Thiophene, tetrahydro-, 1,1-dioxide

• Formula: C₄H₈O₂S
• Molecular weight: 120.170
• IUPAC Standard InChI: InChI=1S/C4H8O2S/c5-7(6)3-1-2-4-7/h1-4H2 Copy

  
• IUPAC Standard InChIKey: HXJUTPCZVOIRIF-UHFFFAOYSA-N Copy
• CAS Registry Number: 126-33-0
• 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 sulfone; Bondelane A; Bondolane A; Cyclic tetramethylene sulfone; Cyclotetramethylene sulfone; Sulfolan; Sulfolane; Sulpholane; Tetrahydrothiophene dioxide; Tetrahydrothiophene 1,1-dioxide; Thiacyclopentane dioxide; Thiophan sulfone; Thiophane dioxide; 1,1-Dioxothiolan; Thiophene, 1,1-dioxide-tetrahydro-; Dihydrobutadiene sulfone; 1,1-Dioxide tetrahydrothiofuran; Dioxothiolan; Tetrahydothiophene-1,1-dioxide; Sulfalone; Sulphoxaline; Thiocyclopentane-1,1-dioxide; Thiolane-1,1-dioxide; 1,1-Dioxidetetrahydrothiophene; 2,3,4,5-Tetrahydrothiophene-1,1-dioxide; Dihydrobutadiene sulphone; Tetrahydrothiofen-1,1-dioxid; Thiophane 1,1-dioxide; NSC 46443
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• Information on this page:
  • Phase change data
  • Gas phase ion energetics data
  • Mass spectrum (electron ionization)
  • References
  • Notes
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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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
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

Enthalpy of vaporization

Enthalpy of fusion

Entropy of fusion

Gas phase ion energetics 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:
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

Ionization energy determinations

Mass spectrum (electron ionization)

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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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Additional Data

References

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Lee, 1986
Lee, F.-M., Use of Organic Sulfones as the Extractive Distillation SOlvent for Aromatic Recovery, Ind. Eng. Chem. Process Des. Dev., 1986, 25, 949-57. [all data]

Tripathi, RajaRam, et al., 1975
Tripathi, R.P.; RajaRam, A.; Bhimeshwararao, P., Liquid-liquid equilibria in ternary system toluene + n-heptane + sulfolane, J. Chem. Eng. Data, 1975, 20, 261-4. [all data]

Jannelli and Pansini, 1985
Jannelli, L.; Pansini, M., Thermodynamic properties of dilute solutions of C2-C6 n-alkanoic acids in sulfolane, J. Chem. Eng. Data, 1985, 30, 349. [all data]

Jannelli and Pansini, 1985, 2
Jannelli, L.; Pansini, M., Solid-Liquid Phase Diagram and Excess Propertiers at 303.16 and 313.16 K of Dimethyl Sulfoxide (1) + Sulfolane (2) Binary System, J. Chem. Eng. Data, 1985, 30, 428. [all data]

Lopez, Jannelli, et al., 1983
Lopez, A.; Jannelli, L.; Pansini, M., Thermodynamic and Physical Properties of Binary Systems Involving Sulfolane + 2-Methylpropionitrile and Sulfolane + 2,2-Dimethylpropionitrile dimethylpropionitrile., J. Chem. Eng. Data, 1983, 28, 176. [all data]

Sacco and Jannelli, 1972
Sacco, A.; Jannelli, L., Thermodynamic behavior of binary mixtures involving sulfolane: I excess volumes of sulfolane with benzene, carbon tetrachloride, and dioxan, J. Chem. Thermodyn., 1972, 4, 191-7. [all data]

Steele, Chirico, et al., 1997
Steele, W.V.; Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A., Vapor Pressure, Heat Capacity, and Density along the Saturted Line, Measurements for Cyclohexanol, 2-Cyclohexen-1-one, 1,2-Dichloropropane, 1,4-Di-tert-butylbenzene, (±)-2-Ethylhexanoic Acid, 1-(m, J. Chem. Eng. Data, 1997, 42, 1021-36. [all data]

Morais, Matos, et al., 2004
Morais, Victor M.F.; Matos, M. Agostinha R.; Miranda, Margarida S.; Liebman, Joel F., Surprises with strain energy and sulpholane (tetrahydrothiophene 1,1-dioxide): a combined experimental and theoretical investigation, Molecular Physics, 2004, 102, 5, 525-530, https://doi.org/10.1080/002689710410001671558 . [all data]

Steele, Chirico, et al., 1997, 2
Steele, W.V.; Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A., Vapor Pressure, Heat Capacity, and Density along the Saturation Line, Measurements for Cyclohexanol, 2-Cyclohexen-1-one, 1,2-Dichloropropane, 1,4-Di- tert -butylbenzene, (±)-2-Ethylhexanoic Acid, 2-(Methylamino)ethanol, Perfluoro- n -heptane, and Sulfolane, J. Chem. Eng. Data, 1997, 42, 6, 1021-1036, https://doi.org/10.1021/je9701036 . [all data]

Al-Najjar and Al-Sammerrai, 2007
Al-Najjar, Hazim; Al-Sammerrai, Dhoaib, Thermogravimetric determination of the heat of vaporization of some highly polar solvents, J. Chem. Technol. Biotechnol., 2007, 37, 3, 145-152, https://doi.org/10.1002/jctb.280370302 . [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]

Shcherbina, Kaporovskii, et al., 1984
Shcherbina, A.E.; Kaporovskii, L.M.; Shcherbina, E.A., Zh. Prikl. Khim. (Leningrad), 1984, 57, 1910. [all data]

Ahlers, Lohmann, et al., 1999
Ahlers, Jens; Lohmann, Jürgen; Gmehling, Jürgen, Binary Solid-Liquid Equilibria of Organic Systems Containing Different Amides and Sulfolane, J. Chem. Eng. Data, 1999, 44, 4, 727-730, https://doi.org/10.1021/je9802975 . [all data]

Domanska, Moollan, et al., 1996
Domanska, Urszula; Moollan, Warren C.; Letcher, Trevor M., Solubility of Sulfolane in Selected Organic Solvents, J. Chem. Eng. Data, 1996, 41, 2, 261-265, https://doi.org/10.1021/je950236w . [all data]

Domanska, Moollan, et al., 1996, 2
Domanska, U.; Moollan, W.C.; Letcher, T.M., Solubility of Sulfolane in Selected Organic Solvents, J. Chem. Eng. Data, 1996, 41, 2, 261, https://doi.org/10.1021/je950236w . [all data]

Aitken, Gosney, et al., 1984
Aitken, R.A.; Gosney, I.; Farries, H.; Palmer, M.H.; Simpson, I.; Cadogan, J.I.G.; Tinley, E.J., Chemical repercussions of orbital interactions through bond and through space. The reactivity of the double bond in unsaturated cyclic sulphones towards aziridine formation and epoxidation, Tetrahedron, 1984, 40, 2487. [all data]

Evlasheva, Puchkova, et al., 1975
Evlasheva, T.I.; Puchkova, V.V.; Potapov, V.K.; Gur'yanova, E.N., Ionisation potentials and electron-donating properties of sulphones, Russ. J. Phys. Chem., 1975, 49, 453. [all data]

Muller, Schweig, et al., 1974
Muller, C.; Schweig, A.; Mock, W.L., Through-conjugation through the sulfone group in 2,5-di-tert- butylthiophene 1,1-dioxide, J. Am. Chem. Soc., 1974, 96, 280. [all data]

Notes

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• Symbols used in this document:
  

  Pc	Critical pressure
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  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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