2-Cyclohexen-1-one, 2,6,6-trimethyl-
- Formula: C9H14O
- Molecular weight: 138.2069
- IUPAC Standard InChI: InChI=1S/C9H14O/c1-7-5-4-6-9(2,3)8(7)10/h5H,4,6H2,1-3H3
- IUPAC Standard InChIKey: NAXZOZQQIIMORY-UHFFFAOYSA-N
- CAS Registry Number: 20013-73-4
- 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: 2,6,6-Trimethyl-2-cyclohexenone; 2,6,6-trimethylcyclohex-2-en-1-one; 2,6,6-Trimethylcyclohex-2-enone; 2,6,6-trimethyl-2-cyclohexen-1-one; 5-Cyclohexen-1-one, 2,2,6-trimethyl
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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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | -233. | kJ/mol | Semi | Stewart, 2004 | |
| ΔfH°gas | -44.2 ± 2.2 | kJ/mol | Ccb | Gerasimov and Gubareva, 1985 | ALS |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔcH°liquid | -5355.2 ± 2.2 | kJ/mol | Ccb | Gerasimov and Gubareva, 1985 | Corresponding ΔfHºliquid = -187.2 kJ/mol (simple calculation by NIST; no Washburn corrections) |
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
Kovats' RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | OV-101 | 1046. | Yamaguchi and Shibamoto, 1981 | N2, 2. K/min; Column length: 70. m; Column diameter: 0.28 mm; Tstart: 80. C; Tend: 200. C |
| Capillary | OV-101 | 1054. | Yamaguchi and Shibamoto, 1981 | N2, 2. K/min; Column length: 70. m; Column diameter: 0.28 mm; Tstart: 80. C; Tend: 200. C |
Kovats' RI, polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | Carbowax 20M | 1384. | Yamaguchi and Shibamoto, 1981 | N2, 2. K/min; Column length: 70. m; Column diameter: 0.28 mm; Tstart: 80. C; Tend: 200. C |
| Capillary | Carbowax 20M | 1386. | Yamaguchi and Shibamoto, 1981 | N2, 2. K/min; Column length: 70. m; Column diameter: 0.28 mm; Tstart: 80. C; Tend: 200. C |
Normal alkane RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | HP-5 | 1057.1 | Leffingwell and Alford, 2005 | 60. m/0.32 mm/0.25 μm, He, 30. C @ 2. min, 2. K/min, 260. C @ 28. min |
| Capillary | PONA | 1049. | Ramalho, de Freitas, et al., 1999 | 50. m/0.2 mm/0.5 μm, He, 40. C @ 5. min, 6. K/min; Tend: 250. C |
| Capillary | DB-1 | 1036. | Habu, Flath, et al., 1985 | 3. K/min; Column length: 50. m; Column diameter: 0.32 mm; Tstart: 0. C; Tend: 250. C |
| Capillary | DB-1 | 1032. | Habu, Flath, et al., 1985 | 3. K/min; Column length: 50. m; Column diameter: 0.32 mm; Tstart: 50. C; Tend: 250. C |
Normal alkane RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | TR-5 MS | 1051. | Kurashov, Mitrukova, et al., 2014 | 15. m/0.25 mm/0.25 μm, Helium; Program: 35 0C (3 min) 2 0C/min -> 60 0C (3 min) 2 0C/min -> 80 0C (3 min) 4 0C/min -> 120 0C (3 min) 5 0C/min -> 150 0C (3 min) 15 0C/min -> 240 0C (10 min) |
| Capillary | CP Sil 5 CB | 1040. | Weyerstahl, Marschall, et al., 1998 | He; Column length: 25. m; Phase thickness: 0.39 μm; Program: not specified |
| Capillary | DB-1 | 1040. | Buttery, Teranishi, et al., 1990 | Column length: 60. m; Column diameter: 0.32 mm; Program: not specified |
Normal alkane RI, polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | Carbowax 20M | 1376. | Kawakami, Kobayashi, et al., 1993 | He, 60. C @ 4. min, 2. K/min; Column length: 50. m; Column diameter: 0.25 mm; Tend: 180. C |
| Capillary | Carbowax 20M | 1376. | Kawakami and Kobayashi, 1991 | He, 60. C @ 4. min, 2. K/min; Column length: 50. m; Column diameter: 0.25 mm; Tend: 180. C |
| Capillary | Carbowax 20M | 1400. | Kanasawud and Crouzet, 1990 | 50. C @ 10. min, 4. K/min; Column length: 40. m; Column diameter: 0.4 mm; Tend: 170. C |
