Molecular structure of benzo(a)pyrene 4,5-oxide. 1976

J P Glusker, and D E Zacharias, and H L Carrell, and P P Fu, and R G Harvey

An X-ray crystallographic study of benzo(a)pyrene 4,5-oxide, a metabolite of the carcinogen benzo(a)pyrene (BP), as given information on the geometry of this molecule. The carbon skeleton of BP itself has been shown by others to be early planar; the planarity of the carbon skeleton has been shown by this work to be perturbed very little by epoxidation of the 4,5-double bond. Epoxidation has, however, increased the double bond character of C-11--C-12, C-9--C-10, and C-7--C-8. The hydrogen atom on C-3 points directly toward the oxygen atom of another molecule. This C--H... O interaction, although weak, suggests that C-3 might be slightly acidic. An analysis of the experimentally determined bond lengths indicates that, after the highly reactive epoxide ring, the most reactive positions are at C-1, C-6, C-7, C-11, and C-12. The oxide ring of BP, unlike that for the K-region oxide of 7,12-dimethylbenz(a)anthracene, is symmetrical (with C--O distances equivalent within experimental error). The C--O distances are longer than those found in most oxides, including those in 7,12-dimethylbenz(a)anthracene-5,6-oxide. Thus it has been shown that the oxide rings of the K-region oxides of the two potent carcinogens BP and 7,12-dimethylbenz(a)anthracene are not similar in dimensions.

UI MeSH Term Description Entries
D008958 Models, Molecular Models used experimentally or theoretically to study molecular shape, electronic properties, or interactions; includes analogous molecules, computer-generated graphics, and mechanical structures. Molecular Models,Model, Molecular,Molecular Model
D008968 Molecular Conformation The characteristic three-dimensional shape of a molecule. Molecular Configuration,3D Molecular Structure,Configuration, Molecular,Molecular Structure, Three Dimensional,Three Dimensional Molecular Structure,3D Molecular Structures,Configurations, Molecular,Conformation, Molecular,Conformations, Molecular,Molecular Configurations,Molecular Conformations,Molecular Structure, 3D,Molecular Structures, 3D,Structure, 3D Molecular,Structures, 3D Molecular
D002621 Chemistry A basic science concerned with the composition, structure, and properties of matter; and the reactions that occur between substances and the associated energy exchange.
D004988 Ethers, Cyclic Compounds of the general formula R-O-R arranged in a ring or crown formation. Cyclic Ether,Cyclic Ethers,Ether, Cyclic
D001580 Benzopyrenes A class of chemicals that contain an anthracene ring with a naphthalene ring attached to it. Benzpyrene
D014961 X-Ray Diffraction The scattering of x-rays by matter, especially crystals, with accompanying variation in intensity due to interference effects. Analysis of the crystal structure of materials is performed by passing x-rays through them and registering the diffraction image of the rays (CRYSTALLOGRAPHY, X-RAY). (From McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed) Xray Diffraction,Diffraction, X-Ray,Diffraction, Xray,Diffractions, X-Ray,Diffractions, Xray,X Ray Diffraction,X-Ray Diffractions,Xray Diffractions
D055598 Chemical Phenomena The composition, structure, conformation, and properties of atoms and molecules, and their reaction and interaction processes. Chemical Concepts,Chemical Processes,Physical Chemistry Concepts,Physical Chemistry Processes,Physicochemical Concepts,Physicochemical Phenomena,Physicochemical Processes,Chemical Phenomenon,Chemical Process,Physical Chemistry Phenomena,Physical Chemistry Process,Physicochemical Phenomenon,Physicochemical Process,Chemical Concept,Chemistry Process, Physical,Chemistry Processes, Physical,Concept, Chemical,Concept, Physical Chemistry,Concept, Physicochemical,Concepts, Chemical,Concepts, Physical Chemistry,Concepts, Physicochemical,Phenomena, Chemical,Phenomena, Physical Chemistry,Phenomena, Physicochemical,Phenomenon, Chemical,Phenomenon, Physicochemical,Physical Chemistry Concept,Physicochemical Concept,Process, Chemical,Process, Physical Chemistry,Process, Physicochemical,Processes, Chemical,Processes, Physical Chemistry,Processes, Physicochemical

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