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

Go To: Top, Phase change data, Mass spectrum (electron ionization), 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:
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)

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

Spectrum

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Additional Data

References

Go To: Top, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), Notes

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

Go To: Top, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), References

• 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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