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
- IUPAC Standard InChIKey: BADXJIPKFRBFOT-UHFFFAOYSA-N
- 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
View 3d structure (requires JavaScript / HTML 5) - 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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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
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | -383.6 ± 1.9 | kJ/mol | Ccb | Pilcher, Parchment, et al., 1993 |
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
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 9.28 ± 0.05 | PE | Houk, Davis, et al., 1973 | LLK |
De-protonation reactions
C8H11O2- + =
By formula: C8H11O2- + H+ = C8H12O2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1418. ± 8.8 | kJ/mol | G+TS | Cumming and Kebarle, 1978 | gas phase; Acid: dimedone; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1385. ± 8.4 | kJ/mol | IMRE | Cumming and Kebarle, 1978 | gas phase; Acid: dimedone; B |
IR Spectrum
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, UV/Visible spectrum, References, Notes
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
UV/Visible spectrum
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, IR Spectrum, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Spectrum
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Additional Data
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| Source | Timmons, 1966 |
|---|---|
| Owner | INEP CP RAS, NIST OSRD Collection (C) 2007 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
| Origin | INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS |
| Source reference | RAS UV No. 19945 |
| Instrument | Unicam SP 700 |
| Melting point | 147-149 |
References
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, IR Spectrum, UV/Visible spectrum, Notes
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]
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]
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]
Timmons, 1966
Timmons, C.J.,
UV atlas of organic compounds, 1966, 1, B5/3. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, IR Spectrum, UV/Visible spectrum, References
- Symbols used in this document:
ΔfH°gas Enthalpy of formation of gas at standard conditions 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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