Abstract
A recent publication of a general carbocation rearrangement mechanism highlighted protonated cyclopropane (PCP+) intermediates, whose structures are meso between the nonclassical hypotheses of edge-PCP+ and corner-PCP+. Unlike the nonclassical structures, which possess 3-centre–2-electron bonds, the meso-PCP+ structures appear as closed classical structures. The 2-norbornyl ion, however, is known to have a nonclassical corner-PCP+ structure, and here we explore (using computational chemistry) the reasons why. The main reasons are due to the three 5-membered carbon rings, whose ring strain resist relaxation to a meso-PCP+ structure, but an additional reason is the trisubstitution on one side of the PCP+ face, which causes unfavourable C–C bond eclipsing.
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