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Issue 30, 2017
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Entropy-driven homochiral self-sorting of a dynamic library

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Abstract

A dynamic mixture of stereoisomeric macrocycles derived from glutamic acid displayed a homochiral self-selection when increasing the acetonitrile content of the aqueous mixed medium. The homochiral self-sorting required the anionic form of the side chains and increased at higher temperature, implying an entropic origin. Conformational analysis (NMR and MD simulations) allowed us to explain the observed behaviour. The results show that entropy can play a role in the homochiral self-sorting in adaptive bio-inspired chemical systems.

Graphical abstract: Entropy-driven homochiral self-sorting of a dynamic library

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Publication details

The article was received on 13 Feb 2017, accepted on 23 Mar 2017 and first published on 23 Mar 2017


Article type: Communication
DOI: 10.1039/C7CC01153A
Citation: Chem. Commun., 2017,53, 4274-4277
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    Entropy-driven homochiral self-sorting of a dynamic library

    J. Atcher, J. Bujons and I. Alfonso, Chem. Commun., 2017, 53, 4274
    DOI: 10.1039/C7CC01153A

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