Thiophene, tetrahydro-
- Formula: C4H8S
- Molecular weight: 88.171
- IUPAC Standard InChIKey: RAOIDOHSFRTOEL-UHFFFAOYSA-N
- CAS Registry Number: 110-01-0
- 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: Tetramethylene sulfide; Tetrahydrothiophene; Tetrahydrothiophen; Thiacyclopentane; Thilane; Thiolane; Thiophane; Tetramethylene sulphide; Thiolan; THT; Tetrahydrothiofen; Thiofan; UN 2412; Pennodorant 1013; NSC 5272
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Mass spectrum (electron ionization), UV/Visible spectrum, 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 | -33.6 ± 1.2 | kJ/mol | Ccr | Davies and Sunner, 1962 | see Sunner, 1963 |
ΔfH°gas | -34.5 ± 1.5 | kJ/mol | Ccr | Hubbard, Katz, et al., 1954 | Heat of combustion calculated author's U=-773.80 |
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 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 | -72.8 ± 1.2 | kJ/mol | Ccr | Davies and Sunner, 1962 | see Sunner, 1963; ALS |
ΔfH°liquid | -73.1 ± 1.5 | kJ/mol | Ccr | Hubbard, Katz, et al., 1954 | Heat of combustion calculated author's U=-773.80; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -3246.8 ± 1.0 | kJ/mol | Ccr | Davies and Sunner, 1962 | see Sunner, 1963; ALS |
ΔcH°liquid | -3246.2 ± 1.3 | kJ/mol | Ccr | Hubbard, Katz, et al., 1954 | Heat of combustion calculated author's U=-773.80; ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 207.82 | J/mol*K | N/A | Hubbard, Finke, et al., 1952 | DH |
Constant pressure heat capacity of liquid
Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
140.16 | 298.15 | Hubbard, Finke, et al., 1952 | T = 13 to 333 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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 393. ± 3. | K | AVG | N/A | Average of 7 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 174.35 | K | N/A | Davies and Sunner, 1962, 2 | Uncertainty assigned by TRC = 1. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 176.98 | K | N/A | Hubbard, Finke, et al., 1952, 2 | Uncertainty assigned by TRC = 0.06 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 632. | K | N/A | Majer and Svoboda, 1985 | |
Tc | 632. | K | N/A | Cheng, McCoubrey, et al., 1962 | Uncertainty assigned by TRC = 1. K; extrapolated to zero time to correct for decompostion calibr. vs NPL thermometer J.C.McCoubrey, A.R.Ubbelohde Trans. Faraday Soc. 1960,56,114; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 39.0 ± 0.6 | kJ/mol | AVG | N/A | Average of 6 values; Individual data points |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
34.66 | 394.3 | N/A | Majer and Svoboda, 1985 | |
37.1 | 358. | A,EB | Stephenson and Malanowski, 1987 | Based on data from 343. to 434. K. See also Hubbard, Finke, et al., 1952 and Osborn and Douslin, 1966.; AC |
37.7 | 346. | EB | White, Barnard--Smith, et al., 1952 | Based on data from 331. to 401. K.; AC |
Enthalpy of vaporization
ΔvapH =
A exp(-βTr) (1 − Tr)β
ΔvapH =
Enthalpy of vaporization (at saturation pressure)
(kJ/mol)
Tr = reduced temperature (T / Tc)
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Temperature (K) | A (kJ/mol) | β | Tc (K) | Reference | Comment |
---|---|---|---|---|---|
350. to 394. | 52.76 | 0.2624 | 632. | Majer and Svoboda, 1985 |
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 |
---|---|---|---|---|---|
333.4 to 373.5 | 5.00861 | 1979.981 | 2.346 | Eon, Pommier, et al., 1971 | Coefficents calculated by NIST from author's data. |
344.33 to 433.60 | 4.1203 | 1401.939 | -53.543 | Osborn and Douslin, 1966 |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
7.3521 | 176.98 | Hubbard, Finke, et al., 1952 | DH |
7.35 | 177. | Lange, 1985 | AC |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
41.54 | 176.98 | Hubbard, Finke, et al., 1952 | DH |
Reaction 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: Michael M. Meot-Ner (Mautner) and Sharon G. Lias
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: (C4H8S+ • C4H8S) + C4H8S = (C4H8S+ • 2C4H8S)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 33. | kJ/mol | PHPMS | Hiraoka, Takimoto, et al., 1987 | gas phase; Entropy change calculated or estimated |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 75. | J/mol*K | N/A | Hiraoka, Takimoto, et al., 1987 | gas phase; Entropy change calculated or estimated |
By formula: (C4H9S+ • C4H8S) + C4H8S = (C4H9S+ • 2C4H8S)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 33. | kJ/mol | PHPMS | Hiraoka, Takimoto, et al., 1987 | gas phase; Entropy change calculated or estimated |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 75. | J/mol*K | N/A | Hiraoka, Takimoto, et al., 1987 | gas phase; Entropy change calculated or estimated |
By formula: C4H9S+ + C4H8S = (C4H9S+ • C4H8S)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 70.7 | kJ/mol | PHPMS | Hiraoka, Takimoto, et al., 1987 | gas phase |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 87.9 | J/mol*K | PHPMS | Hiraoka, Takimoto, et al., 1987 | gas phase |
By formula: C4H8S+ + C4H8S = (C4H8S+ • C4H8S)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 70.7 | kJ/mol | PHPMS | Hiraoka, Takimoto, et al., 1987 | gas phase; ΔrH< |
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, UV/Visible spectrum, 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
Spectrum
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Additional Data
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Due to licensing restrictions, this spectrum cannot be downloaded.
Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
NIST MS number | 694 |
UV/Visible spectrum
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Spectrum
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Additional Data
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Download spectrum in JCAMP-DX format.
Source | Fehnel and Carmack, 1949 |
---|---|
Owner | INEP CP RAS, NIST OSRD Collection (C) 2007 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
Origin | INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS |
Source reference | RAS UV No. 10651 |
Instrument | Beckman DU |
Melting point | - 96.1 |
Boiling point | 121 |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Mass spectrum (electron ionization), UV/Visible spectrum, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Davies and Sunner, 1962
Davies, J.V.; Sunner, S.,
Heats of combustion and formation of thiolane and of the thiolenes,
Acta Chem. Scand., 1962, 16, 1870-1876. [all data]
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]
Hubbard, Katz, et al., 1954
Hubbard, W.N.; Katz, C.; Waddington, G.,
A rotating combustion bomb for precision calorimetry. Heats of combustion of some sulfur-containing compounds,
J. Phys. Chem., 1954, 58, 142. [all data]
Hubbard, Finke, et al., 1952
Hubbard, W.N.; Finke, H.L.; Scott, D.W.; McCullough, J.P.; Katz, C.; Gross, M.E.; Messerly, J.F.; Pennington, R.E.; Waddington, G.,
Thiacyclopentane: heat capacity, heats of fusion and vaporization, vapor pressure, entropy, heat of formation and thermodynamic functions,
J. Am. Chem. Soc., 1952, 74, 6025-6030. [all data]
Davies and Sunner, 1962, 2
Davies, J.V.; Sunner, S.,
Heats of Combustion and Formation of Thiolane and the Thiolenes,
Acta Chem. Scand., 1962, 16, 1870. [all data]
Hubbard, Finke, et al., 1952, 2
Hubbard, W.N.; Finke, H.L.; Scott, D.W.; McCullough, J.P.; Katz, C.; Gross, M.E.; Messerly, J.F.; Pennington, R.E.; Waddington, G.,
Thiacyclopentyane: Heat Capacity, Heats of Fusion and Vaporization, Vapor Pressure, Entropy, Heat of Formation and Thermo. Functions,
J. Am. Chem. Soc., 1952, 74, 6025-30. [all data]
Majer and Svoboda, 1985
Majer, V.; Svoboda, V.,
Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]
Cheng, McCoubrey, et al., 1962
Cheng, D.C.H.; McCoubrey, J.C.; Phillips, D.G.,
Critical Temperatures of Some Organic Cyclic Compounds,
Trans. Faraday Soc., 1962, 58, 224. [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]
Osborn and Douslin, 1966
Osborn, A.G.; Douslin, D.R.,
Vapor Pressure Relations of 36 Sulfur Compounds Present in Petroleum.,
J. Chem. Eng. Data, 1966, 11, 4, 502-509, https://doi.org/10.1021/je60031a014
. [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]
Eon, Pommier, et al., 1971
Eon, C.; Pommier, C.; Guiochon, G.,
Vapor pressures and second virial coefficients of some five-membered heterocyclic derivatives,
J. Chem. Eng. Data, 1971, 16, 4, 408-410, https://doi.org/10.1021/je60051a008
. [all data]
Lange, 1985
Lange, N.A.,
Lange's Handbook of Chemistry, 13th Edition, J.A. Dean, ed(s)., McGraw-Hill, New York, NY, 1985, 1792. [all data]
Hiraoka, Takimoto, et al., 1987
Hiraoka, K.; Takimoto, H.; Yamabe, S.,
Stabilities and Structures in Cluster Ions of Five-Membered Heterocyclic Compounds Containing O, N and S Atoms,
J. Am. Chem. Soc., 1987, 109, 24, 7346, https://doi.org/10.1021/ja00258a018
. [all data]
Fehnel and Carmack, 1949
Fehnel, E.A.; Carmack, M.,
J. Am. Chem. Soc., 1949, 71, 84. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Mass spectrum (electron ionization), UV/Visible spectrum, 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 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 ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy of reaction at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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