The separation of the aromatic stabilization energy (ASE) of cyclobutadiene (CBD) into a sigma- and a pi-component is reinvestigated. Eight different reactions are considered for this purpose. As expected, the total destabilization energies that result from these reactions depend only on the reference compound and not on the reaction itself.
View Article and Find Full Text PDFA well-established quantity for specifying the aromaticity or antiaromaticity of cyclic conjugated molecules is the so-called aromatic stabilization energy (ASE), which can be derived-either experimentally or theoretically-from appropriate homodesmotic reactions. To gain further insight into the origin of aromaticity, several schemes have been devised to partition ASE into nuclear and electronic as well as sigma and pi contributions, some of which have resulted in contradictory statements about the driving force of aromatic stabilization. Currently, these contradictions have not been resolved and have resulted in a confusing distinction between two different types of aromaticity: extrinsic and intrinsic aromaticity.
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