In the previous post, it was noted that Möbius annulenes are intrinsically chiral, and should therefore in principle be capable of resolution into enantiomers. The synthesis of such an annulene by Herges and co-workers was a racemic one; no attempt was reported at any resolution into such enantiomers. Here theory can help, since calculating the optical rotation [α]D is nowadays a relatively reliable process for rigid molecules. The rotation (in °) calculated for that Möbius annulene was relatively large compared to that normally measured for most small molecules.
Posts Tagged ‘chiroptical’
The Chirality of Lemniscular Octaphyrins
Tuesday, April 28th, 2009The chirality of Möbius annulenes
Wednesday, April 22nd, 2009Much like climbing Mt. Everest because its there, some hypothetical molecules are just too tantalizing for chemists to resist attempting a synthesis. Thus in 1964, Edgar Heilbronner speculated on whether a conjugated annulene ring might be twistable into a Möbius strip. It was essentially a fun thing to try to do, rather than the effort being based on some anticipated (and useful) property it might have. If you read the original article (rumour has it the idea arose during a lunchtime conversation, and the manuscript was completed by the next day), you will notice one aspect of these molecules that is curious by its absence. There is no mention (10.1016/S0040-4039(01)89474-0) that such Möbius systems will be chiral. By their nature, they have only axes of symmetry, and no planes of symmetry, and such molecules therefore cannot be superimposed upon their mirror image; as is required of a chiral system (for a discussion of the origins and etymology of the term, see 10.1002/chir.20699).