6533b7d1fe1ef96bd125ccdb
RESEARCH PRODUCT
Effect of a Rigid Sulfonamide Bond on Molecular Folding: A Case Study
Aku SuhonenKaisa HelttunenHeikki M. TuononenMaija NissinenElisa NauhaIan S. Morgansubject
HydrogenStereochemistrychemistry.chemical_elementmolecular foldingkonformeeritorgaaninen synteesiCrystalSide chainmolecular conformersGeneral Materials Sciencemolekyylien laskostuminenta116sulfonamidisidosConformational isomerismX-ray crystallographychemistry.chemical_classificationHydrogen bondsulfonamide bondGeneral Chemistryorganic synthesisCondensed Matter PhysicsSulfonamideFolding (chemistry)chemistryIntramolecular forceröntgenkristallografiadescription
A disulfonamide compound with bulky aromatic side chains was prepared, and its properties as a potential building block for foldamers were evaluated. Two different solvate crystal forms of the compound were identified and compared to the structures of an analogous oligoamide and related disulfonamides. The disulfonamide is unfolded in one of the solvates, whereas in the other one, a loosely folded conformer stabilized by an intramolecular hydrogen bond is found. Density functional calculations indicated that the loosely folded conformer is slightly more stable than its unfolded isomer. The calculations also identified a third, more tightly folded and more extensively hydrogen bonded, conformer that is even lower in energy. peerReviewed
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2015-05-19 | Crystal Growth & Design |