Acetylacetone

• Formula: C₅H₈O₂
• Molecular weight: 100.1158
• IUPAC Standard InChI: InChI=1S/C5H8O2/c1-4(6)3-5(2)7/h3H2,1-2H3 Copy

  
• IUPAC Standard InChIKey: YRKCREAYFQTBPV-UHFFFAOYSA-N Copy
• CAS Registry Number: 123-54-6
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
  The 3d structure may be viewed using Java or Javascript.
• Other names: 2,4-Pentanedione; Acetoacetone; Diacetylmethane; Pentane-2,4-dione; 2-Propanone, acetyl-; 2,4-Dioxopentane; 2,4-Pentadione; CH3COCH2COCH3; Acetone, acetyl-; ACAC; Pentanedione; Pentanedione-2,4; Acetyl 2-propanone; UN 2310; 2,4-Pentandione; Pentan-2,4-dione; NSC 5575
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• Information on this page:
  • Gas phase ion energetics data
  • Mass spectrum (electron ionization)
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Ion clustering data
  • IR Spectrum
  • UV/Visible spectrum
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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Gas phase ion energetics data

Go To: Top, Mass spectrum (electron ionization), Gas Chromatography, References, Notes

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

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

C₅H₇O₂^- +  =

By formula: C₅H₇O₂^- + H⁺ = C₅H₈O₂

Mass spectrum (electron ionization)

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

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

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Additional Data

Gas Chromatography

Go To: Top, Gas phase ion energetics data, Mass spectrum (electron ionization), References, Notes

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

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Kovats' RI, non-polar column, isothermal

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Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Van Den Dool and Kratz RI, non-polar column, custom temperature program

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Van Den Dool and Kratz RI, polar column, custom temperature program

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Normal alkane RI, non-polar column, temperature ramp

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Normal alkane RI, non-polar column, custom temperature program

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Normal alkane RI, polar column, temperature ramp

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Normal alkane RI, polar column, custom temperature program

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References

Go To: Top, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, 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 β-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]

Mijin and Antonovic, 2004
Mijin, D.Z.; Antonovic, D.G., Temperature dependence of the Kovats retention indices for alkyl 1,3-diketones on a DB-5 capillary column, J. Serb. Chem. Soc., 2004, 69, 10, 759-767, https://doi.org/10.2298/JSC0410759M . [all data]

Tiess, 1984
Tiess, D., Gaschromatographische Retentionsindices von 125 leicht- bis mittelflüchtigen organischen Substanzen toxikologisch-analytischer Relevanz auf SE-30, Wiss. Z. Wilhelm-Pieck-Univ. Rostock Math. Naturwiss. Reihe, 1984, 33, 6-9. [all data]

Bogoslovsky, Anvaer, et al., 1978
Bogoslovsky, Yu.N.; Anvaer, B.I.; Vigdergauz, M.S., Chromatographic constants in gas chromatography (in Russian), Standards Publ. House, Moscow, 1978, 192. [all data]

Haken, Ho, et al., 1975
Haken, J.K.; Ho, D.K.M.; Vaughan, C.E., Gas chromatography of homologous esters. VII. The retention behaviour of pyruvate esters and related carbonyl and carboxyl compounds, J. Chromatogr., 1975, 106, 2, 317-325, https://doi.org/10.1016/S0021-9673(00)93839-1 . [all data]

Vernon and Edwards, 1975
Vernon, F.; Edwards, G.T., Gas-liquid chromatography on fluorinated stationary phases. II. Fluorinated compounds containing a functional group, J. Chromatogr., 1975, 114, 1, 87-93, https://doi.org/10.1016/S0021-9673(00)85245-0 . [all data]

Pino, Mesa, et al., 2005
Pino, J.A.; Mesa, J.; Muñoz, Y.; Martí, M.P.; Marbot, R., Volatile components from mango (Mangifera indica L.) cultivars, J. Agric. Food Chem., 2005, 53, 6, 2213-2223, https://doi.org/10.1021/jf0402633 . [all data]

Whitfield and Mottram, 1999
Whitfield, F.B.; Mottram, D.S., Investigation of the reaction between 4-hydroxy-5-methyl-3(2H)-furanone and cysteine or hydrogen sulfide at pH 4.5, J. Agric. Food Chem., 1999, 47, 4, 1626-1634, https://doi.org/10.1021/jf980980v . [all data]

Madruga and Mottram, 1998
Madruga, M.S.; Mottram, D.S., The effect of pH on the formation of volatile compounds produced by heating a model system containing 5'-imp and cysteine, J. Braz. Chem. Soc., 1998, 9, 3, 261-271, https://doi.org/10.1590/S0103-50531998000300010 . [all data]

Kuo and Ho, 1992
Kuo, M.-C.; Ho, C.-T., Volatile constituents of the solvent extracts of Welsh onions (Allium fistulosum L. variety Maichuon) and scallions (A. fistulosum L. variety caepitosum), J. Agric. Food Chem., 1992, 40, 10, 1906-1910, https://doi.org/10.1021/jf00022a036 . [all data]

Zhang and Ho, 1991
Zhang, Y.; Ho, C.-T., Formation of meatlike aroma compounds from thermal reaction of inosine 5'-monophosphate with cysteine and glutathione, J. Agric. Food Chem., 1991, 39, 6, 1145-1148, https://doi.org/10.1021/jf00006a031 . [all data]

