Journal of the American Chemical Society, Vol.133, No.33, 12918-12921, 2011
Planar Hydrocarbons More Optically Active Than Their Isomeric Helicenes
Comparisons are made of the calculated optical rotation tensors of C(2v)-symmetric, polyaromatic hydrocarbons and their [S]helicene, [6]helicene, and [7]helicene isomers. Seven boolean AND-shaped, planar compounds had, in each case, larger computed tensor elements than the chiral helicenes. Merely obviating the condition of solution averaging wholly changes expectations of the magnitudes and etiologies of optical activity. Symmetries of achiral compounds facilitate semiquantitative correlations between structure and optical rotation.