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RECORD NUMBER: 14 OF 83

Main Title Comparative Analysis of the Electrostatic Potentials of Some Structural Analogues of 2,3,7,8-Tetrachlorodibenzo-p-dioxin and of Related Aromatic Systems.
Author Murray, J. S. ; Evans, P. ; Politzer., P. ;
CORP Author New Orleans Univ., LA. Dept. of Chemistry.;Health Effects Research Lab., Research Triangle Park, NC.
Publisher c1990
Year Published 1990
Report Number EPA/600/J-90/141;
Stock Number PB91-109793
Additional Subjects Electrostatic charge ; Oxygen ; Toxicity ; Aromatic compounds ; Quantum chemistry ; Atomic orbitals ; Pyrenes ; Benzanthracenes ; Flavones ; Hazardous materials ; Biochemistry ; Reprints ; Dioxin/Tetrachloro-dibenzo ; Comparative evaluations ; Benzopyrenes ; Hydroxylase
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NTIS  PB91-109793 Some EPA libraries have a fiche copy filed under the call number shown. 07/26/2022
Collation 21p
Abstract
An ab initio STO-5G computational analysis of the electrostatic potentials of four structural analogs of the highly toxic 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) and four related aromatic systems (benzo(a)pyrene, benz(a)anthracene and two isomeric benzoflavones) was carried out. The systems, to varying degrees, induce aryl hydrocarbon hydroxylase activity and are believed to interact with the same cytosolic receptor in initiating their biochemical responses. It was found that a high degree of activity appears to require negative potentials that are non-overlapping above all or most of the lateral regions, with an observed optimum range of magnitudes. In systems with central oxygens, it is required that the negative oxygen potentials be small and weak; however, oxygen negative regions in the molecule are not necessary for high activity. The observed differences between the potential patterns of the four aromatic systems and those of TCDD and its active analogs may reflect an inherent dissimilarity in the nature of their interactions with the cytosolic receptor.