurement of the ion-molecule equilibria RH + Cl- = RHCl-, Can. J. Chem., 1982, 60, 1907. [all data]

Caldwell, Masucci, et al., 1989
Caldwell, G.W.; Masucci, J.A.; Ikonomou, M.G., Negative Ion Chemical Ionization Mass Spectrometry - Binding of Molecules to Bromide and Iodide Anions, Org. Mass Spectrom., 1989, 24, 1, 8, https://doi.org/10.1002/oms.1210240103 . [all data]

Folkendt, Weiss-Lopez, et al., 1985
Folkendt, M.M.; Weiss-Lopez, B.E.; Chauvel, J.P., Jr.; True, N.S., Gas-phase 1H NMR studies of keto-enol tautomerism of acetylacetone, methyl acetoacetate, and ethyl acetoacetate, J. Phys. Chem., 1985, 89, 3347-3352. [all data]

Mines and Thompson, 1975
Mines, G.W.; Thompson, H., Infrared and photoelectron spectra, and keto-enol tautomerism of acetylacetones and acetoacetic esters, Proc. Roy. Soc. London A, 1975, 342, 327-339. [all data]


Notes

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