The use of the word disruption reminds of Henry Armstrong’s use of the same word, in more or less the same context, in 1890, 35 years earlier (for the context, replace Armstrong’s use of the words cycle of affinity, by Robinson’s use of the word electrons). It seems quite probable that Robinson and Armstrong met, since they were both alive at this period.

Anyway, my point here is that Robinson, entranced by the aromatic sextet he has (re?)discovered, was determined that one cannot have too much of a good thing, and creates two sextets in naphthalene. The comments about borrowing two (what we now know as σ) electrons from the central C-C bond is (in 1925) no difficulty. I suppose perhaps we should instead give Robinson credit for inventing the homo-aromatic bond? At any rate, posterity has judged Armstrong’s 1990 representations of the polycyclic aromatics as having survived extremely well, whereas Robinson’s has not.

And something that we have access to, but was not even a twinkle in Robinson’s eye is high level solutions of Schroedinger’s equation, which addresses the point Igor makes above. This will give an answer as to what sort of species the structure on the right actually is. It could be a stable valence bond isomer of nitrosobenzene, or it could be a transition state interconverting two bent forms. I will comment on the results of this shortly.