Organic Chemistry in Confining Media by Zory Vlad Todres

Author:Zory Vlad Todres
Language: eng
Format: epub
Publisher: Springer International Publishing, Heidelberg

Scheme 4.1H-bond complexation of benzene dicarboxylates with hexaazamacrocycle

(Mateus et al. 2012) prepared polyamine macrobicyclic receptors that exhibit unprecedented selectivity for fumarate over other dicarboxylate competitors, including its cis isomer maleate (Scheme 4.2). The receptors work in water at pH of about 4. Oxalate, malonate, succinate, glutarate, maleate, and fumarate were tested. The authors ascribed the lower affinity of all of them (excluding fumarate) to worse fit to the receptor cavity arising from their own conformational preferences and flexibility. The fumarate anion has the right size, shape, and rigidity to fit into the cavity of the receptors. Namely, fumarate can be retained inside the cavity through four hydrogen bonds. Scheme 4.2 shows that maleate forms only two hydrogen bonds and two coordinative ones, therefore being held more weakly.

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