The thermal cis-to-trans isomerization of an azobenzene covalently-bridged to azacrown ether occurs via the inversion mechanism, and the rotational mechanism is not allowed owing to the rigid ring structure. By using the “standard” azobenzene, it was demonstrated that the thermal isomerization of most cis-azobenzenes occurs via the inversion mechanism, the activation parameters being subject to a good ΔH–ΔS compensation relationship.
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Shinkai et al. (1980) studied this question.
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