4H-Thiopyran-4-one, tetrahydro-
- Formula: C5H8OS
- Molecular weight: 116.181
- IUPAC Standard InChI: InChI=1S/C5H8OS/c6-5-1-3-7-4-2-5/h1-4H2
- IUPAC Standard InChIKey: OVRJVKCZJCNSOW-UHFFFAOYSA-N
- CAS Registry Number: 1072-72-6
- 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: 1-Thiacyclohexan-4-one; 4-Thiacyclohexanone; Penthianone; Tetrahydro-1-thio-γ-pyrone; Tetrahydro-1-thio-4-pyrone; Tetrahydro-1,4-thiapyrone; Tetrahydro-4-thiopyrone; Tetrahydro-4H-thiopyran-4-one; Tetrahydrothiopyran-4-one; 2,3,5,6-Tetrahydro-4-thiopyranone; 4-Oxotetrahydrothiopyran; 4-Oxothiane; Tetrahydrothia-4-pyranone; Tetrahydro-4H-thiapyran-4-one; 4H-tetrahydrothiopyran-4-one; 4-Thianone; NSC 41599
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | -37.1 ± 0.65 | kcal/mol | Ccb | Geiseler and Sawistowsky, 1972 |
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
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔcH°liquid | -833.0 ± 0.50 | kcal/mol | Ccb | Geiseler and Sawistowsky, 1972 |
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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔvapH° | 17.36 | kcal/mol | V | Geiseler and Sawistowsky, 1972 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔsubH° | 17.4 ± 0.41 | kcal/mol | N/A | Geiseler and Sawistowsky, 1972, 2 | See also Pedley and Rylance, 1977.; AC |
Enthalpy of sublimation
| ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 17.1 ± 0.41 | 317. | I | Geiseler and Sawistowsky, 1972, 2 | AC |
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:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 8.90 ± 0.05 | PE | Colonna, Distefano, et al., 1980 | LLK |
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
Van Den Dool and Kratz RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | DB-1 | 1011. | Zhang and Ho, 1991 | 60. m/0.25 mm/0.25 μm, He, 2. K/min, 220. C @ 10. min; Tstart: 40. C |
| Capillary | DB-1 | 1017. | Zhang and Ho, 1991, 2 | 60. m/0.25 mm/0.25 μm, He, 2. K/min, 220. C @ 10. min; Tstart: 40. C |
Normal alkane RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | SPB-1 | 1017. | Frerot, Velluz, et al., 2008 | 30. m/0.25 mm/1.0 μm, Helium, 60. C @ 5. min, 5. K/min; Tend: 250. C |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Geiseler and Sawistowsky, 1972
Geiseler, V.G.; Sawistowsky, J.,
Bildungsenthalpien und Mesomerieenergien von π-Bindungssystemen. 4. Mitteilung: Bildungsenthalpien einiger Thiacyclannone,
Z. Phys. Chem. (Leipzig), 1972, 250, 43-48. [all data]
Geiseler and Sawistowsky, 1972, 2
Geiseler, G.; Sawistowsky, J.,
Z. Phys. Chem. (Leipzig), 1972, 250, 1-2, 43. [all data]
Pedley and Rylance, 1977
Pedley, J.B.; Rylance, J.,
, Computer Analysed Thermochemical Data: Organic and Organometallic Compounds, University of Sussex, Brighton, 1977. [all data]
Colonna, Distefano, et al., 1980
Colonna, F.P.; Distefano, G.; Guerra, M.; Jones, D.,
Photoelectron (He(I), He(II) and X-ray) spectroscopy of γ-pyrone and its related sulphur derivatives: valence and core ionization energies shake-up satellites,
J. Electron Spectrosc. Relat. Phenom., 1980, 18, 309. [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]
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]
Notes
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- 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 ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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