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:
  • Reaction thermochemistry data
  • Vibrational and/or electronic energy levels
  • References
  • Notes
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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
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

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

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

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:
  

  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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