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By analogy with the homocyclopropenyl (1) and homotropylium cations (2), cyclohexadienyl anions (3) might also be expected to be nonplanar, homoaromatic species. Several such anions, prepared by proton abstraction from the correspond- ing 1,3- and 1,4-cyclohexadienes, were studied by IH and I3C NMR spectroscopy in ND3 solution. Interpretation of the chemi- cal shifts, coupling constants, and the results of low-temperature studies at 300 (IH NMR) and 67.88 MHz (I3C NMR) indi- cated these cyclohexadienyl anions rather to be planar nonhomoaromatic species. MIND0/3 calculations on the parent cyclo- hexadienyl anion agreed; the planar form was found to be a shallow energy minimum. The large spatial separation between the *-system termini and the stabilizing interaction of T* (CH2) with the HOMO of the pentadienyl fragment are responsible for the absence of the expected homoaromaticity

Carbanions. 3. Nuclear magnetic resonance spectroscopic and theoretical study of homoaromaticity in cyclohexadienyl anions