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Acetylacetone

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Gas phase ion energetics 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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

Quantity Value Units Method Reference Comment
IE (evaluated)8.85 ± 0.02eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)873.5kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity836.8kJ/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
8.85 ± 0.05PEHouk, Davis, et al., 1973LLK
8.82 ± 0.02PIShigorin, Filyugina, et al., 1967RDSH
8.87 ± 0.03PIWatanabe, Nakayama, et al., 1962RDSH
9.63 ± 0.01PEHush, Livett, et al., 1987Vertical value; LBLHLM
9.15PECauletti, Furlani, et al., 1980Vertical value; LLK
9.00PESchweig, Vermeer, et al., 1974Vertical value; LLK
9.18 ± 0.07PEEvans, Hamnett, et al., 1972Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C4H5O2+10.7 ± 0.1CH3EIReichert and Westmore, 1969RDSH
C4H5O2+10.24CH3PIShigorin, Filyugina, et al., 1967RDSH

De-protonation 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

References

Go To: Top, Gas phase ion energetics data, Notes

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

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [all data]

Houk, Davis, et al., 1973
Houk, K.N.; Davis, L.P.; Newkome, G.R.; Duke, R.E., Jr.; Nauman, R.V., Photoelectron spectroscopy of cyclic «beta»-diketones their enolone tautomers, J. Am. Chem. Soc., 1973, 95, 8364. [all data]

Shigorin, Filyugina, et al., 1967
Shigorin, D.N.; Filyugina, A.D.; Potapov, V.K., Role of intramolecular hydrogen bonding in the ionisation and dissociation of compounds, Zh. Fiz. Khim., 1967, 41, 2336, In original 1255. [all data]

Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J., Ionization potentials of some molecules, J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [all data]

Hush, Livett, et al., 1987
Hush, N.S.; Livett, M.K.; Peel, J.B.; Willett, G.D., Variable-temperature ultraviolet photoelectron spectroscopy of the keto-enol tautomers of pentane-2,4-dione, Aust. J. Chem., 1987, 40, 599. [all data]

Cauletti, Furlani, et al., 1980
Cauletti, C.; Furlani, C.; Storto, G., Coordinative bond d-shell ionisations in the UV photoelectron spectra of bis({beta}-diketonato) cobalt (II) copper (II) complexes, their thio analogues, J. Electron Spectrosc. Relat. Phenom., 1980, 18, 329. [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. [all data]

Evans, Hamnett, et al., 1972
Evans, S.; Hamnett, A.; Orchard, A.F.; Lloyd, D.R., Study of the metal-oxygen bond in simple tris-chelate complexes by He(I) photoelectron spectroscopy, Faraday Discuss. Chem. Soc., 1972, 54, 227. [all data]

Reichert and Westmore, 1969
Reichert, C.; Westmore, J.B., Mass spectral studies of metal chelates. IV.Mass spectra, appearance potentials, and coordinate bond energies of bis(acetylacetonate)metal(II) complexes of the first transition series, Inorg. Chem., 1969, 8, 1012. [all data]

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]


Notes

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