Thietane
- Formula: C3H6S
- Molecular weight: 74.145
- IUPAC Standard InChIKey: XSROQCDVUIHRSI-UHFFFAOYSA-N
- CAS Registry Number: 287-27-4
- 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: Trimethylene sulfide; Propane, 1,3-epithio-; Thiacyclobutane
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Phase change data
Go To: Top, 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 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 | 367.9 | K | N/A | Weast and Grasselli, 1989 | BS |
Tboil | 368.1 | K | N/A | Majer and Svoboda, 1985 | |
Tboil | 367. | K | N/A | Brandsma and Wijers, 1963 | Uncertainty assigned by TRC = 3. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 199.91 | K | N/A | Scott, Finke, et al., 1953 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.01 K; approach to equilibrium is slow; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 36.01 | kJ/mol | N/A | Majer and Svoboda, 1985 | |
ΔvapH° | 35.8 | kJ/mol | N/A | Reid, 1972 | AC |
ΔvapH° | 35.9 | kJ/mol | N/A | Hubbard, Katz, et al., 1954 | DRB |
ΔvapH° | 35.9 ± 0.2 | kJ/mol | V | Scott, Finke, et al., 1953, 2 | ALS |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
32.32 | 368.1 | N/A | Majer and Svoboda, 1985 | |
36.5 | 290. | N/A | Dykyj, Svoboda, et al., 1999 | Based on data from 275. to 393. K.; AC |
34.6 | 336. | A,EB | Stephenson and Malanowski, 1987 | Based on data from 321. to 404. K. See also Scott, Finke, et al., 1953, 3 and Osborn and Douslin, 1966.; AC |
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 |
---|---|---|---|---|
321.51 to 404.79 | 4.14157 | 1321.331 | -48.637 | Osborn and Douslin, 1966 |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
8.24 | 199.9 | Domalski and Hearing, 1996 | AC |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
3.77 | 176.7 | Domalski and Hearing, 1996 | CAL |
41.25 | 199.9 |
Enthalpy of phase transition
ΔHtrs (kJ/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
0.6686 | 176.7 | crystaline, II | crystaline, I | Scott, Finke, et al., 1953, 3 | DH |
8.2483 | 199.91 | crystaline, I | liquid | Scott, Finke, et al., 1953, 3 | DH |
Entropy of phase transition
ΔStrs (J/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
3.78 | 176.7 | crystaline, II | crystaline, I | Scott, Finke, et al., 1953, 3 | DH |
41.26 | 199.91 | crystaline, I | liquid | Scott, Finke, et al., 1953, 3 | DH |
Gas phase ion energetics data
Go To: Top, 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 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 C3H6S+ (ion structure unspecified)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 8.61 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 834.8 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 805.0 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.61 | PIPECO | Butler and Baer, 1983 | LBLHLM |
8.5 | PE | Aue and Bowers, 1979 | LLK |
8.65 ± 0.01 | PI | Trofimov, Mel'der, et al., 1975 | LLK |
8.65 | S | Whiteside and Warsop, 1969 | RDSH |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
CHS+ | 10.5 ± 0.1 | C2H5 | PI | Butler and Baer, 1982 | T = 0K; LBLHLM |
CHS+ | 10.4 ± 0.1 | C2H5 | PI | Butler and Baer, 1982 | T = 298K; LBLHLM |
CHS+ | 13.9 ± 0.2 | ? | EI | Gallegos and Kiser, 1962 | RDSH |
CH2S+ | 9.9 | C2H4 | PIPECO | Butler and Baer, 1983 | LBLHLM |
CH2S+ | 10.4 ± 0.1 | ? | EI | Jones and Lossing, 1967 | RDSH |
CH3S+ | 12.3 ± 0.15 | ? | EI | Gallegos and Kiser, 1962 | RDSH |
C2H2+ | 17.1 ± 0.4 | ? | EI | Gallegos and Kiser, 1962 | RDSH |
C2H3+ | 16.7 ± 0.2 | ? | EI | Gallegos and Kiser, 1962 | RDSH |
C2H3S+ | 10.0 | CH3 | PIPECO | Butler and Baer, 1983 | LBLHLM |
C2H4+ | 13.6 ± 0.2 | ? | EI | Gallegos and Kiser, 1962 | RDSH |
C3H3+ | 15.3 ± 0.4 | ? | EI | Gallegos and Kiser, 1962 | RDSH |
C3H5+ | 12.2 ± 0.2 | SH? | EI | Gallegos and Kiser, 1962 | RDSH |
C3H5S+ | 10.8 | H | PIPECO | Butler and Baer, 1983 | LBLHLM |
References
Go To: Top, Phase change data, Gas phase ion energetics data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
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]
Brandsma and Wijers, 1963
Brandsma, L.; Wijers, H.,
A Simple Laboratory Scale Preparation Method for Dialkyl Sulfides, Selenides, Telluridles, Thiols and Selenols,
Recl. Trav. Chim. Pays-Bas, 1963, 82, 68. [all data]
Scott, Finke, et al., 1953
Scott, D.W.; Finke, H.L.; Hubbard, W.N.; McCullough, J.P.; Katz, C.; Gross, M.E.; Messerly, J.F.; Pennington, R.E.; Waddington, G.,
Thiacyclobutane: Heat Capacity, Heats of Transition, Fusion and Vaporization, Vapor Pressure, Entropy, Heat of Formation and Thermodynamic Functions,
J. Am. Chem. Soc., 1953, 75, 2795-800. [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]
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]
Scott, Finke, et al., 1953, 2
Scott, D.W.; Finke, H.L.; Hubbard, W.N.; McCullough, J.P.; Katz, C.; Gross, M.E.; Messerly, J.F.; Pennington, R.E.; Waddington, G.,
Thiacyclobutane: Heat capacity, heats of transition, fusion and vaporization, vapor pressure, entropy, heat of formation and thermodynamic functions,
J. Am. Chem. Soc., 1953, 75, 2795-28. [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]
Scott, Finke, et al., 1953, 3
Scott, D.W.; Finke, H.L.; Hubbard, W.N.; McCullough, J.P.; Katz, C.; Gross, M.E.; Messerly, J.F.; Pennington, R.E.; Waddington, G.,
Thiacyclobutane: heat capacity, heats of transition, fusion and vaporization, vapor pressure, entropy, heat of formation and thermodynamic functions,
J. Am. Chem. Soc., 1953, 75, 2795-2800. [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]
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]
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]
Aue and Bowers, 1979
Aue, D.H.; Bowers, M.T.,
Chapter 9. Stabilities of positive ions from equilibrium gas phase basicity measurements
in Ions Chemistry,, ed. M.T. Bowers, 1979. [all data]
Trofimov, Mel'der, et al., 1975
Trofimov, B.A.; Mel'der, U.K.; Pikver, R.I.; Vyalykh, E.P.,
Ionization potentials of unsaturated and sulfides the participation of neighboring multiple bonds of heteroatoms in the stabilization of the radical cation,
Teor. Eksp. Khim., 1975, 11, 129. [all data]
Whiteside and Warsop, 1969
Whiteside, J.A.B.; Warsop, P.A.,
The electronic spectrum of trimethylene sulfide,
J. Mol. Spectry., 1969, 29, 1. [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]
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]
Jones and Lossing, 1967
Jones, A.; Lossing, F.P.,
The ionization potential and heat of formation of thioformaldehyde,
J. Phys. Chem., 1967, 71, 4111. [all data]
Notes
Go To: Top, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy IE (evaluated) Recommended ionization energy Tboil Boiling point Ttriple Triple point temperature ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion 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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