2H-Thiopyran, tetrahydro-

Data at NIST subscription sites:

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.


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
Δfgas-63.3kJ/molN/ASunner, 1963Value 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
Δfgas-63.5 ± 1.0kJ/molCcrMcCullough, Finke, et al., 1954Reanalyzed 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
Δfliquid-106. ± 1.kJ/molCcrSunner, 1963See Sunner, 1962; ALS
Δfliquid-106.2 ± 0.88kJ/molCcrMcCullough, Finke, et al., 1954Reanalyzed by Cox and Pilcher, 1970, Original value = -105.4 ± 0.84 kJ/mol; ALS
Quantity Value Units Method Reference Comment
Δcliquid-3892.5kJ/molCcrSunner, 1963See Sunner, 1962; ALS
Δcliquid-3892.5 ± 0.71kJ/molCcrMcCullough, Finke, et al., 1954Reanalyzed by Cox and Pilcher, 1970, Original value = -3892.2 ± 0.71 kJ/mol; ALS
Quantity Value Units Method Reference Comment
liquid218.24J/mol*KN/AMcCullough, Finke, et al., 1954, 2DH

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
163.30298.15McCullough, Finke, et al., 1954, 2T = 13 to 340 K.; DH

Phase change data

Go To: Top, Gas phase thermochemistry data, Condensed 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 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
Tboil414.9KN/AWeast and Grasselli, 1989BS
Tboil415.0KN/AHaines, Helm, et al., 1956Uncertainty assigned by TRC = 0.4 K; TRC
Quantity Value Units Method Reference Comment
Tfus291.5KN/AHaines and Gilson, 1989Crystal phase 1 phase; Uncertainty assigned by TRC = 0.1 K; TRC
Tfus292.14KN/AHaines, Helm, et al., 1956Uncertainty assigned by TRC = 0.05 K; TRC
Quantity Value Units Method Reference Comment
Ttriple292.25KN/AMcCullough, Finke, et al., 1954, 3Crystal phase 1 phase; Uncertainty assigned by TRC = 0.07 K; accompanied by lambda-type transition; TRC
Quantity Value Units Method Reference Comment
Tc684.KN/AAnselme and Teja, 1990Uncertainty assigned by TRC = 22. K; TRC
Quantity Value Units Method Reference Comment
ρc2.84mol/lN/AAnselme and Teja, 1990Uncertainty assigned by TRC = 0.39 mol/l; TRC
Quantity Value Units Method Reference Comment
Δvap42.8kJ/molCReid, 1972AC
Δvap42.7kJ/molN/AMcCullough, Finke, et al., 1954DRB

Enthalpy of vaporization

ΔvapH (kJ/mol) Temperature (K) Method Reference Comment
41.4325.N/ADykyj, Svoboda, et al., 1999Based on data from 310. to 443. K.; AC
39.5362.A,EBStephenson and Malanowski, 1987Based on data from 347. to 423. K. See also White, Barnard--Smith, et al., 1952.; AC
37.2345.EBPalczewska-Tulinska, Cholinski, et al., 1984Based on data from 338. to 393. K.; AC
42.8 ± 0.2350.VMcCullough, Finke, et al., 1954ALS
39.7351.N/AMcCullough, Finke, et al., 1954, 2AC

Antoine Equation Parameters

log10(P) = A − (B / (T + C))
    P = vapor pressure (bar)
    T = temperature (K)

View plot Requires a JavaScript / HTML 5 canvas capable browser.

Temperature (K) A B C Reference Comment
351.43 to 414.904.02701420.424-61.672McCullough, Finke, et al., 1954, 2Coefficents calculated by NIST from author's data.

Enthalpy of fusion

ΔfusH (kJ/mol) Temperature (K) Reference Comment
2.45292.3Domalski and Hearing, 1996AC

Entropy of fusion

ΔfusS (J/mol*K) Temperature (K) Reference Comment
5.44201.4Domalski and Hearing, 1996CAL
32.38240.0
8.37292.3

Enthalpy of phase transition

ΔHtrs (kJ/mol) Temperature (K) Initial Phase Final Phase Reference Comment
1.0979201.4crystaline, IIIcrystaline, IIMcCullough, Finke, et al., 1954, 2DH
7.7751240.02crystaline, IIcrystaline, IMcCullough, Finke, et al., 1954, 2DH
2.4485292.25crystaline, IliquidMcCullough, Finke, et al., 1954, 2DH

Entropy of phase transition

ΔStrs (J/mol*K) Temperature (K) Initial Phase Final Phase Reference Comment
5.45201.4crystaline, IIIcrystaline, IIMcCullough, Finke, et al., 1954, 2DH
32.39240.02crystaline, IIcrystaline, IMcCullough, Finke, et al., 1954, 2DH
8.38292.25crystaline, IliquidMcCullough, Finke, et al., 1954, 2DH

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


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

View large format table.

Column type Active phase Temperature (C) I Reference Comment
CapillaryOV-101100.880.Gal'pern, Gollandskikh, et al., 1976H2; Column length: 100. m; Column diameter: 0.25 mm

Normal alkane RI, non-polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryCP-Sil 5842.Damste, van Dalen, et al., 198825. m/0.32 mm/0.45 μm, Helium, 0. C @ 5. min, 3. K/min; Tend: 300. C
CapillaryCP Sil 5 CB842.Damste, Kock-van Dalen, et al., 198825. m/0.32 mm/0.45 μm, He, 3. K/min; Tstart: 50. C; Tend: 300. C
CapillaryOV-101880.Limin, Jichun, et al., 198875. 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

View large format table.

Column type Active phase I Reference Comment
CapillaryMethyl Silicone850.Farkas, Héberger, et al., 2004Program: not specified
CapillarySE-52860.van Langenhove and Schamp, 1986Column 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