Isoxazolinyldioxepins. Part 2. The partitioning characteristics and the complexing ability of some oxazolinyldioxepin diastereoisomers

Abstract

The octanol–water partition coefficients (P) of pairs of isoxazolinyldioxepin diastereoisomers were measured. It was found that one type of diastereoisomer had a lower partition coefficient than the corresponding analogue from the other type. These differences were attributed to variations in molecular conformation. Quantum-mechanical studies have also shown major differences in the electronic distribution of the two types of diastereoisomers. These findings were finally confirmed by experiments designed to test the ability of the two types of isoxazolinyldioxepin to complex with mono-cations such as Li⁺, Na⁺, K⁺, Cs⁺, and Cu⁺.