Elmar Kaufmann

(CH2LiF)2: the effect of dimerization on the structure and dissociation energy of carbenoids

Ab initio molecular orbital theory suggests that the non-tetrahedral structural features of the prototype carbenoid, CH2LiF, are retained in its dimer; however, dissociation of singlet methylene is thermodynamically much more favourable from the dimer than from the monomer.

Stabilization of the alleged ‘bishomoromatic’ bicyclo[3.2.1]octa-2,6-dienyl anion by counterion interactions and by hyperconjugation

Hyperconjugation and inductive effects, rather than homoaromaticity, are responsible for the stabilization of the title anion in the gas phase; interaction of the double bond with the Li+ gegenion in the endo geometry contributes additionally in solution.