9,10-Dehydroanthracene: p-Benzyne-type biradicals abstract hydrogen unusually slowly

Journal of the American Chemical Society

Volumn 118, Issue 20, 1996, Pages 4896-4903

  Schottelius, Marc J ^a   Chen, Peter ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ANTHRACENE DERIVATIVE;

ARTICLE; DNA BINDING; DRUG STRUCTURE;

EID: 0029884874     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja960181y     Document Type: Article

References (56)

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24. EI mass spectra with fragmentation patterns are also reported in the literature for 9-methoxy- and 9-ethoxyanthracene: Gillis, R. G.; Long, G. J.; Moritz, A. G.; Occolowitz, J. L. Org. Mass. Spedrosc. 1968, 1, 527. Klasinc, L.; Komadinovic, S.; Stefanovic, D.; Guesten, H. Croat. Chem. Acta 1976, 48, 109.
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26. For the slowest decay, τ = 1.0 ms, the decay could be followed out for <2 lifetimes. Although the decay is first-order as far as we can determine, we do not exclude the possibility that instrumental limitations prevent us from seeing nonexponential behavior in the longest-lived transient. Error bounds were determined on the decay rates rather than on the lifetimes, and are reported with those rate measurements.
27. As can be inferred from the identification of the slow transient (see later text), its longer lifetime and much lower ∈ at 251 nm mean that only that fraction of 1 which decays by hydrogen abstraction should contribute to the growth of anthracene absorbance on the microsecond time scale.
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33. We do not consider addition products of 1 to solvent, e.g. acetonitrile, because the absorption spectrum of the slow transient is unchanged going from acetonitrile to isopropyl alcohol. The next most abundant species in solution to which a radical-like species could add would be unreacted propel lane 2.
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