Hexasilabenzene aromatic stabilization

In addition to the question of geometry a second point of interest is the degree of aromatic stabilization in hexasilabenzene. Using appropriate bond-separation reactions hexasilabenzene is found to possess approximately half the aromatic stabilization energy... 

More recently, Scheschkewitz and coworkers reported the synthesis of an exotic tricyclic isomer stabilized with six 2,4,6-triisopropylphenyl (named Tip) substituents, which is an attempt toward production of the first hexa-silabenzene (Chart 13.19). In the crystalline form, the tricyclic ring adopted a cyclohexane-like puckered geometry, which is significantly distorted from a planar benzene-like geometry. The isomer showcased a unique aromaticity, called dismutational aromaticity, supported by three Si resonances and high-level density functional theory calculations. This result can lead to the first isolation of an ideal hexasilabenzene with higher molecular symmetry (six- and three-fold) by designing more elaborate substituents and reaction routes. 

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