2H-Thiopyran, tetrahydro-
- Formula: C5H10S
- Molecular weight: 102.198
- IUPAC Standard InChIKey: YPWFISCTZQNZAU-UHFFFAOYSA-N
- CAS Registry Number: 1613-51-0
- 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: Pentamethylene sulfide; Penthiophane; Tetrahydro-2H-thiopyran; Tetrahydrothiapyran; Tetrahydrothiopyran; Thiacyclohexane; Thiane
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change 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 as indicated in comments:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -63.3 | kJ/mol | N/A | Sunner, 1963 | Value computed using ΔfHliquid° value of -106.0±1.0 kj/mol from Sunner, 1963 and ΔvapH° value of 42.7 kj/mol from McCullough, Finke, et al., 1954.; DRB |
ΔfH°gas | -63.5 ± 1.0 | kJ/mol | Ccr | McCullough, Finke, et al., 1954 | Reanalyzed by Cox and Pilcher, 1970, Original value = -62.6 ± 1.0 kJ/mol; ALS |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, Phase change 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 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 | -106. ± 1. | kJ/mol | Ccr | Sunner, 1963 | See Sunner, 1962; ALS |
ΔfH°liquid | -106.2 ± 0.88 | kJ/mol | Ccr | McCullough, Finke, et al., 1954 | Reanalyzed by Cox and Pilcher, 1970, Original value = -105.4 ± 0.84 kJ/mol; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -3892.5 | kJ/mol | Ccr | Sunner, 1963 | See Sunner, 1962; ALS |
ΔcH°liquid | -3892.5 ± 0.71 | kJ/mol | Ccr | McCullough, Finke, et al., 1954 | Reanalyzed by Cox and Pilcher, 1970, Original value = -3892.2 ± 0.71 kJ/mol; ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 218.24 | J/mol*K | N/A | McCullough, Finke, et al., 1954, 2 | DH |
Constant pressure heat capacity of liquid
Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
163.30 | 298.15 | McCullough, Finke, et al., 1954, 2 | T = 13 to 340 K.; DH |
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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 414.9 | K | N/A | Weast and Grasselli, 1989 | BS |
Tboil | 415.0 | K | N/A | Haines, Helm, et al., 1956 | Uncertainty assigned by TRC = 0.4 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 291.5 | K | N/A | Haines and Gilson, 1989 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.1 K; TRC |
Tfus | 292.14 | K | N/A | Haines, Helm, et al., 1956 | Uncertainty assigned by TRC = 0.05 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 292.25 | K | N/A | McCullough, Finke, et al., 1954, 3 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.07 K; accompanied by lambda-type transition; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 684. | K | N/A | Anselme and Teja, 1990 | Uncertainty assigned by TRC = 22. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ρc | 2.84 | mol/l | N/A | Anselme and Teja, 1990 | Uncertainty assigned by TRC = 0.39 mol/l; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 42.8 | kJ/mol | C | Reid, 1972 | AC |
ΔvapH° | 42.7 | kJ/mol | N/A | McCullough, Finke, et al., 1954 | DRB |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
41.4 | 325. | N/A | Dykyj, Svoboda, et al., 1999 | Based on data from 310. to 443. K.; AC |
39.5 | 362. | A,EB | Stephenson and Malanowski, 1987 | Based on data from 347. to 423. K. See also White, Barnard--Smith, et al., 1952.; AC |
37.2 | 345. | EB | Palczewska-Tulinska, Cholinski, et al., 1984 | Based on data from 338. to 393. K.; AC |
42.8 ± 0.2 | 350. | V | McCullough, Finke, et al., 1954 | ALS |
39.7 | 351. | N/A | McCullough, Finke, et al., 1954, 2 | AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
351.43 to 414.90 | 4.0270 | 1420.424 | -61.672 | McCullough, Finke, et al., 1954, 2 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
2.45 | 292.3 | Domalski and Hearing, 1996 | AC |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
