1,3-Cyclohexanedione, 5,5-dimethyl-

• Formula: C₈H₁₂O₂
• Molecular weight: 140.1797
• IUPAC Standard InChI: InChI=1S/C8H12O2/c1-8(2)4-6(9)3-7(10)5-8/h3-5H2,1-2H3 Copy

  
• IUPAC Standard InChIKey: BADXJIPKFRBFOT-UHFFFAOYSA-N Copy
• CAS Registry Number: 126-81-8
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
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• Other names: Cyclomethone; Dimedon; Dimedone; Lu 274; Medon; Methon; Methone; 1,1-Dimethyl-3,5-cyclohexanedione; 1,1-Dimethyl-3,5-diketocyclohexane; 5,5-Dimethyl-1,3-cyclohexanedione; 5,5-Dimethyldihydroresorcinol; 5,5-Dimethylhydroresorcinol; 5,5-Dimethylcyclohexane-1,3-dione; 5,5-Dimethyl-1,3-cyclohexadione; 5,5-Dimethyl-1,3-dihydroresorcinol; NSC 14984
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• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
  • References
  • Notes
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Gas phase 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Condensed phase 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Phase change 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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos

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 by: John E. Bartmess

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

C₈H₁₁O₂^- +  =

By formula: C₈H₁₁O₂^- + H⁺ = C₈H₁₂O₂

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 compiled as indicated in comments:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

Ionization energy determinations

De-protonation reactions

C₈H₁₁O₂^- +  =

By formula: C₈H₁₁O₂^- + H⁺ = C₈H₁₂O₂

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• SOLID (NUJOL MULL); BECKMAN IR-7 (GRATING); DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm^-1 resolution
• SOLUTION (2% IN CHCl3) VS SOLVENT; BECKMAN IR-7 (GRATING); DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm^-1 resolution

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

• gas; HP-GC/MS/IRD

Mass spectrum (electron ionization)

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

Spectrum

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Additional Data

UV/Visible spectrum

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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 by: Victor Talrose, Alexander N. Yermakov, Alexy A. Usov, Antonina A. Goncharova, Axlexander N. Leskin, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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Additional Data

Gas Chromatography

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

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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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.

Pilcher, Parchment, et al., 1993
Pilcher, G.; Parchment, O.G.; Hillier, I.H.; Heatley, F.; Fletcher, D.; Ribeiro da Silva, M.A.V.; Ferrao, M.L.C.C.H.; Monte, J.S.; Jiye, F., Thermochemical and theoretical studies on cyclohexanediones, J. Phys. Chem., 1993, 97, 243-247. [all data]

Wolfrom and Bobbitt, 1956
Wolfrom, M.L.; Bobbitt, J.M., Periodate Oxidation of Cyclic 1,3-Diketones, J. Am. Chem. Soc., 1956, 78, 2489-93. [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]

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]

Timmons, 1966
Timmons, C.J., UV atlas of organic compounds, 1966, 1, B5/3. [all data]

Okumura, 1991
Okumura, T., retention indices of environmental chemicals on methyl silicone capillary column, Journal of Environmental Chemistry (Japan), 1991, 1, 2, 333-358, https://doi.org/10.5985/jec.1.333 . [all data]

Ventanas, Estevez, et al., 2008
Ventanas, S.; Estevez, M.; Andres, A.I.; Ruiz, J., Analysis of volatile compounds of Iberian dry-cured loins with different intramuscular fat contents using SPME-DED, Meat Sci., 2008, 79, 1, 172-180, https://doi.org/10.1016/j.meatsci.2007.08.011 . [all data]

Notes

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• Symbols used in this document:
  

  Tfus	Fusion (melting) point
  ΔcH°solid	Enthalpy of combustion of solid at standard conditions
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfH°solid	Enthalpy of formation of solid at standard conditions
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔsubH°	Enthalpy of sublimation at standard conditions

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