Tetrahydrofuran

• Formula: C₄H₈O
• Molecular weight: 72.1057
• IUPAC Standard InChI: InChI=1S/C4H8O/c1-2-4-5-3-1/h1-4H2 Copy

  
• IUPAC Standard InChIKey: WYURNTSHIVDZCO-UHFFFAOYSA-N Copy
• CAS Registry Number: 109-99-9
• 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: Furan, tetrahydro-; Butane α,δ-oxide; Butane, 1,4-epoxy-; Cyclotetramethylene oxide; Furanidine; Oxacyclopentane; Oxolane; Tetramethylene oxide; THF; Hydrofuran; Tetrahydrofuraan; Tetrahydrofuranne; Tetraidrofurano; NCI-C60560; Rcra waste number U213; UN 2056; Diethylene oxide; Dynasolve 150; Tetrahydrofurane; THF (tetrahydrofuran); NSC 57858
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• Information on this page:
  • Reaction thermochemistry data
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Henry's Law data
  • Gas phase ion energetics data
  • Ion clustering data
  • IR Spectrum
  • Gas Chromatography
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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 as indicated in comments:
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
B - John E. Bartmess
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
MS - José A. Martinho Simões

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

C₄H₉O⁺ +  = (C₄H₉O⁺ • )

By formula: C₄H₉O⁺ + C₄H₈O = (C₄H₉O⁺ • C₄H₈O)

Bond type: Hydrogen bonds of the type OH-O between organics

C₄H₁₁O⁺ +  = (C₄H₁₁O⁺ • )

By formula: C₄H₁₁O⁺ + C₄H₈O = (C₄H₁₁O⁺ • C₄H₈O)

Bond type: Hydrogen bonds of the type OH-O between organics

C₅H₁₁O⁺ +  = (C₅H₁₁O⁺ • )

By formula: C₅H₁₁O⁺ + C₄H₈O = (C₅H₁₁O⁺ • C₄H₈O)

Bond type: Hydrogen bonds of the type OH-O between organics

(C₄H₉O⁺ • ) +  = (C₄H₉O⁺ • 2)

By formula: (C₄H₉O⁺ • C₄H₈O) + C₄H₈O = (C₄H₉O⁺ • 2C₄H₈O)

Bond type: Hydrogen bonds of the type OH-O between organics

C₆H₅NO₂^- +  = (C₆H₅NO₂^- • )

By formula: C₆H₅NO₂^- + C₄H₈O = (C₆H₅NO₂^- • C₄H₈O)

Free energy of reaction

C₇H₄N₂O₂^- +  = (C₇H₄N₂O₂^- • )

By formula: C₇H₄N₂O₂^- + C₄H₈O = (C₇H₄N₂O₂^- • C₄H₈O)

Free energy of reaction

C₆H₄FNO₂^- +  = (C₆H₄FNO₂^- • )

By formula: C₆H₄FNO₂^- + C₄H₈O = (C₆H₄FNO₂^- • C₄H₈O)

Free energy of reaction

C₆H₄FNO₂^- +  = (C₆H₄FNO₂^- • )

By formula: C₆H₄FNO₂^- + C₄H₈O = (C₆H₄FNO₂^- • C₄H₈O)

Free energy of reaction

C₆H₄FNO₂^- +  = (C₆H₄FNO₂^- • )

By formula: C₆H₄FNO₂^- + C₄H₈O = (C₆H₄FNO₂^- • C₄H₈O)

Free energy of reaction

C₇H₇NO₂^- +  = (C₇H₇NO₂^- • )

By formula: C₇H₇NO₂^- + C₄H₈O = (C₇H₇NO₂^- • C₄H₈O)

Free energy of reaction

C₇H₇NO₂^- +  = (C₇H₇NO₂^- • )

By formula: C₇H₇NO₂^- + C₄H₈O = (C₇H₇NO₂^- • C₄H₈O)

Free energy of reaction

C₇H₇NO₂^- +  = (C₇H₇NO₂^- • )

By formula: C₇H₇NO₂^- + C₄H₈O = (C₇H₇NO₂^- • C₄H₈O)

Free energy of reaction

C₇H₄N₂O₂^- +  = (C₇H₄N₂O₂^- • )

By formula: C₇H₄N₂O₂^- + C₄H₈O = (C₇H₄N₂O₂^- • C₄H₈O)

Free energy of reaction

C₇H₄N₂O₂^- +  = (C₇H₄N₂O₂^- • )

By formula: C₇H₄N₂O₂^- + C₄H₈O = (C₇H₄N₂O₂^- • C₄H₈O)

Free energy of reaction

 + 2 =

By formula: C₄H₄O + 2H₂ = C₄H₈O

 +  = ( • )

By formula: Mg⁺ + C₄H₈O = (Mg⁺ • C₄H₈O)

 (solution) +  (solution) = C₉H₈O₆W (solution) +  (solution)

By formula: C₄H₈O (solution) + C₆O₆W (solution) = C₉H₈O₆W (solution) + CO (solution)

C₁₄H₂₁MnO₂ (solution) +  (solution) = C₁₁H₁₃MnO₃ (solution) +  (solution)

By formula: C₁₄H₂₁MnO₂ (solution) + C₄H₈O (solution) = C₁₁H₁₃MnO₃ (solution) + C₇H₁₆ (solution)

C₁₂H₁₆CrO₅ (solution) +  (solution) = C₉H₈CrO₆ (solution) +  (solution)

By formula: C₁₂H₁₆CrO₅ (solution) + C₄H₈O (solution) = C₉H₈CrO₆ (solution) + C₇H₁₆ (solution)

