Dibenzo[a,l]pyrene (dibenzo[def,p]chrysene): fjord-region distortions.
The molecular dimensions of the potent chemical carcinogen dibenzo[def,p]chrysene, also known as dibenzo[a,l]pyrene, have been determined by X-ray diffraction methods. This analysis shows that the molecule is considerably distorted so that it is non-planar with an angle of 27.6 degrees between the outermost rings and a widening of C-C-C bond angles in the fjord region. The dimensions of the molecular distortion due to atomic overcrowding in the fjord region are presented. This polycyclic aromatic hydrocarbon is a more potent carcinogen than is benzo[a]pyrene or its 11-methyl derivative. Comparisons of the distortions in dibenzo[a,l]pyrene with the geometries of various other polycyclic aromatic hydrocarbons containing fjord- or bay-region methyl groups provide structural data on the ratio of angular to torsional distortion in such overcrowded molecules.
Katz
A K
AK
The Institute for Cancer Research, Fox Chase Cancer Center, Philadelphia, PA 19111, USA.
Carrell
H L
HL
Glusker
J P
JP
D001580:Benzopyrenes / Q000737:chemistry*; D002273:Carcinogens / Q000737:chemistry*
D001580:Benzopyrenes; D002273:Carcinogens; C041517:dibenzo(a,l)pyrene