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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 

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The bay-region geometry of some 5-methylchrysenes: steric effects in 5,6- and 5,12-dimethylchrysenes.

The presence of a bay-region methyl group in carcinogenic polycyclic aromatic hydrocarbons leads to considerable distortion in the molecule. This is illustrated in the structures, obtained by X-ray diffraction techniques, of 5,12- and 5,6-dimethylchrysene. The molecular distortions result from steric requirements, such as that the minimum H...H distance is 1.8 A and the minimum C...C distance is 2.90 A; distortions to accommodate these requirements may be both in-plane (by increasing the angles at carbon atoms in the bay-region from 120 degrees to approximately 124 degrees) and out-of-plane by torsion about certain bonds in the bay-region. It is shown that more in-plane distortions are found for 5-methylchrysene derivatives than for methylbenz[a]anthracene derivatives and this, it is suggested, results from the nature of the flexibility of the chrysene compared with the benz[a]anthracene fragment at the bay-region.[1]

References

  1. The bay-region geometry of some 5-methylchrysenes: steric effects in 5,6- and 5,12-dimethylchrysenes. Zacharias, D.E., Kashino, S., Glusker, J.P., Harvey, R.G., Amin, S., Hecht, S.S. Carcinogenesis (1984) [Pubmed]
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