Dibenzofuran

• Formula: C₁₂H₈O
• Molecular weight: 168.1913
• IUPAC Standard InChI: InChI=1S/C12H8O/c1-3-7-11-9(5-1)10-6-2-4-8-12(10)13-11/h1-8H Copy

  
• IUPAC Standard InChIKey: TXCDCPKCNAJMEE-UHFFFAOYSA-N Copy
• CAS Registry Number: 132-64-9
• 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: [1,1'-Biphenyl]-2,2'-diyl oxide; Dibenzo[b,d]furan; Diphenylene oxide; 2,2'-Biphenylene oxide; 2,2'-Biphenylylene oxide; Dibenzofurane
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• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • References
  • Notes
• Other data available:
  • Gas Chromatography
• Data at other public NIST sites:
  • 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:
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

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 solid

Phase change 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
DH - Eugene S. Domalski and Elizabeth D. Hearing
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.

Enthalpy of vaporization

Enthalpy of sublimation

Enthalpy of fusion

Enthalpy of phase transition

Entropy of phase transition

Gas phase ion energetics 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:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

Ionization energy determinations

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• SOLUTION (10% IN CCl4 FOR 3800-1330 CM^-1, 10% IN CS2 FOR 1330-420 CM^-1) VS. SOLVENT; DOW KBr FOREPRISM-GRATING; DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm^-1 resolution

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

• gas

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, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, 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.

Sabbah, 1991
Sabbah, R., Thermodynamic study of fluorene and dibenzofuran, Bull. Soc. Chim. Fr., 1991, 128, 350. [all data]

Sabbah and Antipine, 1987
Sabbah, R.; Antipine, I., Thermodynamic study on four polycycles. Relationship between their energy values and their structure, Bull. Soc. Chim. Fr., 1987, 392-400. [all data]

Chirico, Gammon, et al., 1990
Chirico, R.D.; Gammon, B.E.; Knipmeyer, S.E.; Nguyen, A.; Strube, M.M.; Tsonopoulos, C.; Steele, W.V., The thermodyanmic properties of dibenzofuran, J. Chem. Thermodyn., 1990, 22, 1075-1096. [all data]

Klots T.D., 1996
Klots T.D., Vibrational spectra, structure, assignment, and ideal-gas thermodynamics of a three-ring molecule: dibenzofuran, J. Mol. Struct., 1996, 380, 1-14. [all data]

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]

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]

Cooper, Crowne, et al., 1967
Cooper, A.R.; Crowne, C.W.P.; Farrell, P.G., Gas-Liquid Chromatographic Studies of Electron-Donor-Acceptor Systems, Trans. Faraday Soc., 1967, 63, 447. [all data]

Chirico, Gammon, et al., 1990, 2
Chirico, R.D.; Gammon, B.E.; Kripmeyer, S.E.; Nguyen, A.; Strube, M.M.; Steele, W.V., The thermodynamic properties of dibenzofuran, J. Chem. Thermodyn., 1990, 22, 11, 1075, https://doi.org/10.1016/0021-9614(90)90157-L . [all data]

Lei, Chankalal, et al., 2002
Lei, Ying Duan; Chankalal, Raymond; Chan, Anita; Wania, Frank, Supercooled Liquid Vapor Pressures of the Polycyclic Aromatic Hydrocarbons, J. Chem. Eng. Data, 2002, 47, 4, 801-806, https://doi.org/10.1021/je0155148 . [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]

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]

Li, Shibata, et al., 2004
Li, Xian-Wei; Shibata, Etsuro; Kasai, Eiki; Nakamura, Takashi, VAPOR PRESSURES AND ENTHALPIES OF SUBLIMATION OF 17 POLYCHLORINATED DIBENZO-p-DIOXINS AND FIVE POLYCHLORINATED DIBENZOFURANS, Environ Toxicol Chem, 2004, 23, 2, 348-808, https://doi.org/10.1897/03-193 . [all data]

Rordorf, 1989
Rordorf, Berchtold F., Prediction of vapor pressures, boiling points and enthalpies of fusion for twenty-nine halogenated dibenzo-p-dioxins and fifty-five dibenzofurans by a vapor pressure correlation method, Chemosphere, 1989, 18, 1-6, 783-788, https://doi.org/10.1016/0045-6535(89)90196-3 . [all data]

