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:
  • Condensed phase thermochemistry data
  • Phase change data
  • Henry's Law data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Reaction thermochemistry data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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Condensed phase thermochemistry data

Go To: Top, Phase change data, Henry's Law 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 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

Phase change data

Go To: Top, Condensed phase thermochemistry data, Henry's Law 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 as indicated in comments:
DH - Eugene S. Domalski and Elizabeth D. Hearing
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
BS - Robert L. Brown and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Enthalpy of vaporization

Enthalpy of vaporization

Δ_vapH = A exp(-βT_r) (1 − T_r)^β
    Δ_vapH = Enthalpy of vaporization (at saturation pressure) (kcal/mol)
    T_r = reduced temperature (T / T_c)

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Antoine Equation Parameters

log₁₀(P) = A − (B / (T + C))
    P = vapor pressure (atm)
    T = temperature (K)

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Enthalpy of fusion

Entropy of fusion

Enthalpy of phase transition

Entropy of phase transition

Henry's Law 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 by: Rolf Sander

Henry's Law constant (water solution)

k_H(T) = k°_H exp(d(ln(k_H))/d(1/T) ((1/T) - 1/(298.15 K)))
k°_H = Henry's law constant for solubility in water at 298.15 K (mol/(kg*bar))
d(ln(k_H))/d(1/T) = Temperature dependence constant (K)

Gas phase ion energetics data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Henry's Law 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, Phase change data, Henry's Law 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]

Hayduk, Laudie, et al., 1973
Hayduk, W.; Laudie, H.; Smith, O.H., Viscosity, Freezing Point, Vapor-Liquid Equilibria, and Other Properties of Aqueous-Tetrahydrofuran Solutions, J. Chem. Eng. Data, 1973, 18, 373-6. [all data]

Brooks and Pilcher, 1959
Brooks, J.H.; Pilcher, G., A Simple Melting Point Calorimeter for Moderately Precise Determination of Purity, J. Chem. Soc., 1959, 1959, 1535. [all data]

Boord, Greenlee, et al., 1946
Boord, C.E.; Greenlee, K.W.; Perilstein, W.L., The Synthesis, Purification and Prop. of Hydrocarbons of Low Mol. Weight, Am. Pet. Inst. Res. Proj. 45, Eighth Annu. Rep., Ohio State Univ., June 30, 1946. [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. [all data]

Wilhoit, Chao, et al., 1985
Wilhoit, R.C.; Chao, J.; Hall, K.R., Thermodynamic Properties of Key Organic Compounds in the Carbon Range C1 to C4. Part 1. Properties of Condensed Phases, J. Phys. Chem. Ref. Data, 1985, 14, 1. [all data]

Lebedev, Rabinovich, et al., 1978, 2
Lebedev, B.V.; Rabinovich, I.B.; Milov, V.I.; Sladkov, A.M., Thermodynamic properties of tetrahydrofuran from 8 to 322 k polyaddition products with the bis-ethinyl derivatives of the same metals, J. Chem. Thermodyn., 1978, 10, 321-9. [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]

Cheng, McCoubrey, et al., 1962
Cheng, D.C.H.; McCoubrey, J.C.; Phillips, D.G., Critical Temperatures of Some Organic Cyclic Compounds, Trans. Faraday Soc., 1962, 58, 224. [all data]

Kobe, Ravicz, et al., 1956
Kobe, K.A.; Ravicz, A.E.; Vohra, S.P., Critical Properties and Vapor Pressures of Some Ethers and Heterocyclic Compounds, J. Chem. Eng. Data, 1956, 1, 50. [all data]

Hossenlopp and Scott, 1981
Hossenlopp, I.A.; Scott, D.W., Vapor heat capacities and enthalpies of vaporizaiton of six organic compounds, J. Chem. Thermodyn., 1981, 13, 405-414. [all data]

Moiseev and Antonova, 1970
Moiseev, V.D.; Antonova, N.D., Zh. Fiz. Khim., 1970, 44, 11, 2912. [all data]

Loras, Aucejo, et al., 2001
Loras, Sonia; Aucejo, Antonio; Montón, Juan B.; Wisniak, Jaime; Segura, Hugo, Polyazeotropic Behavior in the Binary System 1,1,1,2,3,4,4,5,5,5-Decafluoropentane + Oxolane, J. Chem. Eng. Data, 2001, 46, 6, 1351-1356, https://doi.org/10.1021/je0100793 . [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]

Borisov and Chugunova, 1976
Borisov, G.K.; Chugunova, S.G., Russ. J. Phys. Chem., 1976, 50, 1791. [all data]

Rivenq, 1975
Rivenq, F., Bull. Soc. Chim. Fr., 1975, 1, 2433. [all data]

Koizumi and Ouchi, 1970
Koizumi, E.; Ouchi, S., Nippon Kagaku Kaishi, 1970, 91, 5, 501. [all data]

Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E., The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [all data]

Scott D.W., 1970
Scott D.W., Tetrahydrofuran: vibrational assignment, chemical thermodynamic properties, and vapor pressure, J. Chem. Thermodyn., 1970, 2, 833-837. [all data]

Klages and Möhler, 1948
Klages, Friedrich; Möhler, Klement, Über das anomale osmotische Verhalten von Kettenmolekülen, VI. Mitteil.: Bestimmung der Dampfdruckerniedrigung von Polydepsiden, Chem. Ber., 1948, 81, 5, 411-417, https://doi.org/10.1002/cber.19480810512 . [all data]

Cass, Fletcher, et al., 1958, 2
Cass, R.C.; Fletcher, S.E.; Mortimer, C.T.; Springall, H.D.; White, T.R., 281. 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, https://doi.org/10.1039/jr9580001406 . [all data]

Acree, 1991
Acree, William E., Thermodynamic properties of organic compounds: enthalpy of fusion and melting point temperature compilation, Thermochimica Acta, 1991, 189, 1, 37-56, https://doi.org/10.1016/0040-6031(91)87098-H . [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, Phase change data, Henry's Law 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
  Pc	Critical pressure
  S°liquid	Entropy of liquid at standard conditions
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  Vc	Critical volume
  d(ln(kH))/d(1/T)	Temperature dependence parameter for Henry's Law constant
  k°H	Henry's Law constant at 298.15K
  ΔHtrs	Enthalpy of phase transition
  ΔStrs	Entropy of phase transition
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  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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