Solid-state examination of conformationally diverse sulfonamide receptors based on Bis(2-anilinoethynyl)pyridine, -bipyridine, and -thiophene

Orion B. Berryman, Charles A. Johnson, Chris L. Vonnegut, Kevin A. Fajardo, Lev N. Zakharov, Darren W. Johnson, Michael M. Haley

Research output: Contribution to journalArticlepeer-review

Abstract

Utilizing an induced-fit model and taking advantage of rotatable acetylenic C(sp)-C(sp2) bonds, we disclose the synthesis and solid-state structures of a series of conformationally diverse bis-sulfonamide arylethynyl receptors using either pyridine, 2,2′-bipyridine, or thiophene as the core aryl group. Whereas the bipyridine and thiophene structures do not appear to bind guests in the solid state, the pyridine receptors form 2 + 2 dimers with water molecules, two halides, or one of each, depending on the protonation state of the pyridine nitrogen atom. Isolation of a related bis-sulfonimide derivative demonstrates the importance of the sulfonamide N-H hydrogen bonds in dimer formation. The pyridine receptors form monomeric structures with larger guests such as BF4- or HSO4-, where the sulfonamide arms rotate to the side opposite the pyridine N atom.

Original languageEnglish
Pages (from-to)1502-1511
Number of pages10
JournalCrystal Growth and Design
Volume15
Issue number3
DOIs
StatePublished - Mar 4 2015

Fingerprint

Dive into the research topics of 'Solid-state examination of conformationally diverse sulfonamide receptors based on Bis(2-anilinoethynyl)pyridine, -bipyridine, and -thiophene'. Together they form a unique fingerprint.

Cite this