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
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Phase change data
  • Henry's Law data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
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  • Gas Phase Kinetics Database
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Condensed phase 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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Constant pressure heat capacity of liquid

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)

Gas phase ion energetics data

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry 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:
LL - Sharon G. Lias and Joel F. Liebman
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 C₄H₈O⁺ (ion structure unspecified)

Ionization energy determinations

Appearance energy determinations

References

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry 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.

Cass, Fletcher, et al., 1958
Cass, R.C.; Fletcher, S.E.; Mortimer, C.T.; Springall, H.D.; White, T.R., Heats of combustion and molecular structure. Part V. The mean bond energy term for the C-O bond in ethers, and the structures of some cyclic ethers, J. Chem. Soc., 1958, 1406-1410. [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]

Skuratov, Strepikheev, et al., 1957
Skuratov, S.M.; Strepikheev, A.A.; Kozina, M.P., About the reaction activity of five and six-membered heterocyclic compounds, Dokl. Akad. Nauk SSSR, 1957, 117, 452-454. [all data]

Lebedev, Lityagov, et al., 1979
Lebedev, B.V.; Lityagov, V.Ya.; Krentsina, T.I.; Milov, V.I., Thermodynamic properties of tetrahydrofuran in the range 8-322 K, Zhur. Fiz. Khim., 1979, 53, 264-265. [all data]

Lebedev, Rabinovich, et al., 1978
Lebedev, B.V.; Rabinovich, I.B.; Milov, V.I.; Lityagov, V.Ya., Thermodynamic properties of tetrahydrofuran from 8 to 322 K, J. Chem. Thermodyn., 1978, 10, 321-329. [all data]

Lebedev and Lityagov, 1977
Lebedev, B.V.; Lityagov, V.Ya., Calorimetric study of tetrahydrofuran and its polymerization in the temperature range 0-400°K, Vysokomol. Soedin., 1977, A19, 2283-2290. [all data]

Costas and Patterson, 1985
Costas, M.; Patterson, D., Heat capacities of water + organic-solvent mixtures, J. Chem. Soc., Faraday Trans. 1, 1985, 81, 2381-2398. [all data]

Costas and Patterson, 1985, 2
Costas, M.; Patterson, D., Self-association of alcohols in inert solvents, J. Chem. Soc., Faraday Trans. 1, 1985, 81, 635-654. [all data]

Inglese, Castagnolo, et al., 1981
Inglese, A.; Castagnolo, M.; Dell'Atti, A.; DeGiglio, A., Thermochim. Acta, 1981, 77-87. [all data]

Kiyohara, D'Arcy, et al., 1979
Kiyohara, O.; D'Arcy, P.J.; Benson, G.C., Ultrasonic velocities, compressibilities, and heat capacities of water + tetrahydrofuran mixtures at 298.15K, Can. J. Chem., 1979, 57, 1006-1010. [all data]

Bonner and Cerutti, 1976
Bonner, O.D.; Cerutti, P.J., The partial molar heat capacities of some solutes in water and deuterium oxide, J. Chem. Thermodynam., 1976, 8, 105-111. [all data]

Conti, Gianni, et al., 1976
Conti, G.; Gianni, P.; Matteoli, E.; Mengheri, M., Capacita termiche molari di alcuni composti organici mono- e bifunzionali nel liquido puro e in soluzione acquosa a 25C, Chim. Ind. (Milan), 1976, 58, 225. [all data]

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]

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]

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]

Holmes and Lossing, 1991
Holmes, J.L.; Lossing, F.P., Ionization energies of homologous organic compounds and correlation with molecular size, Org. Mass Spectrom., 1991, 26, 537. [all data]

Behan, Dean, et al., 1976
Behan, J.M.; Dean, F.M.; Johnstone, R.A.W., Photoelectron spectra of cyclic aromatic ethers. The question of the Mills-Nixon effect, Tetrahedron, 1976, 32, 167. [all data]

Doucet, Sauvageau, et al., 1972
Doucet, J.; Sauvageau, P.; Sandorfy, C., The vacuum ultraviolet spectrum of tetrahydrofuran, Chem. Phys. Lett., 1972, 17, 316. [all data]

Hernandez, 1963
Hernandez, G.J., Vacuum-ultraviolet absorption spectra of the cyclic ethers: trimethylene oxide, tetrahydrofuran, and tetrahydropyran, J. Chem. Phys., 1963, 38, 2233. [all data]

Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J., Ionization potentials of some molecules, J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [all data]

Kimura, Katsumata, et al., 1981
Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki, T.; Iwata, S., Ionization energies, Ab initio assignments, and valence electronic structure for 200 molecules in Handbook of HeI Photoelectron Spectra of Fundamental Organic Compounds, Japan Scientific Soc. Press, Tokyo, 1981. [all data]

Gerson, Worley, et al., 1978
Gerson, S.H.; Worley, S.D.; Bodor, N.; Kaminski, J.J.; Flechtner, T.W., The photoelectron spectra of some heterocyclic compounds which contain N, O, Cl, and Br, J. Electron Spectrosc. Relat. Phenom., 1978, 13, 421. [all data]

Schmidt and Schweig, 1974
Schmidt, H.; Schweig, A., Notiz zur transanularen n/π-Wechselwirkung in 2,5-Dihydrofuran, Chem. Ber., 1974, 107, 725. [all data]

Pignataro and Distefano, 1974
Pignataro, S.; Distefano, G., n-σ mixing in pentatomic heterocyclic compounds of sixth group by photoelectron spectroscopy, Chem. Phys. Lett., 1974, 26, 356. [all data]

Bain, Bunzli, et al., 1973
Bain, A.D.; Bunzli, J.C.; Frost, D.C.; Weiler, L., Photoelectron spectra of cyclic ethers, J. Am. Chem. Soc., 1973, 95, 291. [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]

Collin and Conde-Caprace, 1966
Collin, J.E.; Conde-Caprace, G., Ionization and dissociation of cyclic ethers by electron impact, Intern. J. Mass Spectrom. Ion Phys., 1966, 1, 213. [all data]

Notes

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, References

• Symbols used in this document:
  

  AE	Appearance energy
  Cp,liquid	Constant pressure heat capacity of liquid
  IE (evaluated)	Recommended ionization energy
  S°liquid	Entropy of liquid at standard conditions
  T	Temperature
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  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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