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Science 5 November 1999:
Vol. 286. no. 5442, p. 1049
DOI: 10.1126/science.286.5442.1049c
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This Week in Science
The unusual reactivity and stability of benzene compared to alkenes can be attributed in simple models to resonance interactions between its three double bonds. The stabilization of cyclic unsaturated molecules, or aromatic molecules, in which 4n + 2 electrons (n = 0, 1, 2,...) form p bonds, contrasts with the destabilization of antiaromatic molecules, cyclic species with 4n p-electrons. The most notable example is cyclobutadiene, which is destabilized to such an extent that its high reactivity makes measuring antiaromaticity difficult. Deniz et al. (p. 1119) have now used photoacoustic calorimetry to determine the enthalpy of formation of cyclobutadiene produced in a photochemical reaction. They estimated its antiaromaticity relative to a hypothetical strainless, conjugated diene reference and a reference with isolated double bonds.
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Science. ISSN 0036-8075 (print), 1095-9203 (online)