Rordorf, 1986
Rordorf, Berchtold F., Thermal properties of dioxins, furans and related compounds, Chemosphere, 1986, 15, 9-12, 1325-1332, https://doi.org/10.1016/0045-6535(86)90407-8 . [all data]

Hansen and Eckert, 1986
Hansen, Philip C.; Eckert, Charles A., An improved transpiration method for the measurement of very low vapor pressures, J. Chem. Eng. Data, 1986, 31, 1, 1-3, https://doi.org/10.1021/je00043a001 . [all data]

SATO, INOMATA, et al., 1986
SATO, NOBUYUKI; INOMATA, HIROSHI; ARAI, KUNIO; SAITO, SHOZABURO, Measurement of vapor pressures for coal-related aromatic compounds by gas saturation method., J. Chem. Eng. Japan / JCEJ, 1986, 19, 2, 145-147, https://doi.org/10.1252/jcej.19.145 . [all data]

Kestens, Auclair, et al., 2010
Kestens, Vikram; Auclair, Guy; Drozdzewska, Katarzyna; Held, Andrea; Roebben, Gert; Linsinger, Thomas, Thermodynamic property values of selected polycyclic aromatic hydrocarbons measured by differential scanning calorimetry, J Therm Anal Calorim, 2010, 99, 1, 245-261, https://doi.org/10.1007/s10973-009-0440-6 . [all data]

Hafsaoui and Mahmoud, 2007
Hafsaoui, S.L.; Mahmoud, R., Solid-liquid equilibria of binary systems containing n-tetracosane with naphthalene or dibenzofuran, J Therm Anal Calorim, 2007, 88, 2, 565-570, https://doi.org/10.1007/s10973-006-8084-2 . [all data]

Lisicki and Jamróz, 2000
Lisicki, Zygmunt; Jamróz, Malgorzata E., (Solid + liquid) equilibria in (polynuclear aromatic+ tertiary amide) systems, The Journal of Chemical Thermodynamics, 2000, 32, 10, 1335-1353, https://doi.org/10.1006/jcht.2000.0685 . [all data]

Mahmoud, Solimando, et al., 2000
Mahmoud, R.; Solimando, R.; Bouroukba, M.; Rogalski, M., Solid-Liquid Equilibrium and Excess Enthalpy Measurements in Binary {Dibenzofuran or Xanthene + Normal Long-Chain Alkane} Systems, J. Chem. Eng. Data, 2000, 45, 3, 433-436, https://doi.org/10.1021/je9902084 . [all data]

Terlouw, Heerma, et al., 1974
Terlouw, J.K.; Heerma, W.; Frintrop, P.C.M.; Dijkstra, G.; Meinema, H.A., Electron-impact induced fragmentation of some heterocyclic-tin compounds, J. Organomet. Chem., 1974, 64, 205. [all data]

Dewar, Harget, et al., 1970
Dewar, M.J.S.; Harget, A.J.; Trinajstic, N.; Worley, S.D., Ground states of conjugated molecules-XXI.Benzofurans and benzopyrroles, Tetrahedron, 1970, 26, 4505. [all data]

Eland, 1969
Eland, J.H.D., Photoelectron spectra of conjugated hydrocarbons and heteromolecules, Intern. J. Mass Spectrom. Ion Phys., 1969, 2, 471. [all data]

Ruscic, Kovac, et al., 1978
Ruscic, B.; Kovac, B.; Klasinc, L.; Gusten, H., Photoelectron spectroscopy of J. Heterocycl. Chem.. Fluorene analogues, Z. Naturforsch. A:, 1978, 33, 1006. [all data]

Tarbell, Frank, et al., 1946
Tarbell, D.S.; Frank, H.R.; Fanta, P.E., Studies on the structure of colchicine, J. Am. Chem. Soc., 1946, 68, 502-506. [all data]

Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, References

• Symbols used in this document:
  

  Cp,gas	Constant pressure heat capacity of gas
  Cp,solid	Constant pressure heat capacity of solid
  Pc	Critical pressure
  S°solid,1 bar	Entropy of solid at standard conditions (1 bar)
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  ΔHtrs	Enthalpy of phase transition
  ΔStrs	Entropy of phase transition
  ΔcH°solid	Enthalpy of combustion of solid at standard conditions
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfH°solid	Enthalpy of formation of solid at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔsubH	Enthalpy of sublimation
  ΔsubH°	Enthalpy of sublimation at standard conditions
  ΔvapH	Enthalpy of vaporization
  ρc	Critical density

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