5.44 | 201.4 | Domalski and Hearing, 1996 | CAL |
32.38 | 240.0 | ||
8.37 | 292.3 |
Enthalpy of phase transition
ΔHtrs (kJ/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
1.0979 | 201.4 | crystaline, III | crystaline, II | McCullough, Finke, et al., 1954, 2 | DH |
7.7751 | 240.02 | crystaline, II | crystaline, I | McCullough, Finke, et al., 1954, 2 | DH |
2.4485 | 292.25 | crystaline, I | liquid | McCullough, Finke, et al., 1954, 2 | DH |
Entropy of phase transition
ΔStrs (J/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
5.45 | 201.4 | crystaline, III | crystaline, II | McCullough, Finke, et al., 1954, 2 | DH |
32.39 | 240.02 | crystaline, II | crystaline, I | McCullough, Finke, et al., 1954, 2 | DH |
8.38 | 292.25 | crystaline, I | liquid | McCullough, Finke, et al., 1954, 2 | DH |
Gas Chromatography
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change 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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Kovats' RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | OV-101 | 100. | 880. | Gal'pern, Gollandskikh, et al., 1976 | H2; Column length: 100. m; Column diameter: 0.25 mm |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | CP-Sil 5 | 842. | Damste, van Dalen, et al., 1988 | 25. m/0.32 mm/0.45 μm, Helium, 0. C @ 5. min, 3. K/min; Tend: 300. C |
Capillary | CP Sil 5 CB | 842. | Damste, Kock-van Dalen, et al., 1988 | 25. m/0.32 mm/0.45 μm, He, 3. K/min; Tstart: 50. C; Tend: 300. C |
Capillary | OV-101 | 880. | Limin, Jichun, et al., 1988 | 75. C @ 8. min, 2. K/min; Column length: 25. m; Column diameter: 0.25 mm; Tend: 130. C |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Methyl Silicone | 850. | Farkas, Héberger, et al., 2004 | Program: not specified |
Capillary | SE-52 | 860. | van Langenhove and Schamp, 1986 | Column length: 100. m; Column diameter: 0.50 mm; Program: not specified |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Sunner, 1963
Sunner, S.,
Corrected heat of combustion and formation values for a number of organic sulphur compounds,
Acta Chem. Scand., 1963, 17, 728-730. [all data]
McCullough, Finke, et al., 1954
McCullough, J.P.; Finke, H.L.; Hubbard, W.N.; Good, W.D.; Pennington, R.E.; Messerly, J.F.; Waddington, G.,
The chemical thermodynamic properties of thiacyclohexane from 0 to 1000°K,
J. Am. Chem. Soc., 1954, 76, 2661-26. [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]
Sunner, 1962
Sunner, S.,
Corrected heat of combustion and formation values for a number of organic sulphur compounds,
Private communication, 1962, 1-4. [all data]
McCullough, Finke, et al., 1954, 2
McCullough, J.P.; Finke, H.L.; Hubbard, W.N.; Good, W.D.; Pennington, R.E.; Messerly, J.F.; Waddington, G.,
The chemical thermodynamic properties of thiacyclohexane from 0 to 100 K,
J. Am. Chem. Soc., 1954, 76, 2661-2669. [all data]
Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]
Haines, Helm, et al., 1956
Haines, W.E.; Helm, R.V.; Cook, G.L.; Ball, J.S.,
Purification and Properties of Organic Sulfur Compounds,
J. Phys. Chem., 1956, 60, 549-55. [all data]
Haines and Gilson, 1989
Haines, J.; Gilson, D.F.R.,
Phase transisions in solid pentamethylene sulfide,
J. Phys. Chem., 1989, 93, 6237. [all data]
McCullough, Finke, et al., 1954, 3
McCullough, J.P.; Finke, H.L.; Hubbard, W.N.; Good, W.D.; Pennington, R.E.; Messerly, J.F.; Waddington, G.,
The Chemical Thermodynamic Properties of Thiacyclohexane from 0 to 1000 K,
J. Am. Chem. Soc., 1954, 76, 2661-9. [all data]
Anselme and Teja, 1990
Anselme, M.J.; Teja, A.S.,
The critical properties of rapidly reacting substances,
AIChE Symp. Ser., 1990, 86, 279, 128-32. [all data]
Reid, 1972
Reid, Robert C.,
Handbook on vapor pressure and heats of vaporization of hydrocarbons and related compounds, R. C. Wilhort and B. J. Zwolinski, Texas A Research Foundation. College Station, Texas(1971). 329 pages.$10.00,
