Assessing Benzene Dimer Interactions in Solution With a Molecular Balance

ABSTRACT We present a combined experimental and computational study of a 1,4/1,6‐dibenzyl substituted cyclooctatetraene (COT)‐based molecular balance as a model to assess the benzene dimer interactions in solution. This is accomplished by investigating the equilibrium between the unfolded 1,4‐ versus folded 1,6‐dibenzyl COT in a variety of common organic solvents. NMR measurements demonstrate that the 1,6‐COT isomer, in which the phenyl moieties are in proximity, is always favored over the unfolded and sterically less hindered 1,4‐COT by ∼0.3 kcal mol −1 , irrespective of solvent. Computations identify London dispersion (LD) interactions between the aromatic moieties in 1,6‐COT as the main stabilizing force.