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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Phase change data
Go To: Top, Gas phase ion energetics data, Ion clustering 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:
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 | Uncertainty assigned by TRC = 1. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 176.98 | K | N/A | Hubbard, Finke, et al., 1952 | 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, 2 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)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
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)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
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, 2 | 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, 2 | DH |
Gas phase ion energetics data
Go To: Top, Phase change data, Ion clustering data, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias
Data compiled as indicated in comments:
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
View reactions leading to C4H8S+ (ion structure unspecified)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 8.38 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 849.1 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 819.3 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.38 | PIPECO | Butler and Baer, 1983 | LBLHLM |
8.62 ± 0.05 | EI | Distefano, Foffani, et al., 1971 | LLK |
8.62 | EI | Distefano, Foffani, et al., 1971, 2 | LLK |
8.57 ± 0.15 | EI | Gallegos and Kiser, 1962 | RDSH |
8.40 | PE | Schmidt and Schweig, 1973 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
CHS+ | 11.0 ± 0.1 | C3H7 | PI | Butler and Baer, 1982 | T = 298K; LBLHLM |
CHS+ | 11.1 ± 0.1 | C3H7 | PI | Butler and Baer, 1982 | T = 0K; LBLHLM |
CHS+ | 13.8 ± 0.2 | ? | EI | Gallegos and Kiser, 1962 | RDSH |
CH2S+ | 10.5 | C3H6 | PIPECO | Butler and Baer, 1983 | LBLHLM |
CH2S+ | 13.0 ± 0.2 | ? | EI | Gallegos and Kiser, 1962 | RDSH |
CH3S+ | 11.1 | C3H5 | PIPECO | Butler and Baer, 1983 | LBLHLM |
CH3S+ | 14.0 ± 0.2 | ? | EI | Gallegos and Kiser, 1962 | RDSH |
C2H2S+ | 17.0 ± 0.3 | ? | EI | Gallegos and Kiser, 1962 | RDSH |
C2H3+ | 18.0 ± 0.4 | ? | EI | Gallegos and Kiser, 1962 | RDSH |
C2H3S+ | 10.36 | C2H5 | PIPECO | Butler and Baer, 1983 | LBLHLM |
C2H3S+ | 15.7 ± 0.4 | ? | EI | Gallegos and Kiser, 1962 | RDSH |
C2H4S+ | 11.7 ± 0.3 | ? | EI | Gallegos and Kiser, 1962 | RDSH |
C3H3+ | 17.2 ± 0.2 | ? | EI | Gallegos and Kiser, 1962 | RDSH |
C3H5+ | 15.5 ± 0.2 | ? | EI | Gallegos and Kiser, 1962 | RDSH |
C4H6+ | 11.9 ± 0.2 | ? | EI | Gallegos and Kiser, 1962 | RDSH |
C4H7+ | 12.4 ± 0.2 | SH | EI | Gallegos and Kiser, 1962 | RDSH |
C4H7S+ | 10.1 | H | PIPECO | Butler and Baer, 1983 | LBLHLM |
C4H7S+ | 12.4 ± 0.3 | H | EI | Gallegos and Kiser, 1962 | RDSH |
C4H8S+ | 10.21 | C2H4 | PIPECO | Butler and Baer, 1983 | LBLHLM |
Ion clustering data
Go To: Top, Phase change data, Gas phase ion energetics 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: 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. Searches may be limited to ion clustering reactions. A general reaction search form is also available.
Clustering reactions
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< |
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 = (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: (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 |
References
Go To: Top, Phase change data, Gas phase ion energetics data, Ion clustering data, 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 the Thiolenes,
Acta Chem. Scand., 1962, 16, 1870. [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.,
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]
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.,
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]
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]
Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G.,
Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update,
J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018
. [all data]
Butler and Baer, 1983
Butler, J.J.; Baer, T.,
A photoionization study of organosulfur ring compounds: Thiirane, thietane and tetrahydrothiophene,
Org. Mass Spectrom., 1983, 18, 248. [all data]
Distefano, Foffani, et al., 1971
Distefano, G.; Foffani, A.; Innorta, G.; Pignataro, S.,
Mass spectrometric study of transition metal complexes with ligands having nitrogen or sulphur as donor atom,
Adv. Mass Spectrom., 1971, 5, 696. [all data]
Distefano, Foffani, et al., 1971, 2
Distefano, G.; Foffani, A.; Innorta, G.; Pignataro, S.,
Electron impact ionization potentials of some manganese, chromium and tungsten organometallic derivatives,
Int. J. Mass Spectrom. Ion Phys., 1971, 7, 383. [all data]
Gallegos and Kiser, 1962
Gallegos, E.J.; Kiser, R.W.,
Electron impact spectroscopy of the four- and five-membered, saturated heterocyclic compounds containing nitrogen, oxygen and sulfur,
J. Phys. Chem., 1962, 66, 136. [all data]
Schmidt and Schweig, 1973
Schmidt, H.; Schweig, A.,
Ausschluss transanularer Wechselwirkung in 2.5-Dihydrothiophen,
Tetrahedron Lett., 1973, 1437. [all data]
Butler and Baer, 1982
Butler, J.J.; Baer, T.,
Photoionization study of the heat of formation of HCS+,
J. Am. Chem. Soc., 1982, 104, 5016. [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]
Notes
Go To: Top, Phase change data, Gas phase ion energetics data, Ion clustering data, References
- Symbols used in this document:
AE Appearance energy IE (evaluated) Recommended ionization energy Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point Ttriple Triple point temperature 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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