Proton-triggered conformational switching: Unsymmetrically linked phenolic oligoamides fold into a turn conformation from a linear conformation following the deprotonation of the phenol groups (see scheme). Deprotonation induces a rearrangement of the hydrogen-bonding mode within each unit from OH⋅⋅⋅OC (linear) to NH⋅⋅⋅O(oxyanion) such that all of the phenolate O− atoms are directed toward the inside of the turn.
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Kanamori et al. (2004) studied this question.
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