AIChE J., 1972, 18, 6, 1278-1278, https://doi.org/10.1002/aic.690180637
. [all data]
Dykyj, Svoboda, et al., 1999
Dykyj, J.; Svoboda, J.; Wilhoit, R.C.; Frenkel, M.L.; Hall, K.R.,
Vapor Pressure of Chemicals: Part A. Vapor Pressure and Antoine Constants for Hydrocarbons and Sulfur, Selenium, Tellurium and Hydrogen Containing Organic Compounds, Springer, Berlin, 1999, 373. [all data]
Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw,
Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2
. [all data]
White, Barnard--Smith, et al., 1952
White, P.T.; Barnard--Smith, D.G.; Fidler, F.A.,
Vapor Pressure--Temperature Relationships of Sulfur Compounds Related to Petroleum,
Ind. Eng. Chem., 1952, 44, 6, 1430-1438, https://doi.org/10.1021/ie50510a064
. [all data]
Palczewska-Tulinska, Cholinski, et al., 1984
Palczewska-Tulinska, Marcela; Cholinski, Jacek; Szafranski, Andrzej M.; Wyrzykowska-Stankiewicz, Danuta,
Experimental vapor pressures and maximum-likelihood Antoine-equation constants for 1,1,1-methoxydimethylpropane, thiacyclopentane and 1,4-butanediol,
Fluid Phase Equilibria, 1984, 15, 3, 295-307, https://doi.org/10.1016/0378-3812(84)87014-4
. [all data]
Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D.,
Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III,
J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985
. [all data]
Gal'pern, Gollandskikh, et al., 1976
Gal'pern, G.D.; Gollandskikh, N.I.; Gordadze, G.N.,
Application of methylene-insertion reactions to cyclic sulphides (C4H8S, C5H10S and C6H12S) to produce standard compounds for gas chromatography,
J. Chromatogr., 1976, 124, 1, 43-51, https://doi.org/10.1016/S0021-9673(00)87835-8
. [all data]
Damste, van Dalen, et al., 1988
Damste, J.S.S.; van Dalen, A.C.K.; de Leeuw, J.W.; Schenck, P.A.,
Identification of homologous series of alkylated thiophenes, thiolanes, thianes and benzothiophenes present in pyrolisates of sulfur-rich kerogenes,
J. Chromatogr., 1988, 435, 435-452, https://doi.org/10.1016/S0021-9673(01)82208-1
. [all data]
Damste, Kock-van Dalen, et al., 1988
Damste, J.S.S.; Kock-van Dalen, A.C.; de Leeuw, J.W.; Schenk, P.A.,
Identification of homologous series of alkylated thiophenes, thiolanes, thianes and benzothiophenes present in pyrolysates of sulphur-rich kerogens,
J. Chromatogr., 1988, 435, 435-452, https://doi.org/10.1016/S0021-9673(01)82208-1
. [all data]
Limin, Jichun, et al., 1988
Limin, Z.; Jichun, J.; Shiyi, L.; Keman, S.,
Identification of sulfur ethers in Jianghan naphtha fractions,
Acta Petrolei Sinica, 1988, 4, 1, 100-107. [all data]
Farkas, Héberger, et al., 2004
Farkas, O.; Héberger, K.; Zenkevich, I.G.,
Quantitative structure-retention relationships. XIV. Prediction of gas chromatographic retention indices for saturated O-, N-, and S-heterocyclic compounds,
Chemom. Intell. Lab. Syst., 2004, 72, 2, 173-184, https://doi.org/10.1016/j.chemolab.2004.01.012
. [all data]
van Langenhove and Schamp, 1986
van Langenhove, H.; Schamp, N.,
Identification of Volatiles in the Head Space of Acid-Treated Phosphate Rock by Gas Chromatography-Mass Spectromety,
J. Chromatogr., 1986, 351, 65-75, https://doi.org/10.1016/S0021-9673(01)83473-7
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas Chromatography, References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid S°liquid Entropy of liquid at standard conditions Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point Ttriple Triple point temperature ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition 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 ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions ρc Critical density - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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