Paradigms and Paradoxes: Resonance Stabilization in Diazophenoxides (Quinone Diazides) |
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Authors: | Hosmane Ramachandra S. Liebman Joel F. |
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Affiliation: | (1) Department of Chemistry and Biochemistry, University of Maryland, Baltimore County, Baltimore, Maryland, 21250 |
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Abstract: | Diazophenoxides (quinone diazides) constitute an interesting class of compounds that are seemingly high-energy species on the nonaromatic/aromatic interface. With appropriate substitution and/or annelation, they have found use in the fields of explosives, medicine, and photolithography. Thermochemical information about them is sparse. To aid further understanding of these important chemical species, the current paper discusses a few extant enthalpies of formation from which we tentatively derive a resonance energy of ca. 15 kJ-mol–1 for the parent, p-species, 4-diazo-2,5-cyclohexadiene-1-one. Interestingly, this value is nearly identical to that recently found for the likewise conjugated diazo compound, ethyl diazoacetate. |
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Keywords: | o- and p-diazophenoxides o- and p-quinone diazides diazocyclohexadienones enthalpies of combustion enthalpies of formation resonance energy and stabilization |
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