Normal alkane RI, polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | Supelcowax-10 | 1424. | Ramalho, de Freitas, et al., 1999 | 60. m/0.25 mm/1. μm; Program: 50 C(5min) => 3C/min => 200C(4min) => 3C/min => 250C |
| Capillary | DB-Wax | 1417. | Weyerstahl, Marschall, et al., 1998 | N2; Column length: 60. m; Phase thickness: 0.25 μm; Program: not specified |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Stewart, 2004
Stewart, J.J.P.,
Comparison of the accuracy of semiempirical and some DFT methods for predicting heats of formation,
J. Mol. Model, 2004, 10, 1, 6-10, https://doi.org/10.1007/s00894-003-0157-6
. [all data]
Gerasimov and Gubareva, 1985
Gerasimov, P.A.; Gubareva, A.I.,
Physical chemical properties of vitamin A precursor ketones,
Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol., 1985, 28, 106-109. [all data]
Yamaguchi and Shibamoto, 1981
Yamaguchi, K.; Shibamoto, T.,
Volatile constituents of green tea, Gyokuro (Camellia sinensis L. var Yabukita),
J. Agric. Food Chem., 1981, 29, 2, 366-370, https://doi.org/10.1021/jf00104a035
. [all data]
Leffingwell and Alford, 2005
Leffingwell, J.C.; Alford, E.D.,
Volatile constituents of Perique tobacco,
Electron. J. Environ. Agric. Food Chem., 2005, 4, 2, 899-915. [all data]
Ramalho, de Freitas, et al., 1999
Ramalho, P.S.; de Freitas, V.A.P.; Macedo, A.; Silva, G.; Silva, A.M.S.,
Volatile components of Cistus ladanifer leaves,
Flavour Fragr. J., 1999, 14, 5, 300-302, https://doi.org/10.1002/(SICI)1099-1026(199909/10)14:5<300::AID-FFJ830>3.0.CO;2-X
. [all data]
Habu, Flath, et al., 1985
Habu, T.; Flath, R.A.; Mon, T.R.; Morton, J.F.,
Volatile components of Rooibos tea (Aspalathus linearis),
J. Agric. Food Chem., 1985, 33, 2, 249-254, https://doi.org/10.1021/jf00062a024
. [all data]
Kurashov, Mitrukova, et al., 2014
Kurashov, E.A.; Mitrukova, G.G.; Krylova, Yu.V.,
Variations in the component composition of essential oil of Ceratophyllum demersum (Ceratophyllaceae) during vegetation (in press),
Plant Resources (Rastitel'nye Resursy), 2014, 1, 000-000. [all data]
Weyerstahl, Marschall, et al., 1998
Weyerstahl, P.; Marschall, H.; Weirauch, M.; Thefeld, K.; Surburg, H.,
Constituents of commercial Labdanum oil,
Flavour Fragr. J., 1998, 13, 5, 295-318, https://doi.org/10.1002/(SICI)1099-1026(1998090)13:5<295::AID-FFJ751>3.0.CO;2-I
. [all data]
Buttery, Teranishi, et al., 1990
Buttery, R.G.; Teranishi, R.; Flath, R.A.; Ling, L.C.,
Identification of additional tomato paste volatiles,
J. Agric. Food Chem., 1990, 38, 3, 792-795, https://doi.org/10.1021/jf00093a042
. [all data]
Kawakami, Kobayashi, et al., 1993
Kawakami, M.; Kobayashi, A.; Kator, K.,
Volatile constituents of Rooibos tea (Aspalathus linearis) as affected by extraction process,
J. Agric. Food Chem., 1993, 41, 4, 633-636, https://doi.org/10.1021/jf00028a023
. [all data]
Kawakami and Kobayashi, 1991
Kawakami, M.; Kobayashi, A.,
Volatitle constituents of greem mate and roasted mate,
J. Agric. Food Chem., 1991, 39, 7, 1275-1279, https://doi.org/10.1021/jf00007a016
. [all data]
Kanasawud and Crouzet, 1990
Kanasawud, P.; Crouzet, J.C.,
Mechanism of formation of volatile compounds by thermal degradation of carotenoids in aqueous medium. 1. β-Carotene degradation,
J. Agric. Food Chem., 1990, 38, 1, 237-243, https://doi.org/10.1021/jf00091a052
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Gas Chromatography, References
- Symbols used in this document:
ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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