title: Solid-State Examination of Conformationally Diverse Sulfonamide Receptors Based on Bis(2-anilinoethynyl)pyridine, -Bipyridine, and -Thiophene.
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.
authors.affiliation: Department of Chemistry & Biochemistry and the Materials Science Institute, University of Oregon, Eugene, Oregon 97403-1253, United States.
authors.forename: Orion B
authors.initials: OB
authors.lastname: Berryman
authors.affiliation: Department of Chemistry & Biochemistry and the Materials Science Institute, University of Oregon, Eugene, Oregon 97403-1253, United States.
authors.forename: Charles A
authors.initials: CA
authors.lastname: Johnson
authors.affiliation: Department of Chemistry & Biochemistry and the Materials Science Institute, University of Oregon, Eugene, Oregon 97403-1253, United States.
authors.forename: Chris L
authors.initials: CL
authors.lastname: Vonnegut
authors.affiliation: Department of Chemistry & Biochemistry and the Materials Science Institute, University of Oregon, Eugene, Oregon 97403-1253, United States.
authors.forename: Kevin A
authors.initials: KA
authors.lastname: Fajardo
authors.affiliation: CAMCOR, University of Oregon, 1443 East 13th Avenue, Eugene, Oregon 97403, United States.
authors.forename: Lev N
authors.initials: LN
authors.lastname: Zakharov
authors.affiliation: Department of Chemistry & Biochemistry and the Materials Science Institute, University of Oregon, Eugene, Oregon 97403-1253, United States.
authors.forename: Darren W
authors.initials: DW
authors.lastname: Johnson
authors.affiliation: Department of Chemistry & Biochemistry and the Materials Science Institute, University of Oregon, Eugene, Oregon 97403-1253, United States.
authors.forename: Michael M
authors.initials: MM
authors.lastname: Haley