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

David E. Zacharias, Setsuo Kashino, Jenny P. Glusker, Ronald G. Harvey, Shantu Amin, Stephen S. Hecht

Research output: Contribution to journalArticlepeer-review

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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{combining triple dot above}H distance is 1.8 Å and the minimum C{combining triple dot above}C distance is 2.90 Å; distortions to accommodate these requirements may be both in-plane (by increasing the angles at carbon atoms in the bay-region from 120° to ̃ 124°) 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.

Original languageEnglish (US)
Pages (from-to)1421-1430
Number of pages10
Issue number11
StatePublished - Nov 1984

All Science Journal Classification (ASJC) codes

  • Cancer Research


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