Judging on host-guest binding mode uniqueness: Association entropy as an indicator in enantioselection

Vinod D. Jadhav, Franz P. Schmidtchen

Research output: Contribution to journalArticlepeer-review

46 Scopus citations

Abstract

Supramolecular enantiodifferentiation was studied by isothermal titration calorimetry in an effort to address the order-disorder distinction in the diastereomeric complexes formed from a chiral macrocyclic host and enantiomeric carboxylates. As a result, the association entropy component TAS emerged as an indicator in the enantioselection of tartrate 14 and aspartate 15 by the macrocycle 13 containing two guanidinium anchor groups connected to each other by four urea units. The parent monotopic guanidinium compounds 1 or 2 did not show any enantioselection for chiral carboxylates.

Original languageEnglish
Pages (from-to)2329-2332
Number of pages4
JournalOrganic Letters
Volume8
Issue number11
DOIs
StatePublished - 25 May 2006

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