Effect of a Rigid Sulfonamide Bond on Molecular Folding: A Case Study
Suhonen, A., Morgan, I., Nauha, E., Helttunen, K., Tuononen, H., & Nissinen, M. (2015). Effect of a Rigid Sulfonamide Bond on Molecular Folding: A Case Study. Crystal Growth and Design, 15 (6), 2602-2608. doi:10.1021/acs.cgd.5b00424
Published inCrystal Growth and Design
© 2015 American Chemical Society. This is a final draft version of an article whose final and definitive form has been published by ACS. Published in this repository with the kind permission of the publisher.
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.