Structural analysis by diffraction of polychlorinated dioxins and dibenzofurans

Cantrell, J. S.; Beiter, T. A.; Tomlin, D. W.

doi:10.1016/0045-6535(89)90304-4

Cited by 3 publications

(3 citation statements)

References 15 publications

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“…This compound is a metabolite of PCB 77 (Doi et al, 2006;Koga et al, 1989) and has a strong affinity to both human estrogen sulfotransferase (Shevtsov et al, 2003) and thyroxine (McKinney et al, 1987). 3,3′,5,5′-tetrachloro-4,4′-dihydroxybiphenyl, like chlorinated dioxins Cantrell et al, 1989;Cantrell et al, 1969;Koester et al, 1988), is essentially coplanar in the solid state, and thus adopts a conformation that is significantly different from that of PCB 77. The tendency of this dihydroxylated PCB derivative to adopt a more planar conformation in the solid state is due to the stabilizing intermolecular interactions resulting, in part, from a stacking arrangement of the benzene rings (McKinney and Singh, 1988).…”

Section: Resultsmentioning

confidence: 99%

The three-dimensional structure of 3,3′,4,4′-tetrachlorobiphenyl, a dioxin-like polychlorinated biphenyl (PCB)

et al. 2008

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Section: Resultsmentioning

confidence: 99%

The three-dimensional structure of 3,3′,4,4′-tetrachlorobiphenyl, a dioxin-like polychlorinated biphenyl (PCB)

et al. 2008

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“…It seems that the C-Cl bonds get shorter as more chlorines get added. With octachlorodioxin, the C-Cl bond is 1.71 Å instead of 1.74 Å [34]. This can do two things.…”

Section: Resultsmentioning

confidence: 92%

Predicting hydration free energies of polychlorinated aromatic compounds from the SAMPL-3 data set with FiSH and LIE models

Sulea

Purisima

2011

J Comput Aided Mol Des

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Next-generation solvation models are devised to mimic the accuracy and generality of explicit solvation models at the speed of current popular implicit solvation models. One such method is the first-shell of hydration (FiSH) continuum model that was trained on hydration energetics from LIE calculations and molecular dynamics simulations in explicit solvent. Here we tested prospectively the FiSH model on the SAMPL-3 hydration data set that zooms in the effect of chlorination on solvation. We compare these FiSH predictions with those from retrospective LIE calculations. We find that neither FiSH nor LIE can reproduce well the absolute values and the trend of hydration free energies in the biphenyl and dioxin aromatic chlorination series. Some of the hypotheses behind this performance are discussed and tested. The LIE explicit-solvent model shows some improvement relative to the FiSH continuum model, and we correct a systematic deviation in the continuum van der Waals term of FiSH associated with aromatic Cl atom type.

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“…Moreover, PCDD differ from PCDF in terms of geometric structure and electronic properties. The former was determined by the analysis of crystal structure of congeners (15). Among the latter, the PCDF aromatic properties and the PCDD nonaromatic character were investigated with very simple models such as Hu ¨ckel's 4n + 2 rule (16) as well as with more rigorous ab initio calculations (17).…”

Section: Resultsmentioning

confidence: 99%

Prevention of PCDD/F Formation and Minimization of Their Emission at the Stack of a Secondary Aluminum Casting Plant

Pitea

Bortolami

Collina

et al. 2008

Environ. Sci. Technol.

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Results of an extensive 5 year study on a full-scale plant with the specific aim to investigate polychlorinated dibenzo-p-dioxin (PCDD) and polychlorinated dibenzo furan (PCDF) formation and release in a secondary aluminum casting plant are reported. PCDD and PCDF concentrations were evaluated for all the gaseous and solid streams (no liquid stream was present) as well as for the flue gas upstream and downstream of every single unit of the flue gas cleaning system. The study highlights PCDD and PCDF formation particularly in the narrow 320-360 degrees C range. To prevent formation reactions and/or minimize PCDD and PCDF concentration at the stack, effects of the fabric filter substitution, a quenching chamber and a postcombustor installation together with working conditions are investigated. The flue gas cleaning system results in PCDD and PCDF emission at stack of 0.1-0.2 ng I-TEQ/N m3 and in a mass flow of 250-550 nmol/h. The total PCDD and PCDF release into the environment is 0.06 g I-TEQ/yr and the corresponding emission factor, 0.35 microg I-TEQ/ton. It is shown that the global effects of the technological innovation on the reaction mechanisms are the prevention of PCDD/F formation by de novo synthesis and the minimization of their emission.

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Structural analysis by diffraction of polychlorinated dioxins and dibenzofurans

Cited by 3 publications

References 15 publications

The three-dimensional structure of 3,3′,4,4′-tetrachlorobiphenyl, a dioxin-like polychlorinated biphenyl (PCB)

The three-dimensional structure of 3,3′,4,4′-tetrachlorobiphenyl, a dioxin-like polychlorinated biphenyl (PCB)

Predicting hydration free energies of polychlorinated aromatic compounds from the SAMPL-3 data set with FiSH and LIE models

Prevention of PCDD/F Formation and Minimization of Their Emission at the Stack of a Secondary Aluminum Casting Plant

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