Supramolecular Recognition and Energy Frameworks in Host-Guest Complexes of 18-Crown-6 and Sulfonamides

Ming Shi, Sajesh Thomas, George Koutsantonis, Mark Spackman

Research output: Contribution to journalArticlepeer-review

34 Citations (Scopus)

Abstract

© 2015 American Chemical Society. Crystalline molecular complexes of 18-crown-6 with three sulfonamide analogues (methane, benzene, and toluene sulfonamides) have been synthesized and characterized. Among these, the 18-crown-6:benzenesulfonamide complex exhibits three crystal forms, including a polymorphic pair. Interaction energy calculations show that the host-guest binding energies in these complexes are very high (∼92-104 kJ·mol-1). Energy framework analysis identifies the hierarchy of intermolecular interactions and their topology; a trimeric motif formed by two guest molecules and a crown host is found to be a salient structural feature in these complexes. This study establishes the "sulfonamide-crown motif" as a very robust and predictable supramolecular recognition unit.
Original languageEnglish
Pages (from-to)5892-5900
Number of pages9
JournalCrystal Growth and Design
Volume15
Issue number12
Early online date29 Oct 2015
DOIs
Publication statusPublished - 2 Dec 2015

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