摘要

The representative isodesmic reactions shown in the Abstract graphic for (CH)(4)X-6 hexaheteroadamantane derivatives reveal energetic nonadditivity to remarkably different extents: while the electropositive element stabilizations are exceptionally large and the pnictide and hexaoxaadamantane stabilizations are more modest, the sulfur and selenium analogues are destabilized. Similar behavior Is exhibited by (CH2)(6)X-4 tetraheteroadamantanes. Analysis shows that aromaticity is not involved; the sign and magnitude of the nonadditivity depends on the Interplay of hyperconjugation, electrostatic, and steric (lone pair repulsion) effects.