Concerning restricted rotations in pyridinyl anisoles and pyridinyl phenols bearing saturated handles, and their solid state structures

The variable-temperature («dynamic») NMR measurements of series of pyridinyl anisoles and pyridinyl phenols each of them bearing ortho, ortho′ handles of various lengths at oxygenated ring lead to the following results: (i) at room temperature, a restricted rotation around the intercyclic bond of pyridinyl anisoles and pyridinyl phenol bearing short handles formed by 9–10 atoms is underscored, (ii) all handles at the former derivatives are blocked on one side of the oxygenated ring face, and (iii) handles of 11–12 atoms long at phenol rings are able to move freely. The solid-state packing indicates that all saturated chains are substantially perpendicular to the oxygenated ring.