Dibenzo[a,l]pyrene (dibenzo[def,p]chrysene): fjord-region distortions

Carcinogenesis. 1998 Sep;19(9):1641-8. doi: 10.1093/carcin/19.9.1641.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Benzopyrenes / chemistry*
  • Carcinogens / chemistry*

Substances

  • Benzopyrenes
  • Carcinogens
  • dibenzo(a,l)pyrene