Zhang and Ho, 1991, 2
Zhang, Y.; Ho, C.-T., Comparison of the volatile compounds formed from the thermal reaction of glucose with cysteine and glutathione, J. Agric. Food Chem., 1991, 39, 4, 760-763, https://doi.org/10.1021/jf00004a029 . [all data]

Flath, Light, et al., 1990
Flath, R.A.; Light, D.M.; Jang, E.B.; Mon, T.R.; John, J.O., Headspace Examination of Volatile Emissions from Ripening Papaya (Carica papaya L., Solo Variety), J. Agric. Food Chem., 1990, 38, 4, 1060-1063, https://doi.org/10.1021/jf00094a032 . [all data]

Parker, Hassell, et al., 2000
Parker, J.K.; Hassell, G.M.E.; Mottram, D.S.; Guy, R.C.E., Sensory and instrumental analyses of volatiles generated during the extrusion cooking of oat flours, J. Agric. Food Chem., 2000, 48, 8, 3497-3506, https://doi.org/10.1021/jf991302r . [all data]

Bianchi, Careri, et al., 2007
Bianchi, F.; Careri, M.; Mangia, A.; Musci, M., Retention indices in the analysis of food aroma volatile compounds in temperature-programmed gas chromatography: Database creation and evaluation of precision and robustness, J. Sep. Sci., 2007, 39, 4, 563-572, https://doi.org/10.1002/jssc.200600393 . [all data]

Leffingwell and Alford, 2011
Leffingwell, J.; Alford, E.D., Volatile constituents of the giant pufball mushroom (Calvatia gigantea), Leffingwell Rep., 2011, 4, 1-17. [all data]

Radulovic, Blagojevic, et al., 2010
Radulovic, N.; Blagojevic, P.; Palic, R., Comparative study of the leaf volatiles of Arctostaphylos uva-ursi (L.) Spreng. and Vaccinium vitis-idaea L. (Ericaceae), Molecules, 2010, 15, 9, 6168-6185, https://doi.org/10.3390/molecules15096168 . [all data]

Frerot, Velluz, et al., 2008
Frerot, E.; Velluz, A.; Bagnoud, A.; Delort, E., Analysis of the volatile constituents of cooked petai beans (Parkia speciosa) using high-resolution GC/TOF-MS, Flav. Fragr. J., 2008, 23, 6, 434-440, https://doi.org/10.1002/ffj.1902 . [all data]

Pino, Marbot, et al., 2003
Pino, J.A.; Marbot, R.; Fuentes, V., Characterization of volatiles in Bullock's heart (Annona reticulata L.) fruit cultivars from Cuba, J. Agric. Food Chem., 2003, 51, 13, 3836-3839, https://doi.org/10.1021/jf020733y . [all data]

Chen, 2008
Chen, H.-F., Quantitative prediction of gas chromatography retention indices with support vector machines, radial basis neutral networks and multiple linear regression, Anal. Chim. Acta, 2008, 609, 1, 24-36, https://doi.org/10.1016/j.aca.2008.01.003 . [all data]

Flanagan, Streete, et al., 1997
Flanagan, R.J.; Streete, P.J.; Ramsey, J.D., Volatile Substance Abuse, UNODC Technical Series, No 5, United Nations, Office on Drugs and Crime, Vienna International Centre, PO Box 500, A-1400 Vienna, Austria, 1997, 56, retrieved from http://www.odccp.org/pdf/technical_series₁997-01-01₁.pdf. [all data]

Strete, Ruprah, et al., 1992
Strete, P.J.; Ruprah, M.; Ramsey, J.D.; Flanagan, R.J., Detection and identification of volatile substances by headspace capillary gas chromatography to aid the diagnosis of acute poisoning, Analyst, 1992, 117, 7, 1111-1127, https://doi.org/10.1039/an9921701111 . [all data]

Schutz and Wollrab A., 1988
Schutz, H.; Wollrab A., The significance of the retention index in toxicologic analysis II, Pharmazie in unzerer Zeit, 1988, 17, 4, 97-101. [all data]

Ramsey and Flanagan, 1982
Ramsey, J.D.; Flanagan, R.J., Detection and Identification of Volatile Organic Compounds in Blood by Headspace Gas Chromatography as an Aid to the Diagnosis of Solvent Abuse, J. Chromatogr., 1982, 240, 2, 423-444, https://doi.org/10.1016/S0021-9673(00)99622-5 . [all data]

Kiss, Csoka, et al., 2011
Kiss, M.; Csoka, M.; Gyorfi, J.; Korany, K., Comparison of the fragrance constituents of Tuber aestivium and Tuber Brumale gathered in Hungary, J. Appl. Botany Food Quality, 2011, 84, 102-110. [all data]

Seifert and King, 1982
Seifert, R.M.; King, A.D., Jr., Identification of some volatile constituents of Aspergillus clavatus, J. Agric. Food Chem., 1982, 30, 4, 786-790, https://doi.org/10.1021/jf00112a044 . [all data]

Notes

Go To: Top, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, References

• Symbols used in this document:
  

  AE	Appearance energy
  IE (evaluated)	Recommended ionization energy
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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