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Online corrected version: (2006) "Homoaromatic". Aromatic molecules typically display enhanced chemical stability, compared to similar non-aromatic molecules. 18 (6): 833839. doi:10.1039/c2cc33521b. It is argued that he also anticipated the nature of wave mechanics, since he recognized that his affinities had direction, not merely being point particles, and collectively having a distribution that could be altered by introducing substituents onto the benzene ring (much as the distribution of the electric charge in a body is altered by bringing it near to another body). p.515. Benzene, as well as most other annulenes (cyclodecapentaene excepted) with the formula CnHn where n is an even number, such as cyclotetradecaheptaene.

Hence, cyclobutadiene is non-aromatic; the strain of the asymmetric configuration outweighs the anti-aromatic destabilization that would afflict the symmetric, square configuration. Polynuclear heterocyclic aromatic types. A. doi:10.1098/rspl.1856.0002. To avoid the instability of antiaromaticity, molecules may change shape, becoming non-planar and therefore breaking some of the interactions. By the same mechanism, the signals of protons located near the ring axis are shifted upfield. doi:10.1021/ja01429a002. J Chem Phys.

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