Dibenzo-p-dioxin

• Formula: C₁₂H₈O₂
• Molecular weight: 184.1907
• IUPAC Standard InChI: InChI=1S/C12H8O2/c1-2-6-10-9(5-1)13-11-7-3-4-8-12(11)14-10/h1-8H Copy

  
• IUPAC Standard InChIKey: NFBOHOGPQUYFRF-UHFFFAOYSA-N Copy
• CAS Registry Number: 262-12-4
• 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: Dibenzo[b,e][1,4]dioxin; Dibenzo[1,4]dioxin; Diphenylene dioxide; Oxanthrene; Phenodioxin; Dibenzodioxin; NCI-C03656
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Phase change data
  • Gas phase ion energetics data
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Mass spectrum (electron ionization)
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
• Options:
  • Switch to calorie-based units

Data at NIST subscription sites:

• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.

Gas phase thermochemistry data

Go To: Top, Phase change data, Gas phase ion energetics data, Gas Chromatography, 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
DRB - Donald R. Burgess, Jr.
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Constant pressure heat capacity of gas

Phase change data

Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, Gas Chromatography, 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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Enthalpy of sublimation

Enthalpy of fusion

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, Phase change data, Gas Chromatography, 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:
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

Ionization energy determinations

Gas Chromatography

Go To: Top, Gas phase thermochemistry data, Phase change 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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Van Den Dool and Kratz RI, non-polar column, temperature ramp

View large format table.

Lee's RI, non-polar column, temperature ramp

View large format table.

References

Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, Gas Chromatography, Notes

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

Luk'yanova, Kolesov, et al., 1997
Luk'yanova, V.A.; Kolesov, V.P.; Avramenko, N.V.; Vorob'eva, V.P.; Golovkov, V.F., Standard enthalpy of formation of dibenzo-p-dioxine, Russ. J. Phys. Chem. (Engl. Transl.), 1997, 71, 338-340, In original 406. [all data]

Dorofeeva O.V., 1997
Dorofeeva O.V., Unpublished results. Thermocenter of Russian Academy of Science, Moscow, 1997. [all data]

Shaub, 1982
Shaub, W.M., Estimated thermodynamic functions for some chlorinated benzenes, phenols and dioxins, Thermochim. Acta, 1982, 58, 11-44. [all data]

Rordorf, 1986
Rordorf, B.F., Proc. 5th Interna. Sympo. on Chlorinated Dioxins and Related Compounds, Bayreuth, 1986. [all data]

Cullinane and Rees, 1940
Cullinane, N.M.; Rees, W.T., Isomorphous relationships of some organic compounds of analogous constitution, Trans. Faraday Soc., 1940, 36, 507. [all data]

Pimenova, Melkhanova, et al., 2002
Pimenova, S.M.; Melkhanova, S.V.; Kolesov, V.P.; Demyanov, P.I.; Fedotov, A.N.; Vorobieva, V.P., Experimental determination of the enthalpy of formation of dibenzo- p-dioxin, The Journal of Chemical Thermodynamics, 2002, 34, 3, 385-390, https://doi.org/10.1006/jcht.2001.0951 . [all data]

Kolesov, Dorofeeva, et al., 1999
Kolesov, Victor P.; Dorofeeva, Olga V.; Iorish, Vladimir S.; Papina, Tatiana S.; Lukyanova, Vera A.; Melkhanova, Svetlana V., Experimental measurements and a group additivity approach for estimating the standard molar enthalpies of formation of dioxins, Mendeleev Communications, 1999, 9, 4, 143-144, https://doi.org/10.1070/MC1999v009n04ABEH001074 . [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]

Luk'yanova, Kolesov, et al., 1997, 2
Luk'yanova, V.A.; Kolesov, V.P.; Avramenko, N.V.; Vorob'eva, V.P.; Golovkov, V.F., Standard enthalpy of formation of dibenzo-p-dioxin, Zh. Fiz. Khim., 1997, 71, 3, 406. [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, 2
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]

Rordorf, 1986, 3
Rordorf, B.F., , Proceedings of the Fifth International Symposium on Chlorinated Dioxins and Related Compounds (16-19 September), Bayreuth, Germany, 1986. [all data]

Zimmermann, Boesl, et al., 1995
Zimmermann, R.; Boesl, U.; Lenoir, D.; Kettrup, A.; Grebner, T.L.; Neusser, H.J., The ionization energies of polychlorinated dibenzo-p-dioxins: new experimental results and theoretical studies, Int. J. Mass Spectrom. Ion Processes, 1995, 145, 97. [all data]

Colonna, Distefano, et al., 1978
Colonna, F.P.; Distefano, G.; Galasso, V.; Irgolic, K.J.; King, C.E.; Pappalardo, G.C., The conformation, uv-absorption spectra and photoelectron spectra of phenoxachalcogenins, J. Organometal. Chem., 1978, 146, 235. [all data]

Nounou, 1966
Nounou, P., Etude des composes aromatiques par spectrometrie de masse. I. Mesure des potentials d'ionisation et d'apparition par la methode du potential retardateur et interpretation des courbes d'ionisation differentielle, J. Chim. Phys., 1966, 63, 994. [all data]

Kuboyama, 1964
Kuboyama, A., Molecular complexes and their spectra. XVII.The iodine and the chloranil complexes with thianthrene analogs, J. Am. Chem. Soc., 1964, 86, 164. [all data]

Donnelly, Munslow, et al., 1991
Donnelly, J.R.; Munslow, W.D.; Grange, A.H.; Pettit, T.L.; Simmons, R.D.; Sovocool, G.W., Correlation of structure with linear retention index for bromo- and bromochlorodibenzo-p-dioxins and bromodibenzofurans, J. Chromatogr., 1991, 540, 293-310, https://doi.org/10.1016/S0021-9673(01)88817-8 . [all data]

Donnelly, Munslow, et al., 1991, 2
Donnelly, J.R.; Munslow, W.D.; Grange, A.H.; Pettit, T.L.; Simmons, R.D.; Kumar, K.S.; Sovocool, G.W., A gas chromatographic/mass spectrometric approach for isomer-specific environmental monitoring of the 1700 bromo-, chloro-, and bromoschloro-dibenzo-p-dioxins, Biol. Mass Spectrom., 1991, 20, 5, 329-337, https://doi.org/10.1002/bms.1200200515 . [all data]

Lee, Vassilaros, et al., 1979
Lee, M.L.; Vassilaros, D.L.; White, C.M.; Novotny, M., Retention Indices for Programmed-Temperature Capillary-Column Gas Chromatography of Polycyclic Aromatic Hydrocarbons, Anal. Chem., 1979, 51, 6, 768-773, https://doi.org/10.1021/ac50042a043 . [all data]

Notes

Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, Gas Chromatography, References

• Symbols used in this document:
  

  Cp,gas	Constant pressure heat capacity of gas
  IE (evaluated)	Recommended ionization energy
  Tfus	Fusion (melting) point
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔsubH	Enthalpy of sublimation
  ΔsubH°	Enthalpy of sublimation at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
• The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
• Customer support for NIST Standard Reference Data products.