The reaction coordinate is usually chosen to be a simple function of the bonds that are broken or
formed in a chemical reaction. Although such an approach is adequate for the analysis of isolated reaction
processes, it does not provide a general metric that allows ready comparison between different chemical reactions.
In this paper, we introduce hybridization as a unifying metric for the degree of structural progress in organic
reaction processes and illustrate the usefulness of such an analysis by reference to the Hammond postulate and
electrocyclic reactions.
As part of an investigation into new synthetic routes to poly(peri-naphthalene), the synthesis and cycloaromatization of tetraethynylbiphenyls is described. The temperature-dependent cyclization of biphenyls containing unsubstituted alkynes provides the desired perylene in good yield.
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