Abstract
Proximity effects occur between vicinal functional groups or between a group and a specific molecular fragment in close proximity, for example an endocyclic N atom in the ortho position relative to the group. They are a combination of through-bond inductive and resonance effects, and through-space interactions, which can be either attractive or repulsive. In this review, we discuss quantum-chemical tools and examples from the literature that explore the structural and physicochemical implications of proximity effects. We focus on derivatives of small molecules: benzene, small polycyclic aromatic hydrocarbons, simple heterocycles, and lastly, purine derivatives.
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