X-ray Diffraction Evidence for a "Cyclotriene" Motif in the
Molecular Structure of Trisbicyclo[2.1.1]hexabenzene: Bond Alternation After
Burgi, H.-B.; Baldridge, K.K.; Hardcastle, K.; Frank, N.L.; Siegel, J.S.
Contribution from the University of Bern, Switzerland, California State University-Northridge, San Diego Supercomputer Center, and the University of California, San Diego
Angew. Chem. Int. Ed. Engl. 1994, 34, 1454.
Benzene Structure with Localized Double Bonds
SDSC Staff Scientist Kim Baldridge and UCSD Chemistry Professor Jay S.
Siegel computationally designed and then chemically synthesized
trisbicyclo[2.1.1]hexabenzene, the first simple benzene structure with
localized double bonds. Synthesis of this kind of molecular structure has
been a goal of chemists for over 60 years. The blue transparent shell
around the molecule represents the total electron density at a specified
contour level, while the inner net surfaces represent the highest occupied
molecular orbital of this structure (the two colors are representative of
the two phases of this orbital). Graphics generated by Kim Baldridge and
Jerry Greenberg using QMView (Quantum Mechanical viewing tool).