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 journalArticle

50 Citations (Scopus)

Abstract

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
JournalCarcinogenesis
Volume5
Issue number11
DOIs
StatePublished - Nov 1 1984

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Polycyclic Aromatic Hydrocarbons
X-Ray Diffraction
Carbon
5,6-dimethylchrysene
5,12-dimethylchrysene
5-methylchrysene
anthracene
chrysene
benz(a)anthracene

All Science Journal Classification (ASJC) codes

  • Cancer Research

Cite this

Zacharias, David E. ; Kashino, Setsuo ; Glusker, Jenny P. ; Harvey, Ronald G. ; Amin, Shantu ; Hecht, Stephen S. / The bay-region geometry of some 5-methylchrysenes : Steric effects in 5,6- and 5,12-dimethylchrysenes. In: Carcinogenesis. 1984 ; Vol. 5, No. 11. pp. 1421-1430.
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abstract = "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 {\AA} and the minimum C{combining triple dot above}C distance is 2.90 {\AA}; 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.",
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The bay-region geometry of some 5-methylchrysenes : Steric effects in 5,6- and 5,12-dimethylchrysenes. / Zacharias, David E.; Kashino, Setsuo; Glusker, Jenny P.; Harvey, Ronald G.; Amin, Shantu; Hecht, Stephen S.

In: Carcinogenesis, Vol. 5, No. 11, 01.11.1984, p. 1421-1430.

Research output: Contribution to journalArticle

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T2 - Steric effects in 5,6- and 5,12-dimethylchrysenes

AU - Zacharias, David E.

AU - Kashino, Setsuo

AU - Glusker, Jenny P.

AU - Harvey, Ronald G.

AU - Amin, Shantu

AU - Hecht, Stephen S.

PY - 1984/11/1

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N2 - 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.

AB - 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.

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