ArticleAngewandte Chemie (International ed. in English)2026
The Nonadiabatic Nature of the Substituent Effects in Azobenzene.
Article in Angewandte Chemie (International ed. in English), 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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5 authors.
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Abstract
The mechanism of thermal Z → E isomerization in azobenzenes has been debated for nearly a century, with inversion, rotation, and nonadiabatic pathways proposed to account for the nonlinear substituent dependence of the reaction rate. Here, we combine systematic kinetic analysis with temperature-dependent Eyring and isokinetic evaluations to experimentally evaluate the origin of this behavior. A series of para-substituted azobenzenes exhibits uniformly negative entropies of activation, suggesting a single nonadiabatic rotational mechanism is operative across all substituents. We found that the characteristic "V-shaped" Hammett correlation of azobenzene arises not from a mechanistic change, but from the inadequacy of the σ
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