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
- IUPAC Standard InChIKey: NFBOHOGPQUYFRF-UHFFFAOYSA-N
- 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
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Gas phase thermochemistry data
Go To: Top, Condensed 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 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
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | -14.1 ± 1.1 | kcal/mol | Ccb | Luk'yanova, Kolesov, et al., 1997 | ALS |
| ΔfH°gas | -14.1 ± 1.1 | kcal/mol | Ccb | Luk'yanova, Kolesov, et al., 1997 | ALS |
| ΔfH°gas | -14.1 | kcal/mol | N/A | Luk'yanova, Kolesov, et al., 1997 | Value computed using ΔfHsolid° value of -148.7±4.4 kj/mol from Luk'yanova, Kolesov, et al., 1997 and ΔsubH° value of 89.5 kj/mol from Luk'yanova, Kolesov, et al., 1997.; DRB |
Constant pressure heat capacity of gas
| Cp,gas (cal/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 10.81 | 50. | Dorofeeva O.V., 1997 | These S(T) and Cp(T) values were calculated using estimated vibrational frequencies. Thermodynamic functions calculated earlier by [ Shaub, 1982] are lower than selected ones by 8.8-11.2 J/mol*K for S(T) and 0.1-4.0 J/mol*K for Cp(T).; GT |
| 15.39 | 100. | ||
| 21.47 | 150. | ||
| 28.461 | 200. | ||
| 39.364 | 273.15 | ||
| 43.08 ± 0.72 | 298.15 | ||
| 43.351 | 300. | ||
| 57.168 | 400. | ||
| 68.640 | 500. | ||
| 77.784 | 600. | ||
| 85.062 | 700. | ||
| 90.925 | 800. | ||
| 95.719 | 900. | ||
| 99.687 | 1000. | ||
| 103.00 | 1100. | ||
| 105.80 | 1200. | ||
| 108.17 | 1300. | ||
| 110.20 | 1400. | ||
| 111.93 | 1500. |
Condensed phase thermochemistry 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 compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°solid | -35.5 ± 1.1 | kcal/mol | Ccb | Luk'yanova, Kolesov, et al., 1997 | |
| ΔfH°solid | -35.5 ± 1.1 | kcal/mol | Ccb | Luk'yanova, Kolesov, et al., 1997 | |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -1366.3 ± 0.98 | kcal/mol | Ccb | Luk'yanova, Kolesov, et al., 1997 | Corresponding ΔfHºsolid = -35.54 kcal/mol (simple calculation by NIST; no Washburn corrections) |
| ΔcH°solid | -1366.3 ± 0.98 | kcal/mol | Ccb | Luk'yanova, Kolesov, et al., 1997 | Corresponding ΔfHºsolid = -35.54 kcal/mol (simple calculation by NIST; no Washburn corrections) |
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:
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
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Tfus | 395.7 | K | N/A | Rordorf, 1986 | Uncertainty assigned by TRC = 0.1 K; TRC |
| Tfus | 393.05 | K | N/A | Cullinane and Rees, 1940 | Uncertainty assigned by TRC = 0.5 K; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔsubH° | 21.9 ± 0.2 | kcal/mol | C | Pimenova, Melkhanova, et al., 2002 | AC |
| ΔsubH° | 21.4 ± 0.2 | kcal/mol | C | Kolesov, Dorofeeva, et al., 1999 | AC |
| ΔsubH° | 21.4 | kcal/mol | N/A | Luk'yanova, Kolesov, et al., 1997 | DRB |
Enthalpy of sublimation
| ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 22.4 ± 0.29 | 318. | ME | Li, Shibata, et al., 2004 | Based on data from 303. to 333. K.; AC |
| 21.40 ± 0.17 | 318. | C | Luk'yanova, Kolesov, et al., 1997 | ALS |
| 21.40 | 318. | C | Luk'yanova, Kolesov, et al., 1997 | ALS |
| 21.4 ± 0.2 | 318. | C | Luk'yanova, Kolesov, et al., 1997, 2 | AC |
| 22.1 | 318. | T | Rordorf, 1989 | Based on data from 303. to 333. K. See also Rordorf, 1986, 2.; AC |
Enthalpy of fusion
| ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 5.54 | 395.7 | Rordorf, 1986, 3 | AC |
Gas Chromatography
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change 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
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | RTX-5 | 1612. | Donnelly, Munslow, et al., 1991 | 30. m/0.25 mm/0.25 μm, He, 170. C @ 1. min, 2. K/min; Tend: 320. C |
| Capillary | RTX-5 | 1612. | Donnelly, Munslow, et al., 1991, 2 | 30. m/0.25 mm/0.25 μm, He, 170. C @ 1. min, 2. K/min; Tend: 320. C |
Lee's RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | SE-52 | 267.27 | Lee, Vassilaros, et al., 1979 | 12. m/0.3 mm/0.34 μm, He, 2. K/min; Tstart: 50. C; Tend: 250. C |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change 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]
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, Condensed phase thermochemistry data, Phase change data, Gas Chromatography, References
- Symbols used in this document:
Cp,gas Constant pressure heat capacity of gas Tfus Fusion (melting) point 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 - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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