Tetrahydropyran
- Formula: C5H10O
- Molecular weight: 86.1323
- IUPAC Standard InChI: InChI=1S/C5H10O/c1-2-4-6-5-3-1/h1-5H2
- IUPAC Standard InChIKey: DHXVGJBLRPWPCS-UHFFFAOYSA-N
- CAS Registry Number: 142-68-7
- 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: Oxacyclohexane; Oxane; 2H-Pyran, tetrahydro-; Pentamethylene oxide; Tetrahydro-2H-pyran; THP
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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
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | -53.50 ± 0.24 | kcal/mol | Cm | Pell and Pilcher, 1965 | ALS |
| ΔfH°gas | -52.6 ± 0.6 | kcal/mol | Ccb | Snelson and Skinner, 1961 | ALS |
| ΔfH°gas | -53.39 ± 0.37 | kcal/mol | Ccb | Cass, Fletcher, et al., 1958 | Reanalyzed by Cox and Pilcher, 1970, Original value = -50.7 kcal/mol; ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°gas | -758.44 ± 0.23 | kcal/mol | Cm | Pell and Pilcher, 1965 | Corresponding ΔfHºgas = -53.39 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Constant pressure heat capacity of gas
| Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 8.102 | 50. | Dorofeeva O.V., 1992 | p=1 bar. Selected values are in close agreement with those calculated by [ Vedal D., 1975].; GT |
| 9.947 | 100. | ||
| 12.68 | 150. | ||
| 15.84 | 200. | ||
| 21.52 | 273.15 | ||
| 23.70 ± 0.72 | 298.15 | ||
| 23.86 | 300. | ||
| 32.765 | 400. | ||
| 40.872 | 500. | ||
| 47.729 | 600. | ||
| 53.456 | 700. | ||
| 58.270 | 800. | ||
| 62.340 | 900. | ||
| 65.803 | 1000. | ||
| 68.757 | 1100. | ||
| 71.286 | 1200. | ||
| 73.456 | 1300. | ||
| 75.325 | 1400. | ||
| 76.941 | 1500. |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, References, Notes
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
DH - Eugene S. Domalski and Elizabeth D. Hearing
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°liquid | -60.9 ± 0.4 | kcal/mol | Ccb | Snelson and Skinner, 1961 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -750.94 ± 0.31 | kcal/mol | Ccb | Snelson and Skinner, 1961 | Corresponding ΔfHºliquid = -60.89 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°liquid | -752.8 ± 1.5 | kcal/mol | Ccb | Cass, Fletcher, et al., 1958 | Corresponding ΔfHºliquid = -59.0 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°liquid | -749.90 ± 0.20 | kcal/mol | Ccb | Skuratov, Strepikheev, et al., 1957 | Reanalyzed by Cox and Pilcher, 1970, Original value = -750.1 ± 0.2 kcal/mol; Combustion at 293 K; Corresponding ΔfHºliquid = -61.93 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS |
Constant pressure heat capacity of liquid
| Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 35.755 | 298.15 | Inglese, Grolier, et al., 1984 | DH |
| 35.662 | 298.15 | Inglese, Castagnolo, et al., 1981 | DH |
| 33.60 | 298. | Conti, Gianni, et al., 1976 | DH |
| 36.121 | 297.62 | Moelwyn-Hughes and Thorpe, 1964 | T = 297 to 327 K.; DH |
Reaction thermochemistry data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, 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
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
+
=
By formula: C5H8O + H2 = C5H10O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -24.69 ± 0.24 | kcal/mol | Chyd | Allinger, Glaser, et al., 1981 | liquid phase; solvent: Hexane |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Pell and Pilcher, 1965
Pell, A.S.; Pilcher, G.,
Measurements of heats of combustion by flame calorimetry. Part 3.-Ethylene oxide, trimethylene oxide, tetrahydrofuran and tetrahydropy,
Trans. Faraday Soc., 1965, 61, 71-77. [all data]
Snelson and Skinner, 1961
Snelson, A.; Skinner, H.A.,
Heats of combustion: sec-propanol, 1,4-dioxan, 1,3-dioxan and tetrahydropyran,
Trans. Faraday Soc., 1961, 57, 2125-2131. [all data]
Cass, Fletcher, et al., 1958
Cass, R.C.; Fletcher, S.E.; Mortimer, C.T.; Springall, H.D.; White, T.R.,
Heats of combustion and molecular structure. Part V. The mean bond energy term for the C-O bond in ethers, and the structures of some cyclic ethers,
J. Chem. Soc., 1958, 1406-1410. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]
Dorofeeva O.V., 1992
Dorofeeva O.V.,
Ideal gas thermodynamic properties of oxygen heterocyclic compounds. Part 2. Six-membered, seven-membered and eight-membered rings,
Thermochim. Acta, 1992, 200, 121-150. [all data]
Vedal D., 1975
Vedal D.,
Vibrational spectra of pentamethylene sulfide and selenide,
Spectrochim. Acta, 1975, A31, 355-372. [all data]
Skuratov, Strepikheev, et al., 1957
Skuratov, S.M.; Strepikheev, A.A.; Kozina, M.P.,
About the reaction activity of five and six-membered heterocyclic compounds,
Dokl. Akad. Nauk SSSR, 1957, 117, 452-454. [all data]
Inglese, Grolier, et al., 1984
Inglese, A.; Grolier, J.-P.E.; Wilhelm, E.,
Excess volumes and excess heat capacities of oxane + cyclohexane and 1,4-dioxane + cyclohexane,
Fluid Phase Equilibria, 1984, 15, 287-294. [all data]
Inglese, Castagnolo, et al., 1981
Inglese, A.; Castagnolo, M.; Dell'Atti, A.; DeGiglio, A.,
Thermochim. Acta, 1981, 77-87. [all data]
Conti, Gianni, et al., 1976
Conti, G.; Gianni, P.; Matteoli, E.; Mengheri, M.,
Capacita termiche molari di alcuni composti organici mono- e bifunzionali nel liquido puro e in soluzione acquosa a 25C,
Chim. Ind. (Milan), 1976, 58, 225. [all data]
Moelwyn-Hughes and Thorpe, 1964
Moelwyn-Hughes, E.A.; Thorpe, P.L.,
The physical and thermodynamic properties of some associated solutions. II. Heat capacities and compressibilities,
Proc. Roy. Soc. (London), 1964, 278A, 574-587. [all data]
Allinger, Glaser, et al., 1981
Allinger, N.L.; Glaser, J.A.; Davis, H.E.,
Heats of hydrogenation of some vinyl ethers and related compounds,
J. Org. Chem., 1981, 46, 658-661. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, References
- Symbols used in this document:
Cp,gas Constant pressure heat capacity of gas Cp,liquid Constant pressure heat capacity of liquid ΔcH°gas Enthalpy of combustion of gas at standard conditions ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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