Dibenzofuran
- Formula: C12H8O
- Molecular weight: 168.1913
- IUPAC Standard InChIKey: TXCDCPKCNAJMEE-UHFFFAOYSA-N
- 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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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), 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
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | 47.3 ± 4.8 | kJ/mol | Ccb | Sabbah, 1991 | see Sabbah and Antipine, 1987 and Chirico, Gammon, et al., 1990; ALS |
Constant pressure heat capacity of gas
Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
104.68 | 200. | Klots T.D., 1996 | GT |
133.95 | 250. | ||
163.05 | 298.15 | ||
164.21 | 300. | ||
193.48 | 350. | ||
220.83 | 400. | ||
245.61 | 450. | ||
267.81 | 500. | ||
287.52 | 550. | ||
305.14 | 600. | ||
329.34 | 650. | ||
334.74 | 700. |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), 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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°solid | -29.2 ± 4.8 | kJ/mol | Ccb | Sabbah, 1991 | see Sabbah and Antipine, 1987 and Chirico, Gammon, et al., 1990; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -5836.3 ± 4.7 | kJ/mol | Ccb | Sabbah, 1991 | see Sabbah and Antipine, 1987 and Chirico, Gammon, et al., 1990; Corresponding ΔfHºsolid = -29.1 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°solid | -5859.7 ± 4.2 | kJ/mol | Ccb | Cass, Fletcher, et al., 1958 | Corresponding ΔfHºsolid = -5.9 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°solid,1 bar | 196.18 | J/mol*K | N/A | Chirico, Gammon, et al., 1990 | crystaline, I phase; S (298.15 K, liq) = 244.97 J/mol*K.; DH |
Constant pressure heat capacity of solid
Cp,solid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
199.01 | 298.15 | Chirico, Gammon, et al., 1990 | crystaline, I phase; T = 5 to 720 K. Data graphically extrapolated. Cp (298.15 K, liq) = 237.57 J/mol*K, graphically extrapolated.; DH |
Phase change data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), 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:
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.
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 558.2 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
Tboil | 560.2 | K | N/A | Weast and Grasselli, 1989 | BS |
Tboil | 560.15 | K | N/A | Cooper, Crowne, et al., 1967 | Uncertainty assigned by TRC = 0.6 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 355. ± 3. | K | AVG | N/A | Average of 6 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 355.31 | K | N/A | Chirico, Gammon, et al., 1990, 2 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.02 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 824. | K | N/A | Chirico, Gammon, et al., 1990, 2 | Uncertainty assigned by TRC = 4. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 36.40 | bar | N/A | Chirico, Gammon, et al., 1990, 2 | Uncertainty assigned by TRC = 1.00 bar; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ρc | 2.02 | mol/l | N/A | Chirico, Gammon, et al., 1990, 2 | Uncertainty assigned by TRC = 0.03 mol/l; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 81. ± 9. | kJ/mol | AVG | N/A | Average of 6 values; Individual data points |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
66.2 | 398. | GC | Lei, Chankalal, et al., 2002 | Based on data from 323. to 473. K.; AC |
55.1 | 418. | A | Stephenson and Malanowski, 1987 | Based on data from 403. to 559. K.; AC |
66.2 | 410. | N/A | Cass, Fletcher, et al., 1958, 2 | Based on data from 403. to 418. K.; AC |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
82.1 ± 1.5 | 307. | ME | Li, Shibata, et al., 2004 | Based on data from 295. to 318. K.; AC |
85.6 | 324. | T | Rordorf, 1989 | Based on data from 304. to 343. K. See also Rordorf, 1986.; AC |
79.1 | 323. | N/A | Hansen and Eckert, 1986 | Based on data from 303. to 343. K.; AC |
76.7 | 323. | GS | SATO, INOMATA, et al., 1986 | Based on data from 299. to 346. K.; AC |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
18.6 | 354.7 | DSC | Kestens, Auclair, et al., 2010 | AC |
19.41 | 355.1 | N/A | Hafsaoui and Mahmoud, 2007 | AC |
20.5 | 355.8 | DSC | Lisicki and Jamróz, 2000 | AC |
17.6 | 355.2 | DSC | Mahmoud, Solimando, et al., 2000 | AC |
18.6 | 355.7 | N/A | Chirico, Gammon, et al., 1990 | AC |
Enthalpy of phase transition
ΔHtrs (kJ/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
0.00 | 292.5 | crystaline, II | crystaline, I | Chirico, Gammon, et al., 1990 | DH |
19.29365 | 355.31 | crystaline, I | liquid | Chirico, Gammon, et al., 1990 | DH |
Entropy of phase transition
ΔStrs (J/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
54.30 | 355.31 | crystaline, I | liquid | Chirico, Gammon, et al., 1990 | DH |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, IR Spectrum, Mass spectrum (electron ionization), 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:
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
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.77 | EI | Terlouw, Heerma, et al., 1974 | LLK |
8.22 | PE | Dewar, Harget, et al., 1970 | RDSH |
7.9 ± 0.05 | PE | Eland, 1969 | RDSH |
8.09 | PE | Ruscic, Kovac, et al., 1978 | Vertical value; LLK |
IR Spectrum
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), References, Notes
Data compiled by: Coblentz Society, Inc.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, References, Notes
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
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Due to licensing restrictions, this spectrum cannot be downloaded.
Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | Japan AIST/NIMC Database- Spectrum MS-NW- 354 |
NIST MS number | 228192 |
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), 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]
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), 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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