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Hydrogen transfer from 9,10-dihydrophenanthrene to anthracene

✍ Scribed by R. Billmers; R. L. Brown; S. E. Stein

Publisher: John Wiley and Sons
Year: 1989
Tongue: English
Weight: 559 KB
Volume: 21
Category: Article
ISSN: 0538-8066
DOI: 10.1002/kin.550210602

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✦ Synopsis

Kinetic studies of t h e transfer of hydrogen from 9,lO-dihydrophenanthrene t o anthracene were done at 350°C in the liquid phase. Principal products were phenanthrene and 9,lO-dihydroanthracene. Autocatalysis occurred at low extents of reaction, where H-transfer from 9,lO-dihydroanthracene to anthracene caused an increase in free radical concentrations. At higher extents of reaction, 9,lO-dihydroanthracene inhibited rates by diverting intermediate 9-hydrophenanthryl radicals back to reactants. A quantitative kinetic model based on literature rate and thermodynamic data fits the observations well. A key net reaction is the transfer of an H-atom from a radical (9-hydrophenanthryl) to a molecule (anthracene). It is shown that this process does not involve a free H-atom intermediate. The derived rate constant for this exothermic process (7.5 x lo3 M-' s-') is considerably greater than that for the related, but thermoneutral H-transfer between anthracene moieties (120 M s-').

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