Furan

• Formula: C₄H₄O
• Molecular weight: 68.0740
• IUPAC Standard InChI: InChI=1S/C4H4O/c1-2-4-5-3-1/h1-4H Copy

  
• IUPAC Standard InChIKey: YLQBMQCUIZJEEH-UHFFFAOYSA-N Copy
• CAS Registry Number: 110-00-9
• 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: Divinylene oxide; Furfuran; Oxacyclopentadiene; Oxole; Tetrole; Furane; Furfurane; NCI-C56202; Rcra waste number U124; UN 2389; 1,4-Epoxy-1,3-butadiene
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• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • Henry's Law data
  • Vibrational and/or electronic energy levels
  • References
  • Notes
• Other data available:
  • Phase change data
  • Gas phase ion energetics data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
• Data at other public NIST sites:
  • Computational Chemistry Comparison and Benchmark Database
  • Gas Phase Kinetics Database
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Gas 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:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Constant pressure heat capacity of gas

Constant pressure heat capacity of gas

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
RCD - Robert C. Dunbar

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

C₄H₅O⁺ +  = (C₄H₅O⁺ • )

By formula: C₄H₅O⁺ + C₄H₄O = (C₄H₅O⁺ • C₄H₄O)

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

Free energy of reaction

C₄H₃O^- +  =

By formula: C₄H₃O^- + H⁺ = C₄H₄O

 + 2 =

By formula: C₄H₄O + 2H₂ = C₄H₈O

C₄H₄O⁺ +  = (C₄H₄O⁺ • )

By formula: C₄H₄O⁺ + C₄H₄O = (C₄H₄O⁺ • C₄H₄O)

(C₄H₄O⁺ • ) +  = (C₄H₄O⁺ • 2)

By formula: (C₄H₄O⁺ • C₄H₄O) + C₄H₄O = (C₄H₄O⁺ • 2C₄H₄O)

 +  = ( • )

By formula: Na⁺ + C₄H₄O = (Na⁺ • C₄H₄O)

Free energy of reaction

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)

Vibrational and/or electronic energy levels

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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: Takehiko Shimanouchi

Symmetry:   C_2ν     Symmetry Number σ = 2

Source: Shimanouchi, 1972

Notes

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Henry's Law data, Vibrational and/or electronic energy levels, Notes

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

Zaheeruddin and Lodhi, 1991
Zaheeruddin, M.; Lodhi, Z.H., Enthalpies of formation of some cyclic compounds, Phys. Chem. (Peshawar Pak.), 1991, 10, 111-118. [all data]

Guthrie, Scott, et al., 1952
Guthrie, G.B., Jr.; Scott, D.W.; Hubbard, W.N.; Katz, C.; McCullough, J.P.; Gross, M.E.; Williamson, K.D.; Waddington, G., Thermodynamic properties of furan, J. Am. Chem. Soc., 1952, 74, 4662-46. [all data]

Landrieu, Baylocq, et al., 1929
Landrieu, P.; Baylocq, F.; Johnson, J.R., Etude thermochimique dans la serie furanique, Bull. Soc. Chim. France, 1929, 45, 36-49. [all data]

Dorofeeva O.V., 1992
Dorofeeva O.V., Ideal gas thermodynamic properties of oxygen heterocyclic compounds. Part 1. Three-membered, four-membered and five-membered rings, Thermochim. Acta, 1992, 194, 9-46. [all data]

Guthrie G.B., 1952
Guthrie G.B., Jr., Thermodynamic properties of furan, J. Am. Chem. Soc., 1952, 74, 4662-4669. [all data]

Bak B., 1955
Bak B., Infrared absorption spectra of alpha and beta monodeutero, and alpha, alpha' dideutero furan vapors. Heat capacity and entropy of furan, Acta Chem. Scand., 1955, 9, 749-762. [all data]

Rico M., 1967
Rico M., Fundamental vibrations of furan and deuterated derivatives, J. Mol. Spectrosc., 1967, 24, 133-148. [all data]

Soptrajanov B., 1968
Soptrajanov B., Thermodynamic functions of furan and deuterated furans, Croat. Chem. Acta, 1968, 40, 241-245. [all data]

Chao J., 1986
Chao J., Thermodynamic properties of key organic oxygen compounds in the carbon range C1 to C4. Part 2. Ideal gas properties, J. Phys. Chem. Ref. Data, 1986, 15, 1369-1436. [all data]

Klots T.D., 1994
Klots T.D., Complete vapor phase assignment for the fundamental vibrations of furan, pyrrole and thiophene, Spectrochim. Acta, 1994, A50, 765-795. [all data]

Guthrie, Scott, et al., 1952, 2
Guthrie, G.B., Jr.; Scott, D.W.; Hubbard, W.N.; Katz, C.; McCullough, J.P.; Gross, M.E.; Williamson, K.D.; Waddington, G., Thermodynamic properties of furan, J. Am. Chem. Soc., 1952, 74, 4662-4669. [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]

Meot-Ner (Mautner), Ross, et al., 1985
Meot-Ner (Mautner), M.; Ross, M.M.; Campana, J.E., Stable Hydrogen - Bonded Isomers of Covalent Ions, J. Am. Chem. Soc., 1985, 107, 4835. [all data]

Grabowski and Owusu
Grabowski, J.J.; Owusu, D., , as cited in 98CLI/WEN. [all data]

DePuy, Kass, et al., 1988
DePuy, C.H.; Kass, S.R.; Bean, G.P., Formation and Reactions of Heteroaromatic Anions in the Gas Phase, J. Org. Chem., 1988, 53, 19, 4427, https://doi.org/10.1021/jo00254a001 . [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]

McMahon and Ohanessian, 2000
McMahon, T.B.; Ohanessian, G., An Experimental and Ab Initio Study of the Nature of the Binding in Gas-Phase Complexes of Sodium Ions, Chem. Eur. J., 2000, 6, 16, 2931, https://doi.org/10.1002/1521-3765(20000818)6:16<2931::AID-CHEM2931>3.0.CO;2-7 . [all data]

Shimanouchi, 1972
Shimanouchi, T., Tables of Molecular Vibrational Frequencies Consolidated Volume I, National Bureau of Standards, 1972, 1-160. [all data]

Notes

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• Symbols used in this document:
  

  Cp,gas	Constant pressure heat capacity of gas
  Cp,liquid	Constant pressure heat capacity of liquid
  S°liquid	Entropy of liquid at standard conditions
  T	Temperature
  d(ln(kH))/d(1/T)	Temperature dependence parameter for Henry's Law constant
  k°H	Henry's Law constant at 298.15K
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfH°liquid	Enthalpy of formation 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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