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Weakly bound carbon - Carbon bonds in acenaphthene derivatives and hexaphenylethane

Journal of Physical Chemistry A, ISSN: 1089-5639, Vol: 114, Issue: 2, Page: 1161-1168
2010
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A class of acenaphthene derivatives is shown to contain weak central carbon - carbon bonds that may be easily cleaved at high temperatures or even at ambient conditions to yield persistent free diradicals. To demonstrate the weak C - C bond strength, density functional theory calculations were carried out at several levels of theory for both the parent molecules and the diradicals resulting from the C - C bond cleavage. To assess the accuracy of the calculations, hexaphenylethane was chosen as a model compound due to its similarity with the molecules studied here, its great resonance stabilization, and long-standing history within the chemistry community. The C - C bond dissociation energy of hexaphenylethane was determined to be 11.3 ± 1.4 kcal/ mol using a combination of isodesmic reactions and calculations at the M06-2X/6-31+G(d,p) level of theory. The types of molecules presented here are proposed as strong possibilities for the natural existence of free radicals in young and mature soot formed in hydrocarbon combustion. © 2010 American Chemical Society.

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