Abstract
AbstractThe present personal perspective sheds light on the checkered history of hexaphenylethane (HPE) and some of its key derivatives, including successes and failures in interpreting experimental as well as computational data. HPE has become a testing ground for chemical theory since the groundbreaking work of Gomberg in 1900. It sparked the growth of theoretical carbon chemistry beyond tetravalency, forced chemists to improve theory of color and chemical bonding by mesomeric resonance, and challenged the purely repulsive view on substituent effects. Understanding the origin of the instability of HPE on the one hand and the stability of the sterically much more crowded all‐meta tBu‐substituted HPE on the other hand may well be considered an important turning point in the appreciation of London dispersion (LD) and the analytical power of computational chemistry.
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