 +  =

By formula: C₄H₆O + H₂ = C₄H₈O

 +  =

By formula: H₂ + C₄H₆O = C₄H₈O

 (solution) + C₂₀H₃₀Sm (solution) = C₂₄H₃₈OSm (solution)

By formula: C₄H₈O (solution) + C₂₀H₃₀Sm (solution) = C₂₄H₃₈OSm (solution)

C₂₄H₃₈OSm (solution) +  (solution) = C₂₈H₄₆O₂Sm (solution)

By formula: C₂₄H₃₈OSm (solution) + C₄H₈O (solution) = C₂₈H₄₆O₂Sm (solution)

C₂₄H₃₉Si₃U (solution) +  (solution) = C₂₈H₄₇OSi₃U (solution)

By formula: C₂₄H₃₉Si₃U (solution) + C₄H₈O (solution) = C₂₈H₄₇OSi₃U (solution)

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

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.

Data compiled by: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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Additional Data

References

Go To: Top, 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.

Hiraoka and Takimoto, 1986
Hiraoka, K.; Takimoto, H., Gas-Phase Stabilities of Symmetric Proton-Held Dimer Cations, J. Phys. Chem., 1986, 90, 22, 5910, https://doi.org/10.1021/j100280a090 . [all data]

Larson and McMahon, 1982
Larson, J.W.; McMahon, T.B., Formation, Thermochemistry, and Relative Stabilities of Proton - Bound dimers of Oxygen n - Donor Bases from Ion Cyclotron Resonance Solvent - Exchange Equilibria Measurements, J. Am. Chem. Soc., 1982, 104, 23, 6255, https://doi.org/10.1021/ja00387a016 . [all data]

Grimsrud and Kebarle, 1973
Grimsrud, E.P.; Kebarle, P., Gas Phase Ion Equilibria Studies of the Solvation of the Hydrogen Ion by Methanol, Dimethyl Ether and Water. Effect of Hydrogen Bonding, J. Am. Chem. Soc., 1973, 95, 24, 7939, https://doi.org/10.1021/ja00805a002 . [all data]

Lias, Liebman, et al., 1984
Lias, S.G.; Liebman, J.F.; Levin, R.D., Evaluated gas phase basicities and proton affinities of molecules heats of formation of protonated molecules, J. Phys. Chem. Ref. Data, 1984, 13, 695. [all data]

Keesee and Castleman, 1986
Keesee, R.G.; Castleman, A.W., Jr., Thermochemical data on Ggs-phase ion-molecule association and clustering reactions, J. Phys. Chem. Ref. Data, 1986, 15, 1011. [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]

Chowdhury, Grimsrud, et al., 1987
Chowdhury, S.; Grimsrud, E.P.; Kebarle, P., Bonding of Charged Delocalized Anions to Protic and Dipolar Aprotic Solvent Molecules, J. Phys. Chem., 1987, 91, 10, 2551, https://doi.org/10.1021/j100294a021 . [all data]

Chowdhury, 1987
Chowdhury, S. Grimsrud, Bonding of Charge Delocalized Anions to Protic and Dipolar Aprotic Solvents, J. Phys. Chem., 1987, 91, 10, 2551, https://doi.org/10.1021/j100294a021 . [all data]

Dolliver, Gresham, et al., 1938
Dolliver, M.A.; Gresham, T.L.; Kistiakowsky, G.B.; Smith, E.A.; Vaughan, W.E., Heats of organic reactions. VI. Heats of hydrogenation of some oxygen-containing compounds, J. Am. Chem. Soc., 1938, 60, 440-450. [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

Operti, Tews, et al., 1988
Operti, L.; Tews, E.C.; Freiser, B.S., Determination of Gas-Phase Ligand Binding Energies to Mg+ by FTMS Techniques, J. Am. Chem. Soc., 1988, 110, 12, 3847, https://doi.org/10.1021/ja00220a020 . [all data]

Nakashima and Adamson, 1982
Nakashima, M.; Adamson, A.W., J. Phys. Chem., 1982, 86, 2905. [all data]

Klassen, Selke, et al., 1990
Klassen, J.K.; Selke, M.; Sorensen, A.A.; Yang, G.K., J. Am. Chem. Soc., 1990, 112, 1267. [all data]

Yang, Peters, et al., 1986
Yang, G.K.; Peters, K.S.; Vaida, V., Chem. Phys. Lett., 1986, 125, 566. [all data]

Allinger, Glaser, et al., 1981
Allinger, N.L.; Glaser, J.A.; Davis, H.E., Heats of hydrogenation of some vinyl ethers and related compounds, J. Org. Chem., 1981, 46, 658-661. [all data]

Nolan, Stern, et al., 1989
Nolan, S.P.; Stern, D.; Marks, T.J., J. Am. Chem. Soc., 1989, 111, 7844. [all data]

Schock, Seyam, et al., 1988
Schock, L.E.; Seyam, A.M.; Sabat, M.; Marks, T.J., Polyhedron, 1988, 7, 1517. [all data]

Pickett, Hoeflich, et al., 1951
Pickett, L.W.; Hoeflich, N.J.; Liu, T.-C., The vacuum ultraviolet absorption spectra of cyclic compounds. II. Tetrahydrofuran, tetrahydropyran, 1,4-dioxane and furan, J. Am. Chem. Soc., 1951, 73, 4865-4869. [all data]

Notes

Go To: Top, Reaction thermochemistry data, Mass spectrum (electron ionization), UV/Visible spectrum, References

• Symbols used in this document:
  

  T	Temperature
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔrS°	Entropy of reaction at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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